141–150 of 152 posts
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 ?
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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…
> 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 have if you quit. Maybe they really enjoy the work itself too.
I 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.
> So much bureaucratic stuff to become one though. You usually have to be someone's friend or start a company yourself. How so? I think it's possible. Network, linkedin etc. And in startups it's not that bureaucratic in my experience. I think you can achieve that ;)
I 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.
If 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.
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If 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.
Building 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.
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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.
Companies do not make the world better.
Also, companies are not the only kind of group someone can join (for money or not) with the goal of improving the world.
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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 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…
See perhaps Nick Maggiulli's post "The Ideal Level of Wealth":
> Financial Independence (28.6x Your Annual Spending): $3.5M. Assuming you never wanted to work again, you would need about 28.6x your annual spending to cover your costs indefinitely [$120,000 * 28.6 ~ $3,500,000]. This 28.6 comes from the Kitces research[1] showing that the 3.5% Rule[2] is the safe withdrawal rate for a 40-year time horizon and beyond. This research suggests that if you can make it 40 years while withdrawing 3.5% per year, then you’ll likely make it 50 years (or more).
[…]
> Whether your goal is Coast FIRE or full financial independence, the ideal level of wealth in the U.S. is in the low-to-mid range of Level 4 ($1M-$10M), or $2M-$5M. I know this is a lot of money and many people will never reach it, but that’s why it’s an ideal. It’s something to strive for. It’s enough where you don’t have to worry about money anymore, but not so much that it becomes a burden or warps your identity.
* https://ofdollarsanddata.com/the-ideal-level-of-wealth/
Adjust the $120k annual spend for your own lifestyle and cost of living.
You're not going to fly private, but it will take most of the worry out of life. Morgan Housel, author of the recently release The Art of Spending Money (and previously The Psychology of Money):
> 00:50:16 […] You have the independence to be who you are and wake up every morning and say, I can do whatever I want today. That’s wealth.
* https://ritholtz.com/2025/11/transcript-morgan-housel-spend/
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raising the round is them selling part of the company. enough of the company that they no longer ever have to worry about money again. yeah that removes a lot of potential stress. the company can fail now and it won't ruin him. gives him more freedom to keep building.
“more freedom to keep building” This is the disconnect to me. This phrase has tech industry cult vibes to me. I don’t see “freedom” and “building” as words that mesh together. I see “building” as something I’m obligated to do to pay my bills. I do it because it’s preferable to other forms of labor. As soon as I have the financial means to stop doing it, I’m out.
I’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…
If that group is necessary then it's a damning indictment of the product/engineering culture. The CTO's job should be to fix the broken culture, not try to side-step it.
But HN now is full of people completely removed from any kind of entrepreneurial mindset, people who aren’t “hackers” even in the most generous sense. They will not agree.
Keyboard warriors is probably the best descriptor of HN demo now.