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My role as a founder-CTO: year 8
- raw_anon_1111 9mo agoSaying you want to control your company and you want to be around 10 years and then raising VC funding is either naive or dishonest. VCs aren’t interested in a lifestyle business throwing them maybe a small dividend and a miniscule number of companies go public. Look at YC, they have invested in thousands of companies and only around 20 have gone public and only 3 have had positive returns since going public https://medium.com/@Arakunrin/the-post-ipo-performance-of-y-combinator-companies-a-mixed-bag-of-success-and-struggle-58e9a4006f01 https://medium.com/@Arakunrin/the-post-ipo-performance-of-y-...
- airstrike 9mo agoThe problem with that analysis is it ignores all the companies that exited through an acquisition rather than public markets. If anything, it's an endorsement of M&A.
- raw_anon_1111 9mo agoMy “analysis” was the idea of a private company that seems to want to stay independent and control their own destrone like the author of the submission wants. There are only two ways to stay independent - stay private forever or go public. Once you take outside funding, you really have no choice but an acquisition or go public. VCs don’t want to get tiny dividend checks. Even public shareholders will insist on a sale at the right price
- airstrike 9mo agoGoing public doesn't keep you independent, though, unless you were already the kind of unicorn that has enough pull to own a massive amount of shares and/or a special class of them
- raw_anon_1111 9mo agoIsn’t that what I just said? > Even public shareholders will insist on a sale at the right price
- airstrike 9mo agoYes, but that isn't all you said and it isn't even right. Public shareholders generally don't insist on anything as they are dispersed. They may elect directors to the board, but that question gets into all sorts of dynamics about who actually really votes when annual meetings come around, board independence, activist shareholders and whatnot. Put all of that aside and assume for a second that directors are a perfect representation of shareholder interests. Boards do not "insist on a sale". Instead, they may have the _fiduciary duty_ to consider bona fide acquisition offers and take the decision that maximizes shareholder value, triggered upon certain conditions (cf Revlon Duties)
- raw_anon_1111 9mo agoHow many times have the board refused a sell for the right amount of money.
- airstrike 9mo agoThat is not "insisting on a sale". Selling for the right amount of money is literally the right decision to make!
- raw_anon_1111 9mo agoThe entire submission is about someone who doesn’t want to be acquired even at “the right price”. You don’t have that option when you take outside investors.
- elwatto 9mo agoNot at all, we believe the asset is worth a lot more :)
- Lionga 9mo agoTalk about dumping your trash on retail, YC is a lot smarter then I thought
- trollbridge 9mo agoThe house always wins.
- adiazyc 9mo ago[dead]
- fourseventy 9mo agoUnless you are already worth billions if an exit would net you 9 figures its a no-brainer to sell.
- riazrizvi 9mo agoIs it? So you can what? Buy exotic vehicles? Buy extra houses? Buy surgeries? Buy expensive experiences? All you find is stuff, presented as super valuable, and people very very keen to sell it to you. They’ll do whatever you want. It attracts a certain kind of person. The people who have the means for this lifestyle seem mostly disappointed. It’s not the situation this guy has created for himself. His life has meaning, he’s of value to his employees and customers and partners.
- dmacj 9mo agoI’m sure there are many other more meaningful options, none of which start with the word “buy”.
- trollbridge 9mo agoBut then money has nothing at all to do with such options.
- websiteapi 9mo agoyou're seriously lacking in imagination if all you can think of is that.
- afavour 9mo agoSo that you have security for the rest of your life and your children have security for the rest of theirs. And likely their children as well. Not everthing bought with money is superficial. Certainly a lot is less superficial than dedicating your life to “in app payments made easy”. Turning down generational wealth so you can continue to pursue your dream of being a tech CEO seems like a wildly selfish decision to me. Just start a new company!
- farceSpherule 9mo ago[flagged]
- themanmaran 9mo agoDid you just generate a GPT rant and find-replace every — with --?
- farceSpherule 9mo agoWhy does everyone assume that everything posted is based on GPT? There are people in this world who know how to write.
- lovich 9mo agoBecause your account was created after general access to chatGPT and other LLMs was available to the public and your writing style looks similar. Anonymous text on the internet, especially from accounts made after 2022/2023, are like steel post nuclear tests. Everything on the planet is tainted and the only things that can be relatively trusted are steel/text created prior to the tainting event
- HHaan 9mo agoBecause only a complete sociopath (or someone replacing AI's –) would have this much -- in their copy
- thaw13579 9mo agoThose were most likely from a multi-line list that was converted to a single line when the comment was processed on submission.
