[HN Gopher] My role as a founder-CTO: year 8
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My role as a founder-CTO: year 8
Author : ridruejo
Score : 64 points
Date : 2025-12-26 19:43 UTC (5 days ago)
(HTM) web link (miguelcarranza.es)
(TXT) w3m dump (miguelcarranza.es)
| raw_anon_1111 wrote:
| 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 wrote:
| 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 wrote:
| 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 wrote:
| 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 wrote:
| Isn't that what I just said?
|
| > _Even public shareholders will insist on a sale at the
| right price_
| airstrike wrote:
| 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 wrote:
| How many times have the board refused a sell for the
| right amount of money.
| airstrike wrote:
| That is not "insisting on a sale". Selling for the right
| amount of money is literally the right decision to make!
| Lionga wrote:
| Talk about dumping your trash on retail, YC is a lot smarter
| then I thought
| trollbridge wrote:
| The house always wins.
| fourseventy wrote:
| Unless you are already worth billions if an exit would net you 9
| figures its a no-brainer to sell.
| riazrizvi wrote:
| 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.
| dmacj wrote:
| I'm sure there are many other more meaningful options, none
| of which start with the word "buy".
| trollbridge wrote:
| But then money has nothing at all to do with such options.
| websiteapi wrote:
| you're seriously lacking in imagination if all you can think
| of is that.
| afavour wrote:
| 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!
| ryandrake wrote:
| 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 wrote:
| > _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 wrote:
| You can just say "sociopath", it's faster.
| fragmede wrote:
| 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 wrote:
| Companies do not make the world better.
| riazrizvi wrote:
| 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 wrote:
| 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 wrote:
| 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 wrote:
| 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.
| bcantrill wrote:
| 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 wrote:
| > 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 wrote:
| 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 wrote:
| 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 wrote:
| Correct. The secondary provides the safety net to
| confidently swing for the fences.
| nawgz wrote:
| 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!
| chollida1 wrote:
| > 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.
| louthy wrote:
| > 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 wrote:
| 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 wrote:
| > 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 wrote:
| 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 wrote:
| Nah see you live in a SRO in Chinatown and get all your
| meals at the Catholic mission.
| jwilber wrote:
| 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.
| asah wrote:
| almost: just cut a deal to allow partial liquidity, ideally via
| a vehicle that avoids tax events, e.g. loan
| OGEnthusiast wrote:
| Not taking a nine-figure exit is insane to me.
| __turbobrew__ wrote:
| 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 wrote:
| They do another startup of course.
| lizknope wrote:
| 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.
| weslleyskah wrote:
| 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.
| iancmceachern wrote:
| 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.
| mjr00 wrote:
| > 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 wrote:
| Everybody wants to be the CTO until it's time to do CTO
| things.
| weslleyskah wrote:
| 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 wrote:
| 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 wrote:
| 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 wrote:
| 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 wrote:
| 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!"
| orliesaurus wrote:
| 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_ wrote:
| 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 wrote:
| Oh wow you just described our last CTO to a T.
| elwatto wrote:
| That 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.
| harmonic18374 wrote:
| 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.
| lizknope wrote:
| 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 wrote:
| 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 wrote:
| > 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 wrote:
| 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.
| throw03172019 wrote:
| 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 wrote:
| 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).
| theptip wrote:
| I 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.
| ezekg wrote:
| 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.
| IncreasePosts wrote:
| 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.
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