[HN Gopher] Peter Thiel turned a Roth IRA into a $5B tax-free pi...
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       Peter Thiel turned a Roth IRA into a $5B tax-free piggy bank
        
       Author : giuliomagnifico
       Score  : 329 points
       Date   : 2021-06-24 11:20 UTC (11 hours ago)
        
 (HTM) web link (www.propublica.org)
 (TXT) w3m dump (www.propublica.org)
        
       | Tycho wrote:
       | The negativity here is misled. Thiel made investments in
       | companies which he thought might one day be of enormous value to
       | society. Their current valuations, and the size of his IRA, prove
       | him right. We can thank early investors like Thiel for bringing
       | this potential to fruition. And not only that, but Thiel has not
       | consumed any of this well-earned wealth, instead leaving it
       | untouched, hasn't converted it into scarce goods and services,
       | presumably because he didn't see virtue in the gross materialism
       | that consuming it would entail. These investments are heroic acts
       | by Thiel.
        
         | steve_adams_86 wrote:
         | > heroic acts
         | 
         | I don't understand - can you elaborate on why exactly this is
         | heroic?
        
           | Tycho wrote:
           | In the sense that he developed his business acumen and
           | foresight to an exquisite degree and was then able to take
           | well-informed risks with his own resources that in the end
           | produced a great outcome for society (and himself). Many
           | people fail to develop their talents, or squander them, or
           | are too over-cautious to use them, and they and society are
           | the worse for it.
        
         | verall wrote:
         | Yup, no companies are quite as valuable to society as Paypal
         | and Palantir. I can think of few companies that have done more
         | _good_ for more people, and Thiel deserves every dime of that
         | $5B for ratfucking the populace.
        
       | calkuta wrote:
       | Good. What's wrong, the government doesn't have enough money?
        
       | oxymoran wrote:
       | He's a quasi libertarian that doesn't trust the government with
       | his tax money. What was expected? Further, if you know that's
       | what he think and it's within the law, what are we doing here
       | with this expose? It would be one thing if he was critical of
       | other people for working within the law to avoid taxes and you
       | caught him being a hypocrite but this is not that. If we are
       | going to be critical here, it should be of whatever loop holes
       | allow this.
        
         | mywittyname wrote:
         | He has no problem taking the government's money though. If he
         | didn't trust the government, I would expect that he'd refuse to
         | work with them on the grounds of not being able to trust them.
        
           | missedthecue wrote:
           | I believe that the parent is implying that Thiel doesn't
           | trust the government to use his money prudently, not that the
           | government is liable to cheat him out of a contract.
           | 
           | That's not really a double standard any more than taking a
           | paycheck from google while using duckduckgo on your PC at
           | home is a double standard.
        
       | w0mbat wrote:
       | Headline could be "Person uses retirement account to save money
       | for retirement."
        
         | shanecleveland wrote:
         | ... in ways that are not accessible to the everyday person.
        
         | xkjkls wrote:
         | The fact that someone used a vehicle that limits your yearly
         | contribution to $5500 a year to amass $5 billion is worth
         | investigating. The investment return needed for that is close
         | to 60% annually, an inconceivably high rate of return for any
         | long period of time.
        
           | seafoam wrote:
           | "an inconceivably high rate of return"
           | 
           | I don't think that word means what you think it means
        
             | medvezhenok wrote:
             | I mean, considering no-one has achieved that rate of return
             | (in the public markets) with compounding ever, that's
             | probably a fair observation. The closest was the Medallion
             | Fund, but that's a non-compounded return at $10B AUM.
             | 
             | But also somewhat irrelevant as the main point of the
             | article focuses on that first investment ($2K -> $33M in
             | 2-3 years via private Paypal shares).
        
               | gravypod wrote:
               | I have no skin in the game but "in the public markets" is
               | a very key part of this discussion. If he did purchase
               | his stock allocations from founding PayPal (regardless of
               | of if this was legal) this would have _not_ been in the
               | public market. This is an extremely high risk time and
               | money investment that could have been worth $0 the next
               | day. This is why a lot of people end up trying to start a
               | startup. To get huge financial gains for themselves.
        
           | jppope wrote:
           | Yes... the investment return from Facebook
        
         | _jal wrote:
         | Why not? Similarly, another of today's headlines could also be
         | 'Property damage inconveniences some in Florida'.
        
         | [deleted]
        
         | crispyambulance wrote:
         | > "Person uses retirement account to save money for
         | retirement."
         | 
         | ... with a few extra "twists" that utterly subvert the
         | intention of the Roth IRA, making it possible to accumulate an
         | astronomical dynastic fortune without having to pay taxes on it
         | like normal people.
        
         | sushid wrote:
         | The intent of the article is to point out how the rich truly
         | take advantage of existing tax laws/loopholes to stay even more
         | rich.
         | 
         | No one is claiming Thiel did anything illegal. But it does seem
         | a bit preposterous that billionaires can amass $5B Roth IRA
         | accounts.
        
           | ne0flex wrote:
           | I'm curious how he was able to get a Roth IRA in the first
           | place. Apparently Roth IRA began in 1997 and there's a
           | contribution limit if you make above a certain amount.Given
           | that Thiel started "Thiel Capital Management" in 1996, I'm
           | willing to bet he was above the earning limit.
        
             | lordnacho wrote:
             | Says in the article he was below the limit.
             | 
             | If you're reasonably wealthy and you start a firm, there's
             | no problem just taking a smaller salary. It's a little bit
             | surprising that the rules don't address this though. Why
             | not just say Roth IRA is for people with net worth under
             | some figure? Or as mentioned in the article, put a cap on
             | the amount of tax exempt money?
        
             | hammeiam wrote:
             | Anybody can have a Roth IRA. Even if you're over the income
             | limit for a Roth, you can still convert a traditional to a
             | Roth IRA after you pay taxes on the amount. These
             | conversions are pretty common and well known.
        
             | xkjkls wrote:
             | Probably by a traditional IRA to Roth IRA conversion.
        
             | anonAndOn wrote:
             | Like every other SV startup, he was paid a decent salary
             | with lots of stock and thus qualified under the income
             | limits.
        
           | jppope wrote:
           | The intent of ProPublica's entire series of articles is to
           | imply that wealthy Americans are immorally building their
           | wealth. They are taking advantage of the fact that the public
           | doesn't have basic financial literacy to turn the public
           | against wealthy Americans and some of our most important
           | systems in America (Entrepreneurship, Joint-stock companies,
           | etc).
           | 
           | Thiel bought a lotto ticket in his Roth IRA, after which he
           | invested the earnings into other high-risk ventures which
           | also worked out.
        
             | FabHK wrote:
             | I have basic financial literacy, and found that article
             | insightful and alarming. Maybe your political views
             | coloured your dismissal of the article series and "the
             | public".
             | 
             | I don't think tax shelters for retirement accounts were
             | designed to let financiers such as Thiel and Romney buy
             | undervalued promising lottery tickets from themselves or
             | their buddies, or should be used as such.
        
             | medvezhenok wrote:
             | The big argument was whether it was a true lotto ticket
             | (say buying Bitcoin at 1 cent, where everyone accepts it's
             | valued at 1 cent), or whether it was actually self dealing
             | (real best-estimate value of shares was maybe $0.10 a
             | share, and he bought in IRA for $0.001 a share). That means
             | the true value of his IRA "contribution" becomes $170,000
             | instead of $1,700, which is clearly tax evasion.
             | 
             | Still a lotto ticket, but that first transaction becomes a
             | lot less innocent.
        
             | nickpp wrote:
             | It is fascinating how the ProPublica articles are
             | redistributed in mainstream media (BBC, CNN, etc) even
             | though they are obviously wrong, biased and even based on
             | stolen private data.
             | 
             | It's almost as if someone is having an agenda...
        
           | NonEUCitizen wrote:
           | He wasn't a billionaire when he started the IRA account.
        
       | SamReidHughes wrote:
       | This is based on stolen personal data.
        
         | scop wrote:
         | Indeed. I'm surprised this is not a main part of the HN
         | conversation. It concerns me that the IRS leaking personal
         | financial information is not the main story.
        
       | [deleted]
        
       | giantg2 wrote:
       | I'd love to even double my IRA. Sadly, I dont think this article
       | will be helpful to me.
        
       | bawana wrote:
       | Another example of fine financial engineering. Money from
       | financial instruments (interest income, capital gains, etc)
       | should be restricted in its use. That money should only be usable
       | in purchasing real goods (not options) real products and real
       | labor. By allowing investment gains to be used for further
       | investment, we allow increasing demand for financial instruments
       | to drive up their prices and attract even more money. Instead of
       | building roads, schools and paying our teachers, we are using our
       | money to 'buy more money', an abstraction that does not really
       | benefit us.
        
       | [deleted]
        
       | suyash wrote:
       | That's a genius move, we should all learn from this and take
       | advantage. Nice job Peter!
        
       | arbitragy wrote:
       | 1.7m shares of Paypal at .001 is worth 5B at the current share
       | price of 295.
       | 
       | Obviously debatable whether you can mark shares of your own
       | company / PE firm sponsor equity / etc at near zero in a tax
       | sheltered vehicle. But if Thiel held shares in a personal account
       | and borrowed against them he wouldn't have owed tax either, as
       | unrealized capital gains are not taxed.
       | 
       | Buffett, Musk, Bloomberg, etc. all have the vast majority of
       | their wealth in businesses they founded, and have subsequently
       | paid de minimuis taxes relative to their net worth.
       | 
       | All have arguably made significant contributions to society and
       | world at large, magnitudes higher than their net worth and taxes
       | paid.
        
         | vineyardmike wrote:
         | > All have arguably made significant contributions to society
         | and world at large, magnitudes higher than their net worth and
         | taxes paid.
         | 
         | Very arguable. I would take up that argument. I don't believe
         | this too be true.
        
       | breck wrote:
       | The data here is super interesting. The tone and editorializing
       | are idiotic.
       | 
       | That being said, ultimately lawmakers are at fault.
       | 
       | We need to start thinking of law as code. We want to minimize the
       | complexity of law, just like you want to minimize the complexity
       | of code.
       | 
       | I have a new way to do that:
       | 
       | https://github.com/treenotation/research/blob/master/papers/...
       | 
       | 2D Languages will be the future of the law and democracy.
        
         | quickthrower2 wrote:
         | What is a 2D language?
        
           | breck wrote:
           | A language that can be near completely specified by a stack
           | of 2D grammars of increasing abstraction.
           | 
           | Binary notation is a general purpose syntax in 1 dimension.
           | There exists a 2D general purpose syntax, where you not only
           | have columns but all rows, and from there you can build
           | abstractions from binary to numeral systems to letters to
           | words to structs to systems.
        
         | vmception wrote:
         | All the "rich people tax" articles have an idiotic tone as if
         | they've found a smoking gun of .... something
         | 
         | They really prey on ignorance
        
           | rglover wrote:
           | As well as envy and greed, though, they'll never admit it.
        
         | MomoXenosaga wrote:
         | The lawmakers are quite literally the same people who advise
         | rich people on taxes.
         | 
         | The funniest thing I ever saw was an African civil servant who
         | had gone private now telling foreign companies how to fuck the
         | government he used to work for.
        
         | [deleted]
        
       | cannabis_sam wrote:
       | Tax is a joke to rich people, and that's the exact reasons
       | economic inequality is a problem..
        
         | missedthecue wrote:
         | In the USA, the top 1% make 20% of the income but pay almost
         | 40% of the taxes. That seems very progressive, not a 'joke'.
        
           | tomjakubowski wrote:
           | Careful. The top 1% pay 40% of federal income tax, not of all
           | taxes. Federal income tax is around half of total federal tax
           | revenue.
           | 
           | I also wonder, is that "20% of all income" figure 20% of all
           | taxable income, or all declared income?
        
             | richwater wrote:
             | > figure 20% of all taxable income, or all declared income?
             | 
             | Since we're baselessly speculating, it might be 100!
        
       | listless wrote:
       | > Yet, from the start, a small number of entrepreneurs, like
       | Thiel, made an end run around the rules: Open a Roth with $2,000
       | or less. Get a sweetheart deal to buy a stake in a startup that
       | has a good chance of one day exploding in value. Pay just
       | fractions of a penny per share, a price low enough to buy huge
       | numbers of shares. Watch as all the gains on that stock -- no
       | matter how giant -- are shielded from taxes forever, as long as
       | the IRA remains untouched until age 59 and a half. Then use the
       | proceeds, still inside the Roth, to make other investments.
       | 
       | What? Am I missing something or is that a horrible explanation of
       | how this works? I still don't understand how he used a Roth to
       | shield 5 billion from taxes. I'm much more alarmed that he gets
       | deals on startups that nobody else does. That hardly seems fair.
        
       | maxk42 wrote:
       | Utterly astounded and dismayed to see this much of HN's audience
       | completely fail to comprehend what they've read here and paint
       | this as some sort of sinister theft.
       | 
       | This is the law functioning as intended. Thiel's case is a one-
       | in-100-million+ event. He may have the only Roth IRA in existence
       | that's valued at over $5 billion. But he didn't do it by
       | exploiting some sort of "loophole" or paying high-priced
       | accountants to shield his assets in foreign entities offshore. He
       | put his investments in a Roth IRA just like any of you can do.
       | The only difference is his investments were in the top 0.0001% in
       | terms of performance. That's generally how people get to be
       | billionaires.
       | 
       | And that's not even to mention that the assets in a Roth IRA are
       | essentially worthless to him - he's not old enough to make
       | withdrawals or take distributions tax-free and you can't borrow
       | against a Roth IRA. The funds are essentially unavailable to him
       | for years to come unless he wants to pay taxes and penalties.
       | 
       | Again - this isn't a tax dodge. This is someone who used the law
       | exactly as intended without any illegal or shady dealings and
       | happened to be incredibly fortunate.
       | 
       | The whole article is a hit piece designed to get whip people into
       | a furor. And lately I've been noticing propublica publishing a
       | lot of those.
        
         | onlyfortoday2 wrote:
         | this is a forum for programmers. they know nothing about
         | finance
        
         | hyperpape wrote:
         | You're right that this is legal, and that it does not seem to
         | involve any trickery. It's not clear that it's even a loophole
         | per se.
         | 
         | But that is not the same as intended, which is a stricter bar.
         | Arguably a provision capping the tax-exempt returns to a mere
         | 10000% (just spitballing, surely there are better ways to write
         | such a provision) would have been more in keeping with the
         | intent of the law.
        
           | vmception wrote:
           | A stricter bar because?
           | 
           | What issue do you have with people having post tax dollars? I
           | don't really understand this sentiment, it seems to be at
           | odds with even the government's goals.
        
             | hyperpape wrote:
             | You misinterpret. I mean a stricter bar for interpretation.
             | 
             | My own opinion on taxes is irrelevant--the parent poster
             | cannot say "it's legal, so it's the intent of the law".
             | 
             | This is true whether it's a good or a bad law.
        
         | eplanit wrote:
         | > The whole article is a hit piece designed to get whip people
         | into a furor. And lately I've been noticing propublica
         | publishing a lot of those.
         | 
         | Yes. The story is shaped and told to feed "Capitalism and
         | Wealthy People are Bad" narrative.
        
         | vmception wrote:
         | From what I can tell, people don't want to learn, they have a
         | warped view of taxes at all which drives their furor
         | 
         | I disagree about the Roth IRA being unavailable to him though.
         | He listed it as an asset on his New Zealand citizenship
         | application and it didnt hurt. If push comes to shove he can
         | take any amount out of it and pay the "penalty" which is income
         | tax + 10%, so worst case in this country is around 60% on the
         | portion taken out if the tax residency - that specific year -
         | was in a high tax state instead one of the many zero income tax
         | states where it would just be 47% or so. Some European
         | countries have it worse at relatively low amounts.
        
         | tomdell wrote:
         | PayPal shares were purchased by the CEO at fractions of a penny
         | - an obviously fraudulent valuation - effectively turning
         | Thiel's $2k fund into a multimillion dollar fund overnight in
         | actual fact and circumventing the intent of the law.
        
         | aeturnum wrote:
         | I think you're missing the thrust of ProPublica's reporting.
         | This is not an article claiming that laws have been broken. It
         | is pointing out the difference in intent and reality for a part
         | of our financial law. It is not that Thiel is getting huge
         | windfalls from this account now (he is a billionaire, he does
         | not need them), it's that this is another example of a
         | billionaire getting abnormally large absolute benefits from a
         | financial instrument.
         | 
         | The message is not that Thiel has committed some crime, but
         | that he has cleverly and successfully used an instrument
         | designed for the 'middle class' to shelter billions in
         | earnings. The implication is that we should _reform these tax
         | vehicles so that the ultra-wealthy cannot use them_ - not that
         | Thiel is cheating the system as it exists. The lines which talk
         | about contribution limits to Roths are to emphasize that _this
         | was not intended to shelter this kind of wealth_.
         | 
         | > _This is someone who used the law exactly as intended_
         | 
         | I 100% agree Thiel has broken no crime and I think you should
         | be *embarrassed* to say that the people who created the Roth
         | intended this. There is no evidence of that. We should
         | recognize that this Roth IRA is sheltering more money than
         | people expected and make (or refrain from making) regulatory
         | changes in response.
        
           | marris wrote:
           | If they intended something else, then why didn't they write
           | the rules to reflect "else"? The truth is that they didn't
           | think that any Roth IRA investor would be as successful as
           | Thiel. He showed that he can be. Good for him.
        
             | TaylorAlexander wrote:
             | The law is an evolving code as we discover new scenarios.
             | This reporting is exploring one of those unexpected
             | scenarios so we can understand the need to change the law.
        
               | lefrenchy wrote:
               | Not to mention that rich people can pay the smartest
               | legal scholars and financial gurus to find workarounds
               | and engineer ways to make more money.
        
             | aeturnum wrote:
             | > _If they intended something else, then why didn 't they
             | write the rules to reflect "else"?_
             | 
             | If the web server didn't intend to allow a buffer overflow
             | on POST requests, why did it improperly allocate memory?
             | 
             | I agree with you that we have a choice: should this be
             | allowed? If not, how do we transition? If yes, do we want
             | to place any limits on it in the future?
        
               | marris wrote:
               | When you create a tax shelter, someone _always_ asks
               | "what if someone uses this to create an enormous amount
               | of wealth"? This is not just true for the US tax code,
               | but has been true for probably every tax code in history.
               | When that question is raised, the first thing to
               | contemplate is how likely it is to occur. And if it is
               | not considered likely, then this risk is accepted.
               | 
               | Fuzzing may be a good analogy. Fuzzing can be used to
               | test POST request processing when the logic is too
               | complicated to validate via more formal means. We try a
               | large sample of inputs. If they pass, then the test
               | passes, even though we cannot be confident that the code
               | will handle every input string correctly.
        
               | aeturnum wrote:
               | Right, but like - if you later find a buffer overflow
               | that the fuzzing missed - you'll fix it right?
        
               | marris wrote:
               | Sure, if you can reproduce the input and if you agree
               | that it is misuse. This is a scenario where we don't know
               | the formula to create $5B, and and there is no consensus
               | that it ("making an extremely successful investment in a
               | tax shelter") is misuse.
        
               | beaner wrote:
               | Why wouldn't it be allowed? If my investments into my
               | Roth IRA performed so we'll i became a billionaire, I
               | wouldn't want to be treated differently. And I wouldn't
               | want my mom or my neighbor to either. They essentially
               | got lucky, they're not taking anything from me in being
               | so fortunate.
               | 
               | The "problem" in this case is that Thiel was already a
               | billionaire to begin with, and such luck on top of
               | existing wealth is what irrationally bothers people.
        
               | aeturnum wrote:
               | We have a progressive tax system, which generally taxes
               | higher incomes at greater rates. Maybe we do want the
               | Roth to be an unlimited shelter, but that has generally
               | not been the approach we have taken.
               | 
               | > _The "problem" in this case is that Thiel was already a
               | billionaire to begin with, and such luck on top of
               | existing wealth is what irrationally bothers people._
               | 
               | This isn't how I feel and I don't actually think that is
               | the case ProPublica is making. Tax breaks can also be
               | understood as payments - is it in the interest of the US
               | to pay Thiel to put his money in a Roth? How much should
               | the US pay? How many of your tax dollars would you want
               | to go to funding tax breaks for Thiel?
               | 
               | I am sure people are vindictive as well, but the tax
               | questions seem both meaningful and work asking to me.
        
               | marris wrote:
               | > Is it in the interest of the US to pay Thiel to put his
               | money in a Roth? How much should the US pay? How many of
               | your tax dollars would you want to go to funding tax
               | breaks for Thiel?
               | 
               | I submit that yes, it is in the interest of the US to do
               | this, provided that Thiel is creating value for the US
               | (and to some extent the world) with that money. $5B is
               | approximately one day of US government spending (maybe
               | less now). Letting Thiel invest $5B may not be the _best_
               | investment decision that the USG has ever made (e.g.
               | Internet funding, Telsa support), but it is way higher
               | than the mean decision.
        
               | noodle wrote:
               | The difference is also that the investments your mom or
               | your neighbor put into their Roth IRA are going to be
               | publicly traded companies and similar. Thiel, an
               | accredited investor, sold himself shares of his own
               | company at a very low price to put into his white glove
               | managed Roth IRA.
               | 
               | The average person does not have the ability to do this.
        
             | jychang wrote:
             | Are you seriously trying to say that lawmakers can't write
             | buggy code with edge cases they didn't consider?
        
               | marris wrote:
               | Sure they can.
               | 
               | Here, I think some lawmakers probably thought (a) "if
               | someone can use this tool that well, then more power to
               | him", or (b) I don't like it, but it is so unlikely, and
               | I can probably live with it.
               | 
               | I don't think it was a scenario of someone failing to
               | "consider the case."
        
