[HN Gopher] Part II: The failure points from $5M to $100M in ARR
       ___________________________________________________________________
        
       Part II: The failure points from $5M to $100M in ARR
        
       Author : tyoung
       Score  : 159 points
       Date   : 2023-01-12 17:23 UTC (5 hours ago)
        
 (HTM) web link (tracy.posthaven.com)
 (TXT) w3m dump (tracy.posthaven.com)
        
       | candybar wrote:
       | On the whole, this is a fairly good write-up but this is just not
       | right:
       | 
       | > Being at a startup is hard in a way that is almost
       | indescribable to anyone who hasn't experienced it.
       | 
       | Being at a startup as an employee isn't necessarily hard. You
       | hear this type of "startup is so hard" because running companies
       | well is hard and successful startups will often grow faster than
       | their founders are able to grow their own ability to run
       | companies, which makes their own job challenging. And a lot of
       | startups are poorly run in ways that are entirely avoidable
       | (often as a result of their CEOs not being able to grow as
       | quickly as their company) which can make life hard for the
       | employees as well. But this isn't a necessary part of the startup
       | experience.
        
         | metadat wrote:
         | Most non-startup jobs tend to be well-defined and come with a
         | pre-existing business strategy and existing resources, such as
         | a project codebase and existing at least semi-working solution
         | to which one can inspect and add to.
         | 
         | Contrast this with startup companies, where it's often required
         | to explore and build completely new things from the thin air of
         | the ether. I'm not saying other jobs don't also have elements
         | of this, as new projects and opportunities do emerge, but being
         | at a startup is definitely an extreme situation and arguably a
         | different game. In the meta lens, it can be viewed as the act
         | of mining the veins of market realities for golden ideas.
         | 
         | It's for the risk takers and adventurers. I've witnessed many a
         | great engineer learn it's too undefined which can be
         | uncomfortable, and is not a good fit for them.
         | 
         | It's nothing personal, along the exact same lines as some folks
         | who can't stand working for a large company.
         | 
         | Different strokes and all that. This form of diversity is one
         | of the beautiful things about the spectrum of humanity. In
         | aggregate, it works!
        
       | kolbe wrote:
       | I got the impression that the 2022 late stage funding implosion
       | was also the death of ARR as a be-all growth metric. It got
       | Goodhart's Law'd to death after all the companies that went
       | public at huge valuations based on ARR turned out to not be as
       | "recurring" as investors would have liked.
        
         | Ataraxic wrote:
         | I wonder if you have more context or numbers. What companies
         | are you thinking of. I remember companies like WeWork and
         | Coinbase dropping in valuation but what more traditional Saas
         | companies have run into this sort of hurdle?
         | 
         | I'd argue that ARR is still a good measure just not the growth
         | at all costs, w/e it takes to get toe 100M ARR/Unicorn status
         | anymore. After all, sales is sales and if you don't have
         | repeatable sales you probably don't have much of anything.
        
           | kolbe wrote:
           | There are many shenanigans that startups can play to juice
           | ARR to render it meaningless. The idea isn't terrible, but
           | that's why I invoked Goodhart's Law.
           | 
           | > After all, sales is sales and if you don't have repeatable
           | sales you probably don't have much of anything.
           | 
           | That's right, but you're missing the key that it's a
           | necessary, but _not sufficient_ requirement. When the pool of
           | investments is 90% with ARR are honest and straightforward,
           | then it 's good to use ARR as a metric. But when the pool
           | changes to 50% or less who are honest (as Goodhart would
           | predict), the metric loses value.
        
       | georgeecollins wrote:
       | I hate this BS about A managers hire A people, B people hire C
       | etc. This is total MBA thinking (I think it comes form GE, or at
       | least they espoused it) on a forum where people routinely mock
       | MBAs.
       | 
       | I have been lucky to work in a field where teams frequently work
       | in parallel and success or failure is pretty clear cut. And teams
       | are often stratified based on the priority of project. Many
       | times-- not always -- the "B" team crushes the "A" team. Why?
       | Some reasons include: the A team is performative and focused on
       | the things that burnish the careers and reputation of its
       | members. B teams have more of a sense of the wolf being at the
       | door and that if they don't perform their task they will feel the
       | consequence. Being underdogs promotes teamwork.
       | 
       | Obviously people have profound differences in their strengths and
       | weaknesses and some people are completely inappropriate. But
       | calling people stars or A player covers up a lot of lazy thinking
       | that includes a lot of bias. I have worked at smaller startups
       | that say "we only hire A players". Obviously that is delusional
       | but worse it covered up the more profound questions. Why did you
       | hire the wrong person? Why did that person or team fail?
        