- farceSpherule 9mo ago[flagged]
- cityzen 9mo ago[flagged]
- OGEnthusiast 9mo agoNot taking a nine-figure exit is insane to me.
- __turbobrew__ 9mo ago[flagged]
- operatingthetan 9mo agoThey do another startup of course.
- lizknope 9mo agoYeah. I know someone that started 4 companies and another that started 5. Out of those they had about a 50% success rate in selling to a larger company, stay about 3-4 years to vest, then leave to make a new start and repeat the cycle. Unfortunately I worked at 2 of the startups that failed.
- seawsurf 9mo agoWhy this industry has such a claustrophobic atmosphere? If he was a doctor and had a calling for the profession, I would understand. I was doing an unrelated degree (Econ), but now I am doing a tech degree and I never saw such a depressive mentality towards life among peers. It is like these people are hell bound to the work culture, diehard workaholics. They don't know anything else outside of a computer screen. Honestly disgracefully.
- deleted 9mo ago[deleted]
- iancmceachern 9mo agoTotally. There is a real mentality in many of the teams I've worked with that the "grind", "sacrifice", as the pound of flesh that must be offered up for success. In reality it's far different. We need to make something of value and charge fairly for that value. Teams can do this without the grind, and still be wildly successful. Teams can do the grind only and are typically not. It's a false idol, and a lot of folks in the industry only have this to look up to so they don't know better. It's because those of us doing the opposite, getting there with balance, aren't writing career focused articles around the holidays. Virtue signaling our work ethic. We're spending time with ourselves, our families, quietly succeeding.
- mjr00 9mo ago> It is like these people are hell bound to the work culture, diehard workaholics. They don't know anything else outside of a computer screen. This is a founder/CTO. You don't get to be a founder or C-level without making work a lot more of your life than just a 9-5. As much as people complain about the C-suite not doing anything and spending all their time golfing, they're basically on work mode 24/7. I've never worked with a C-level who didn't check emails on the weekend, wasn't willing to travel at a moment's notice to close a deal, not willing to work to resolve business or tech emergencies at 1am, etc. On top of that they always represent the company, even in their off time. Stuff that wouldn't matter for a regular employee might lead to termination or forced resignation. For example, kissing a woman who isn't your wife at a concert.[0] This is all true even outside of tech. Ever talk to someone who owns a restaurant? They spend weekends and nights talking to suppliers, figuring out staffing, etc... This doesn't represent typical non-executive jobs in the software industry. Most are largely 9-5. The ones with oncall expectations tend to pay more. [0] https://www.cnn.com/2025/07/19/business/andy-byron-astronomer-ceo-resigns https://www.cnn.com/2025/07/19/business/andy-byron-astronome...
- orliesaurus 9mo agoThe wild part to me isn’t 9 figures is good/bad, it’s that in year 8 the company still has a single human as the default DRI for culture, zero‑to‑one work, and existential decisions. If you’re going to turn down generational wealth, the least responsible version is keeping everything psychologically and operationally coupled to you; the grown‑up move is making yourself cheap to replace and designing a succession plan you’d actually be willing to trigger on bad news, not just a term sheet
- stefan_ 9mo agoThat's never quite how it happens, they can't let go. You can see it in the "Office of the CTO" thing. I've seen that one many times before: when confronted with the endless complexity and depth of building a real global product, they recoil. Everything takes too long, is too uninteresting. They instead build up this parallel engineering organization that is showered with money, headcount and C-level attention to build the new moonshots, with the subtext that whenever it's "ready", it will be thrown over the wall to the actual engineering org. It's a speedrun to make your engineering talent leave.
- throwway120385 9mo agoOh wow you just described our last CTO to a T.
- elwatto 9mo agoThat was the whole point of writing this series: to show how my role evolves and what I’ve had to give up. Trust me, if it were up to me, I’d still be having fun coding (even more so these days). There’s an entire section on delegation in this year’s post. I’m not the single DRI for culture at all. We have many strong culture carriers, which has made scaling to 100 people much easier than scaling to 20. That said, culture is still one of the core responsibilities of founders, in my opinion. Also, OCTO isn’t about me wanting to innovate. It’s about giving certain engineers permission to not be tied to a roadmap and to stay fluid.
- dangus 9mo ago
- harmonic18374 9mo agoI feel RevenueCat is on shaky ground, their market position can only get worse and worse as Apple and Google improve their complimentary offerings and they are forced into more A/B testing that directly competes with others. Recent StoreKit changes this year close a lot of the remaining gap. I would have sold. I wonder why they chose not to.