           | jupp0r wrote:
           | I think you are missing the point of GP. There is nothing
           | billionaire specific about what Thiel did. You could have
           | done the same with the same Roth contributions. If the law is
           | changed it will not only limit Peter Thiel from doing this
           | but also you and me.
        
             | mediaman wrote:
             | It's clear that the IRA system was created to encourage
             | saving for retirement through tax deferral.
             | 
             | It was not intended for billionaires, because for them it
             | serves no purpose in encouraging them to save for
             | retirement. (Financial security in retirement is not
             | something billionaires worry about.)
             | 
             | The idea that there is no way the law could exclude this
             | sort of benefit while not hurting the middle class is
             | absurd. There are any number of ways to do it: for example,
             | any plan with more than $10 million in capital gains could
             | have gains above that amount lose their tax-exempt status.
        
               | lotsofpulp wrote:
               | >It's clear that the IRA system was created to encourage
               | saving for retirement through tax deferral.
               | 
               | It is not clear to me that IRAs were created for this
               | reason. As far as I can tell, they seem to exist only to
               | provide plausible deniability (and poorly at that) for
               | 401ks giving an advantage to big businesses that can
               | afford to implement them (pre Vanguard/cheap passive
               | investing days) over smaller businesses that could not
               | afford to implement 401ks.
               | 
               | Otherwise, I see no reason why people who work for
               | employers that can afford to offer 401ks should have a
               | leg up in tax advantaged retirement savings over people
               | who do not and have to rely on IRAs (which have
               | drastically lower contribution limits).
               | 
               | >It was not intended for billionaires,
               | 
               | It would have been simple to write in a limit for maximum
               | amount of tax free gains in Roths.
        
             | et-al wrote:
             | There is actually something _millionaire_ specific about
             | what Thiel did. He was an accredited investor that was able
             | to buy private shares that the general public cannot buy.
             | 
             | If IRAs were only allowed to purchase publicly-listed
             | stock, this wouldn't have happened.
        
               | Scoundreller wrote:
               | Which also gives the accredited investors another
               | advantage: with less capital available, the valuations
               | are inherently depressed.
        
             | [deleted]
        
             | ska wrote:
             | > If the law is changed it will not only limit Peter Thiel
             | from doing this but also you and me.
             | 
             | That obviously not necessarily true. One can imagine a
             | change in law that limits tax sheltering of this type for
             | any individual to say, 10mm. A tiny fraction of the
             | population would be affected.
        
               | tablespoon wrote:
               | > That obviously not necessarily true. One can imagine a
               | change in law that limits tax sheltering of this type for
               | any individual to say, 10mm. A tiny fraction of the
               | population would be affected.
               | 
               | Or limit the types of assets that can be held in an IRA
               | to those that are publicly traded and can be bought on
               | the open market. It seems like an important part of this
               | scheme was Thiel basically got to set the price of some
               | shares he sold himself, because they weren't publicly
               | traded at the time.
        
               | s1artibartfast wrote:
               | Then you are limiting what people can do with their money
               | 2 inflating stock prices of giant companies. What if I
               | want to invest in a friend's business or buy a rental
               | property. Are you saying it should be illegal for me to
               | do that with my IRA?
        
               | walshemj wrote:
               | Your being very optimistic here and changes will make the
               | existing v poor US pensions system worse.
               | 
               | edge cases make bad law eg using the small number of
               | social security cheats to reduce entitlements to all or
               | the tiny tiny number of cases of elector fraud to
               | disenfranchise the poor and BAME.
               | 
               | Dunblane and the Dangerous dogs act in the UK are
               | related.
               | 
               | This is the sort of thing that fringe "hobbyist"
               | activists do assuming they aren't paid agent
               | provocateur's
        
               | ska wrote:
               | > Your being very optimistic here
               | 
               | I'm not being optimistic or pessimistic, just pointing
               | out a logical fallacy.
        
             | aeturnum wrote:
             | "The law, in its majestic equality, forbids rich and poor
             | alike to sleep under bridges, to beg in the streets, and to
             | steal their bread."
             | 
             | I think there are about 4 billion billionaire-specific
             | things Thiel is getting out of this arrangement that aren't
             | accessible to me (or, I suspect, to you).
        
             | markdown wrote:
             | That's the point. It should limit temporarily embarrassed
             | billionaires like you and me from doing this if we regain
             | our riches.
        
           | peytoncasper wrote:
           | What is your limit on how much money should be "sheltered" by
           | a Roth IRA?
           | 
           | At the time Thiel was not an ultra-wealthy billionaire. From
           | the article.
           | 
           | "I said, 'If you really think this is going to be big, you
           | know, you might want to consider this new Roth,'" recalled
           | Anderson
           | 
           | The Roth IRA is intended to be a retirement vehicle for
           | people to make contributions too with the intention of it not
           | being touched till after retirement. As a perk, it is not
           | taxed.
           | 
           | Maybe its not within the "spirit" of the law, but I hardly
           | see how trying to create incredibly granular restrictions on
           | start up founders or people that believe they have a better
           | investing strategy is the right approach.
           | 
           | What about making it easier for normal people to have access
           | to the same IPOs that Thiel had access to?
        
             | aeturnum wrote:
             | > _What is your limit on how much money should be
             | "sheltered" by a Roth IRA?_
             | 
             | This is what I am saying the article is raising!
             | 
             | I'd limit it to $10m myself. Seems like that would be
             | enough to retire on. Probably tie it to inflation?
             | 
             | What number would you pick?
             | 
             | > _What about making it easier for normal people to have
             | access to the same IPOs that Thiel had access to?_
             | 
             | I would be fine with that but it seems like a separate
             | issue?
        
               | manigandham wrote:
               | I wouldn't pick a number. Who are you to decide how much
               | wealth someone else has?
        
               | unstatusthequo wrote:
               | How about freedom and no limit? Why limit?
        
               | peytoncasper wrote:
               | I'm not sure I would pick a number if I am honest, but I
               | can understand that a number probably exists.
               | 
               | If this wasn't Thiel but rather someone else who made
               | 60k/yr or 120k/yr, I don't think this would even be a
               | conversation. So what if they turned their Roth IRA into
               | 100 million.
               | 
               | In my opinion that is encouraging the right behavior and
               | the intent. Investing 2,000 per year of their wages and
               | trying to be somewhat forward thinking about their
               | retirement.
               | 
               | Now there is the open question of if an average person is
               | able to truly analyze such investments, but I think that
               | is a separate issue as well.
        
             | sp332 wrote:
             | And Roth IRAs are funded post-tax. That means he paid taxes
             | on the income already, before he put the money into the
             | IRA. That's why it's "tax-free".
        
               | peytoncasper wrote:
               | I think that's fair, although, and correct me if I am
               | wrong. Its his current income tax, so it's highly likely
               | that his income tax bracket is lower than the cap gains
               | tax that would normally be applied on investments like
               | this.
               | 
               | That being said, I tend to agree. Its to prevent double
               | tax in which you're trying to promote a better
               | investment. Your long term health and retirement.
        
               | pontifk8r wrote:
               | I'm correcting you: Unless he makes less than $40,000 in
               | salary, the capital gains tax rates are going to be lower
               | than the tax rate for ordinary income. The chart in this
               | article reveals more:
               | https://www.investopedia.com/articles/personal-
               | finance/10151...
        
           | lend000 wrote:
           | > successfully used an instrument designed for the 'middle
           | class' to shelter billions in earnings
           | 
           | A Roth IRA is beneficial if positions are being changed
           | (taxable events), because those taxes are deferred. For very
           | long term holding, the benefit caps out at 20% in exchange
           | for tying up the assets for decades.
           | 
           | He will eventually benefit, if the company is still valuable
           | when he comes of retirement age, by avoiding the single long
           | term capital gains hit he would otherwise pay. It'll be more
           | of a story, then, if the stock is near an all time high
           | value, but frankly, this is not a scalable investment
           | strategy for the wealthy sheltering their wealth (which would
           | be a more interesting story). This only worked because he has
           | been an exceptionally successful investor. This wouldn't be a
           | good strategy for every startup founder, because even if the
           | startup was mega-successful, the founders would not be rich
           | until retirement.
        
             | birken wrote:
             | He has been constantly changing his positions and using the
             | proceeds to invest in other companies. The benefit isn't
             | one time, it is compounding over time, because he gets to
             | keep investing the 20% of extra money he would have had to
             | pay in capital gains, over and over again, as he shifts his
             | money between investments.
             | 
             | He also doesn't have to keep all of his wealth in this Roth
             | IRA, just a percentage. It clearly is a scalable strategy
             | because lots of people are doing it.
        
         | SavantIdiot wrote:
         | This reminds me of Trump supporters who said, "Because he beat
         | the IRS and paid zero taxes means he's smarter than the
         | system."
         | 
         | Your argument is along the same lines: Theil followed the law,
         | ergo nothing "sinister" happened.
         | 
         | Which is the same as: "It isn't sinister because there is no
         | law."
         | 
         | Yet, where did laws come from? Oh right, from people who have
         | ethics. Because our ethics do not come from laws; our morals
         | do, but not our ethics. Morality is an invented extension of
         | ethics, which is codified into law when people think something
         | shitty is happening (well, that's how it SHOULD happen... but
         | that's the School-House-Rock version)
         | 
         | IMHO, and many others (sadly, to your "dismay") Theil is being
         | a greedy pig exploiting vagaries of the law for his MASSIVE
         | gain, and there needs to be laws to prevent this kind of
         | behavior because it is only available to the super wealthy, and
         | it makes the elite class even more untouchable (plus a thousand
         | other second-order effects).
        
           | bpodgursky wrote:
           | This isn't some complicated double-dutch tax sheltering
           | scheme though. It's functionally the same as using your Roth
           | IRA to buy a lottery ticket and winning. The vast majority of
           | startups fail.
           | 
           | It's just a super simple investment that succeeded because
           | his startup won.
        
             | SavantIdiot wrote:
             | Again: I have a problem with someone investing in their
             | startup using a government tax-protected shelter, and then
             | making a killing off of it: that is double dipping, and
             | scum-baggy.
             | 
             | Simple law: you cannot invest in your own company in your
             | own Roth IRA because it is blatantly unfair to other
             | investors who don't have similar insider trading abilities.
             | 
             | Done.
        
               | nrmitchi wrote:
               | I mean, you're already not allowed to use a Roth to
               | invest in a company that you're an officer of, major
               | shareholder in, etc (with many other restrictions), so
               | I'm not sure how adding a new law would have changed this
               | (since the existing ones appear to have just been
               | ignored)
        
               | cscurmudgeon wrote:
               | > Simple law: you cannot invest in your own company in
               | your own Roth IRA because it is blatantly unfair to other
               | investors who don't have similar insider trading
               | abilities.
               | 
               | Why can't other investors create their own startups and
               | invest their money similarly?
               | 
               | Startup founders take a lot of risk. There is a big
               | chance his investment could have been zero. It is strange
               | that ProPublica does not understand this basic concept.
               | 
               | Where is their report on millions of Roth accounts that
               | went to zero?
        
               | SavantIdiot wrote:
               | > It is strange ProPublica not understand this basic
               | concept.
               | 
               | One could ask how you demonstrably cannot understand the
               | conflation of two unrelated concepts?
               | 
               | Concept A: taking a risk to create a startup that you
               | hope becomes a profitable company by executing to its
               | core competency
               | 
               | Concept B: investing in your own company through a tax
               | vagary with an investment device that has nothing to do
               | with startup (or a particular startup)
               | 
               | Seems clear as day to me.
               | 
               | https://www.youtube.com/watch?v=BPX-wuplDvc
        
               | diob wrote:
               | The paltry amount he invested was hardly a risk. Had it
               | not panned out, he would have been out basically zilch.
        
         | chrisseaton wrote:
         | > That's generally how people get to be billionaires.
         | 
         | I think generally they inherit?
        
           | hyperpape wrote:
           | I believe that this has been true at some points in the past,
           | but is not true for the majority of the current slate of
           | billionaires, most of whose wealth comes from activities
           | during their lifetime.
           | 
           | It's a robber baron period, not a dynastic wealth period.
        
             | chrisseaton wrote:
             | > but is not true for the majority of the current slate of
             | billionaires, most of whose wealth comes from activities
             | during their lifetime
             | 
             | Huh you're right. I guess that's a source of hope!
        
               | [deleted]
        
         | outside1234 wrote:
         | Uh huh - I think we will need a full accounting on what exactly
         | happened here in an IRS audit to confirm that - I'm pretty
         | dubious.
        
           | DantesKite wrote:
           | The US government is pretty aggressive about getting their
           | tax dollars (no matter who it is).
           | 
           | See John McAfee, Al Capone.
        
             | DoreenMichele wrote:
             | I'm pretty sure Al Capone was not about aggressive tax
             | collecting but was instead about putting him away on the
             | one thing they could actually prove and make it stick.
        
             | diob wrote:
             | They're gone on record saying they only go after the small
             | fry though. The big ones hold them up in litigation.
        
             | nrmitchi wrote:
             | Really? IF the US is that aggressive about their tax
             | dollars, what was the full fallout of the Panama Papers
             | again?
             | 
             | I'm not going to say anything about McAfee at at this time,
             | but your other example was not really a target for
             | inditement based _solely_ on his tax crimes.
        
             | mapt wrote:
             | That was before 40 years of billionaires largely
             | controlling the agenda of government, with the past 15
             | years in particular seeing audit rates for this class drop
             | below audit rates for waitresses.
        
         | 1-more wrote:
         | > Again - this isn't a tax dodge. This is someone who used the
         | law exactly as intended without any illegal or shady dealings
         | and happened to be incredibly fortunate.
         | 
         | To quote Daniel Ellsberg: the scandal isn't that they're
         | breaking the law, the scandal is that what they're doing is
         | legal.
        
         | sida wrote:
         | I don't think that's true right. Peter Thiel purchased shares
         | in Paypal at $0.001 per share, which is far below fair market
         | value.
         | 
         | The "theft" here is the undervaluation of the shares with which
         | he purchased at
        
           | onlyfortoday2 wrote:
           | waffle talk
        
           | concreteblock wrote:
           | Who sold him those shares?
        
             | sida wrote:
             | It is in the article "Mr. Thiel purchased his founders'
             | shares in PayPal through his Roth IRA during PayPal's
             | formation"
             | 
             | I am willing the venture a guess that the initial valuation
             | was far greater than 0.001 per share. And this was all an
             | accounting trick to exploit IRA
        
               | throwaway5752 wrote:
               | I'd guess $.001 is the par value and there was no 409A
               | valuation. The initial basis doesn't really matter if it
               | is essentially zero or $1 or $5 in this case. The implied
               | current price on the founders shares is approximately
               | $2500.
               | 
               | I agree with Propublica's take
               | 
               |  _Yet, from the start, a small number of entrepreneurs,
               | like Thiel, made an end run around the rules: Open a Roth
               | with $2,000 or less. Get a sweetheart deal to buy a stake
               | in a startup that has a good chance of one day exploding
               | in value. Pay just fractions of a penny per share, a
               | price low enough to buy huge numbers of shares. Watch as
               | all the gains on that stock -- no matter how giant -- are
               | shielded from taxes forever, as long as the IRA remains
               | untouched until age 59 and a half. Then use the proceeds,
               | still inside the Roth, to make other investments._
               | 
               | I also think that there should be a cap on tax free
               | distributions sheltered by Roths, and they should not be
               | transferable upon death.
        
               | nerfhammer wrote:
               | The key is knowing exactly which startup to put your
               | $2000 in.
        
               | tablespoon wrote:
               | > The key here is that if you have to reliably identify
               | exactly which startup to put your $2000 in.
               | 
               | No. Theil was _already_ making a risky startup bet, so
               | the  "reliably identify" point is moot. All this maneuver
               | did was let him avoid all the taxes he'd owe if it paid
               | off.
        
               | marris wrote:
               | I disagree with ProPublica's take. If it was as simple as
               | "pay just fractions of a penny per share... watch as all
               | the gains..." then we would all do it. Not just with Roth
               | IRAs, but with our _entire portfolios._ The reason we don
               | 't all do this is because startups are very very risky.
               | Some people will succeed and walk away with windfalls.
               | Other people will lose their shirts. If there was
               | arbitrage, there would be a an "app for that" and there
               | would be more billionaires walking around.
        
               | lordnacho wrote:
               | What they seem to be suggesting is that a fair valuation
               | (well reasoned given all information) of the shares would
               | have put the investment at millions of dollars, but due
               | to a peculiarity of historical accounting, they could be
               | put at worth $2K because that was the creation price and
               | the last print.
               | 
               | For instance, it might be that a funding round was about
               | to happen. This is never a sure thing, so you could claim
               | that the shares are not worth the full price (and in any
               | case the only trade was at 2K), while privately thinking
               | "hmm, my shares are now worth x millions".
               | 
               | You then sell the shares to the Roth, thinking yourself
               | that you're putting x millions in the vehicle while
               | reporting 2K.
               | 
               | Doesn't sound illegal to me, but it also doesn't sound
               | like things are supposed to work this way.
        
               | Scoundreller wrote:
               | Or just exclude private shares from Roth IRAs.
               | 
               | Most people are non-accredited investors and therefore
               | ineligible to buy them.
               | 
               | Startups won't miss out on the $2000/yr from the few that
               | are eligible.
        
               | bpodgursky wrote:
               | Forcing all IRA investment through publicly listed
               | companies sounds like exactly the law a hedge fund would
               | write. Why allow people to invest in assets you can own
               | without going through a Wall Street investment bank?
               | 
               | Regulatory capture is forcing the entire economy through
               | your cartel in the name of nominal protection.
        
               | doggosphere wrote:
               | Publicly listed companies are equally available
               | opportunities for anyone participating in the
               | contribution rate-limited game of Roth IRA maximization.
               | 
               | Private share contributions give huge asymmetric upside
               | to private investors/founders. Yes they take risk in that
               | their shares still have to end up being worth something
               | one day, but clearly the upside tax advantages are
               | ridiculously unbalanced against the middle class because
               | not everyone has access to early stage investments.
               | 
               | So, even the playing field by:
               | 
               | - Letting anyone invest in early stage companies (this
               | has many other implications)
               | 
               | Or
               | 
               | - Only allow cash contributions to IRAs
        
               | Scoundreller wrote:
               | You can buy publicly traded companies without going
               | through brokers/stock exchanges.
               | 
               | What can be assured is that the exchange can be booked at
               | a market value, which can never be guaranteed in a
               | private sale in an opaque market, risking shenanigans to
               | shift value beyond the contribution limit.
               | 
               | (You can say a corp's initial shares have zero value, but
               | we can all agree here that a Corp formed to execute on a
               | startup team's plan/idea absolutely does have value).
        
               | woah wrote:
               | Are you saying that Peter Thiel should have known that he
               | would turn PayPal into a multibillion dollar business,
               | and because of this, the shares were not really
               | worthless?
               | 
               | EDIT: That was sarcastic, but re-reading, that basically
               | is what the article is saying:
               | 
               | > Get a sweetheart deal to buy a stake in a startup that
               | has a good chance of one day exploding in value.
               | 
               | 20-20 hindsight
        
               | vmception wrote:
               | it's honestly no wonder that the masses assumes
               | inaccessibly expensive accountants are necessary to
               | simply think clearly
        
               | ajju wrote:
               | All shares issued at founding have a near-zero cost
               | because, while you technically need to buy the shares,
               | the company (by definition) is worth $0 on the day you
               | start it.
               | 
               | There is no tax gimmick involved in that part. If you
               | require entrepreneurs to buy shares of their own company
               | for large sums of money on the day they start the
               | company, it would dissuade many entrepreneurs. On the day
               | I incorporated my company in Delaware, my debt exceeded
               | my assets and the startup was going to be my only
               | profession.
        
               | machinebun wrote:
               | Sure - there's no problem with valuing those shares at
               | $0.001 in general, because there's not much that
               | valuation matters for in the short term (eventually you
               | will pay different taxes depending on the end result of
               | your company).
               | 
               | However, Roth IRAs specifically are a tax shelter and
               | have contribution limits, so valuations matter a whole
               | lot for them (difference in $0.01 per share vs $0.001 per
               | share would be a difference of $500M vs $5B today).
               | That's why I think illiquid (or non-market cleared)
               | securities should not be allowed in Roth IRAs.
        
               | ska wrote:
               | > That's why I think illiquid (or non-market cleared)
               | securities should not be allowed in Roth IRAs.
               | 
               | That + a cap on tax shelter would solve the issue, if it
               | needs solving.
               | 
               | Perhaps also prohibit equity from any source where you
               | aren't arms length.
        
               | Scoundreller wrote:
               | > the company (by definition) is worth $0 on the day you
               | start it.
               | 
               | Is it?
               | 
               | If Elon Musk forms a corporation tomorrow, its market
               | value is more than $0 before he does a single thing with
               | it.
               | 
               | And that's all the IRS should care about for Roth
               | contribution limits: market value.
               | 
               | If I buy 1000 shares of PayPal from my mom for $2000 (mkt
               | value: a lot more!) and put that into my IRA and tell the
               | IRS that $2000 is the price we agreed (in the marketplace
               | of the dinner table).
        
               | vmception wrote:
               | Its still surprising to me that you got this backwards.
               | There is no reason to ever choose a higher par value than
               | that then when forming a company.
        
               | tylermenezes wrote:
               | When the company is formed the valuation is genuinely
               | very small because it has no assets, customers, etc.
               | Buying some of your shares in a Roth IRA at this point is
               | relatively common, enough so that I've heard multiple
               | people suggest that founders do it.
        
