My role as a founder-CTO: year 8

(miguelcarranza.es)

57 points | by ridruejo 5 days ago

14 comments

  • orliesaurus 1 hour ago
    The 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_ 1 hour ago
      That'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 33 minutes ago
        Oh wow you just described our last CTO to a T.
  • ezekg 21 minutes ago
    Good 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.
  • harmonic18374 1 hour ago
    I 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.
  • throw03172019 55 minutes ago
    I’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 34 minutes ago
      The 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).
  • IncreasePosts 11 minutes ago
    Unless 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.
  • lizknope 1 hour ago
    I 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 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.

    • moomoo11 36 minutes ago
      Startups (businesses in general) are a game and the employees are resources.

      Don’t take it so personally. I did once too.

      If the employees think they know better, there’s nothing stopping them from starting their own businesses and destroying their boss.

      • lizknope 28 minutes ago
        > Don’t take it so personally. I did once too.

        This is easier said than done.

        The founders of many startups are extremely charismatic. They can get you to sacrifice your personal / family life and work long hours by dangling the big pay day in front of you.

        The second startup I worked at let the first 8 employees buy into the company for Class A shares. These in theory were worth more than the Class B shares I was given. This later led to some marital issues when one guy invested $100K into the startup based on the founder taking everyone out to dinner and assuring the wives it was a great idea. Then 3 years later they have turned down 2 possible sales, no exit plan in site, and that $100K would have been useful for the children's tuition who are about to go to college.

        I write these posts are warnings to people who get excited about the appeal of working for a startup.

        So I would really love to hear the author talk about what his employees thought about turning down the deal and how much money they would have got.

      • eptcyka 13 minutes ago
        Yeah, just don’t get emotionally invested in a chance of paying off your mortgage immediately. Don’t get your hopes up about materially bringing down your retirement age.

        It isn’t reasonable to expect the founders to do an employee’s bidding when it comes to selling a company, but it is reasonable for the employees to feel emotionally invested.

  • OGEnthusiast 2 hours ago
    Not taking a nine-figure exit is insane to me.
    • __turbobrew__ 1 hour ago
      I get the vibe of the dog doesn’t know what to do when they catch the car. Catching the car has been their whole life, and once lost there is nothing left.
      • operatingthetan 52 minutes ago
        They do another startup of course.
        • lizknope 36 minutes ago
          Yeah. 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.
  • fourseventy 3 hours ago
    Unless you are already worth billions if an exit would net you 9 figures its a no-brainer to sell.
    • asah 2 hours ago
      almost: just cut a deal to allow partial liquidity, ideally via a vehicle that avoids tax events, e.g. loan
    • riazrizvi 2 hours ago
      Is 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.

      • afavour 2 hours ago
        So 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!

        • bcantrill 2 hours ago
          I know from the outside this seems very simple, but it's more complicated than that. Certainly, if the objective is (merely) security for one's children, that can be secured with much (much) less money (and likely was secured in the secondary that the author makes reference to); having nine figures of wealth is not an unvarnished good, and in particular makes raising grounded, self-reliant kids pretty complicated. To appreciate this dynamic, read Graeme Wood's outstanding 2011 piece in The Atlantic, "The Secret Fears of the Super-Rich"[0].

          [0] https://web.archive.org/web/20190422235813/https://www.theat...

          • afavour 1 hour ago
            > having nine figures of wealth is not an unvarnished good, and in particular makes raising grounded, self-reliant kids pretty complicated

            Sure, but I’m pretty sure if you asked those parents if they’d rather lose all their money to make parenting easier their answer would be a resounding “no”.

            • bcantrill 1 hour ago
              Those aren't the choices. You don't understand how the poster passed on nine figures -- but if the secondary sale netted 7 figures (likely), the choice is in fact between having enough wealth to have total security for one's family versus having so much wealth that the wealth itself creates anxiety.
              • afavour 1 hour ago
                Then have someone manage the money away from you. Put it in a lifetime trust, whatever. The idea that you’d turn down that sum of money because of the anxiety it would cause you is simply not logical.
              • ridruejo 42 minutes ago
                Correct. The secondary provides the safety net to confidently swing for the fences.
        • ryandrake 2 hours ago
          I just don't understand the mentality of the author. 9 figures is generational wealth, potentially perpetually with good multi-generational money management plan. With that kind of money invested, you have beaten the game, and can literally do any side quest you want to do, forever. This is the biggest no-brainer ever. What the fuck are you waiting for?