         | Swizec wrote:
         | An A player from Google will fail at a 10 person startup. An A
         | player from a 10 person startup will choke on FAANG bureaucracy
         | and fail.
         | 
         | Fit matters. You wouldn't hire Jim Carey for a DiCaprio role.
        
           | mooreds wrote:
           | This is an underappreciated truth.
           | 
           | The corollary is: find out where you thrive and go there.
           | 
           | Don't beat yourself up if you get spun out of a FAANG, or a
           | startup or a smallco or a bootstrap or a founding role or a
           | mid-tier enterprise. Don't contort to a role or company that
           | isn't a fit.
           | 
           | If you have solid skills, you can find a place.
        
           | albertgoeswoof wrote:
           | You obviously haven't seen eternal sunshine of the spotless
           | mind
        
             | Swizec wrote:
             | I have. Pretty sure I've seen every movie he was in, huge
             | fan.
             | 
             | He's a great actor, but he hasn't shown the range that
             | other A-listers have. Whether that's because of skill,
             | interest, or typecasting, I couldn't say.
        
               | rockostrich wrote:
               | Kind of dumb to say an actor that's clearly proven he has
               | immense range when there are so many other obvious
               | choices. Vin Diesel for example is an A-list star who
               | clearly does not have anywhere the range that Carrey or
               | DiCaprio have.
        
             | lencastre wrote:
             | Bestest movie together with Lost in Translation
        
               | googlryas wrote:
               | Can I guess you're between 37 and 42 years old.
        
           | pryelluw wrote:
           | Jim Carey as the protagonist of titanic does sound like a
           | great movie. I'm sure he would have found space on that piece
           | of wood and survived.
        
             | kingforaday wrote:
             | I saw this over the holiday period last month. James
             | Cameron commissioned a study because he got sick of people
             | yelling at him for killing Jack.
             | 
             | https://www.insider.com/james-cameron-had-forensic-
             | analysis-...
        
               | neilv wrote:
               | > _" We took two stunt people who were the same body mass
               | of Kate and Leo and we put sensors all over them and
               | inside them and we put them in ice water and we tested to
               | see whether they could have survived through a variety of
               | methods and the answer was, there was no way they both
               | could have survived. Only one could survive," he said._
               | 
               | This is peak underappreciated stuntpeople.
        
           | rockostrich wrote:
           | Speaking in absolutes is never useful even though I think
           | this advice might apply when looking for a new role, but
           | small companies tend to grow if you help them succeed so it
           | would be difficult to say your fit is at 10 person companies
           | when that means you would have to jump ship every year just
           | to stay in your comfort zone.
           | 
           | I joined my current company when it was 40 people (and around
           | 10 developers). Almost 6 years later we're ~1500 and the
           | engineering org is something like 200-300. I think I was most
           | comfortable around 20 or so developers but that doesn't mean
           | I can't make continue to have meaningful impact now that
           | there's an order of magnitude more people and the org has
           | completely changed.
           | 
           | I've seen folks who were supposedly "A player"s from small
           | start-ups and FAANG join the company at different stages.
           | Some succeed and some fail but I never noticed any
           | correlation between current size of the company they're
           | currently thriving at and our size when they joined.
           | 
           | Fit is never going to be perfect so don't give up on
           | something just because it might be a little uncomfortable.
           | Give up if you've tried to make it work and it's clear you
           | can't find a way to have impact.
        
         | vasco wrote:
         | In general good people will be able to identify good people
         | (colloquially: game recognizes game). And good people will know
         | they are being interviewed by someone who is not so good, and
         | they won't want to join. A hires A.
         | 
         | Additionally, people who are not so good tend to be threatened
         | by good people. So they will rather hire someone that won't
         | threaten or "find them out". B hires C.
        