               | Scoundreller wrote:
               | Yeah, I doubt Thiel came up with this himself. Was
               | probably recommended by accountants whom should all be
               | familiar with Roth IRAs.
               | 
               | But the possibilities of windfall tax-free profits made
               | sure everyone kept quiet about it.
        
             | enahs-sf wrote:
             | As a founder you can grant yourself options or shares at
             | essentially infinitesimally small values in the very early
             | days of the company and pay virtually no tax.
        
               | bcrl wrote:
               | Other countries only allow shares of publicly traded
               | companies to be added to tax shelter savings accounts.
               | This seems like a reasonably fair way to prevent people
               | with significant resources from taking advantage of the
               | system in ways the general public cannot. Someone getting
               | returns in excess of hundreds of thousands of percent
               | should be able to afford paying a few percent in tax to
               | help pay for the infrastructure society has provided to
               | make success in industry possible.
        
               | walshemj wrote:
               | The UK doesn't there are a number of schemes that allow
               | this.
               | 
               | Everyone in the private company I work for has EMI
               | options that trigger on change of control.
        
               | enahs-sf wrote:
               | Forgive my ignorance but I was under the impression this
               | was startup founders standard operating procedure.
               | 
               | 1. Form a C Corp
               | 
               | 2. Grant founders shares at $0.000x/share
               | 
               | 3. Early exercise all of said shares at basically nothing
               | 
               | 4. Make 83(b) election to IRS
               | 
               | 5. Take advantage of long term cap gains and qsbs
               | 
               | I'm sure plenty of folks in this forum have done similar
               | things, the only difference is mr. thiel put it into his
               | Roth account, essentially betting on himself and it paid
               | off big time.
        
             | maxk42 wrote:
             | That's not how it works. When you incorporate, the
             | corporation has shares split among the founders. The
             | founders themselves determine the "par" value of each share
             | - essentially its intrinsic worth.
             | 
             | You have to pay this amount of money to acquire the shares
             | upon incorporation. (Each state does it a little
             | differently.) So it's generally made a very low value
             | between $0.0001 and $0.01. You'd pay the same amount if you
             | were to incorporate a new business. That's it. He put some
             | of his founding shares in Paypal in the Roth IRA when he
             | founded the company and he got incredibly lucky. Nothing
             | sinister happened.
        
               | phonon wrote:
               | Except if these were founder shares, he would likely be
               | disqualified. "Disqualified person...an officer, director
               | (or an individual having powers or responsibilities
               | similar to those of officers or directors), a 10 percent
               | or more shareholder, or a highly compensated employee
               | (earning 10 percent or more of the yearly wages of an
               | employer)"                 (2)Disqualified person
               | For purposes of this section, the term "disqualified
               | person" means a person who is--       (A)a fiduciary;
               | (B)a person providing services to the plan;       (C)an
               | employer any of whose employees are covered by the plan;
               | (D)an employee organization any of whose members are
               | covered by the plan;       (E)an owner, direct or
               | indirect, of 50 percent or more of--       (i)the
               | combined voting power of all classes of stock entitled to
               | vote or the total value of shares of all        classes
               | of stock of a corporation,       (ii)the capital interest
               | or the profits interest of a partnership, or
               | (iii)the beneficial interest of a trust or unincorporated
               | enterprise,       which is an employer or an employee
               | organization described in subparagraph (C) or (D);
               | (F)a member of the family (as defined in paragraph (6))
               | of any individual described in subparagraph (A),
               | (B), (C), or (E);       (G)a corporation, partnership, or
               | trust or estate of which (or in which) 50 percent or more
               | of--       (i)the combined voting power of all classes of
               | stock entitled to vote or the total value of shares of
               | all        classes of stock of such corporation,
               | (ii)the capital interest or profits interest of such
               | partnership, or       (iii)the beneficial interest of
               | such trust or estate,       is owned directly or
               | indirectly, or held by persons described in subparagraph
               | (A), (B), (C), (D), or (E);       (H)an officer, director
               | (or an individual having powers or responsibilities
               | similar to those of officers or        directors), a 10
               | percent or more shareholder, or a highly compensated
               | employee (earning 10 percent or more        of the yearly
               | wages of an employer) of a person described in
               | subparagraph (C), (D), (E), or (G); or       (I)a 10
               | percent or more (in capital or profits) partner or joint
               | venturer of a person described in        subparagraph
               | (C), (D), (E), or (G).       The Secretary, after
               | consultation and coordination with the Secretary of Labor
               | or his delegate, may by        regulation prescribe a
               | percentage lower than 50 percent for subparagraphs (E)
               | and (G) and lower than 10        percent for
               | subparagraphs (H) and (I).
               | 
               | https://www.law.cornell.edu/uscode/text/26/4975
        
           | ghufran_syed wrote:
           | You realize that when forming a company, the number of shares
           | you issue is arbitrary, right? If three founders each put in
           | $1 capital, and each get 1 share, then the price per share is
           | $1. If instead the founders get 1 million shares each, then
           | each share is worth 1 millionth of a dollar. What economic
           | difference does it make?
           | 
           | Or are you claiming that on the day that he paid $0.001 per
           | share, someone else paid more per share? If that didn't
           | happen, there is NO WAY to determine after the fact what the
           | "true" market value was on that date.
        
             | Scoundreller wrote:
             | > Or are you claiming that on the day that he paid $0.001
             | per share, someone else paid more per share
             | 
             | I suspect this was the case. Hypothetical example: Class A
             | shares were available for $100 each, and Class B shares for
             | $0.0001 each, but you could only get a B share by buying an
             | A share. With the implicit (or explicit?) promise to merge
             | the share classes together eventually to cause the prices
             | to converge and massively inflate the Roth IRA side of the
             | investment where you stashed the B shares.
             | 
             | So the $0.0001 shares all cost you $100 each to buy, but
             | that $100 comes from outside your $2000 contribution limit.
        
               | vmception wrote:
               | You don't need two classes of shares for this you are
               | over complicating things
        
               | Scoundreller wrote:
               | Yeah, could just do the share issuance in 2 stages: the
               | first at $0.000001 then later at >$1 to raise useful
               | capital.
               | 
               | But multiple share classes often exist anyway for various
               | reasons (different preferences upon liquidation,
               | different voting polices, different retraction policies,
               | different dividend policies, etc)
        
               | vmception wrote:
               | Yes
               | 
               | I believe Bain Capital used separate share classes to
               | pump their employees 401ks
               | 
               | That level of collaboration and financial engineering
               | should be encouraged
        
         | cdolan wrote:
         | The true theft is the thousands of private documents on private
         | citizens stolen from the IRS and provided to ProPublica
        
           | justanotherguy0 wrote:
           | Yeah this vigilantism from careerists in the federal
           | bureaucracy must be punished.
           | 
           | We're never going to hear about the ins and outs of their
           | darlings like AOC and Sanders (whose wife defrauded and
           | destroyed a college she was put in charge of).
           | 
           | Instead this is a hit on people they dislike or disagree
           | with.
           | 
           | Edit: y'all can downvote me all you want. I used to work in
           | DC and I know the difference between a law, signed off on by
           | elected officials who represent you, official rules, that go
           | through a rule making process, and guidance, which is being
           | routinely abused.
           | 
           | I also know that activists and bureaucrats are actively
           | conspiring to push policy without winning a single election.
           | 
           | Everybody loves when people they agree with bend the rules,
           | but what we've seen over the last several decades is a
           | warping and poisoning of our policy infrastructure.
        
           | kyrra wrote:
           | Per their about page[0]:
           | 
           | > We dig deep into important issues, shining a light on
           | abuses of power and betrayals of public trust -- and we stick
           | with those issues as long as it takes to hold power to
           | account.
           | 
           | As you said, the "abuse of power" here is someone (likely) at
           | the IRS leaked these documents. Someone with the power over
           | others taxes chose to share that info. Then ProPublica is
           | then using this information to push a tax story that they
           | want.
           | 
           | [0] https://www.propublica.org/about
        
         | FabHK wrote:
         | - "Ah, Mr Thiel, I see you're holding some shares there of a
         | precious little company. Would you want to sell me some to put
         | in this here tax shelter maybe?"
         | 
         | - "Why, yes, Mr Thiel, I'd love to sell you some of my shares
         | here for your fine tax shelter there, let's say, hmm, 1.7
         | million shares."
         | 
         | - "Aye, let's do it then, Mr Thiel. Mind you though: you can
         | only sell yourself up to $2000 worth, Mr Thiel, per year. Now
         | say, Mr Thiel, how much are those shares there worth, you
         | reckon, Mr Thiel?"
         | 
         | - "Well, Mr Thiel, I'll write you receipt over $0.001 per
         | share. What do you say, Mr Thiel?"
         | 
         | - "Very well, Mr Thiel, that sounds about right. $1700, of
         | course, Mr Thiel, just under the $2000 limit, what a happy
         | coincidence, Mr Thiel. You're so savvy in valuing shares!"
         | 
         | - "Of course, Mr Thiel, thank you, always eager to help, Mr
         | Thiel."
         | 
         | - "The pleasure is all mine, Mr Thiel. We are so fortunate, are
         | we not?"
        
           | vmception wrote:
           | These are the exact conversations I have with myself even
           | doling out shares to my self directed 401k and private
           | foundation
           | 
           | Here nothing abnormal or discounted occurred with the share
           | price
           | 
           | The par value at formation time would have been that
        
         | Aunche wrote:
         | This was my first reaction as well, but on second thought, this
         | seems like a flagrant abuse of the Roth IRA. I'm not saying
         | Thiel should be punished, but something is clearly wrong here.
         | Let's say I invest in a freelancing company that only employs
         | myself, and buy 100% of the equity for $500, which I use to buy
         | a work laptop. I only take 1/3 of my income as salary and then
         | leave the rest of the money in the freelancing company, which
         | invests it in stocks. Combine this with a Double Irish
         | arrangement, and I could basically avoid paying taxes
         | completely.
        
           | walshemj wrote:
           | You'd be trading as an investment company then
        
         | [deleted]
        
         | dustingetz wrote:
         | you "withdraw" by getting a bank line of credit with the IRA as
         | collateral
        
           | ska wrote:
           | That's not allowed.
           | 
           | I expect if you have enough there, you could use the same
           | sorts of schemes as other illiquid wealth.
        
           | maxk42 wrote:
           | It's explicitly prohibited for Roth IRAs.
        
           | [deleted]
        
           | [deleted]
        
           | gravypod wrote:
           | I don't think you are allowed to borrow _against_ a Roth IRA.
           | You are able to borrow _from_ an IRA in a very small set of
           | situations. I think they are mainly buying your first house,
           | going to college, becoming disabled, or adopting a child.
           | 
           | I am not a lawyer so take it with a grain of salt and I am
           | very probably wrong.
        
         | seventytwo wrote:
         | Of course it's all legal. That's not the point.
         | 
         | The point is that this is one more example of how the wealthy
         | and powerful have more opportunity than others, even given the
         | same laws.
         | 
         | This is no different in that aspect than the problem of rich
         | people being able to hire the best lawyers to defend
         | themselves, while the poor receive overworked public defenders.
         | Everything equal, the wealthy have more opportunity.
         | 
         | If we want a society that is _equal opportunity_ , our laws and
         | regulations need to account for the natural emergent properties
         | of wealth. Our progressive tax system is a narrow, feeble
         | attempt at doing that, but it's certainly not enough.
        
         | [deleted]
        
         | tablespoon wrote:
         | > This is the law functioning as intended. Thiel's case is a
         | one-in-100-million+ event. He may have the only Roth IRA in
         | existence that's valued at over $5 billion. But he didn't do it
         | by exploiting some sort of "loophole" or paying high-priced
         | accountants to shield his assets in foreign entities offshore.
         | He put his investments in a Roth IRA just like any of you can
         | do. The only difference is his investments were in the top
         | 0.0001% in terms of performance. That's generally how people
         | get to be billionaires.
         | 
         | No. Roth IRA's have contribution limits, and at a minimum I'm
         | sure he exploited some loophole to get his adjusted gross
         | income down below $110,000 so he could make that $2000
         | contribution in 1999 (https://www.irs.gov/pub/irs-prior/p590--
         | 1999.pdf). Look at his work history:
         | 
         | > https://en.wikipedia.org/wiki/Peter_Thiel: He then earned his
         | J.D. from Stanford Law School in 1992.[7] After graduation, he
         | worked as a judicial law clerk for Judge James Larry Edmondson
         | of the U.S. Court of Appeals for the Eleventh Circuit, as a
         | securities lawyer for Sullivan & Cromwell, as a speechwriter
         | for former-U.S. Secretary of Education William Bennett, and as
         | a derivatives trader at Credit Suisse. He founded Thiel Capital
         | Management in 1996. He co-founded PayPal in 1999, serving as
         | chief executive officer until its sale to eBay in 2002 for $1.5
         | billion.
        
           | vmception wrote:
           | Its per year. Founders often are not taking salary or much of
           | one for several years.
           | 
           | You can have millions of liquid assets and not have any
           | income and be eligible for income related thresholds.
           | 
           | You dont need to be taking advantage of net operating losses
           | or charitable deductions for any of this.
        
           | jeremy_k wrote:
           | It's called Backdoor Roth Contribution [1]. It only really
           | works if you don't have any normal IRA accounts.
           | 
           | 1 - https://www.investopedia.com/terms/b/backdoor-roth-
           | ira.asp
        
           | marris wrote:
           | He could have saved it up from prior years of work. Starting
           | salaries can in fact be lower than $110K.
        
             | tablespoon wrote:
             | The OP said he made the contribution in 1999, after he did
             | things like work as a securities lawyer and founding a
             | hedge fund.
        
         | kolbe wrote:
         | Just as "they" are being presumptuous about how he got that
         | much money in there, so are you. He may very well have made an
         | extraordinarily good investment with his Roth IRA, but he may
         | have transferred tens of millions of dollars worth of stock
         | into it at below market rates.
        
           | maxk42 wrote:
           | The article explicitly states: "Mr. Thiel purchased his
           | founders' shares in PayPal through his Roth IRA during
           | PayPal's formation."
           | 
           | That's literally the market rate.
        
             | machinebun wrote:
             | > purchased his founders' shares in PayPal through his Roth
             | IRA during PayPal's formation."
             | 
             | > That's literally the market rate.
             | 
             | That's not a market rate, that's a price-fixed rate. A
             | market rate involves actual buyer and seller transactions
             | and an actual market (a couple of people shuffling stock
             | amongst themselves does not a market make)
             | 
             | If he had put Bitcoin in there at $0.01 back when it was
             | trading at $0.01 - that would be a market rate transaction
             | (since there was a market for Bitcoin at the time). That
             | would have been much less problematic than what actually
             | happened (and there would be no "substantial control"
             | problems either with the Bitcoin investment).
        
         | lukeschlather wrote:
         | > And that's not even to mention that the assets in a Roth IRA
         | are essentially worthless to him - he's not old enough to make
         | withdrawals or take distributions tax-free and you can't borrow
         | against a Roth IRA
         | 
         | I don't think that's remotely true. For a normal person with
         | tens of thousands or even a few hundred thousand in an IRA that
         | money is basically useless.
         | 
         | But for someone with billions in an IRA? He can almost
         | certainly start a public company and use a maze of shell
         | companies to let him do whatever he wants with the money.
        
         | tzs wrote:
         | > And that's not even to mention that the assets in a Roth IRA
         | are essentially worthless to him - he's not old enough to make
         | withdrawals or take distributions tax-free and you can't borrow
         | against a Roth IRA. The funds are essentially unavailable to
         | him for years to come unless he wants to pay taxes and
         | penalties.
         | 
         | If he took all of that money out now he'd be looking at losing
         | half of it to taxes and penalties, leaving him with about $2.5B
         | which is several of orders of magnitude more than he put into
         | it. That's far from "essentially worthless".
        
       | throw0101a wrote:
       | Method:
       | 
       | > _Yet, from the start, a small number of entrepreneurs, like
       | Thiel, made an end run around the rules: Open a Roth with $2,000
       | or less. Get a sweetheart deal to buy a stake in a startup that
       | has a good chance of one day exploding in value. Pay just
       | fractions of a penny per share, a price low enough to buy huge
       | numbers of shares. Watch as all the gains on that stock -- no
       | matter how giant -- are shielded from taxes forever, as long as
       | the IRA remains untouched until age 59 and a half. Then use the
       | proceeds, still inside the Roth, to make other investments._
        
         | patentatt wrote:
         | I also wonder if they can borrow against it. It would seem a
         | pretty low risk loan for a banker to make, and it would allow
         | people to access the money arbitrarily, negating the one
         | downside or limitation. So yet another way that the rich can
         | basically avoid paying any taxes. Does anyone know of any
         | limitations or rules restricting what you can invest the
         | contents of an IRA in? Can you set up a business, sell your IRA
         | shares of the business, then borrow against that value?
         | Basically a foolproof way to avoid paying any taxes ever. The
         | best part is the interest rate just has to be lower than the
         | tax rate, not even the rate of return, right? Incredible. I
         | think Romney was roasted for doing the same thing with his IRA.
         | Seems like any wealthy person could and should be doing this.
        
           | HWR_14 wrote:
           | Roths are bad collateral in general, because they are a
           | special asset that survives bankruptcy (up to a certain
           | level). Now, Thiel would actually care about his Roth getting
           | chopped to only a few million, so in this case we'd have to
           | look at what laws prevent that, which I don't know.
           | 
           | Edit: Using a Roth as collateral is apparently prohibited
           | under IRS rules 4975(c)(1)(B)
        
         | nickpp wrote:
         | > buy a stake in a startup that has a good chance of one day
         | exploding in value
         | 
         | Sounds easy and straightforward.
        
         | dehrmann wrote:
         | > Open a Roth with $2,000 or less
         | 
         | You need a MAGI of less than $139,000 to do that. That includes
         | dividends and capital gains, so it's unlikely post-Paypal Thiel
         | ever made that little. Pre-Paypal Thiel might have.
         | 
         | > Get a sweetheart deal to buy a stake in a startup that has a
         | good chance of one day exploding in value.
         | 
         | This might happen for post-Paypal Thiel. Definitely not pre.
         | This is way easier said than done unless you have good access
         | to deal flow (he does) and founders willing to pay for the
         | privilege of having you as an investor vs. some random VC.
         | 
         | > Pay just fractions of a penny per share
         | 
         | You're not paying fractions of a penny per share for something
         | that has a "good chance of one day exploding in value." This
         | investment doesn't exist.
         | 
         | I'd love to see his specific investments. I have a feeling a
         | handful from a specific time window made up the bulk his his
         | returns.
        
           | junar wrote:
           | As reported in the article, Thiel's income was below the
           | income limit in the year of contribution, and he only needed
           | one year's contribution to execute the strategy.
           | 
           | Also, income doesn't matter nowadays. Because Congress
           | removed the income limit on Roth conversions (also reported
           | in the article), anyone is free to make a nondeductible
           | traditional IRA contribution and convert it to Roth, which
           | achieves a similar effect.
        
           | temp_praneshp wrote:
           | > > Open a Roth with $2,000 or less > You need a MAGI of less
           | than $139,000 to do that.
           | 
           | Is there a reason trad -> roth doesn't work in this scenario?
        
           | didibus wrote:
           | > This might happen for post-Paypal Thiel. Definitely not
           | pre. This is way easier said than done unless you have good
           | access to deal flow (he does) and founders willing to pay for
           | the privilege of having you as an investor vs. some random
           | VC.
           | 
           | He purchased shares of PayPal at 0.001 when he first founded
           | it using his Roth IRA, it's all explained in the article.
           | 
           | > You're not paying fractions of a penny per share for
           | something that has a "good chance of one day exploding in
           | value." This investment doesn't exist
           | 
           | That's where the article alludes to something maybe slightly
           | fraudulent, for him to have his PayPal startup at the
           | beginning sell shares to himself at 0.001$, as a special
           | declared "employee discount rate".
           | 
           | He then managed to make 28 million in his Roth IRA from the
           | IPO of PayPal which he paid no taxes on, because his private
           | PayPal shares were all in the Roth IRA. Then he took that 28
           | million and reinvested it in Facebook, his Hedge Fund, his
           | other startup Palantir and others, and those investment
           | further did not get taxed, because the whole pool of money
           | was all in the Roth IRA from this point on.
        
         | mywittyname wrote:
         | I hope a law is passed that hits this kind of behavior with
         | stiff penalties. Thiel isn't the first to do something like
         | this. It is incredibly common. The letter of the law is that
         | annual contributions are capped, and the spirit of that law is
         | that this is done to keep these accounts from becoming tax-
         | free, judgement-proof shelters for insane amounts of wealth.
         | 
         | Perhaps caps on Roth the value of Roth IRAs and a limit of the
         | type of assets held in them to certain bonds and publicly
         | traded stocks. Somewhere between $1MM and $10MM with an annual
         | CPI adjustment is probably a fair cap amount.
        
           | prpl wrote:
           | Not the first but there's not a ton of people who can
           | squirrel away $5B in a Roth IRA, so likely the most
           | egregious.
        
             | nostrademons wrote:
             | They're not squirreling away $5B in a Roth IRA, they're
             | squirreling away $2000 and putting it in an asset whose
             | value grows from $2000 -> $5B. In theory someone who put
             | Dogecoin in their Roth IRA in 2014 could do the same.
             | 
             | It would make sense to limit Roth IRAs to publicly-traded
             | assets. If you're investing in securities that you need to
             | be an "accredited investor" for (> $1M liquid net worth),
             | that's not really a tool for the middle class.
        
               | lotsofpulp wrote:
               | It would make more sense to get rid of all
               | deductions/credits/exemptions, so that there would be no
               | unintended consequences.
        