- DANmode 9mo agoUsers, while not at the top of the list, is probably on the list.
- lizknope 9mo agoI had never heard of the company RevenueCat. It looks like a system for mobile app developers to make in app purchases. A few Internet sources say that RevenueCat has about 120 employees. I'm in a completely different field so I'm not going to claim to understand all of that but I have worked for 2 startups. The author talks about himself and his co-founder Jacob and they went back and forth on whether to sell or not. I am very interested in what the other 118 employees thought. Did they want the co-founders to sell? What was their equity in the company? What kind of deal would they get? Accelerated vesting? Much larger than normal RSU stock grant at the acquiring company compared to a normal new hire there? Nothing? I post this link in many threads about startups about how the normal employees often get nothing. The author says "So we decided to raise another round" and I wonder if the co-founders share the liquidation preferences and captables with the other 118 employees. https://www.reddit.com/r/startups/comments/a8f6xz/why_didnt_i_get_any_money_from_my_startup_a_guide/ https://www.reddit.com/r/startups/comments/a8f6xz/why_didnt_... I posted this comment in a different startup related thread last month but I really wish the CEOs of both startups would have accepted these lower offers. I don't know what the captable was at the first startup but at the second I would have got around $300K. This would have been a large amount of money for me but the founders wanted more so they rejected the offer. Almost every "normal" level employee thought we should have taken the deal and then we would have also gotten jobs with normal RSU grants and bonuses at the acquiring company which was a well established company. It made me decide to never work at a startup again. I don't want a single person to be able to control my financial situation that much. I'd rather have the relatively guaranteed yearly raise, bonus, and RSU grant, and not have to drink the Kool-Aid of the founders. > I worked at 2 startups. Both failed. > The first had been around for about 4 years when I joined and had products that made money. They were trying to get acquired. They had partnered with 2 companies making products specifically for them. One of them offered to buy the company for $30 million but the founders thought their company was worth $300 million. They said no and then money started to run out and people started leaving. In the end the assets were sold for $2 million. > The second startup was created by former coworkers and I joined after it had existed for 4 months. We worked like crazy for the first year and got our prototype out. We had a lot of interest but it took me a while to realize that the 3 founders already had net worths from $5 million to billionaire level. When I heard about offers in the $30 million range they just weren't interested in selling for so little. I left after 3 years and the company floundered another 2 years until they shut it down as people left.
- throw03172019 9mo agoI’d take the money, spend time with family (he mentioned toddler) and then figure out what to do next. Retiring isn’t everyone’s dream but at least having generational wealth is a big relief.
- ridruejo 9mo agoThe secondary provided that relief. Continuing to work on the company makes perfect sense if you enjoy it, which he clearly does (with the inescapable ups and downs of every start up of course).
- theptip 9mo agoI dunno man. A useful psychological trick in this scenario is to imagine you were on the other side of the transaction. Say you have nine figures in your account. Would you push it all into this company to be able to have a fun job? Seems completely insane to me. F You Money means you can spin up whatever projects you want for the rest of your life. Even if your dream job is worth $100m to you, is the delta between this job and your realistic best alternative really worth that much? Speaking as a co-founder CTO, I believe there is a very insidious kind of attachment that forms when you’re dancing with burnout, and working on a successful company that you’ve built from the ground up. “I want to leave a dent in the universe” I told myself. After 3 months in a hammock decompressing, I very quickly realized that there is more to life than work, and it’s really easy to find fulfillment building things if you get bored. But this viewpoint is really hard to hold onto when you’re buried in the day to day excitement of the job.
- cj 9mo ago> Even if your dream job is worth $100m to you, is the delta between this job and your realistic best alternative really worth that much? At least for me, regular financial decision making breaks down once the numbers are above a certain amount. E.g. You won’t feel 10x better about a $100m windfall vs. a $10m windfall. The best case scenario for a lot of founders is to do a secondary, cash out / de-risk, and keep on building. That’s the route I took. Paired with obsessive focus on work/life balance, I don’t regret taking this route.
- deleted 9mo ago[deleted]
- ezekg 9mo agoGood read. I had an offer for a mere 7 figures and that was hard enough to turn down. I couldn't imagine 9 figures! But I think I do get it, at least as much as I can get it at my level. It's hard to give up something you've poured so much of your life into -- "your baby." You lose the autonomy to continue shaping what independence looks like for yourself, or at least it felt that way to me.