         | toss1 wrote:
         | Yup, this is the one thing that struck me wrong in the essay.
         | 
         | After spending multiple paragraphs about how they found that
         | they had to dig much deeper into the background of every exec,
         | getting 10+ references from reports, peers, and their managers,
         | and developing specific lists of red flags . . .they end the
         | section with: "Takeaway: Always trust your gut on people. "
         | 
         | Yes, for sure, if you 'gut' tells you something is off about
         | someone, seriously consider and trust that also, but what was
         | really effective was not gut-trusting, but gathering more hard
         | data and observations to evaluate.
         | 
         | Just seems like the author didn't really think it through.
        
           | naijaboiler wrote:
           | I have hired before. A few times. "Trust my gut" is still the
           | best predictor of success for me. Every hire i have talked
           | myself into didn't end up working out. Nowadays for hiring, i
           | live by, "if it's not a strong yes, it's not a yes"
        
           | candybar wrote:
           | This is just garden-variety narcissism telling you that when
           | you made the right decision, you were right and even when you
           | made the wrong decision, you were actually right all along,
           | you just let your true self be overridden. In reality, a lot
           | of difficult decisions involve you being on both sides of the
           | decision at different times, so it's very easy to look back
           | on any wrong decision you made and decide that the real issue
           | was not trusting yourself.
           | 
           | I'm also a bit surprised that she's throwing the "big company
           | executive" under the bus here, given that it's very easy to
           | identify who this is. She doesn't seem to be merely saying
           | that the fit was the issue, given this:
           | 
           | > 1. They frequently use the wrong pronoun "I" followed by
           | "[contribution to the company]".
           | 
           | > 2. You dread having 1-1s with them.
           | 
           | > 3. They blame you or their peers.
           | 
           | > 4. They complain laterally and downwards.
        
           | methyl wrote:
           | I think it's trusting your gut when it says ,,no", not that
           | you can trust only your gut when it comes to hiring. Wasn't
           | clear but that's how I understand it and agree.
        
         | gumby wrote:
         | > A managers hire A people, B people hire C etc
         | 
         | If that is the case, how do the B people get jobs in the first
         | place? Who hires them?
        
           | Nevermark wrote:
           | The same reason A engineers can put out B work:
           | resource/time/reward tradeoffs and the inevitable unknowns.
        
           | nikanj wrote:
           | Nepotism
        
           | [deleted]
        
         | [deleted]
        
         | mbesto wrote:
         | > Many times-- not always -- the "B" team crushes the "A" team.
         | Being underdogs promotes teamwork.
         | 
         | It's clear you don't understand what A and B people are then.
         | If the "B team" is crushing the "A Team", then they aren't the
         | "B team". Also, notice how you switched "player" with "team"?
         | The quote is "A players hire A players", not "team".
         | 
         | The point is that top tier individuals typically hire top tier
         | individuals. The reason this notion isn't so clear cut is
         | because its hard to identify A players before the fact. It's a
         | retrospective truthism.
        
           | endisneigh wrote:
           | Seems like a no true Scotsman
        
       | reasonabl_human wrote:
       | Thanks so much for sharing these insights! Especially the
       | humanizing points around life still unfolding around you
       | regardless of how much success you achieve.
        
       | lbriner wrote:
       | A common theme seems to be founders who want to keep all the cool
       | stuff about being a small business while they scale to the ARR of
       | a corporate. It can't happen. 1000 people don't all care about
       | some new feature shipped by someone over in the payments team so
       | don't subject them to it.
       | 
       | Most of us have been there in the painfull all-hands meeting
       | falling asleep because the more people you have, the less they
       | will care about the business. In a a team of 5, I have a lot of
       | skin in the game and also a lot of influence. In a company with
       | 100K employees, most of us are just a cog and some cogs don't
       | even move anything!
        