               | ajmurmann wrote:
               | The harm here isn't that he invested in startups, but
               | that it's become such an insanely high profit that's now
               | entirely shielded from taxes. What would preventing
               | startup investments accomplish that a simple cap on
               | shielded gains (let's say 10 or 20 million) wouldn't?
        
               | NonEUCitizen wrote:
               | What is the harm?
        
               | [deleted]
        
               | megaman821 wrote:
               | All the money coming into the Roth IRA is post tax money,
               | whether it was cash or IRA conversion. Once in the Roth
               | IRA, you can sell for a profit and rebuy different stocks
               | without paying tax on that profit. Outside the Roth IRA
               | selling for a profit would be a taxable event. Trading
               | stale stocks for fresh new winners without paying the tax
               | inbetween is an incredible advantage to growing your
               | wealth.
        
               | nostrademons wrote:
               | That's the intended benefit of Roth IRAs though, even for
               | middle-class investors. That you can buy & sell within
               | them without paying capital gains tax.
               | 
               | It's not usually a huge problem in the public markets
               | because they're extremely liquid, with generally
               | symmetric information across all participants, and that
               | liquidity makes it hard to generate extremely excessive
               | investment returns except by luck. But private companies
               | are illiquid, oftentimes with huge asymmetries of
               | information, and that lets you generate 10,000%+
               | investment gains by happening to have an opportunity to
               | invest in a rocket ship that other people can't get into.
        
           | ajmurmann wrote:
           | I'm not sure if it's bad that he invested in startups with
           | that money. It's quite risky and if discourage it for that
           | reason. If we implemented your proposal of capping the amount
           | of shielded returns the problem would be gone. Most of this
           | problem word be gone even with a very high cap in the tens
           | millions.
           | 
           | On the other hand, are we optimizing for an edge case that
           | gets media attention but is ultimately insignificant? Edge
           | cases often make bad laws.
        
             | mywittyname wrote:
             | This isn't an edge case though. This is a common case. And
             | it's frankly, a common _abuse_ case. This stuff is famous
             | for the being used by the Mitt Romneys and Pete Thiels of
             | the world, but I know people who 've bragged about doing
             | the same thing on a much smaller scale. It just happens to
             | work better the more money/influence one has.
             | 
             | All you need is a tax attorney and enough money to found a
             | business to exploit this cheat. Start a business worth
             | $5000, and move it into a Roth. Then shovel other
             | investments into this new business and viola, you have a
             | several million bucks parked in a tax-free, judgement-proof
             | vehicle that can be passed onto your kids and grow until
             | the end of the USA.
             | 
             | The longer we wait to fix this, the more it's going to
             | distort our economy.
             | 
             | An asset cap is a simple solution and it hurts nobody who
             | using this as an actual retirement vehicle. But there are
             | other solutions as well that, again, don't hurt people who
             | intend to take distributions in retirement but prevent
             | abuse like this (minimum required distributions, like 401ks
             | have); dissolution of the Roth upon transfer due to death
             | of the owner, etc.
        
           | Chris2048 wrote:
           | There is no "spirit of that law", law is as written. If there
           | is a spirit that the letter excludes, then it is the fault of
           | the lawmakers - why shouldn't _they_ face penalties instead?
        
             | ABCLAW wrote:
             | There are many legal traditions in the world, and most of
             | them (both by number, volume of territory, amount of people
             | governed, etc) take the opposite approach.
             | 
             | Only a very narrow English line of black letter law that
             | ascribes to the black letter above all else... and even in
             | that system a completely twinned system of courts allowed
             | for ethical adjustments to law through the courts of
             | equity.
             | 
             | Most continental systems of law and currently standard
             | constitutional constructions provide very clear, very
             | codified release valves for situations in which the written
             | law is bullshit. Which is often.
        
       | vmception wrote:
       | I do this with my 401ks and IRAs and Roth products too and unlike
       | my non-profit entities in the 501 tax section the big trouble
       | with the 400 tax section is that you cant do in-kind
       | contributions
       | 
       | So you cant contribute assets you have to contribute cash and
       | then buy the assets, whereas with nonprofits you can also
       | contribute assets directly
       | 
       | This is just a small administrative hurdle, when you have
       | contractual authority over an organization you can write options
       | agreements and other grants that your 400 section tax deferred
       | entity can afford. Self directed 400 section entities are
       | typically formed as trusts, so it is easy to interact with them
       | as distinct investors even if you are signing both sides of every
       | contract.
       | 
       | I think its funny in the article where the person quoted said
       | they were "in favor of change" to the tax code. Add in kind
       | contribution to tax deferred products like 401ks and IRAs!
        
       | nickpinkston wrote:
       | I can't really blame Peter for taking advantage of the law.
       | 
       | We should mostly blame our lawmakers for allowing our pro-
       | oligarchy legal/financial system to exist.
        
       | papito wrote:
       | I am sweating here the fact that I am making more than is allowed
       | in order to contribute. Fidelity lets me, so I do, but someone
       | like Thiel, of course, can find ways.
       | 
       | How in the f*k do you invest into startups with something that is
       | not publicly traded anyway? Was PayPal over the counter? Why was
       | it so cheap?
        
         | NonEUCitizen wrote:
         | Did you read the article? It mentions he used Pensco, an IRA
         | custodian that allows alternative investments. Pensco is now
         | Pacific Premier Trust.
        
         | caseysoftware wrote:
         | > _How in the f_ k do you invest into startups with something
         | that is not publicly traded anyway? Was PayPal over the
         | counter? Why was it so cheap?*
         | 
         | He was one of the founders of Paypal. At that stage, the strike
         | price of the shares would have been fractions of a cent. More
         | importantly, the "fair market value" of the shares of a non-
         | public company is what the board says it to be which pre-
         | funding is whatever they choose. Post-funding, there's usually
         | a floor set because outsiders (aka investors) have done some
         | analysis.
         | 
         | Normal people pay X% tax on the difference between strike and
         | FMV. (X varies based on a bunch of things.)
         | 
         | That's all Stock Options 101.
         | 
         | Normal people can take advantage of the situation by executing
         | as soon as they have the strike price. That makes the
         | difference $0 so any % of that is still zero. The risk is that
         | the actual value of the shares could go to zero too.
         | 
         | The "loophole" with Thiel is doing it all with an IRA.. which
         | legally anyone can do _BUT_ it 's complicated and requires a
         | specific process.
         | 
         | I've followed RocketDollar the past few years because they help
         | with that and document all of it properly.
        
         | HWR_14 wrote:
         | You can invest in many asset classes in a Roth. You can buy a
         | house. What I'm interested in is if Theil offered to invest
         | $100 from his Roth at a $1,000 valuation with a handshake that
         | he would then invest $1,000,000 at a $100,000,000 valuation. Or
         | numbers that make more sense.
         | 
         | Of course, if you're not an accredited investor, you cannot
         | invest in startups. The idea is you could not recover from a
         | loss. So I have no idea why a Roth should be allowed to invest
         | as an accredited investor.
        
           | missedthecue wrote:
           | The accredited investor rules irk me. Not because investing
           | in startups is a good way to accumulate wealth, but because
           | of the double standard. The government happily separates
           | literally tens of billions of dollars from poor people every
           | year through the lottery, why can't we let those people
           | crowdfund interesting new ideas if they want to?
        
             | Retric wrote:
             | Due to the long history of investment scams. The lottery
             | takes large sums in aggregate, but doesn't use high
             | pressure sales tactics or let people easily place their
             | life savings in it. Aka, it would take significant effort
             | to buy 500,000$ worth of lottery tickets.
        
             | jdavis703 wrote:
             | The lottery gives players a moment to fantasize about what
             | it'd be like to be rich. I see no difference to buying a
             | beer for a few moments of entertainment.
             | 
             | Obviously people can overdo gambling, but the same goes for
             | beer.
        
             | nceqs3 wrote:
             | Look at the SPAC boom. Letting retail in creates many
             | problems. There are too many scam artists in the world.
        
             | manicennui wrote:
             | Thanks to Regulation Crowdfunding, people can. Sites like
             | Wefunder make it easy to do so.
        
             | throwaway803453 wrote:
             | There is a secondary benefit in that it influenced people
             | like me to save, invest, and work very very hard to get
             | that status. I invested in one YC startup after achieving
             | it and that felt like a major personal win.
             | 
             | However, the financial goal posts were set 20+ years ago
             | should have been periodically updated for inflation.
        
             | mywittyname wrote:
             | Blame scam artists. Before these rules were in place,
             | scammers were taking people's life savings through shoddy
             | investments. This happened often enough that people asked
             | the government to step in to protect these people. And the
             | "Accredited Investor" was born.
             | 
             | Maybe things would be better today if they revoked the
             | rules. Or maybe they would be worse. But either way it
             | exists for a reason.
             | 
             | And to be honest, $1MM is not a huge hurdle to overcome.
             | Anyone looking to invest in risky ventures would be wise to
             | accumulate a meaningful amount of wealth in order to shield
             | them from the loss of capital they will very likely incur.
             | Plus, there are ways around this in certain situations.
             | 
             | A better approach would be to address the reporting
             | requirements that are preventing startups from going public
             | earlier. Startups used to IPO a few years after founding,
             | but now they are going for 10+years.
        
             | ajmurmann wrote:
             | Fortunately, you can now also become an accredited investor
             | by taking a class rather than meeting income or wealth
             | requirements.
        
               | iammisc wrote:
               | This is the right approach IMO.
        
               | jb775 wrote:
               | Do you have any info on where to take this class?
        
               | ajmurmann wrote:
               | Unfortunately, I don't. Here is more about it though:
               | https://www.investor.gov/introduction-investing/general-
               | reso...
               | 
               | I also have seen that some Angel Investment firms will
               | pay cost of accreditation from your fees to them.
        
           | toephu2 wrote:
           | How can I put a Single Family House I buy in my Roth IRA?
        
             | NonEUCitizen wrote:
             | I think you can have houses that are bought for investment
             | (e.g. rented out to others) but not a house you live in.
             | You need IRA custodians that allow alternative investments.
        
         | twostorytower wrote:
         | You should be very careful. There is another way to do this,
         | it's called a backdoor Roth. Despite the sketchy name, it's
         | perfectly legal and used in practice by millions of people. A
         | simple way is to contribute $6,000 of post-tax money into a
         | traditional Roth, then submit what is called a Roth conversion
         | to convert the $6,000 into a Roth IRA account. Do this through
         | the proper channels so all the documentation is there.
         | 
         | This is not financial advice.
        
         | greyface- wrote:
         | > Fidelity lets me, so I do
         | 
         | This is inadvisable. There is a legal way to do this.
         | https://en.wikipedia.org/wiki/Roth_IRA#Traditional_IRA_conve...
         | 
         | If you're making direct Roth contributions over the limit,
         | those are disallowed and may come back to bite you. It may be
         | possible to recharacterize your already-done disallowed
         | contributions as Traditional IRA conversions; I would talk with
         | Fidelity or a tax advisor.
        
           | lotsofpulp wrote:
           | I am curious as to what compels someone to admit in writing
           | to committing fraud.
        
             | papito wrote:
             | I push a button that says "Contribute", and it's fraud.
             | Donald Trump buys land in New Jersey for $2 million to
             | develop a golf course, the golf course is deep sixed by the
             | town, he writes "$100 million loss because that is what it
             | is worth in my opinion", and it's fine.
             | 
             | God forbid I make a few thousand dollars tax-free, let
             | alone by accident.
        
               | lotsofpulp wrote:
               | But you just wrote you did it on purpose, not by
               | accident.
        
               | papito wrote:
               | I realized after the fact that I have been contributing
               | above my income level - I was sort of aware I might have
               | been out of the range but I never paid attention. The
               | screens are nagging you about being at $0 contributions.
        
               | lotsofpulp wrote:
               | So now that you have acknowledged it, you have to take
               | steps to fix its. Otherwise, it is fraud.
        
               | astrange wrote:
               | Turbotax will yell at you when you report it and make you
               | unwind (recharacterize) the transaction.
               | 
               | There is a proper way to do it though. Contribute to a
               | traditional IRA and immediately convert it.
        
           | [deleted]
        
           | papito wrote:
           | The last time I did it I got totally torched on taxes. You
           | can only convert from scratch - not after the fact.
        
       | incogitomode wrote:
       | I wonder why the Roth didn't include any sort of cap or maximum
       | exemption? It seems like that would have been an easy safety to
       | build in, like a stop-loss for the government to avoid
       | intentional and unintentional abuse leading to tax shortfalls.
       | The federal gift tax has a limit of $11.7 million, seems like a
       | gift to your older self might be considered similarly.
        
         | xkjkls wrote:
         | I think they just never expected someone could use it to amass
         | this much money. A $5500 a year contribution limit seems
         | incredibly limiting.
        
       | pjfin123 wrote:
       | How has all this information form the IRS leaked? ProPublica
       | seems to have accessed many of the richest American's tax data.
       | Is this something one person could do? How many people have that
       | kind of access?
        
         | nullc wrote:
         | Based on their claims of how they validated it by comparing the
         | data with 60 some persons whos tax filings were public (e.g.
         | politicans) it would be reasonable to assume that ProPublica
         | received detailed tax records on a considerable fraction of all
         | Americans. Certainly whomever collected the data had access to
         | that.
        
         | [deleted]
        
         | gwern wrote:
         | An IRS insider leaked it, obviously. Super illegal and against
         | the IRS culture, but now it's out there.
         | 
         | What's puzzling is how apparently selective the leaked material
         | all is. ProPublica has all these very specific memos and tax
         | return info about Thiel's Roth IRA, and yet, they are only
         | aware _of_ Thiel 's long IRS mega-audit (and that he won 100%),
         | and don't know that it was in fact all about auditing his use
         | of the Roth IRA trick? (Or that Fortune reported about the
         | Paypal mafia's use of the Roth IRA back in like 2009?) Very
         | odd.
        
           | astrange wrote:
           | Why do they have info about his Roth IRA anyway? That
           | wouldn't be part of a tax record. Maybe it's from the audit?
           | 
           | (Similar issues came up when people wanted to see Trump's tax
           | returns to find out "if he was really wealthy". They wouldn't
           | show that. Of course they might show a lot of other things.)
        
             | NonEUCitizen wrote:
             | Part of the article mentioned the IRA was disclosed in his
             | application for New Zealand residency. So does NZ publish
             | residency applications? Or was that also leaked?
        
       | ghufran_syed wrote:
       | " buy a stake in a startup that has a good chance of one day
       | exploding in value."
       | 
       | the propublica people must be rich, if they can reliably identify
       | these kind of startups - everything is easy in hindsight. They
       | also missed the bit where thiel _paid tax_ on the $2000, that he
       | invested. The whole idea of retirement accounts is that you
       | either pay the tax at the beginning, or you pay at the end.
        
       | systemBuilder wrote:
       | Any IRA owner with more than 50 years of average family income
       | ($3.5m) should be required to liquidate it. These are not tax
       | shelters for the rich!
       | 
       | But seriously this is no different than if he owned the stock
       | shares outright and he just chose never to sell those shares for
       | 50 years he would pay no tax! It's how the rich have break to the
       | system to favor Capital over labor!
        
       | exabrial wrote:
       | Good for him. I don't think this is a problem for a lot of
       | reasons. First he didn't break any laws, second, US taxes are a
       | waste anyway. They'll either be used to fight pointless wars,
       | sent to special interests (See Pelosi's family), or used to fuel
       | racial injustice with militarization of police. The only way out
       | to is to stop feeding the beast.
        
       | adolph wrote:
       | I guess in 7-10 years Ryan Holiday will have another fun book to
       | write about a news outlet going under via a "this is not kayfabe"
       | lawsuit.
       | 
       | https://www.goodreads.com/book/show/36681909-conspiracy
        
       | [deleted]
        
       | ajaimk wrote:
       | Since when is being smart and successful a crime? I definitely
       | would expect this from ProPublica but not Hacker News?
       | 
       | "Hacker" News!
        
       | anm89 wrote:
       | Wow they sure try to sledgehammer the fact that thiel has a lot
       | of money here with the first 3 paragraphs and visuals making sure
       | that you understand that 5 billion is in fact a lot of money.
        
         | HWR_14 wrote:
         | That's five billion reasons for the IRS to comb through the
         | transactions looking for prohibited self-dealing.
        
           | anm89 wrote:
           | Sure, I absolutely think they should pursue it. I'm just
           | saying, say the guy is rich once. You didn't even need to say
           | it once, 95% of everyone reading knows very well that he is
           | rich as hell. I don't need a visual to explain to me that 5
           | Billion is more than 30k
        
       | NonEUCitizen wrote:
       | They did not write about people who used their IRAs to invest in
       | startups that went belly-up and lost money.
        
       | creddit wrote:
       | The propublica tax leak is monstrously fucked up and I'm
       | constantly shocked at how little anyone seems to question the
       | validity of using personal IRS records for reporting.
        
         | [deleted]
        
         | throwaway2048 wrote:
         | im shedding a single tear for thiel's billions
        
           | jdminhbg wrote:
           | The good news is there's no way this total lack of privacy
           | controls at the IRS will ever be used against non-
           | billionaires.
        
         | nrmitchi wrote:
         | "I'm constantly shocked at how little anyone seems to question
         | the validity of using self-reported evidence that shows our
         | one-sided the US tax system is for reporting"
        
       | Chris2048 wrote:
       | Thiel then used the wealth amassed in his Roth to invest in other
       | startups
       | 
       | How? I thought the whole point is you can't touch this money? Did
       | he take on loans, promising to pay them back once he was 60?
       | In 2004, he provided Facebook's first large outside cash
       | infusion, investing $500K. His Facebook shares would grow tax-
       | free in his Roth.
       | 
       | I'm not sure I understand. Did he invest in FB _and
       | independently_ purchase shares (less than 2k pa) in his Roth? So
       | the 500K was not the private purchase of shares?
        
         | fastball wrote:
         | You buy 2000 shares with your Roth IRA for $1 per share.
         | 
         | They appreciate in value to $1,000 per share.
         | 
         | You sell the shares, now there is $2,000,000 cash value in your
         | Roth IRA, which you can use to make other investments.
         | 
         | Repeat ad infinitum without those transactions incurring any
         | sort of tax burden, as long as you don't withdraw any of that
         | money until you're 60.
        
         | misiti3780 wrote:
         | How did he buy non-public-ally trade FB shares in his Roth?
        
           | missedthecue wrote:
           | With a self-directed IRA, you can make all kinds of
           | investments, including real-estate and private companies.
        
         | s1artibartfast wrote:
         | What do you mean by can't touch the money in a Roth?
         | 
         | It stays in the roth account, but you can buy and sell assets
         | as often as you want with the money you put in.
        
         | naturalauction wrote:
         | It's possible he already had 500k in his Roth by 2004.
        
       | boringg wrote:
       | One of the thing that sucks about all these billionaires running
       | end run around the tax system (outside of the obvious pay your
       | fair share) is that they then have a bigger and bigger war chess
       | to splash around. Anyone else who is competing the investment
       | arena has to either play by the same rules or can't compete. It
       | inherently makes more people have to buy into these end-run tax
       | scenarios or risk being left behind. In this case it looks Peter
       | Thiel just went all in on the ROTH IRA beyond what anyone else
       | did.
       | 
       | Its not to dissimilar from the Countrywide CEO saying he was in a
       | forced situation to get into subprime even though he had not
       | interest and though it was a bad investment. If he didn't the
       | board would vote him out. Recognize it is different but its kind
       | of not unless the rules of the game change (which they may be in
       | real time if this propublica billionaire take down works).
        
         | rs999gti wrote:
         | > One of the thing that sucks about all these billionaires
         | running end run around the tax system (outside of the obvious
         | pay your fair share)
         | 
         | How is what Thiel did an end around? He paid taxes on his
         | contributions - https://www.hrblock.com/tax-
         | center/income/retirement-income/...
        
           | boringg wrote:
           | I don't disagree - I would say that he definitely leaned in
           | on the letter of the law and leaned away from the spirit of
           | the law. $5B in untaxed gains is frankly both impressive in
           | that he generated those returns and also feels a bit unfair
           | to the rest of us who have to pay cap gains on all our
           | smaller wins.
        
         | gist wrote:
         | > One of the thing that sucks about all these billionaires
         | running end run around the tax system
         | 
         | It's not an 'end run around the tax system'. It's either legal
         | or it's not. If illegal they run the risk of getting caught. If
         | legal it's legal. Period. Nothing also to prevent a regular
         | person from doing something somewhat similar other than they
         | don't know how to or don't know it even exists to use or
         | exploit. Now you can say 'oh well the rich can hire people who
         | know' but there (in this day and age) nothing to prevent a
         | regular person from taking the time to research and come up
         | with their own schemes using online research and help from
         | others readily available. Of course if you don't have money to
         | be taxed what's the point of that? If you do that takes effort
         | and most people just want to assume what is being done is wrong
         | because someone has or has access to information and
         | importantly knowledge they don't have.
         | 
         | People who are wealthy have many things that regular people
         | don't have.
        
           | boringg wrote:
           | I would say that tax evasion isn't as black and white as you
           | make it out to be (tax attorneys will take aggressive and
           | passive stances on their interpretation of the law). As well
           | there is the letter of the law and the spirit of the law.
           | 
           | Agree I could also have set up a roth IRA like that. What I
           | don't have access to is the deal flow and the ability to
           | structure the deal on my terms (supposedly i.e. shares for
           | pennies). That's something only power/money and access can
           | get you.
        
         | dcolkitt wrote:
         | I think the central fallacy is that you're assuming more money
         | makes it easier to achieve higher returns. For the vast
         | majority of finance, you get diminishing returns to scale.
         | There are many investment strategies that have limited
         | capacity, and as you get bigger you either have to dilute or
         | take increasingly risky positions.
         | 
         | The phenomenon's pretty ubiquitous among hedge funds. Tons of
         | funds produce stellar returns at $100 million AUM, then use
         | that track record to grow to a $1 billion+ and all of a sudden
         | put up mediocre results.
        