          Similarly, I don't understand why the CxOs in my current (BigTech) company still work. You're done. You can do anything you want and yet you voluntarily continue to amass more?

          • jonas21 21 minutes ago
            > Similarly, I don't understand why the CxOs in my current (BigTech) company still work. You're done. You can do anything you want

            Has it occurred to you that perhaps what they want is to be the CxO of a big tech company? There’s a lot of power, prestige, and impact on society that you can’t easily get if you quit. And maybe they really enjoy the work itself too.

            • scubbo 9 minutes ago
              You can just say "sociopath", it's faster.
          • fragmede 14 minutes ago
            Because it's genuinely not about the money for them. It's hard to believe, but some people really do want to make the world better in their way, with whatever tools they have that their disposal.
            • scubbo 7 minutes ago
              Companies do not make the world better.
        • riazrizvi 2 hours ago
          Anyone can have security by living very safely within their means, by learning how to be satisfied. What people really mean when they say what you are proposing, is “guarantee a certain future lifestyle”. But the appeal of future lifestyles depends on not obtaining them. Without an ability to be satisfied, acquisition is always disappointing. It’s why a pay raise in a job that doesn’t address your needs, loses its shine after a month or so.
          • afavour 2 hours ago
            As someone who has experienced family adversity in my life (health, disability) I couldn’t disagree with you more.

            Things happen. Expensive things. The security to be able to afford expansive cancer care without worry, to pay for therapy and specialized schooling for your child… these are huge, huge things and they happen to you (or your children, or your children’s children) no matter what you do or don’t do. This isn’t just about being happy to be frugal.

            • riazrizvi 1 hour ago
              Things happen, it’s true. And in the world there are many enterprises that spring up to present solutions as long as you fork over all your cash, and here in the USA, based on the market, that means lots and lots of cash.

              That’s just a perspective on hardship, it’s not the only way. People deal with hardships with many many tools. My favorite tools are dignity, grace, courage, personal strength, and ingenuity. Money is another tool, yes, but it tends to prevent mastery of the others.

              Elsewhere in the comments there was talk about legacy. You can give your kids a bank account, and the examples that you had money to pay off problems. Or you can give them something else through your example. I choose the latter.

              • afavour 1 hour ago
                With respect, those words feel very empty. Face the prospect of, say, chemotherapy you can’t afford or death. See how you feel about dignity and grace then.
      • dmacj 2 hours ago
        I’m sure there are many other more meaningful options, none of which start with the word “buy”.
        • trollbridge 2 hours ago
          But then money has nothing at all to do with such options.
      • louthy 2 hours ago
        > Is it? So you can what? Buy exotic vehicles? Buy extra houses? Buy surgeries? Buy expensive experiences?

        Regain your own time. As a former CTO who has recently exited, recovering my own time again is more valuable to me than the money (although the money means I can retain my own time going forward).

        > His life has meaning, he’s of value to his employees and customers and partners.

        Your work is not you and if you think that way, you're gonna be crushed when you come to retire. Even though I loved what I did for a career, it's better to do what you love for yourself, not "employees and customers and partners". Many people have other interests outside of building tech, but even if building tech is your only thing, exiting is a chance at starting something fresh and on your own terms.

        • riazrizvi 1 hour ago
          You can live in the heart of San Francisco on $2k/mo, including rent. You don’t need to work 10hours a week as a software developer, to support that lifestyle.

          I could fit a solar system in the gap between your two options of a) full time CTO or b) 9 figures to ‘win back your time’.

          Personally I believe you’ve been operating on autopilot, and not designing your life to suit your own needs.

          • louthy 1 hour ago
            > Personally I believe you’ve been operating on autopilot, and not designing your life to suit your own needs.

            You have no idea about me at all, so please don't insult me by thinking that you do.

          • jondwillis 28 minutes ago
            Bro, what? $2k? I just double checked and everything available for less than $2k is awful if you care about, IDK, having a family, a pet, a kitchen, outdoor space, green space, not having to share everything, including peace and quiet, with a revolving cast of characters.

            Not that these things are required to “live,” but I certainly am not interested in making these tradeoffs.

            • paradox460 13 minutes ago
              Nah see you live in a SRO in Chinatown and get all your meals at the Catholic mission.
      • chollida1 2 hours ago
        > Is it? So you can what? Buy exotic vehicles? Buy extra houses? Buy surgeries? Buy expensive experiences?

        Buy freedom to chose what to do with your life. I've never sold a company and netted 9 figures but i have been lucky enough to work for a hedge fund and make enough that I and my family can do what ever we want from the age of 30 onwards.