         | dilyevsky wrote:
         | I could see it happening in b2c just not your regular b2b saas
        
         | [deleted]
        
       | xenadu02 wrote:
       | As employee #36 I lived through some of these things first hand
       | and definitely agree with them (I think we were over 200 people
       | when I left).
       | 
       | It was painful going through the enterprise focus transition
       | along with a nonsensical reorg imposed by the aforementioned Big
       | Tech VP. One day we had focused platform-specific teams working
       | on satisfying customers, the next we were moved to cross-
       | functional feature teams and focused on enterprise features that
       | (from our perspective) no one ever asked for.
       | 
       | I also felt the sting from mediocre engineering managers. I
       | remember sitting down with Tracy and Ralph at Uptown Bar and
       | giving them both barrels on what I thought of several managers.
       | To their credit those managers weren't working there very long
       | after that conversation.
       | 
       | IIRC Ralph asked if I wanted to move to being a manager and I
       | declined but in hindsight I think that was a mistake - we needed
       | good management in engineering more than we needed my code.
       | 
       | Another thing that hurt us was hiring a bunch of PMs. Most of
       | them were condescending, ignorant, or both... but suddenly they
       | were telling the engineers who had built everything what to do?
       | IIRC we could have cut that department down to two people with no
       | loss.
       | 
       | The leader of this product team was a manager that just didn't
       | seem to be doing his job, only pushing paperwork and giving
       | scatterbrained presentations. I never did find out why he was
       | kept on so long. I think I very cheekily asked Tracy one time
       | which of his relatives worked at Y2K or Sequoia such that he
       | couldn't be fired because it was clear everyone in engineering
       | was fed up with his nonsense. I'm pretty sure at least several
       | top engineers quit due to that guy specifically.
       | 
       | Either way I don't regret my time at PlanGrid. It was a great
       | team and I'm proud of what the team did and what I did.
        
         | Ben-G wrote:
         | Hah - what a vivid recollection.
         | 
         | It's been a while - we should catch up soon :)
        
         | fakedang wrote:
         | As an outsider to the tech industry, it seems to me that the
         | Product Manager/Product Owner role seems to be not only the
         | most BS role, but also the most damaging role? Considering that
         | I saw a post a few weeks back, I saw a similar post (I think on
         | HN itself) where PMs were being fired en masse, I wonder if
         | there is any real utility with the product team, or if it's
         | just a holdover from Google doing its thing back in the days
         | that everyone decided to copy.
        
           | ZephyrBlu wrote:
           | PMs tend to have a lot of leverage, so a bad one makes a very
           | large negative impact. A good PM is worth their weight in
           | gold though.
           | 
           | I think of them as basically glue. They just help make shit
           | get done. That could be helping co-ordinate between eng and
           | design, doing customer research, managing expectations, etc.
           | Whole range of things that different PMs do.
        
           | pixiemaster wrote:
           | I wouldn't agree with the BS label, as a good PM/PO can
           | really help along.
           | 
           | but with that kind of role, contribution quality is rarely
           | assed correctly, and at the same time, the sandwhich role
           | between contributors, management, and customers, combined
           | with a usually communication-savvy skillset can be extremely
           | dangerous. even worse in impact than a highly visible ,,bad"
           | EVP/SVP.
        
           | HatchedLake721 wrote:
           | Of course there is.
           | 
           | If not for the PM, who will speak with the customers, gather,
           | analyze and understand their needs and problems?
           | 
           | There should be a person that drives the product in the right
           | direction based on customer conversations.
           | 
           | In the early stages founder is the product owner.
           | 
           | But as the company grows, the role of the founder/CEO
           | changes. You now build the people, and people build the
           | business.
           | 
           | Engineers or CEOs building features no one asked for is IMHO
           | one of the major reasons lots of tech startups fail.
           | 
           | Awesome idea, cool product, but no one asked for that feature
           | you were building for 2 months. (guilty here myself)
        
           | skrtskrt wrote:
           | You need both good PMs and an organization that is set up to
           | utilize PMs well.
        
           | vasco wrote:
           | I good PM does great things if they are very busy across
           | teams and don't have time to hassle people about shenanigans
           | and instead talk to users and understand the product deeply.
           | Many places though have too many PMs that never talk to users
           | and pretend like they know what they want.
        
       | mariambarouma wrote:
       | Ha! one of the slam-your-own-dick-in-the-door moves that startups
       | seem destined to repeat
       | 
       | Seen it SO many times when startups decide they need "grownups"
       | in big positions to be credible externally
        
         | dilyevsky wrote:
         | Hey it worked for google (eric) and facebook (sheryl) so it
         | will work for us!
        