           | xkjkls wrote:
           | More untaxable money definitely makes it easier to achieve
           | higher returns.
        
             | jklein11 wrote:
             | Can you explain how?
        
               | boringg wrote:
               | You simply have more investible dollars to use. Therefore
               | any losses can be spread across a larger base, or,
               | alternatively, you have potentially more gains available
               | to you as a result of more exposure.
               | 
               | It's similar to leverage.
        
               | IG_Semmelweiss wrote:
               | more investments over a greater pool of assets, chasing
               | returns, also increase your surface area of error.
               | Examples abound.
               | 
               | There's a reason its easy for funds to get big with a
               | small LP commitment round, and there's also a reason most
               | funds close after hitting certain numbers, increasing the
               | AUM means increased complexity, and thus, potential
               | implosion.
               | 
               | The real world bears many examples of growing AUM
               | portfolio that blew up past a certain size.
               | 
               | There's no counterexample that I know of , of a fund with
               | a consistent growth pattern that started small, hit size,
               | and then increasing further their size with the same
               | trajectory from having more investment dollars to use.
        
           | boringg wrote:
           | I think you have two things confused. % vs total returns.
           | 
           | Larger funds have a tougher time finding high returns.
           | However if you are getting dollars on a lower cost basis
           | (i.e. untaxed vs 0.8 taxed dollars) you have more money that
           | can be exposed. Therefore allowing for more upside and
           | alternatively any losses can be spread across a larger base.
           | 
           | In no world does not having more money allow for more money
           | to be gained. In venture it also means you have more money
           | you can burn at a loss.
        
       | prezjordan wrote:
       | I miss the days when the unfathomably rich would at least build a
       | university or a park or something. The future is just so boring.
        
         | hardtke wrote:
         | From wikipedia: Billionaire Peter Thiel, a co-founder of PayPal
         | and current Facebook board member, paid $10 million to help
         | finance lawsuits against Gawker Media, including the Bollea
         | lawsuit. He called his financial support of Bollea's case "one
         | of my greater philanthropic things that I've done."
        
         | FanaHOVA wrote:
         | The Thiel Fellowship allowed Vitalik to drop out of school and
         | work full time on ETH. And that's just one of the recipients.
        
           | knz_ wrote:
           | That's not a positive. Ethereum is a premined scam coin.
        
           | gaze wrote:
           | why is that a good thing?
        
             | fastball wrote:
             | Seems fairly equivalent to funding a new building at a
             | university that is already mostly populated by rich kids,
             | who by and large are doing things less useful to society
             | than building a decentralized computing platform used
             | around the world.
        
               | dnautics wrote:
               | Although I'm a pretty huge skeptic of the performance of
               | the thiel fellowship (knowing some fellows personally and
               | also knowing some of the showrunners), I don't think
               | calling it a rich kid's club is fair, with the exception
               | of Austin Russel.
        
               | fastball wrote:
               | I was calling universities a rich kid's club (esp. the
               | ones that get the most gifts from the megarich). Trying
               | to make the point that, while the Thiel Fellowship may
               | not be objectively "good", it seems at least as good or
               | better than the OC's suggestion that it is preferable for
               | the megarich to fund things like universities.
        
               | dnautics wrote:
               | Sorry, I misread.
        
               | gaze wrote:
               | ah yes the two things you can do with lots of money --
               | giving it to a university and doing the thiel fellowship
        
               | arkitaip wrote:
               | Because building for the privileged is the only thing the
               | filthy rich can do. That or funding a shitty
               | decentralized platform.
        
               | [deleted]
        
           | Afforess wrote:
           | That's like saying the foundation supported a scientist
           | working on building more coal-fired power plants. ETH, along
           | with crypto in general, is harmful to society. Weird flex.
        
             | dnautics wrote:
             | The electric grid, too, started on coal fired plants;
             | perhaps we should label it as "harmful to society"
        
               | whydoibother wrote:
               | The grid actually produced something useful though.
        
               | pitaj wrote:
               | Usefulness is subjective.
        
             | quickthrower2 wrote:
             | If you are going to make a point against Ethereum, I
             | recommend this: It encourages scams, gambling addiction,
             | people losing money accidentally, and the usual criminal
             | activity associated with crypto.
        
             | j_walter wrote:
             | ETH will be POS soon, and like any invention in the
             | beginning there are issues that need to be worked out to
             | prevent more harm than good.
        
               | misiti3780 wrote:
               | POS?
        
               | sokoloff wrote:
               | Proof-of-stake (rather than the more energy intensive
               | proof-of-work).
               | 
               | https://www.investopedia.com/terms/p/proof-stake-pos.asp
        
               | xkjkls wrote:
               | I've been hearing ETH will be POS for 3 years. When is
               | this actually going to occur.
        
               | hanniabu wrote:
               | It's already in transition with the beacon chain and is
               | expected to full PoS end of this year or Q1 next year.
        
             | fastball wrote:
             | That's your opinion, which is not shared by a great many
             | people.
        
               | whydoibother wrote:
               | Most people are barely aware of crypto, let alone the
               | negative effects of it. Once people become more informed,
               | hopefully more and more people will see what a plague on
               | society it is.
        
               | Bayart wrote:
               | The people who have that specific stance on crypto are
               | usually those who know just enough to have to form an
               | opinion but not enough to realize how little they know.
        
           | prezjordan wrote:
           | I don't think it's necessary to debate ETH as a public good
           | but... Vitalik is by far the most impactful recipient of the
           | fellowship grant so "just one of the recipients" is doing a
           | lot of work here.
        
             | [deleted]
        
             | missedthecue wrote:
             | The founder of Ocean Cleanup, a nonprofit that engineers
             | technology to clean the oceans is one recipient.
             | 
             | https://en.wikipedia.org/wiki/The_Ocean_Cleanup
             | 
             | Founder of Figma is another.
             | 
             | https://en.wikipedia.org/wiki/Figma_(software)
        
               | quickthrower2 wrote:
               | $100k for him is a punt. Like me spending $10. In return
               | he possibly gets reciprocity from future successful
               | businesses.
        
               | gravypod wrote:
               | Wow, Figma is one of the best UI/UX design tools I've
               | ever used. That's very interesting.
        
           | xkjkls wrote:
           | What else has the Thiel Fellowship created other than Vitalik
           | and ETH? I'm not sure we can judge the success of it on it's
           | single most impactful result.
        
             | dnautics wrote:
             | The fellowship did not create vitalik and eth; he was
             | giving talks about it on the crypto circuit before he
             | accepted a fellowship.
        
             | fastball wrote:
             | Here is a list:
             | https://en.wikipedia.org/wiki/Thiel_Fellowship#Recipients
        
             | programmarchy wrote:
             | There's quite a few impressive fellows. Founder of Figma is
             | probably one you've heard about.
        
       | nickpp wrote:
       | Am I missing something? He didn't seem to do anything illegal.
       | 
       | This is the second article from ProPublica which:
       | 
       | - accuses people of doing something that is perfectly legal
       | 
       | - singles out one or two such people and exposes their private
       | matters
       | 
       | Is that ok just because they are rich? There is another comment
       | thread going on right now where people are absolutely furious
       | that they are tracked for _targeted ads_. How would they feel if
       | their tax info was displayed online for all to see?
        
         | NonEUCitizen wrote:
         | and blames people for following the law instead of congress for
         | writing the law as such.
        
         | medvezhenok wrote:
         | There is an argument whether investing in securities that are
         | non-public and have no official price (especially ones you have
         | a controlling stake in) should be illegal (even if it isn't
         | right now).
         | 
         | I think that's what the article is about. If he contributed
         | $5000, bought bitcoin at 1 cent and had the same amount of
         | money now, it would be a non-issue.
        
       | ve55 wrote:
       | What seems most unfair here is how difficult dealing with private
       | equity is as a normal person; the entire purpose of the Roth IRA
       | is that you do not pay any taxes afterwards, and that is how it
       | functions for everyone, whether you are rich or not. On the other
       | hand, the same cannot be said about the ability to purchase,
       | find, and work with private equity. I understand many
       | publications may dislike certain people (as one can note from who
       | they choose to mention the most), but I don't see a reason why he
       | would decline using tax-advantaged accounts just because he has
       | attained significantly larger wealth and roi than most others
       | using them.
        
         | didibus wrote:
         | I agree about access to private equity, but did you read the
         | whole thing?
         | 
         | He purchased shares of his own startup at 0.001 cents, way
         | below market rate.
         | 
         | To me, that's clearly not the intent of Roth IRA. This means
         | any startup founder can simply put their ownership shares into
         | their Roth IRA and never be taxed on their company growth.
         | 
         | It also doesn't seem they singled out Thiel, he has the biggest
         | Roth IRA they know off, seems logical to discuss him the most.
        
           | technotony wrote:
           | Their claim that the shares were below market value doesn't
           | stack up. They did this when they founded the company, the
           | company has no value at formation so it's fair priced. Just
           | because they raised money a few months later doesn't mean it
           | was worth anything at formation.
        
             | FabHK wrote:
             | That very same year, there were two or three funding
             | rounds, according to the article, for $0.5m and $4.5m. Yet
             | at the end of the year, the shares in the Roth were
             | reported to be worth less than the initial $1700.
        
             | bklyn11201 wrote:
             | If you have knowledge that people want to inject money into
             | your startup (and thus raising the value), then stuffing
             | shares into a Roth IRA before a raise (that you know will
             | happen) would surely be skirting the idea of fair-market
             | value.
        
           | throwkeep wrote:
           | > He purchased shares of his own startup at 0.001 cents, way
           | below market rate.
           | 
           | How do you know that was below market rate? Startups
           | generally begin with shares worth almost nothing.
        
           | [deleted]
        
           | ve55 wrote:
           | I did, but I'm not sure I have enough information to conclude
           | if what was done should be illegal/allowed or not, since this
           | is based on various sections of leaked documents, but it's
           | quite possible some bad things were involved. (One may remark
           | that turning small investments into the many billions quickly
           | clearly is a sign that foul play was involved, but recall
           | that his original 10% stake in FB would be worth almost $100B
           | today in less than 20 years. I do think he sold most of the
           | stake long ago, though.)
        
           | lotsofpulp wrote:
           | > He purchased shares of his own startup at 0.001 cents, way
           | below market rate.
           | 
           | Source?
        
             | garmaine wrote:
             | TFA. Although I think they're wrong on this account. It
             | doesn't matter that the stock was worth more mere months
             | later when the cashed their investment checks.
             | 
             | But what is an issue is the self-dealing of buying shares
             | in a company he holds a major role in the management of.
        
           | vmception wrote:
           | Why don't you think that was the intent of the Roth IRA, or
           | more specifically within the intent.
           | 
           | The intent of Roth products were to give money to a broke
           | government up front. The government created Roth products for
           | that specific reason and there is no further intent. They
           | made the contract with the people and some of the people
           | actually read it. All tax exempt and tax deferred products
           | can invest in and hold whatever they like with prohibitions
           | generally being on level of control or debt financing. Simply
           | having a prohibition on some kind of property ownership
           | doesn't make sense and I would probably challenge it on
           | constitutional grounds.
        
           | [deleted]
        
           | caseysoftware wrote:
           | > _He purchased shares of his own startup at 0.001 cents, way
           | below market rate._
           | 
           | The proper term is "fair market value" and before a company
           | is publicly traded, the FMV is set by the Board and whatever
           | investors have evaluated it and determined it to be.
           | 
           | In this case, it _looks like_ it was before any investors had
           | put in their money so the Board was simply the founders. At
           | that stage, the Board normally sets the strike price (what
           | you get the shares for) the same as the fair market value
           | (what they 're "worth") and you pay taxes on the difference.
           | Fractions of a cent are common at that stage.
           | 
           | The risk is that the fair market value will never go higher
           | and is likely to be zero (aka failed).
        
           | [deleted]
        
           | fastball wrote:
           | How is there a market rate if his startup was not publicly
           | trading?
           | 
           | The nominal value of the shares in my startup are PS0.01.
           | Sure, that's not what we've sold shares for, but the price we
           | _have_ sold them for was purely what the buyer was willing to
           | pay for them.
        
             | GordonS wrote:
             | So, I was reading into this a bit recently after getting an
             | equity offer (also in the UK). The "fair market value" is
             | open to interpretation, but if the inland revenue come
             | calling, you need to be able to explain it. For a startup
             | with no assets that has not previously sold shares, PS0.01.
             | Is just fine. But if you've got assets, or you've
             | previously sold shares as more than that, then quite
             | clearly the market value is more than a penny.
             | 
             | I mean, what better definition of "fair market value" is
             | there than "what the buyer was willing to pay for them"?
        
             | FabHK wrote:
             | Funding rounds constitute a valuation.
        
           | fny wrote:
           | > that's clearly not the intent of Roth IRA
           | 
           | Would you say the same if someone used a Roth to buy Bitcoin
           | when it was trading at pennies or Gamestop before it blew up?
           | 
           | What's wrong with having the right to invest in your own
           | company? That company pays corporate income taxes. You pay
           | income tax as an employee.
           | 
           | Also, everyone seems to forget Peter Thiel was part of the
           | middle class when he did this...
        
             | DeRock wrote:
             | Thats not the right analogy. This would be more akin to
             | selling your own bitcoins to yourself (into an IRA) for
             | pennies on the dollar.
        
             | mullen wrote:
             | The Roth IRA is not suppose to be a tax shelter for people
             | to get super rich off their own creations. You are not
             | getting a reduced priced Bitcoins or Gamestop stock. You
             | are gambling with your own funds based on information that
             | everyone else has and paying the same price as anyone else.
             | If you get Bitcoins and/or Gamestock at a reduced price,
             | then you are abusing the Roth IRA and the IRS should stop
             | and fine you.
        
               | lotsofpulp wrote:
               | Did that happen? Even ProPublica does not claim it.
        
               | medvezhenok wrote:
               | Would Thiel have been willing to sell his shares to
               | someone else at $0.001 at the time he put them into the
               | IRA? Because that's ultimately what market value is
               | about.
               | 
               | It's also one of the valuation proposals for people
               | playing valuation games with illiquid assets. You can
               | declare them at whatever value you want (and pay tax on
               | that value), but you are forced to sell if someone
               | offered you that value for the asset (if you claim your
               | house is worth $1M, we'll let you pay property tax on
               | $1M, but if someone offers you $1.1M for your house,
               | you're forced to sell). That would cut down on people
               | inflating/deflating asset valuations to game tax codes.
        
               | lotsofpulp wrote:
               | I am not interested in what would have, could have, or
               | should have happened. I am trying to find out what did
               | happen, and any evidence to support it.
               | 
               | You have an interesting proposal for valuations though,
               | although, it seems to have a few logistic hurdles that
               | cross my mind.
        
               | machinebun wrote:
               | What happened was Thiel buying 1.7M shares of stock in
               | his own startup at a value of $0.001 per share in 1999 in
               | his Roth IRA (and then cashing out for $30M+ in 2002).
               | It's debatable whether it was legal (because he was an
               | officer/director of the company and that law is on the
               | books), but the better question would be - should it have
               | been illegal, and the answer to that, in my opinion, is a
               | resounding yes.
               | 
               | I believe non-public investments should be banned from
               | Roth IRAs (and that we should close all of the backdoor
               | loopholes to them as well). They were meant for a certain
               | group of people at the outset and were then twisted
               | around in knots to provide more tax-breaks for the well-
               | off (which should be rolled back). I think mega backdoor
               | Roth should not be a thing, rollover Roth IRA should not
               | be a thing - bring Roth back to it's original vision.
        
               | lotsofpulp wrote:
               | >It's debatable whether it was legal (because he was an
               | officer/director of the company and that law is on the
               | books)
               | 
               | I am interested in finding out the answer to this, as
               | others have posted in this thread the text of the law
               | which makes it seem like he should not have been able to,
               | and what reasoning could possibly have made it legal.
        
               | labcomputer wrote:
               | > Would Thiel have been willing to sell his shares to
               | someone else at $0.001 at the time he put them into the
               | IRA? Because that's ultimately what market value is
               | about.
               | 
               | Well... no. (Can't believe I'm defending Peter F-ing
               | Thiel)
               | 
               | I might own some AAPL shares that I think are worth
               | $1000/share--so I'm not willing to sell my AAPL shares
               | for less than $1000 each. The market (today) thinks they
               | are worth $133/share. Who is right?
               | 
               | Thiel might have _really truly_ believed that his 2M
               | shares would be worth a few billion dollars one day. But
               | if you can 't find anyone who is willing to _buy_ them
               | for that price, then it doesn 't matter. The "fair market
               | value" (what the IRS cares about) of those shares is not
               | a few billion dollars. It doesn't become a FMV until you
               | can find an arms-length buyer who is willing to buy the
               | shares for that price.
               | 
               | You could pay someone to create an independent valuation
               | of the shares--but for a brand new company that has no
               | employees and no assets, not even IP, why would you
               | expect the valuation to come back at much more than $2k?
        
         | xkjkls wrote:
         | Also, if you aren't trading public stocks, it seems much easier
         | to get around size limitations. When you spend $5500 buying the
         | SPY, the government is incredibly certain that is the amount of
         | money your investment was valued at. If you buy $5500 of stock
         | in a startup? Who is to say? The opportunity to buy that stock
         | might have been worth 10x that amount the moment that
         | transaction occured, and there's no real way for the government
         | to actually determine that.
        
         | nielsbot wrote:
         | I don't think it's a dislike of certain people or blaming them
         | for doing these (legal) investment moves. It's about changing
         | the rules to provide more financial equality in our society. I
         | think it's now too easy for the rich to get richer and too hard
         | for the poor to come up. I'm not suggesting banning rich
         | people, and we can debate over matter of degree of equality
         | that's good.
         | 
         | (edit: typo)
        
           | ve55 wrote:
           | Generally agree; I mention it since from my point of view, I
           | would have spent most of the article criticizing the rules
           | and policies politically and finding ways to improve them,
           | rather than constantly going on about the personal lives of
           | some that have exploited them (although it does seem like it
           | cannot be helped sometimes).
        
       | hamburga wrote:
       | Is this practice -- putting founder shares in a Roth IRA when
       | they are worthless -- sort of standard practice? Is everybody
       | doing it and Thiel just did it most successfully?
        
       | maerF0x0 wrote:
       | IMO the only thing he did "wrong" was to make excellent returns
       | within the bounds of a tax vehicle and with investment classes
       | that most of us are typically excluded (accreditation, VC
       | exclusivity)
       | 
       | If we should be mad about anything it's that it's so difficult
       | for the general public to get a good slice of diversification
       | including the asset classes that turn 1000s into millions.
       | 
       | Yes we can go work at a startup, but that is all the eggs in one
       | basket. Better to spread that risk around 10+ investments like
       | VCs do
        
         | [deleted]
        
         | r00fus wrote:
         | If what he did was legal, I dare you do do the same. I bet you
         | any financial/tax advisor would strongly suggest you don't.
         | 
         | What he did wasn't actually legal. He just got away with it.
        
         | jgalt212 wrote:
         | I think the fraud to be found here is whether or not the
         | purchases these IRA's made were made at fair value. Given the
         | astronomical rates of return realized by some, not all, of
         | these mammoth IRAs, you can probability establish such facts.
         | Similar to Madoff's eternally steady fund returns being
         | impossible.
         | 
         | A good litmus test would be, what is the rate of return of a
         | person's investments made outside an IRA vs inside the IRA.
        
           | kova12 wrote:
           | are you sure you are not plain jelaous he's good at making
           | money and you are not?
        
             | dane-pgp wrote:
             | "When I was poor and complained about inequality they said
             | I was bitter; now that I'm rich and I complain about
             | inequality they say I'm a hypocrite. I'm beginning to think
             | they just don't want to talk about inequality."
             | 
             | -- Russell Brand
        
               | [deleted]
        
         | rajup wrote:
         | I agree. All the annoying animations and hyperbole in the
         | article notwithstanding, it does not seem as malicious as the
         | article tries to portray it. It is rather disappointing that
         | there are barriers to some of these investments but I think
         | without these barriers you would open the gates for all sorts
         | of malicious actors taking advantage of unsophisticated
         | investors.
        
           | jppope wrote:
           | They actually are opening up to unaccredited investors, you
           | just need to have a CFP or CPA or something like that (not
           | sure of the actual requirements, I just know that they
           | recently changed them)
        
             | astrange wrote:
             | The change is that having one of those certs now makes you
             | an accredited investor.
             | 
             | You don't have to be accredited to invest in something like
             | a VC fund anymore using something like Wefunder. However
             | it's extremely risky and generally painful to even find out
             | if the thing you invested in 3 years ago even still exists.
        
           | maerF0x0 wrote:
           | I wonder if there are good VC firms that would let people
           | participate in funds around the $1000 threshold? Like if I
           | could give Garry Tan $1000 to just participate, no questions
           | or interaction required just fill out the forms sign the
           | check, see you in 10yrs... I know part of the issue is that
           | many VCs have a high touch process for the people signing
           | $100k checks, but maybe if they made it more streamlined they
           | could generate more diverse investor base and just say to
           | them "You wont hear from us, no you cant help, see you in
           | 10yrs" kind of mentality.
        
       | MandieD wrote:
       | I cannot put any money at all into a Roth IRA, despite making a
       | decent but non-astounding IT salary (below the caps), because I'm
       | an American living abroad who had the temerity to marry a
       | foreigner and am stuck in "married, filing separately". I cannot
       | use similar retirement plans in the country I live in, because no
       | brokerage here wants to deal with non-rich people who are US
       | citizens or have US income tax obligations (why I do _not_ file
       | jointly - at least one of us needs to be able to keep paying into
       | a retirement account here!)
       | 
       | Words cannot express my contempt for Thiel, who is apparently
       | still a citizen of the country I live in. I'm pulling for the
       | Finanzamt, however they can swing it.
        