        That is an incredible amount of freedom and one that I wish most people would have.

        You seem to think only in materialistic ways.

        But having enough money to not have to work again allows you to be a better and more available parent. To be able to provide your kids and nieces and nephews with schooling to put them apart from other kids.

        Its not always about owning another home, Just knowing that my kids are set for life before they start their own lives in case something happens to me was enough for me.

        Lots of us think of others before ourselves.

      • websiteapi 2 hours ago
        you're seriously lacking in imagination if all you can think of is that.
      • jwilber 2 hours ago
        You must be fortunate to have a lived experience where the answer isn’t immediately (and obviously) financial security.

        Also: plenty of meaning outside of running a SaaS. Hell, undergraduate research assistants probably contribute more to societal at large.

      • nawgz 2 hours ago
        You're right, financial freedom is completely unfulfilling, instead it's really meaningful and impactful to be involved in a tech economy whose primary value has been in undermining democracy and social systems!
  • raw_anon_1111 3 hours ago
    Saying 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-...

    • airstrike 3 hours ago
      The 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 2 hours ago
        My “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 1 hour ago
          Going 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 55 minutes ago
            Isn’t that what I just said?

            > Even public shareholders will insist on a sale at the right price

            • airstrike 46 minutes ago
              Yes, 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 21 minutes ago
                How many times have the board refused a sell for the right amount of money.
    • Lionga 2 hours ago
      Talk about dumping your trash on retail, YC is a lot smarter then I thought
  • cityzen 2 hours ago
    [flagged]
  • weslleyskah 1 hour ago
    Why 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.

    • mjr00 1 hour 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-astronome...

      • nradov 1 hour ago
        Everybody wants to be the CTO until it's time to do CTO things.
      • weslleyskah 1 hour ago
        Perhaps I'm just a naive young imbecile.

        Even with such a golden ticket ride to the heavens? You could do anything, focus on your family and build your little castle or depersonalize even, change countries, change your identity, make new connections, live a completely different life...

        • mjr00 1 hour ago
          I don't think you're an imbecile. People just like living differently. "Work to live" vs "live to work" and all that.

          Some people like working a stable but boring 9-5. Some people like working a challenging job, even for longer hours and lower pay. Some people like building things; some people like coordinating teams and managing people; some people like maximizing financial returns and seeing numbers go up.

          As to why this specific person didn't take a 9-figure cashout (assuming it's true); I would imagine it's at least partly because this person thinks it could be worth more in the future. Crazy as it sounds, he may not be wrong. Remember that Larry and Sergey tried to sell their "Google" research project to Yahoo for a life-changing amount of $1 million (in 1998, they could have each bought a house!). Or a million-dollar sale that did happen, Roy Raymond selling Victoria's Secret for a million in 1982. (Multiple houses!)

          Obviously 9 figures is a lot different than 7, especially in 2025. But he's also the CTO and has access to financials and company strategy. Who's to say that the $100,000,000 he would get won't be $250,000,000 in an acquisition next year? Even "just" a 25% bump in a year would be an extra $25 million, which in itself is life-changing. It's obviously a risk, but saying "this guy is crazy and/or an idiot for not taking a 9 figure cashout" isn't fair unless you can peer into the future.

          • weslleyskah 58 minutes ago
            I can definitely understand you. Interesting you mentioned Victoria's Secret, another area that I am highly interested and could make money is fashion. I could mention the cases of models (Tatjana Patitz, Gisele Bundchen) climbing this money ladder of luxury, but too off-topic for this site.

            Different adventures, different life obsessions...

      • pydry 1 hour ago
        Ive worked with a lot of people who sent emails at 2am and in each case it was not necessary but it was performative.
        • operatingthetan 47 minutes ago
          Night owls who check in before they go to bed probably. I've done it, and I wasn't like "oh I will get some points for this!"
    • iancmceachern 1 hour ago
      Totally.

      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.

  • farceSpherule 3 hours ago
    [flagged]
    • themanmaran 3 hours ago
      Did you just generate a GPT rant and find-replace every — with --?
      • thaw13579 2 hours ago
        Those were most likely from a multi-line list that was converted to a single line when the comment was processed on submission.
      • farceSpherule 3 hours ago
        Why does everyone assume that everything posted is based on GPT? There are people in this world who know how to write.
        • lovich 2 hours ago
          Because 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 1 hour ago
          Because only a complete sociopath (or someone replacing AI's –) would have this much -- in their copy
  • farceSpherule 3 hours ago
    [flagged]