       | manv1 wrote:
       | A lot of the enterprise requirements he talked about add no
       | actual value to the product; they're just checkboxes on an RFP
       | that are required.
       | 
       | Theoretically applying all of those requirements to your product
       | might make your product more secure, scalable, or reliable. It'll
       | also make your product harder to maintain, harder to test, and
       | harder to improve.
       | 
       | Many of those requirements are there because vendors put them
       | there. If you're part of the RFP process (and you should be if
       | you're actually selling to that sort of customer) you should be
       | actively pushing back on requirements that you feel are
       | pointless...making them optional instead of required, or at the
       | very least providing a delivery date instead of delivering day 1.
       | 
       | In the enterprise space there's no guarantee you'll get the
       | contract; to an extent the decision more political than
       | technical. You should do a brutal assessment of your actual
       | chances before engaging in any work implementing their
       | requirements before the contract is signed. And since the sales
       | cycle will be at least 6-9 months you'll have plenty of time to
       | figure things out.
       | 
       | Lastly, if your product is highly desired the "requirements" can
       | be bent or delayed. They're guidelines and can be overridden, if
       | you have the right relationships.
        
         | donnythecroc wrote:
         | Interesting you assumed the female CEO writing this was male.
        
       | a_c wrote:
       | Hiring is like a code base, you have to have the right
       | abstraction at the right time. Starting out, better everything be
       | a concrete implementation, that is everyone is directly
       | responsible for making things work.
       | 
       | Next is what I found most people doing differently from my ideal
       | - abstract and refactor base on your existing implementation, not
       | because of some framework doing it, nor because the previous
       | project did it this way. Do you need a data access layer, a
       | library, a folder, to talk to database where the first
       | implementation was just storing things as a variable? You
       | probably need a database and plain SQL. Do you need site
       | reliability engineer to keep your site online while your traffic
       | all comes from friends? Do you need a QA for testing? Or do you
       | need a product manager where, as a founder, the value proposition
       | has yet to be proven? How often do you see a code base spinning
       | up all the folders/empty files because "we may need it". And how
       | often when you hire someone, they spin up various incarnation
       | people * time like teams, sprints, squad, function, _BEFORE_
       | understanding the current implementation. This is why you hire
       | the wrong people. And you know it only 1 year down the road.
       | Wrong abstraction. Using framework has its appeal, where a cookie
       | cutter solution mostly work. But it also has its limitation,
       | bloat.
       | 
       | Once a wrong abstraction is in place, the more code/people
       | depends on it, the more effort it takes to refactor
        
         | a_c wrote:
         | Btw, the most important point from OP's is the last one. Life
         | is fragile, treat people well. That's more important than all
         | the three letter acronyms in the world.
        
       | ipaddr wrote:
       | "And remember that A players can recruit other A players, but B
       | players can only recruit C players"
       | 
       | In point one they list this. In point 3 he mentions his biggest
       | mistake was hiring someone with starpower from a public company
       | who didn't work.
       | 
       | Unless the founder is an A player in terms of recruiting everyone
       | hired would be a C player or less. And in point 3 we learn he is
       | not an A player.
       | 
       | How do B players ever get hired?
        
         | georgeecollins wrote:
         | Your point just illustrates how shallow this analysis is.
        
         | oragnediscussy wrote:
         | The point is that B players have a very hard time ever
         | recruiting A players and actually almost always hire people
         | that are worse than themselves (i.e. c players). This is very
         | true and should be something founders watch out for very
         | carefully as they scale.
        
           | sokoloff wrote:
           | "Yes and..." I think a lot of times this is _intentional_.
           | 
           | A player wants to hire A players so the A player can more
           | effectively beat their rivals in the marketplace.
           | 
           | B player wants to hire C players so the B player can more
           | effectively beat their rivals in the company.
        
         | molsongolden wrote:
         | The A player thing is less about how good they are at hiring
         | and more about how strong of a player they are overall.
         | Founders generally need to be A players to be successful
         | founders.
         | 
         | An A player will still make hiring mistakes but they have the
         | skills/ability/aura/whatever to convince other A players to
         | come work with them.
         | 
         | Many A players won't want to work for/with a B or C player
         | because they won't see this as a good opportunity.
         | 
         | Not sure if they actually meant that B players can't hire B
         | players but maybe. This sort of framing is pretty high level
         | though.
        