       | dmoy wrote:
       | They really should replace 401k (and 415(c)(1)(a)), 403b, 457,
       | IRA, etc with just TSP-for-everyone. Don't make it contingent
       | upon employer, and don't allow additional employer-sponsored tax-
       | advantaged space.
       | 
       | The fact that someone working at a large tech company can put
       | away around $70,000/yr into tax advantaged accounts is kind of
       | insane. Not even including the crazy edge cases that come with
       | private equity like this Thiel instance.
        
       | misiti3780 wrote:
       | This is off subject, but given that someone illegally leaked
       | these tax returns on the richest, is anyone else not surprised we
       | have heard zero about Trump's taxes? (I assume they are riddled
       | with stuff like this)
        
         | vineyardmike wrote:
         | they leaked a few years ago.
        
           | misiti3780 wrote:
           | ya that is true, the NYT did that big expose, I forgot about
           | that.
        
       | jb775 wrote:
       | Not his fault the tax rules are broken for the ultra-rich. They
       | always have been throughout history...so I don't expect any
       | changes.
       | 
       | If we tried, it would require regulation on how politicians can
       | be compensated for the rest of their lives after taking office.
       | Need to close the revolving door where politicians help out rich
       | people/corporations while in office, then are compensated
       | indirectly after leaving office.
        
         | gameswithgo wrote:
         | Sure it is, not his alone, but the ultra rich bribe the
         | government to make sure the rules are broken. They are all at
         | fault. Any attempt to fix these things is stopped by the ultra
         | rich. They have even put their own people on the supreme court!
         | (see comments by the Koch brothers stating this explicitly)
        
         | drzaiusapelord wrote:
         | >Not his fault the tax rules are broken for the ultra-rich.
         | 
         | This isn't some accidental software defect. The rich write
         | these laws to their benefit. He's part of the class whose fault
         | it absolutely is and considering his political position as a
         | conservative, he advocates and helps keep up the corrupt system
         | he benefits from directly, even if he didn't lobby for this
         | specific tax regulation.
        
       | nrmitchi wrote:
       | What I don't understand about this whole maneuver is that Roth
       | transactions must be made at arms length; ie, "Transactions must
       | be made at arm's length and not involve the IRA owner or a member
       | of his or her family."
       | 
       | An example of this is that if you use a Roth to invest in
       | property, you are not allowed to use it personally, not allowed
       | to manage it or do maintenance yourself, etc.
       | 
       | Prohibited transactions risk tainting (and thus exposing) the
       | entire account.
       | 
       | How is Thiel investing in _his own company_ not considered a
       | prohibited investment?
        
         | marris wrote:
         | I can think of two reasons: (1) It was not his own company when
         | the IRA made the investment. That is, the IRA invests alongside
         | other investors at the founding. Anyone who wants to buy shares
         | at 0.01 is able to do so. He is not dictating some special
         | price that only he gets. (2) If some investors create an SPV to
         | invest in PayPal (e.g. to limit liability), then his IRA
         | becomes an investor in that SPV. He loses management control
         | over that portion of the investment, but when the SPV sells its
         | PayPal shares, it distributes the cash to all investors,
         | including to the IRA.
        
         | ABCLAW wrote:
         | >"How is Thiel investing in his own company not considered a
         | prohibited investment?"
         | 
         | It should be, but the IRS doesn't catch every cheat, and as
         | with most other white collar crime, the responsibility can be
         | laundered through a number of accountants and other
         | professional staff, resulting in fines rather than jail time.
         | 
         | So a lot of rich people make a lot of questionable calls
         | regarding how their assets are categorized and if they get
         | caught out they generally just pay what they're supposed to
         | have paid, or sometimes slightly less (some countries have
         | legislation prohibition tax authorities from accepting
         | settlement offer at under-assessed amounts, but there are ways
         | around that too). If they're particularly risk-averse and
         | ballsy, they'll ask for an advance ruling certificate or
         | another pre-emptive ruling on their filings to confirm they're
         | correct beforehand. You can bake those too, if needed.
        
           | [deleted]
        
           | fny wrote:
           | 1. Thiel was not rich when he did this. He was 32 with $2K
           | tucked away in a Roth, maybe more in a standard IRA.
           | 
           | 2. What he did was in no way illegal. He did not cheat the
           | system. The IRS would have come down on him with a hammer
           | already, and they haven't managed to figure out how to do it
           | for the last decade.
        
             | ABCLAW wrote:
             | >The IRS would have come down on him with a hammer already
             | 
             | Part of my work is in financial investigations. The
             | finances of large, multi-entity organizations are expensive
             | to create, difficult to parse, and require extensive
             | periods of time of trained, expensive staff to understand.
             | 
             | Assuming that 'things would have been caught' flies in the
             | face of the fact that they almost never are. Accounting
             | rules change frequently, software systems for logging
             | information is changed, and records are lost. Emails have
             | to be read in tandem with entries to understand the
             | intentions.
             | 
             | Even in cases where we have confessions that someone has
             | embezzled money, we often need to spend multiple weeks
             | tracking down records to isolate when/where/how it
             | occurred.
             | 
             | Even during audits, requests for records can be baked.
             | 'Random' samples of given entries can just exclude the
             | questionable ones.
             | 
             | I've appeared in front of federal tax courts in my
             | practice, the game isn't fair - don't base your reasoning
             | on the idea that it must be.
        
               | abra0 wrote:
               | Sorry, what does "bake a request for records" mean?
        
             | s1artibartfast wrote:
             | 1. Thiel was not Mega rich, but he had money, he had worked
             | as a lawer for a few years and managed his own venture
             | capital firm. Either way, this is irrelevant as he met the
             | income requirements to contribute to an IRA.
             | 
             | 2. It very well may have been illegal, as mentioned in the
             | top level post. The purchase price was the legal value, but
             | using an IRA as a vehicle to invest in _your own company_
             | appears be prohibited by IRA regulations. At the time, it
             | was a purchase  <$2000, and may not have been reviewed. If
             | paypal was someone else's company, there would be no legal
             | issue.
        
               | Taniwha wrote:
               | essentially it seems that his venture capital firm IS his
               | Roth IRA - and it was making the investments - definitely
               | not hands off
        
         | avelis wrote:
         | It is IMO but who is going to actually enforce that?
        
           | vmception wrote:
           | Thats not the issue here
        
         | [deleted]
        
         | fny wrote:
         | Easy. He doesn't own the company, shareholders do, and he
         | happens to be a shareholder. If you work for Microsoft, can you
         | buy Microsoft shares in your IRA? Yes. This is why the IRS
         | can't do squat about this. It's completely legal. If he owned a
         | controlling interest (>50%) things would have been different.
         | 
         | If you bought the property as part of an incorporated entity,
         | it would be entirely legal for you to do work or be contracted
         | by that entity.
        
           | runako wrote:
           | It appears this transaction would invalidate the IRA under
           | today's law because he was an officer of the company.
           | 
           | (Unclear whether the original law was written that way or
           | whether this loophole was closed sometime after.)
        
             | fny wrote:
             | It's still completely legal. These disqualifications only
             | kick in when you own a controlling interest (more than 50%)
             | of an entity.
             | 
             | [0]: https://www.irafinancialgroup.com/learn-more/self-
             | directed-i...
        
               | runako wrote:
               | Keep reading the disqualified persons section:
               | 
               | https://news.ycombinator.com/item?id=27621342
               | 
               | It specifically sweeps in classes of people with
               | responsibilities that are held by typical active co-
               | founders: "(H) an officer, director (or an individual
               | having powers or responsibilities similar to those of
               | officers or directors), a 10 percent or more shareholder,
               | or a highly compensated employee (earning 10 percent or
               | more of the yearly wages of an employer) of a person
               | described in subparagraph (C), (D), (E), or (G)"
               | 
               | Very difficult to a) be a cofounder with meaningful
               | equity b) not do any work so this provision doesn't
               | trigger c) keep your equity and d) have it be worth
               | anything.
        
               | jklein11 wrote:
               | Oh that is interesting. This must get very complicated
               | for officers or directors of companies in the S&P 500.
               | Could you not buy index funds that hold shares of the
               | company you work for?
        
               | runako wrote:
               | They probably just have to buy the shares in taxable
               | accounts.
               | 
               | Edit: misread this. I would be surprised if index/mutual
               | funds are subject to the same rules because holders of an
               | index fund don't own shares in any of the underlying
               | securities.
        
               | jklein11 wrote:
               | But then what do they hold in their tax advantaged
               | accounts? Can they not invest in index funds there?
        
               | nrmitchi wrote:
               | I have to assume you're just feigning naivete here.
               | 
               | First, officers or directors of S&P500 companies are
               | almost definitely above the income level to open a new
               | Roth IRA.
               | 
               | Second, you're really grasping at straws here trying to
               | trace a relatively minuscule investment through mutual
               | fund in order to defend Thiel here.
               | 
               | Someone is saying "Bank robbers are bad because they
               | steal other people's money" and you're sitting over here
               | saying "Well technically when I pick up a penny on the
               | ground, it's not mine. So it's basically the same thing.
               | We have to find a solution that solves both problems at
               | the same time".
        
           | ProjectArcturis wrote:
           | He put the shares in when it was still a private company.
        
             | fny wrote:
             | So what? You can use your Roth IRA to invest in private
             | companies, buy gold, houses, whatever too.
        
         | joshfraser wrote:
         | My guess is he used a self-directed IRA that he converted into
         | a Roth.
        
           | vasilipupkin wrote:
           | did he place the shares into IRA before any outside round
           | though? because otherwise, he would have violated
           | contribution limits?
        
             | lotsofpulp wrote:
             | I would assume he did, unless there is any proof otherwise.
             | 
             | ProPublica specifically omitted this information, so
             | assuming that it was all kosher seems reasonable.
        
               | joshfraser wrote:
               | He would have deposited them at company formation when
               | they were essentially worthless.
        
               | vasilipupkin wrote:
               | right, but then how did he convert them to roth? roth has
               | contribution limits, right? Ah, there are no limits for
               | backdoor conversion.
        
               | lotsofpulp wrote:
               | Right, so this is an example of journalism that reduces
               | people's trust. Or at least it did mine with regards to
               | ProPublica, which I had previously held in higher regard.
        
             | nrmitchi wrote:
             | You're also not allowed to put ISOs or anything "earned"
             | into a Roth IRA (or buy it from yourself).
             | 
             | The problem here is that this was clearly a prohibited
             | transaction, but the IRS state of limitations is
             | effectively 3 years for stuff like this (unless you have
             | really pissed someone off). It's likely that by the time
             | the stock was worth enough (in terms of 409A guesstimate)
             | to look in to, or there was any kind of reportable
             | transaction showing a gain, the time frame on investigating
             | the initial transaction was long past.
        
               | lotsofpulp wrote:
               | > The problem here is that this was clearly a prohibited
               | transaction
               | 
               | I have been unable to find any source for this claim.
               | Even ProPublica, the people with the original documents
               | and the most incentivized to break the news, do not claim
               | this.
        
               | nrmitchi wrote:
               | ProPublica making a public claim of a tax crime is much
               | more likely to be considered libel than an insignificant
               | person on HN doing the same.
        
               | lotsofpulp wrote:
               | So people claiming that he committed fraud are just
               | making up stuff.
        
               | nrmitchi wrote:
               | OR they read the basic rules, regulations, and
               | restrictions about contributing to a Roth IRA and came to
               | a logical conclusion.
        
               | TAForObvReasons wrote:
               | > IRS records show that in 1999 Thiel purchased 1.7
               | million shares of his startup, which would soon become
               | PayPal, for just $1,700 -- a tenth of a penny per share
               | 
               | > Even though Thiel's startup received millions in
               | funding within months, Pensco still told the IRS these
               | founders' shares were worth less than $1,700 at the end
               | of 1999.
               | 
               | Under certain circumstances, there is no statute of
               | limitations. If Pensco did knowingly misrepresent the
               | value of the shares, and if the funding round did imply a
               | wildly different valuation, IRS could still pursue the
               | case.
        
               | nrmitchi wrote:
               | Yes, that is true.
               | 
               | But I cannot fathom the cries of "IRS Pursuing
               | Investigation against a single Tax Transaction from 20
               | years ago against vocal Trump supporter" would go over
               | well.
        
               | wizzwizz4 wrote:
               | That's not the IRS's problem.
        
               | [deleted]
        
         | onetimemanytime wrote:
         | All is OK, until they take a closer look (and IRS, I assume
         | will now)
        
         | vmception wrote:
         | IRAs can be shareholders in anything. They can be 100%
         | shareholders as well. They can even form their own companies
         | from the beginning.
         | 
         | Being a minor shareholder in a corporation isn't a prohibited
         | transaction or run afoul of self dealing regulations.
         | 
         | Even in circumstances that they would, you having less than X%
         | of voting shares mitigates that, the X depending on what type
         | of tax deferred or exempt entity is in question. _SOME_ tax
         | deferred /exempt entities have stricter self dealing
         | regulations and even they wouldnt have had an issue here as
         | Peter Thiel was one of several co-founders.
        
           | klipt wrote:
           | But if you work for a company owned mostly by your Roth IRA,
           | that's easily abused.
           | 
           | Suppose you're a consultant and your one-person consulting
           | company is owned by your Roth IRA. You could deliberately
           | draw a very small taxable salary, so that most of your work
           | goes towards increasing the company's untaxed value in your
           | IRA.
           | 
           | You're basically making your earnings tax free.
           | 
           | Obviously, your Roth IRA's company employing you at below
           | market rate isn't a fair, arms length transaction.
        
             | s1artibartfast wrote:
             | The problem would be buying the company with the roth, not
             | the wages afterwards.
             | 
             | It is completely legal to own a company and pay yourself
             | below market rate, or even not at all. In fact, it is how
             | many small business work.
             | 
             | In your example, the company still has to pay corporate
             | tax, even though it is owned by the IRA.
             | 
             | The only tax advantage to your consulting scheme would come
             | at the time you sold it to someone else, or liquidated it.
        
               | bklyn11201 wrote:
               | It is not legal to own an USA S-Corp and pay yourself a
               | below market rate.
        
               | s1artibartfast wrote:
               | That is a good point. S-Corps are an exception, because
               | the corporations do not handle income tax the way a
               | C-corp would.
        
             | vmception wrote:
             | Okay. Don't mess it up.
        
             | jklein11 wrote:
             | >But if you work for a company <i>owned mostly by your Roth
             | IRA</i>, that's easily abused.
             | 
             | As I understand it, you can't own a company that you(or a
             | relative) own a controlling interest in with your IRA. I
             | can see the sense in this because if own 20% the
             | person(people) who own the other 80% have an incentive to
             | make sure I'm not playing any kind of games with the
             | finances.
             | 
             | In the case of Thiel, it seems like he took $2000 and made
             | a moonshot investment in Paypal. At that point his
             | investment could have just as easily went to $0 as it was
             | to hit $5 billion. He took the risk, why shouldn't he have
             | gotten the reward?
        
               | vkou wrote:
               | > He took the risk, why shouldn't he have gotten the
               | reward?
               | 
               | And he should get the reward, minus capital gains tax.
               | 
               | This country provided an environment for that investment
               | to turn into five billion. He couldn't have done the same
               | thing in Somalia, or Vietnam, or Greece. Why shouldn't it
               | reap its share?
               | 
               | Nearly everyone else pays their fair share of taxes.
        
               | exporectomy wrote:
               | > Nearly everyone else pays their fair share of taxes.
               | 
               | It seems the whole point of these Roth IRA is so people
               | don't have to pay their fair share of taxes. I'd blame
               | the government for creating that.
        
               | jklein11 wrote:
               | He invested a tax advantaged $2000. If he had invested
               | that $2000 in the S&P 500 in 1995 he would have a tax
               | advantaged $25,000. He would have been out that tax
               | advantaged $25,000 if paypal didn't take off. Instead he
               | decided to make a much longer shot bet and for him it
               | paid off.
               | 
               | I can understand adding legislation that would tax
               | distributions on Roth IRA's for billionaires. Thiel would
               | be fine if he had to pay taxes on that windfall.
               | 
               | I just think that it is a mischaracterization that he
               | isn't paying his fair share of taxes. To me, it doesn't
               | seem like he did anything wrong. He took advantage of a
               | system that is accessible to everyone.
        
               | Retric wrote:
               | The issue is as far as people can tell he illegally
               | invested 2000$ from an IRA. You're not allowed to invest
               | in a company _with an IRA_ if:
               | 
               |  _an officer, director (or an individual having powers or
               | responsibilities similar to those of officers or
               | directors), a 10 percent or more shareholder, or a highly
               | compensated employee (earning 10 percent or more of the
               | yearly wages of an employer) of a person described in
               | subparagraph (C), (D), (E), or (G)_ https://uscode.house.
               | gov/view.xhtml?hl=false&edition=1994&re...
               | 
               | Being the CEO clearly qualifies. That said, the statute
               | of limitations means you can often get away with things
               | if they go unreported for long enough. It may be he's
               | currently in the clear.
        
               | mattferderer wrote:
               | The article says he was audited.
               | 
               | > In 2011, Thiel caught the attention of the IRS. The
               | agency launched an audit, tax records show. The records
               | don't spell out what the IRS was looking at or if it
               | involved Thiel's Roth. Whatever the case, the audit was
               | closed years later and Thiel didn't owe any more taxes,
               | tax records show.
        
               | Retric wrote:
               | He was CEO of PayPal until 2002, which means in 2011 this
               | would presumably be past the statute of limitations for
               | many things. It's unclear if this falls under Tax Fraud
               | or not.
        
               | eloff wrote:
               | I think the problem is these IRAs were not designed to
               | shield the super rich from taxes. It's meant to help the
               | average person. Implemented properly it should have an
               | upper limit, probably under a million dollars. Letting it
               | grow to five billion tax free is a loophole that
               | shouldn't exist and does not benefit society at large.
        
           | nrmitchi wrote:
           | > IRAs can be shareholders in anything. They can be 100%
           | shareholders as well. They can even form their own companies
           | from the beginning. > Being a minor shareholder in a
           | corporation isn't a prohibited transaction or run afoul of
           | self dealing regulations.
           | 
           | Yes, obviously, and is exactly how the real estate example I
           | provided works. The IRA opened a company. _Obviously_ it is a
           | company in order to financially benefit the owner of the IRA.
           | That 's literally the whole point of investing, and is not
           | what I am debating here.
           | 
           | It is different when you are then taking an active role in
           | the day-to-day management and/or operation of that business,
           | which is obviously what Thiel did at PayPal.
        
             | vmception wrote:
             | Oh by property that to you meant real estate, I didnt catch
             | that
             | 
             | Peter Theil did not have 100% voting shares of Paypal, and
             | if he did that went away very soon after with the other co
             | founders and investors diluting him fast enough for it to
             | satisfy IRS regulations.
             | 
             | That would work now as well, but it is also possible that
             | it worked better 22 years ago as the IRS may have lacked
             | clarity back then.
        
               | nrmitchi wrote:
               | > Peter Theil did not have 100% voting shares of Paypal,
               | 
               | First, that's not the requirement.
               | 
               | > and if he did that went away very soon after with the
               | other co founders and investors diluting him fast enough
               | for it to satisfy IRS regulations.
               | 
               | Your argument here is "even if he made illegal
               | investments into a tax-advantaged account that has set
               | him up to not pay taxes on 50000000000 dollars, we should
               | ignore it because if he made the investment later it
               | wouldn't have been illegal".
               | 
               | By that logic let's just throw out insider trading laws.
               | "Well if he made the investment after the information was
               | public, it would have been fine"
               | 
               | > the IRS may have lacked clarity back then.
               | 
               | They didn't. It was still explicitly not allowed for a
               | officer/director of a company, someone with a similar
               | role, > 10% share-holder, etc to make investments like
               | this with a Roth IRA.
        
         | TuringNYC wrote:
         | >> What I don't understand about this whole maneuver is that
         | Roth transactions must be made at arms length; ie,
         | "Transactions must be made at arm's length and not involve the
         | IRA owner or a member of his or her family."
         | 
         | Wouldnt this be as simple has investing in another company
         | (managed by external managers) that then invests in your
         | company? I'm sure the wealthy have all sorts of ways to get
         | around this.
        
       | bosswipe wrote:
       | The rich have defunded their police, the IRS has no resources to
       | go after complex schemes like these. But they consider it out of
       | bounds when poor people demand the street harrasment police be
       | defunded.
        
         | missedthecue wrote:
         | The article actually says that Thiel was the target of a multi-
         | year IRS audit, which didn't turn up any irregularities.
        
           | vineyardmike wrote:
           | He's known to be a litigious PITA so i'm sure they're worried
           | about maintaining resources for eaasier-to-win audits.
        
       | tapmap wrote:
       | What people are missing here is the fact that Peter Theil is
       | investing in new companies that go on to create thousands of jobs
       | and billions of dollars in taxes every year. He risks his capital
       | to create these new companies, and a lot of his investments go to
       | zero. The next effect of this is that he's generating a lot more
       | tax revenue for the IRS that he's saving from his Roth IRA.
        
       | esotericimpl wrote:
       | watch out propublica, Hulk Hogan might be bankrolling another
       | lawsuit soon.
        
       | underseacables wrote:
       | Can one learn this skill?
        
