61–70 of 152 posts
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.
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…
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 bui…
Earlier 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.
Not that these things are required to “live,” but I certainly am not interested in making these tradeoffs.
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…
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.
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.
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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 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 (BigTec…
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 have if you quit. Maybe they really enjoy the work itself too.
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Isn’t that what I just said? > Even public shareholders will insist on a sale at the right price
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…
Earlier 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 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 (BigTec…
Earlier quoted context omitted.
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.
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.