           | mlhpdx wrote:
           | Yep, just put people in bins so you can keep them organized.
           | It's always worked, so why stop now, right?
           | 
           | It's not as easy as A and B and C people (or any other
           | labels).
           | 
           | I've professionally led a team doing physical labor, and
           | currently a team of teams doing intellectual labor (software
           | development) and several between. They have been excellent,
           | productive and profitable as well as respectful, ethical and
           | honorable.
           | 
           | The reasons behind their success are complicated but always
           | start on the same foundation: respect. Genuine, difficult to
           | come by, and more difficult to maintain, respect. For the
           | customer. For the user. For each other. For other
           | departments. For the community. For the competition.
           | 
           | From there builds trust, and from trust comes ambition and
           | the ability to focus on the purpose of the job (yes, it's a
           | job in most cases, not a mission or vision).
           | 
           | This is what I see some growth CEOs miss. They lack respect
           | for people outside the "right" mold and don't hire (or keep)
           | them. Then to their surprise, their teams become
           | dysfunctional.
           | 
           | Many tired anecdotes teach us about this (too many chefs,
           | etc.) yet the same mistake is made with relentless
           | repetition.
        
         | skrebbel wrote:
         | Meta nitpick, and I'm not certain, but I think the author
         | (named Tracy) is a she. Or a they which lets you avoid the
         | problem altogether.
        
           | eadmund wrote:
           | > Or a they which lets you avoid the problem altogether.
           | 
           | At the cost of being ungrammatical, inelegant and IMHO
           | profoundly disrespectful.
        
           | williamstein wrote:
           | You are correct. The author's pronoun is "she" and there is a
           | bio page about her here: https://leade.rs/speaker/tracy-young
        
           | sieabahlpark wrote:
           | [flagged]
        
         | williamstein wrote:
         | The assumption is: "And remember that A players can recruit
         | other A players, ...", not " "And remember that A players can
         | ONLY recruit other A players, ...".
         | 
         | (Added: My Ph.D. in mathematics is useful for something.)
        
           | bibanez wrote:
           | I cracked a laugh at the end :) I wonder what their faces
           | will look like when they learn about contraposition
        
           | tyoung wrote:
           | This is helpful, thank you.
        
       | triceratops wrote:
       | Any articles about the failure points from $0 to $5M ARR?
        
         | moneywoes wrote:
         | This please, I think 99% of businesses don't even get to $5M
        
           | jrudolph wrote:
           | also on the same blog -> https://tracy.posthaven.com/part-i-
           | founder-led-enterprise-sa...
        
         | [deleted]
        
         | jvanderbot wrote:
         | It's right on the same site. It is called "part 2" after all.
         | 
         | https://tracy.posthaven.com/part-i-founder-led-enterprise-sa...
        
           | riku_iki wrote:
           | part 1 assumes you built strong product with strong market
           | fit already. Author could consider writing part 0 about
           | missing most critical part.
        
       | HorizonXP wrote:
       | Love seeing you back in the game Tracy.
       | 
       | I'm currently knee-deep in the enterprise world, and trust me,
       | the point about selling into these orgs is very true. My team
       | just spent the last year moving our client off a Salesforce
       | Lightning-based solution onto our custom-built one. No one in the
       | org could tell us why they chose to build it in Lightning, but
       | everyone now says they love our solution.
       | 
       | The lessons you learn building a startup are good and always
       | usable, but you need to be ready to learn what it's like to work
       | in and with an enterprise, to figure out how to adapt and sell
       | your product to them. It's an arduous process, but worthwhile.
        
       | [deleted]
        
       | thexumaker wrote:
       | So 3/4 of the main points here are in regards to hiring the right
       | people... Almost makes me wonder if hr teams/operations shouldn't
       | be measured on just headcount but rather getting the right people
       | in
        
         | Ataraxic wrote:
         | Hiring speed, hire quality, compensation (including things like
         | work/life balance, healthcare, flexibility). I think you can
         | try for two.
         | 
         | Once you get large enough your ability to really selectively
         | recruit gets a lot harder when natural attrition means you need
         | to replace X amount of people just to continue operating as
         | before.
         | 
         | Of course earlier on, the fewer the people the larger the
         | impact each one will have so just like the article says about
         | transitioning to enterprise, the focus and requirements of the
         | HR team change as well.
        
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