         | lamontcg wrote:
         | Make a really good bet on a stock in your Roth that pops
         | something like >10,000x.
         | 
         | In his case it was Paypal shares.
         | 
         | Then you have a massive tax-free investment shelter and you can
         | be an angel investor for startups through it and seek out
         | another >100x investment with it.
         | 
         | It helps a lot to have better information and be more plugged
         | into the investment culture than your average person on the
         | street reading the NYT and trying to sort out where to invest
         | their 401k. It also helps to be a sociopath so that all you
         | care about is returns.
         | 
         | There's a bit of an oversight here where the tax-free returns
         | in a Roth shelter are completely unlimited, they probably
         | should have been capped where massive windfalls became taxed
         | some way, but rich people and those who carry water for them,
         | would have flipped out.
        
       | foolzcrow wrote:
       | The writer of this article sounds jealous and intellectually
       | small.
        
       | aurizon wrote:
       | Yes, this is what it was made for. I got mine up to $150,000
       | based on the annual increment and a few smart buy/sell. I wish I
       | had bought $50,000 Apple at $2, it would have turned into $25
       | million. A few like Thiel do better. Want to hurt Thiel? Hurt us
       | all is your only way. Block options etc, so only trading shares
       | can go in. No 'popcorn' shares that expand by 100 to one or more
       | after they vest etc.
        
         | vernie wrote:
         | The usual response to any criticism of Thiel on HN: Actually
         | this rocks!
        
           | aurizon wrote:
           | I did not criticise Thiel at all, he did well. That said he
           | did have the ability to capture the entire leap from option
           | pennies into mature trading stock at many many dollars, and
           | roll that over a few times.
        
             | [deleted]
        
           | cinntaile wrote:
           | It's a pretty smart loophole but it's not like he came up
           | with this. He has tax specialists for that. Now, it's
           | probably not a good idea for loopholes like these to exist.
           | Articles like these can certainly make a difference to close
           | them. Although it's definitely not black and white, excluding
           | private shares would be too broad imo but maybe a different
           | mechanism to determine the value should be used.
           | 
           | More general I'd say Peter Thiel is both loved and hated and
           | everything in between on HN, there is no real consensus.
        
           | papito wrote:
           | Any suggestion on HN that Peter Thiel is a shit-tier human
           | and a monster will get you downvotes.
           | 
           | The funny thing is, there is never any verbal defense - just
           | downvotes.
        
             | peter422 wrote:
             | I thought his book on startups was very well done and
             | interesting.
             | 
             | However this seems quite shady. The rich should still have
             | to pay taxes.
        
               | lotsofpulp wrote:
               | They do have to pay taxes. Maybe Congress should not pass
               | laws that exempt them from paying taxes, or require them
               | to pay more taxes.
        
               | papito wrote:
               | Congress doesn't write laws - people like Peter Thiel do.
               | You sound like these billionaires are innocent virgins.
               | "Oppsies, I made all these billions because the
               | incompetent congress let me do it". Uh huh.
        
         | not2b wrote:
         | No, it isn't what it was made for. You're limited to a $2000
         | contribution. Claiming that the value of a share of PayPal was
         | 1/10 of a cent was nonsense. He found a loophole, sure, but
         | it's morally fraudulent even if legally allowed. To close the
         | loophole, putting private shares into a Roth IRA should be
         | banned because they have no true market price that indicates
         | their worth.
        
           | icedchai wrote:
           | $2000 hasn't been the contribution limit for almost 20 years.
           | It's $6K now, but we could argue that it's still not enough.
           | 
           | Private companies that are raising money have a valuation on
           | them done periodically ("409A valuation"), and this is what
           | private stock options and common shares are based on. This is
           | the IRS's own rules.
        
           | vmception wrote:
           | I dont find this to be a loophole, you just werent aware of
           | it. A plain reading of the tax code would make that
           | possibility fairly obvious.
           | 
           | This approach will just leave you surprised in the 2040s
           | about what anybody with reading comprehension skills is doing
           | in 2020s.
           | 
           | Also greater private equity access was just expanded in the
           | tax code for tax deferred roth products. So the opposite is
           | happening.
        
           | vmception wrote:
           | lol, 22 years late with a knee jerk reaction of trying to
           | change that specific law
           | 
           | I love how this approach will just leave you surprised in the
           | 2040s about what anybody with reading comprehension skills is
           | doing in 2021
        
             | dang wrote:
             | Please don't be an asshole on HN, no matter how uninformed
             | someone else is or you feel they are. It only makes things
             | worse.
             | 
             | https://news.ycombinator.com/newsguidelines.html
        
           | silicon2401 wrote:
           | > He found a loophole, sure, but it's morally fraudulent even
           | if legally allowed.
           | 
           | Morality is relative. You can't legally police other people
           | based on your personal morality. To me, morality is
           | maximizing your self-benefit, so there's nothing wrong with
           | what Thiel did. If other people disagree, then there are
           | plenty of avenues to campaign for outlawing what he did.
        
           | iammisc wrote:
           | > it's morally fraudulent even if legally allowed
           | 
           | Can you detail the immorality?
           | 
           | > To close the loophole, putting private shares into a Roth
           | IRA should be banned because they have no true market price
           | that indicates their worth.
           | 
           | Why should they be banned? Everything has a price. IIRC, in a
           | self-directed IRA you can put anything... paintings, gold,
           | collectibles, houses. Why not random shares?
           | 
           | I see a huge problem here. Roth IRAs were made with certain
           | guarantees. That some people would make outsized returns in a
           | country of almost 400 million should be expected. Why do we
           | find it necessary to then go and 'get our fair share'? Didn't
           | we already set the rules? Why must we now change them since
           | some guy got lucky?
           | 
           | Ideally, we should just say 'good job Mr Thiel', you held up
           | your end of the bargain and we'll hold up ours. The deal was
           | already struck. This is why no one trusts the American
           | government.
           | 
           | Also, I'd point out that the roth IRA mentioned here is only
           | nominally worth $5b. If he were to sell all the shares there
           | would likely be a huge drop in price. Either way, what goes
           | unmentioned is that the $5b wouldn't be taxed anyway if it
           | was all in unrealized capital gains.
        
             | zajd wrote:
             | Imagine being this dumb
        
           | bklyn11201 wrote:
           | Precisely. Was anyone else allowed to buy Paypal shares at
           | 1/10 of a cent in 1999? If he alone marked this price, how
           | would it not be fraudulent?
        
             | jandrese wrote:
             | He basically bought those shares from himself, which is why
             | he was able to set the price arbitrarily low.
             | 
             | The point of the Roth IRA is to encourage middle and lower
             | class people to invest in their retirement by offering a
             | tax incentive. But to avoid being abused by the rich the
             | total yearly contribution limit is set very low. Thiel
             | avoided this limit by simply selling himself a huge amount
             | of stock for fractions of a penny on the dollar, knowing
             | the actual price on the open market would be far higher.
             | However, nobody can prove that the price of the private
             | share would have been higher at the time because they
             | weren't on a market.
             | 
             | It would be like if you were trying to avoid taxes by
             | selling your 1,000 acre mansion to a LLC that you own for
             | $1 and paying the tax on that $1. This doesn't work for
             | real estate, but the Roth IRA system is not as
             | sophisticated so you can get away with it.
        
           | s1artibartfast wrote:
           | >Claiming that the value of a share of PayPal was 1/10 of a
           | cent was nonsense.
           | 
           | It was the valuation at the time and there is nothing illegal
           | about that. You can invest your Roth in penny stocks or sub
           | penny stocks today if you want.
           | 
           | The real question is if it was legal to purchase stocks in a
           | company he also managed.
        
             | medvezhenok wrote:
             | The only way that was a true valuation of the shares at the
             | time would be if he were willing to sell those shares to
             | someone else at that price ($0.001) at the end of 1999. If
             | not, that's not true value, that's just accounting fraud.
             | 
             | For a valuation, there has to be a market and a market
             | clearing price. If there is no market (no buyers and
             | sellers), valuation is meaningless.
        
               | s1artibartfast wrote:
               | That's not how tax law works. When you found a company
               | you buy founder's stock, with an initial valuation filed
               | with the IRS and this is the value until the next
               | qualified valuation event, where it may change. Share
               | prices of $0.01 to $0.00001 are common. I guarantee that
               | $0.001 was the founders share price filed with the IRS at
               | company formation.
               | 
               | https://gust.com/launch/blog/how-to-value-startup-stock
        
               | machinebun wrote:
               | Sure, $0.001 is the value on paper (and under current
               | law). The point is, it's exploitable (let's say I'm an
               | Apple engineer, I start a new company and get a wink wink
               | from some friends in high places who want to invest in my
               | company doing X. I put in my founders stock into IRA in
               | return for first dibs on placement for the investor - 1
               | year later company has valuation, my stock has risen many
               | %%. Sure, I'm technically doing everything legally, but
               | practically it's somewhat equivalent to insider trading +
               | avoids taxes).
               | 
               | I would personally ban non-public investments in Roth
               | IRAs. That way a debate about market value doesn't have
               | to happen.
        
               | NonEUCitizen wrote:
               | Many times, $0.001 turns out to be too high a value for
               | startup shares -- a lot of startup shares end up being
               | worth zero.
        
               | s1artibartfast wrote:
               | seems like the far better solution is banning IRA
               | investments in your own company. This is the current law.
               | 
               | If you make a smart or lucky in somebody else's company,
               | bitcoin, or whatever, it isn't an exploit, it is the
               | point.
        
       | joshe wrote:
       | Anyone actually done this with normal stock options (NSO if it
       | matters) and have advice? My understanding is that it might be
       | achievable with Pensco as the IRA custodian but I'd be interested
       | in hearing how it worked in practice
        
         | vmception wrote:
         | I've done it, you have to have executive authority over the
         | issuing company to do it, as other directors and their legal
         | counsel are too uninspired to do anything outside of the norm.
         | 
         | Your IRA is a legal entity and you can grant an option to it.
         | It needs the cash to exercise it. Options can have shares at
         | any price in them, such as discounted to nothing but it comes
         | down to which consequences you care about. Making a potentially
         | screwy 409a valuation isn't a big deal, but also avoided if
         | done before other investors come in. Either way it can be a
         | tolerable level of consequence.
        
       | ffggvv wrote:
       | i don't get why twitter banned hunter biden discussion or BLM
       | founder because they were private.
       | 
       | but we're all comfortable seeing the private tax records of these
       | individuals that were stolen. the media has such massive biases
        
       | stevenalowe wrote:
       | The key quote: "Get a sweetheart deal to buy a stake in a startup
       | that has a good chance of one day exploding in value"
       | 
       | In other words, use your Roth IRA to invest in startups (or
       | stocks) that do exceptionally well.
       | 
       | I'd be more concerned about the author's access to "secret
       | internal IRS data"...
        
       | gumby wrote:
       | I have tried to do this in the past and always been told it's not
       | possible (as an exec in the startup it wouldn't be arm's length).
       | 
       | I guess that's what I get for following the rules.
       | 
       | Not that my IRA would have reached the billions mark if I had
       | managed to.
        
         | casefields wrote:
         | Just like Trump--or even Thiel himself--you've gotta not be
         | scared to sometimes amass hefty legal bills, and you can get
         | away with a lot.
        
       | [deleted]
        
       | marris wrote:
       | Does anyone know whether this kind of tax planning is available
       | to today's startup investors? Are there any administrators which
       | support this kind of illiquid investment?
        
         | vmception wrote:
         | Yes, Roth IRAs are quite simple as you can literally just have
         | a stack of cash in your apartment labelled "Roth IRA" if you
         | wanted to. All the reindeer games with IRAs are just so the
         | accounting is hard to mess up, with separate usually electronic
         | accounts.
        
       | runako wrote:
       | IANAL but this topic is of interest.
       | 
       | Without commenting on whether this was legal at the time Thiel
       | made this transaction, it appears it would not be permissible
       | under current tax law. (Update: the relevant text in the statute
       | appears to have been in effect as early as 1995:
       | https://uscode.house.gov/view.xhtml?hl=false&edition=1994&re...)
       | Specifically, the law explicitly disqualifies anyone who is:
       | 
       | >an officer, director (or an individual having powers or
       | responsibilities similar to those of officers or directors), a 10
       | percent or more shareholder, or a highly compensated employee
       | (earning 10 percent or more of the yearly wages of an employer)
       | of a person described in subparagraph (C), (D), (E), or (G)
       | 
       | (Source: https://www.law.cornell.edu/uscode/text/26/4975)
       | 
       | So the relatively plain language would almost certainly include
       | anyone who's a co-founder involved in actively managing a company
       | today.
       | 
       | This kind of blatant tax avoidance is going to end badly for our
       | tax regime, which is likely to overcorrect.
        
         | nickpp wrote:
         | Maybe he was already diluted by other investors to under 10%?
         | And usually founders aren't highly compensated.
        
           | runako wrote:
           | "an officer, director (or an individual having powers or
           | responsibilities similar to those of officers or directors)"
        
             | nickpp wrote:
             | Oops I missed that. You are right then. I wonder if this
             | changed since 1999...
        
               | runako wrote:
               | I updated my post. This provision appears to date to at
               | least 1995.
               | 
               | (IANAL so again I could be misreading something.)
        
         | toomuchtodo wrote:
         | Solid finding.
        
       | kyleblarson wrote:
       | Another sensationalist headline about people doing things that
       | are not illegal. This article feels especially egregious since it
       | is based on stolen IRS data.
        
       | JacobDotVI wrote:
       | Mitt Romney did this as well (although only to the tune of
       | $100M). It was discussed in 2012 in various news outlets:
       | https://www.investopedia.com/managing-wealth/grow-ira-100-mi...
        
         | vmception wrote:
         | Thats where I got the inspiration from for thinking about a lot
         | of accounting differently. Financial engineering that people
         | seem to neglect or be to scared of considering.
         | 
         | With him sometimes Bain Capital made separate share classes,
         | and I think they would give massive dividends periodically to
         | the separate share class that only the 401k investors at Bain
         | Capital would receive. I think its a really great strategy!
         | 
         | Buffett should be doing that in Berkshire Hathaway for their
         | employees instead of being sad about how much tax his secretary
         | pays
        
           | xkjkls wrote:
           | Or, the government should change the tax code to not make
           | this possible and make the advantages of doing this moot.
           | People need to be taxed, and we shouldn't have a system which
           | requires a bunch of extra paperwork just for people to avoid
           | it.
        
             | vmception wrote:
             | These simplistic ideas are exactly why it never will happen
             | 
             | Roth versions of tax deferred accounts only exists because
             | the government is an irresponsible spender and needed
             | revenues. It made the contract with the people because its
             | like a degenerate crack addict child scrounging for cash,
             | in its case only to keep convincing international investors
             | that it can slowly pay debt. Wow the contract worked and
             | you just caught on 22 years later.
             | 
             | What is your issue with people making good trades in a tax
             | deferred and tax exempt accounts? That it needs more
             | revenues again? The government will be fine, international
             | investors are content with its revenue sources. These kinds
             | of accounts are already subject to massive penalties and
             | even UBTI regulations
        
               | xkjkls wrote:
               | My issue is that as a society, we want a percentage of
               | the wealth that is created to be democratically
               | controlled. We can debate which percentage and how that
               | should be acquired, but the end social contract is that
               | part of all wealth produced has some democratic component
               | to it. For the last 5 is that decades, we've had groups
               | of people gradually trying to evade more and more of that
               | responsibility, and we aren't going to produce a
               | functioning society that way.
        
       | stretchwithme wrote:
       | What happened is the resources put into this account were
       | invested in highly successful things. If all investment accounts
       | were this successful, society would be 10X or 100X or 1000X more
       | wealthy.
        
       | cdolan wrote:
       | I am aware of the fact its popular to dislike the ultra-rich, but
       | is this not worrying to the general public?
       | ProPublica has obtained a trove of IRS tax return data on
       | thousands of the country's wealthiest people, covering more than
       | 15 years.
       | 
       | Someone leaked not only Gates, Bezos, Musk, etc data, but
       | thousands of private citizen's intimate financial disclosures
       | (edit: seemingly for the purpose of weaponizing the data against
       | them).
       | 
       | What crime were these thousands of people convicted of to deserve
       | this?
        
         | eloff wrote:
         | Some countries have public tax returns (Sweden? Norway? One of
         | those Nordic countries.)
         | 
         | I think probably they should be public data.
         | 
         | That aside, for very rich people, having them be public is in
         | the interest of the public as it reveals the shady stuff they
         | do to dodge taxes (legally.)
        
           | cdolan wrote:
           | Debating wether tax returns should or should not be public is
           | a great debate to have, I agree. The country should be having
           | that debate. And if we decide tax returns should be made
           | public, it should happen in the future so everyone is on the
           | same page.
           | 
           | The fact is that US tax returns are private information,
           | regardless of what other countries are doing or what you and
           | I _think_ should be done.
        
             | walshemj wrote:
             | Welcome to the great panopticon remember the Telescreen
             | sees all citizen.
        
             | machinebun wrote:
             | > Debating wether tax returns should or should not be
             | public is a great debate to have, I agree. The country
             | should be having that debate. And if we decide tax returns
             | should be made public, it should happen in the future so
             | everyone is on the same page.
             | 
             | The same way the Snowden leaks were instrumental into
             | regulation about surveillance, leaks like this are
             | instrumental in crafting better tax policy, so I would say
             | they are a public good. It's also not-quite possible to do
             | it via completely legal means (as vested interest
             | opposition is too big and has too much capital - the only
             | way to battle against them seems to be to do it via not-so-
             | legal means).
             | 
             | So in this case the fight is punching up against people in
             | positions of power, not down onto people that have no
             | power, so I don't see a direct issue with it. If you have
             | power, you should also have the proportionate
             | responsibility.
        
               | cdolan wrote:
               | "Responsibility" is a very strange word in your comment
               | to me.
               | 
               | Snowden leaked government program details. How in the
               | world is that the same about thousands of private
               | citizens (aka not public figures) personal financial
               | details?
               | 
               | How are these individuals not being "responsible"?
               | 
               | The only unresponsible person is the person(s) who leaked
               | the details, and ProPublica for monetizing it.
        
               | machinebun wrote:
               | We have a disagreement in what makes a public figure
               | then. I believe that over a certain level of wealth, the
               | wealth alone makes someone a public figure or a figure of
               | significance (since wealth = power, and public status
               | also = power, and celebrity status = power).
               | 
               | If someone is powerful enough to have power over other
               | people (which the wealthy certainly are), then they
               | should account for that power with appropriate
               | responsibility.
               | 
               | If you don't want to be a public figure, don't accumulate
               | exorbitant amounts of wealth.
        
               | cdolan wrote:
               | When I say public figure (which Mr. Thiel is, despite his
               | harassment by Gawker and other quirks, but I get your
               | point) I am referring to the thousands of non-public
               | figures who have had their personal tax details stolen
               | and shared with ProPublica, who seemingly did nothing to
               | deserve this.
        
           | yupper32 wrote:
           | You want family and friends to know exactly how much you
           | make?
           | 
           | That's extremely problematic for a lot of people.
           | 
           | Congress already has access to tax returns for the purpose of
           | writing tax legislation. It's not perfect but I really don't
           | want my finances public, and I'm not doing anything shady.
        
             | pmoriarty wrote:
             | _" You want family and friends to know exactly how much you
             | make? That's extremely problematic for a lot of people."_
             | 
             | Can you explain why it's problematic?
        
               | babayega2 wrote:
               | I have lived in 4 countries, and 3 continents and
               | everyone I have lived with agreed that it's not useful
               | for the whole family to know how much you make.
               | 
               | Last year I learned that lesson the hard way...
        
               | yupper32 wrote:
               | Family can be very manipulative when they know you have
               | much more money than them. It can end up massively
               | hurting relationships.
               | 
               | I don't even tell my parents how much I make.
        
               | pmoriarty wrote:
               | _" Family can be very manipulative when they know you
               | have much more money than them."_
               | 
               | As I suspected, this is mainly a problem of the rich.
               | 
               | Most of the rest of us don't make much more money than
               | anybody.
               | 
               | So are we going to make our laws to advantage the rich or
               | the vast and ever growing majority of the population who
               | aren't and never will be rich?
        
               | yupper32 wrote:
               | Ah yes, I'm the problem, paying around 40% in taxes.
               | 
               | People making 6-figures a year are not the ones
               | manipulating the financial system. HN is particularly in
               | this category.
               | 
               | But go ahead and lump me in with someone with like 6000x
               | my net worth.
        
               | pmoriarty wrote:
               | You don't have to be a billionaire to be part of the
               | problem (though it helps).
        
             | djmips wrote:
             | I can see some reasons to not wanting your wealth public if
             | you are reasonably worried that it would attract unwanted
             | attention.
        
             | matz1 wrote:
             | Yes, this is the most pragmatic way to deal with privacy
             | issue, as much as possible information has to be make
             | public for everyone.
             | 
             | >You want family and friends to know exactly how much you
             | make?
             | 
             | Not really but I would like the information to be public,
             | that is they don't have to know but if they want to know
             | they can.
             | 
             | Its great that I don't have to hide it or worry about it
             | being leaked.
             | 
             | If this information being public cause me trouble then
             | we'll find a way to solve that issue rather than fixing it
             | by hiding the information.
        
               | yupper32 wrote:
               | > that is they don't have to know but if they want to
               | know they can.
               | 
               | For the people that I'm defending here, there's no
               | difference.
               | 
               | > Its great that I don't have to hide it or worry about
               | it being leaked.
               | 
               | ...so are you saying you're worried about a law like
               | this?
               | 
               | > Yes, this is the most pragmatic way to deal with
               | privacy issue, as much as possible information has to be
               | make public for everyone.
               | 
               | I'm guessing you think the best way to deal with revenge
               | porn is to have everyone post nude photos of themselves
               | publicly?
        