- IncreasePosts 9mo agoUnless he's pulling a lot of cash out every year it seems unwise to not sell. He can then just go create something highly similar, bankroll it as much as he wants, but still have the back stop of vast wealth on case of failure.
- throw03172019 9mo agoI’m curious what kind of secondary sale happened? What is normal these days? Is it $5m $10m? Is that excluded from the $50m raised or comes out of that amount. Thanks!
- cebert 9mo agoI’m a big fan of the idea of an Office of the CTO group reporting directly to the CTO that helps with prototyping greenfield projects and exploring innovative ideas. I believe a group like this would be beneficial for larger organizations, like the one I work in. There are numerous opportunities for market disruption, but it becomes increasingly challenging to make bold bets as the company expands. If I had the power to do so, I’d set this up at my company asap.
- nickelbob 9mo agoShouldn't this live under the VP of Product?
- cebert 9mo agoThat’s a good point. Perhaps where this group lives depends on your organization. Unfortunately, the innovative ideas aren’t necessarily coming from product where I work.
- charlie0 9mo agoNo, product shouldn't be the head of an engineering team.
- ulfw 9mo agoSo you're argueing "prototyping greenfield projects and exploring innovative ideas" is something that should come solely out of engineering with no Product input?
- charlie0 9mo agoThat's not what I'm saying. There needs to be a collaboration with product ofc, product shouldn't be the boss though.
- nickelbob 9mo agoShould engineers be pushing product forward?
- adiazyc 9mo agofirst, congrats to revenuecat team and investors. tl;dr - delusional founder writes AI slop reflection narrative recast as “vision” and “conviction.” Makes more sense given a. prototypical cto ego (and insecurity) amplified by b. he’s Spanish (ifyyk) Thousands of words to justify the rejection of a nine-figure exit and he never seriously addresses what the exit would mean for employees or investors. “I’m a builder,” “I need to work with inspiring people,” “I’d be bored after two weeks.” Hard to ignore the glaring contradictions amidst the AI slop. He sets “networking with executives” as a top annual goal, then says “networking is mostly bullshit.” He calls out two separate “biggest fires” for the year: first, reliability/support issues; later, hiring velocity. On one hand he’s bragging about “not having to do anything,” but takes credit for every success (“my foundation-building,” “org design I set up,” etc). Median senior engineering salaries in Spain are a fraction of those in the U.S. - you can take the founder out of spain…but you can’t… And yet, the “nine-figure” rejection is repeated over and over. If it was such an easy, confident choice, why does it need so much explanation? Can’t wait to read more about CTO insecurity and a need for public validation. What’s Lemkin got to say?
- Sparkyte 9mo agoI kind of want to be a CTO somewhere. So much bureaucratic stuff to become one though. You usually have to be someone's friend or start a company yourself.
- vinnymac 9mo agoSame, I am looking forward to starting my own company in the next year or two, and exploring the CTO role, especially after so many years as a Staff+ operating as an arm of CTOs and learning the ropes.
- elwatto 9mo agoCheck out the earlier posts in the series. They’re probably more relevant for that stage. What I’ve learned over the years is that the CTO role varies a lot depending on the company and personal context. I just tried to share my journey.
- throw-12-16 9mo agoIf you enjoy building its kind of a pain in the ass. I've been the CTO twice in my career, and am in a pure engineering role now and get a lot more satisfaction out of my job.
- calderwoodra 9mo agoBuilding is so much fun, probably my #1 favorite thing to do, but a bad company culture can ruin it. I love being a CTO so I can build and set the culture that keeps it fun.
- Sparkyte 9mo agoI like that a lot.
- Sparkyte 9mo agoI think the problem I see with every place I have been is a lot bad practices. As a CTO I could guide people out of those bad practices. I love engineering too, but every place I have been as of late has been a squeeze on workers and always a lack of focus.
- MagicMoonlight 9mo agoThis guy is going to end up offing himself when the company slowly goes to zero and he could have had 400 million.
- elwatto 9mo agoI wouldn’t have had 400M. But I am fine.
- Geste 9mo agoWorking 8 years to get to more than 100,000,000 $ and saying no to that...Maybe I'm just too poor to understand that. Sure, this is hackernews, so the hustle mindset is stronger here, but the difference you could make in others people lives just with 10 % of that... I mean, you could house, feed or educate people and you chose to...not do that ? To have more ? Is there a endgame you are not sharing with us, a special number that would make it OK to sell ?