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
My role as a founder-CTO: year 8
31–40 of 152 posts
Re: My role as a founder-CTO: year 8
#32Earlier quoted context omitted.
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 m…
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…
> 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”.
Re: My role as a founder-CTO: year 8
#33Earlier quoted context omitted.
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 meani…
> 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 t…
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.
Re: My role as a founder-CTO: year 8
#34Why 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. Hon…
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Re: My role as a founder-CTO: year 8
#35Not taking a nine-figure exit is insane to me.
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Re: My role as a founder-CTO: year 8
#36Earlier quoted context omitted.
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 sh…
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 i…
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.
Re: My role as a founder-CTO: year 8
#37The 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…
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.
Re: My role as a founder-CTO: year 8
#38Why 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. Hon…
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.
Re: My role as a founder-CTO: year 8
#39Earlier quoted context omitted.
> 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 t…
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.
> 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.
Re: My role as a founder-CTO: year 8
#40Why 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. Hon…
> 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...