             | lordnacho wrote:
             | I can see why people tend to err on the side of privacy,
             | but it doesn't seem to have destroyed Norwegian society to
             | have public records.
             | 
             | I think it's a reasonable thing to discuss, then at least
             | we can get some pros and cons out there.
        
             | eigen wrote:
             | seems like corporate tax transparency would be a good first
             | step.
             | 
             | > Congress already has access to tax returns for the
             | purpose of writing tax legislation.
             | 
             | while that is the law that Congress can request/subpoena
             | returns under SS6103(f) of Title 26 [1], if it can just be
             | ignored then Congress doesnt really have access.
             | 
             | [1] https://irc.bloombergtax.com/public/uscode/doc/irc/sect
             | ion_6...
        
               | yupper32 wrote:
               | > if it can just be ignored then Congress doesnt really
               | have access.
               | 
               | Then fix that! Why do you have to go to the absolute
               | extreme here and make everyone's finances public?
        
             | eloff wrote:
             | Imagine hooking up the public tax returns to an image
             | recognition system and database built from social media. It
             | should be possible to create a dating app for women that
             | lets you see the wealth of people on tinder, in the street,
             | at a party. Men might also use that, but they already have
             | their ideal "rating by physical appearance" app in tinder.
             | Some gender differences are persistent throughout all human
             | history.
             | 
             | There are some downsides to be sure.
        
         | loudtieblahblah wrote:
         | It's not about disliking the ultra-rich.
         | 
         | It's about recognizing how the entire system is stacked against
         | working people and that these ultra-rich pay 0% in taxes, while
         | I pay 30%.
         | 
         | The backbone of this nation is funded by the middle class and
         | the poor being taxed, while the rich externalize their expenses
         | to the government and pay little to nothing in taxation.
         | 
         | If some IRS docs need to get leaked, then so be it. The
         | reporting on this has been pretty responsible.
        
           | cscurmudgeon wrote:
           | The fight against the ultra rich usually ends up as a fight
           | against the middle class with some token offensives against
           | the ultra rich.
        
           | cdolan wrote:
           | Government spending is almost entirely leveraged by debt and
           | these documents prove that these "ultra-rich" pay a large
           | absolute dollar amount of taxes (albeit lower than 30%). That
           | is factually non-zero.
           | 
           | I am all for a healthy debate on the topic, but I disagree
           | the reporting is responsible. Responsible reporting, in my
           | opinion, would involve nameless "there is a $5 billion Roth
           | IRA out there... the system isn't working", rather than
           | naming private citizens who believe their tax returns from
           | 2005-2020 are private information.
           | 
           | Edit: And I think it may be of public curiosity to know about
           | what goes on in the billionaire class. I get that, to a
           | degree. My original point was that ProPublica is admitting
           | that they are in control of _thousands!_ of American 's tax
           | returns for the last decade and a half. There is no guarantee
           | that the IT administrator or summer intern is going to keep
           | that data safe.
        
             | pmoriarty wrote:
             | _" these "ultra-rich" pay a large absolute dollar amount of
             | taxes"_
             | 
             | Money is power.
             | 
             | Because of the wealth they get to keep, these ultra rich
             | are in many ways ruling the rest of us and turning more and
             | more of us in to their servants, telling us how to run our
             | lives, raise our kids, and what to believe.
             | 
             | Are you ok with that? I'm not.
        
               | emteycz wrote:
               | Voters decide, not money. And the rich usually want a
               | free world...
        
               | andrepd wrote:
               | I don't recall ever reading such a naive statement x)
        
               | joshjdr wrote:
               | I disagree. Many complain about Bezos making billions and
               | not paying a fair share of taxes; yet they support and
               | empower him to further do so with every purchase they
               | make from Amazon. Sure, voters have power voting in
               | occasional elections, but every other day they vote with
               | their dollars--whether they see that or not.
        
               | pmoriarty wrote:
               | _" Many complain about Bezos making billions and not
               | paying a fair share of taxes; yet they support and
               | empower him to further do so with every purchase they
               | make from Amazon."_
               | 
               | From what I understand, the vast majority of Amazon's
               | profit comes not from the e-commerce website but from
               | AWS.
               | 
               | And the overwhelming majority of Bezos' net worth comes
               | from the value of Amazon's stock, does it not?
               | 
               | So aren't the people who are most responsible for his
               | wealth the purchasers of Amazon's stock, not the users of
               | the e-commerce part of the business?
        
               | dantheman wrote:
               | Notice what the 'fair share' is, is never stated, and at
               | the same time want to encourage behavior via the tax
               | code, but then get mad when people use the incentives.
        
               | [deleted]
        
               | mschuster91 wrote:
               | Given the enormous reliance on advertising in US
               | elections and the mindblowing sums that parties,
               | candidates and PACs burn on them: money buys votes.
        
               | pmoriarty wrote:
               | _" Voters decide, not money."_
               | 
               | The voters are told what to believe by the likes of Peter
               | Thiel and Cambridge Analytica, or by the likes of Hearst,
               | Bezos, and Rupert Murdoch owning newspapers.
               | 
               | The rich very often have the ears of politicians, with
               | which (if they don't directly bribe) they can easily have
               | lunch any day of the week to lobby for their special
               | interest, or propose quid-pro-quo plans.
               | 
               | How often does the average voter have lunch with their
               | elected representatives? For almost all of them the
               | answer is never.
               | 
               | The rich also donate to foundations (if they don't own
               | some outright) that lobby the government for their
               | interests, they fund ads to the tune of millions of
               | dollars, they sometimes use millions of their own money
               | to fund their own campaigns for office (Trump being
               | exhibit #1, and Bloomberg #2), etc.
        
               | ABCLAW wrote:
               | >the rich usually want a free world...
               | 
               | There are plenty of Kleptocrats that aren't concerned
               | with the world being free and fair; they're just happy to
               | sit atop the pile, regardless of what the pile is.
        
             | axbytg wrote:
             | > Government spending is almost entirely leveraged by debt
             | and these documents prove that these "ultra-rich" pay a
             | large absolute dollar amount of taxes (albeit lower than
             | 30%). That is factually non-zero
             | 
             | These are such non points. Who cares about the absolute
             | amount? We measure it in points for a reason, and the
             | effective number of points the ultra rich pay is <1, while
             | I pay ~25. You can't denormalize that away.
        
             | aeturnum wrote:
             | I'm pretty open to the ethical version of this article
             | omitting Thiel's name.
             | 
             | I also think it would be interesting to talk about what it
             | is in this reporting that materially harms Thiel. That he
             | is a billionaire and that he owns PayPal stock was
             | previously public knowledge. This only seems to introduce
             | information about how much tax his Roth is sheltering him
             | from - which the anonymous version of the article would
             | also cover.
        
               | cdolan wrote:
               | Forbes thought his personal wealth was 2 billion.
               | 
               | This reveal puts his ROTH IRA _alone_ at $5 billion (it
               | owns stock in companies other than PayPal and Palantir)
               | 
               | That is a material change in Mr. Thiel's privacy.
        
             | meristohm wrote:
             | In principle it seems unfair. Case-by-case I have a hard
             | time being against this sort of reporting because of how
             | much influence that money might have. How is it that an
             | individual has so much money? My feeling is that it was
             | enabled in part by tax-funded infrastructure and
             | insufficient government regulation. Too much individualism
             | is trouble (see the USA response to COVID-19). Likewise too
             | much central control.
             | 
             | If we're collectively being exploited and some publicity is
             | what is effective at change, so be it. I still see the
             | super-rich as individuals, intrinsically no better or worse
             | than anyone else, worthy of empathy, and answerable for
             | their actions, which generally feel unethical.
             | 
             | Where might we cap wealth? What is a better way to go
             | through life than playing the acquisition game and feeling
             | like we're not adults until we have the fancy, humorless
             | luxury things? How do we otherwise meet the needs of those
             | who thirst for more and more power and resources?
        
             | andrepd wrote:
             | > Government spending is almost entirely leveraged by debt
             | 
             | What does that have to do with anything? I literally have
             | no idea what you're trying to imply.
             | 
             | > these documents prove that these "ultra-rich" pay a large
             | absolute dollar amount of taxes (albeit lower than 30%).
             | 
             | Yes, and they also benefit from the work of society and
             | government many times more than I do! From courts to law
             | enforcement to bailouts to everything else. More generally:
             | _these people are not rich in a vaccum, they are only this
             | rich because the rest of society exists, therefore they owe
             | a debt back to society_.
             | 
             | Absolute values count for nothing. It's preposterous that I
             | work my ass off and get taxed 30 or 40% and they live off
             | capital gains and get taxed zilch.
        
           | dennis_jeeves wrote:
           | >It's about recognizing how the entire system is stacked
           | against working people and that these ultra-rich pay 0% in
           | taxes, while I pay 30%.
           | 
           | Rather that have the rich also pay 30%, don't you think that
           | it would be better if you too have to pay 0%?
        
           | dane-pgp wrote:
           | > these ultra-rich pay 0% in taxes, while I pay 30%.
           | 
           | Then I have a modest proposal. If the median household net
           | worth[0] in the US is about $120k, and the median household
           | federal tax burden[1] is about $10k per year, then let's say
           | that anyone with a net worth more than $1 billion should pay
           | an annual wealth tax of 10%.
           | 
           | The G7 have already agreed to a global minimum corporation
           | tax rate, so let's make this wealth tax global too, and
           | forbid billionaire residents of non-compliant countries from
           | visiting or passing through countries that implement this
           | tax.
           | 
           | [0] https://dqydj.com/average-median-top-net-worth-
           | percentiles/
           | 
           | [1] https://www.propublica.org/article/the-secret-irs-files-
           | trov...
        
             | Swenrekcah wrote:
             | A 10% wealth tax is quite a lot but otherwise I agree hat
             | we absolutely need to move from income to wealth tax.
             | 
             | I'd support a progressive tax, something like 0 for the
             | first 200,000 or something, then slowly rising to a few
             | percent.
             | 
             | The really tricky thing though is that some assets generate
             | income but others don't, and we probably don't want to put
             | even more pressure on people to make rent on their assets
             | than they already have.
             | 
             | So it's a really hard problem but worth thinking about
             | because taxing capital is really the only way to have a
             | fair tax system in a capitalist society.
        
           | Manuel_D wrote:
           | What country are you talking about? Because in the US the top
           | 1% pay about 40% of taxes [1]. The remaining 2-5% pay 20%.
           | Almost all taxes are paid by people in the top quarter.
           | 
           | 1. https://www.heritage.org/taxes/commentary/1-chart-how-
           | much-t....
        
           | listless wrote:
           | I think two things can be true at once here...
           | 
           | 1. We have GOT to close some of these loopholes now that we
           | know what they are and...
           | 
           | 2. Someone should go to federal prison for this leak
           | 
           | We can't undo what we now know about avoiding taxes and we
           | cannot condone egregious invasions of privacy like this.
        
             | machinebun wrote:
             | I believe that if the leak is proven to be in the public
             | interest, no one should go to jail (but that it should be
             | the rare exception).
             | 
             | I also don't believe Snowden deserves to be in jail (or
             | rather that he should be pardoned). Sometimes you can't fix
             | things without breaking the law - everyone does it on a
             | daily basis with few consequences (jaywalking, etc).
             | Sometimes it has to be done on a larger scale in order to
             | shed light on injustices - otherwise the power of the few
             | will prevail over the power of the many.
        
             | dane-pgp wrote:
             | If someone brings to light an injustice which prompts the
             | legislature to fix the laws to better match the public
             | consensus of fairness, that seems a perfect example of what
             | the presidential pardoning power is intended for.
             | 
             | I understand that the word "If" is doing a lot a work in
             | that sentence, and I have some sympathy for law-abiding
             | billionaires who don't deserve to have their privacy
             | invaded, but they should receive some form of compensation
             | rather than legal punishment of the leaker.
        
         | pradn wrote:
         | It's reasonable for good journalistic organizations to have
         | access to secret government records. They just need to be
         | responsible with them. The same discussion happens any time
         | there's a leak of intelligence/surveillance/military documents.
         | What if the info puts soldiers at risk? Well, the ethics of
         | that are up to the journalistic organization to tackle. They're
         | the best equipped to do that, with their training and
         | standards.
         | 
         | Now if someone just sold the records to TMZ or something,
         | that's a different conversation.
        
         | andrepd wrote:
         | > but thousands of private citizen's intimate financial
         | disclosures (edit: seemingly for the purpose of weaponizing the
         | data against them).
         | 
         | Can you point to one instance of some of this data being
         | divulged about random citizen's finances, or used for
         | blackmailing someone? It seems silly to complain about
         | legitimate journalism because the data _might_ , but has not,
         | been used for nefarious purposes.
         | 
         | Google "whistleblowing".
        
           | IG_Semmelweiss wrote:
           | Whistle blowing journalism implies you are reporting on acts
           | breaking the law.
           | 
           | Reporting things that are juicy but not illegal, is
           | effectively gossip / tabloid material.
           | 
           | You don't get to break the law in order to effectively
           | gossip.
           | 
           | Case in point. You don't get to break into the King of
           | England's cell phone to report he's infertile, even if you
           | think means English citizens have a right to know that the
           | country will never have a Prince-heir.
           | 
           | That is not legitimate journalism, and its certainly not
           | whistle-blowing. Its repugnant and tabloid journalism.
           | 
           | Personal privacy is never second to the mob. Period.
           | 
           | EDIT: unsafe, fraud, abuse, corruption, malfeasance of
           | government/company funds, are almost always also breaking
           | fed/state/opco policy or regulations, and as such they are
           | illicit and fall within the spectrum of whistle-blowing.
        
             | cdolan wrote:
             | Well said, take my upvote.
             | 
             | Personal privacy and the belief that you are innocent until
             | proven guilty (no matter how "obviously guilty" you are),
             | are two things we've really forgotten in the USA and
             | perhaps the modern world in general.
        
               | machinebun wrote:
               | The innocent until proven guilty only applies in criminal
               | court, not in civil court by the way.
               | 
               | Personal privacy is good, but there are some societal
               | things that should supersede the right to personal
               | privacy in my opinion - I don't think any single right
               | should be absolute.
        
               | cdolan wrote:
               | The US Constitution would disagree with you.
               | 
               | Edit- the "Bill of Rights" sorry
        
             | andrepd wrote:
             | > A whistleblower (also written as whistle-blower or
             | whistle blower)[1] is a person, usually an employee, who
             | exposes information or activity within a private, public,
             | or government organization that is deemed illegal, illicit,
             | unsafe, or a waste, fraud, or abuse of taxpayer funds.
             | 
             | Morality [?] lawfullness. Many things are perfectly legal
             | but profoundly immoral or unethical. The public has a right
             | to know that they're being cheated like this, that working
             | class people have to pay their taxes but the very rich
             | don't. It's very slimy that you try to equate this to
             | curiosity about royalty.
        
             | luffapi wrote:
             | There is no requirement for whistle blowing to be strictly
             | about illegal activity. Mismanagement, corruption,
             | unethical behavior... are all considered under the term.
             | It's in the public's benefit for this information to be
             | public. All billionaires should be under far more scrutiny
             | then they are. There's no benefit to the rest of us for
             | them to operate with impunity in the shadows.
        
         | legitster wrote:
         | The weird thing is that none of it is terribly surprising or
         | unexpected. So information was stolen just to kind of confirm
         | what everyone already knew?
         | 
         | If this was all new information I might disagree with you, but
         | we already knew capital gains is horrendously undertaxed. And
         | knowing the specific dollar amount doesn't change the
         | conversation much, it just makes it that much more incendiary.
        
           | FabHK wrote:
           | There is a difference between mutual knowledge (everyone
           | knows X) and common knowledge (everyone knows X, and knows
           | that everyone knows X, and knows that everyone knows that
           | everyone knows X, etc. ad infinitum).
           | 
           | This brings the knowledge everyone sort of knew and makes it
           | common knowledge. That can have a powerful impact.
        
           | cdolan wrote:
           | Counter point - Information was stolen and is being held that
           | doesn't change the common narrative or introduce new
           | information ("our tax system needs help").
           | 
           | Have you considered the amount of identity theft that can
           | occur when you have 15-20 years of tax information on
           | thousands of individuals? And that information has obviously
           | been duplicated many times if it made its way from the IRS,
           | through an informant, and into the hands of at least one
           | person at ProPublica?
           | 
           | I don't intend to defend "the system" and the fact ultra-rich
           | can become even more ultra-rich, or the morality/fairness of
           | that. I do find it very alarming that its apparently "OK"
           | that Pro-Publica has intimate financial details of thousands
           | of Americans - enough to completely ruin their lives if in
           | the wrong hands - and its "OK because they have a lot of
           | money".
           | 
           | Thats not OK to have on any American, wealthy or not, in my
           | opinion.
        
         | enahs-sf wrote:
         | I grep'ed the article for the word 'criminal' and came up
         | empty. This is essentially a hit piece. Say what you will about
         | Bezos, Thiel, et al., but they are just high profile targets
         | that propublica is going after for the clicks. I question the
         | ethics of these journalists.
        
           | FabHK wrote:
           | Maybe also grep synonyms:
           | 
           | > Victor Fleischer, a tax law professor at the University of
           | California, Irvine who has written about the valuation of
           | founders' shares, read the PayPal filings at ProPublica's
           | request. Buying startup shares at a discounted $0.001 price
           | with a Roth, he asserts, would be indefensible. "That's a
           | huge scandal," Fleischer said, adding, "How greedy can you
           | get?"
        
           | andrepd wrote:
           | Morality [?] lawfullness. Many things are perfectly legal but
           | profoundly immoral or unethical. The public has every right
           | to know that they're being cheated like this, that working
           | class people have to pay their taxes but the very rich don't.
        
           | luffapi wrote:
           | Who cares if it's criminal? Do you only read crime reports? I
           | was unaware that a Roth IRA could be exploited like this
           | until this piece enlightened me.
        
         | pmoriarty wrote:
         | What's the argument for keeping tax returns secret?
        
           | cdolan wrote:
           | In the USA they have been private for a long time (forever
           | perhaps, I don't know the full 200 year history on them). In
           | modern times (2000 or later) they have certainly been very
           | private, though.
           | 
           | Whats the argument for being selectively harassed by leaking
           | your sensitive financial details?
        
           | paxys wrote:
           | What's the argument for keeping anything secret? Simply that
           | it is my personal info and isn't anyone else's business.
        
           | walshemj wrote:
           | Same argument for regulating Google analytics which seems
           | super popular on here
        
           | packetslave wrote:
           | ask Donald Trump
        
           | bonzini wrote:
           | Mostly that you don't want random people to know how much you
           | make, and unless you are a public figure there's no reason
           | why it should be useful to the public.
        
             | pmoriarty wrote:
             | So what exactly is the problem with a random person knowing
             | how much you make?
        
               | jes wrote:
               | How much do you make?
        
               | pmoriarty wrote:
               | Nothing. I'm out of work.
               | 
               | Your turn.
        
               | adolph wrote:
               | So you got no skin in the game, take a hike.
        
               | Dma54rhs wrote:
               | Why are you out of work. If so, from where do you get the
               | money to cover your expenses. Who and how much pays, or
               | what are your savings?
        
               | claudiawerner wrote:
               | 24k/year.
        
               | bonzini wrote:
               | Relatives or "friends" asking for money, neighborhood
               | rumors, I don't know. The world is full of random shitty
               | people.
        
         | seventytwo wrote:
         | Maybe we should fund and staff the IRS properly so that they
         | can properly police and audit the wealthy unsteady of relying
         | on "leaks"?
         | 
         | It's perfectly ok for the wealthy to lobby Congress so that the
         | IRS is neutered, but when a person leaks their info, it's a
         | crime, huh? Seems like a double standard.
        
         | adolph wrote:
         | The only crime is ProPublica's and some IRS people. Who's next
         | after "the rich?" Some impolite plumber?
        
           | cdolan wrote:
           | Hey thanks for actually answering my (somewhat rhetorical)
           | question haha.
        
       | [deleted]
        
       | m_ke wrote:
       | Twitter thread breaking this down
       | https://mobile.twitter.com/propublica/status/140800243612462...
        
         | lotsofpulp wrote:
         | Why did ProPublica omit exactly when the funding round for
         | additional millions was in tweet 10 and 11?
         | 
         | > 10/ So.
         | 
         | >Right pointing backhand index IRS records show that in 1999
         | Thiel purchased 1.7 million shares of his startup, which would
         | soon become PayPal, for just $1,700 -- a tenth of a penny per
         | share.
         | 
         | > 11/ Even though Thiel's startup received millions in funding
         | within months, Pensco still told the IRS these founders' shares
         | were worth less than $1,700 at the end of 1999.
         | 
         | >See where this is going?
         | 
         | The only reason I can think of is ProPublica intended to
         | suggest Thiel committed fraud by misstating the company's
         | valuation in 1999, but ProPublica wants to maintain plausible
         | deniability because the funding round did not happen in 1999.
         | 
         | It is great that ProPublica is pointing out how tax
         | deductions/exemptions/credits allow for loopholes to exist, but
         | I do not see a reason for them go after specific people for
         | using them.
         | 
         | Edit: copied tweets for easy reference
        
           | sjg007 wrote:
           | I mean, all startup founders should do this.
        
             | nrmitchi wrote:
             | Except it is very clearly not an arms length transaction,
             | and is explicitly not allowed, and the penalty is
             | tainting/exposing-to-tax the entire IRA.
        
       | hash872 wrote:
       | Is it legal for a startup employee to purchase shares with their
       | Roth? I understand that an officer in the company probably
       | cannot, but if you're just an employee- does anyone know if
       | that's permitted? I skimmed about half the comments section here,
       | not sure if anyone answered this already.
       | 
       | If it is legal- pretty great deal for an employee either given
       | RSUs or options to buy them this way, no?
        
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