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I regret selling my startup

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31–40 of 158 posts

Re: I regret selling my startup

#31
post #17

> What you don't know is that when you have a pile of money, you turn into a dragon. The goal becomes to sit on the pile of money and make sure it doesn't get smaller, and ideally grows on its own. Is this universal? If I had at least a several-million post-tax windfall, I think I'd buy a nice home and maybe a little beach house, put the rest in index funds, and spend my time being healthy, and building particular op…

And then you spend your time checking the stock market, which is exactly what this person is talking about.

No, index funds are boring, there's very little to tinker with, and I'd have so much money it doesn't matter whether the market is down for years at a time.

Re: I regret selling my startup

#32
post #17

> What you don't know is that when you have a pile of money, you turn into a dragon. The goal becomes to sit on the pile of money and make sure it doesn't get smaller, and ideally grows on its own. Is this universal? If I had at least a several-million post-tax windfall, I think I'd buy a nice home and maybe a little beach house, put the rest in index funds, and spend my time being healthy, and building particular op…

I am objectively in a comfortable position and cashflow is still something that occupies my mind.

Re: I regret selling my startup

#33
I don't know why people are so negative in the comments or overthinking what the author wanted to say, when it's pretty clear. Running the company is what made him tick, made him feel alive, and ultimately made him happy. He's cashed out, but sitting around thumb twiddling and maintaining the pile of cash might be an ok life, might make some people happy, but it's not making him happy. There's nothing wrong with any of that. The advice you can get from that is, figure out what it is that makes you enjoy life. If it's feeling secure because you have a pile of cash, then you will do the same as him, but be satisfied with the decision.

Re: I regret selling my startup

#34
post #20
post #17

> What you don't know is that when you have a pile of money, you turn into a dragon. The goal becomes to sit on the pile of money and make sure it doesn't get smaller, and ideally grows on its own. Is this universal? If I had at least a several-million post-tax windfall, I think I'd buy a nice home and maybe a little beach house, put the rest in index funds, and spend my time being healthy, and building particular op…

How many million are we talking about? Because if you cash out for 4 million, 2 million of that is a decent new house in a major city, and not some water front property, but a cookie cutter above average new build. Now you have 2 million left, which, to be honest, if you are just living off of index fund earnings, isn't all that much. Figure 7% growth per year, and you need to set aside 3% of that to grow the fund, y…

Why would anyone buy a house in a major city, especially for retirement. You can get something decent for half the price near nature.

Re: I regret selling my startup

#35
post #20
post #17

> What you don't know is that when you have a pile of money, you turn into a dragon. The goal becomes to sit on the pile of money and make sure it doesn't get smaller, and ideally grows on its own. Is this universal? If I had at least a several-million post-tax windfall, I think I'd buy a nice home and maybe a little beach house, put the rest in index funds, and spend my time being healthy, and building particular op…

How many million are we talking about? Because if you cash out for 4 million, 2 million of that is a decent new house in a major city, and not some water front property, but a cookie cutter above average new build. Now you have 2 million left, which, to be honest, if you are just living off of index fund earnings, isn't all that much. Figure 7% growth per year, and you need to set aside 3% of that to grow the fund, y…

Don't forget the 2 million in taxes.

Re: I regret selling my startup

#36
post #20
post #17

> What you don't know is that when you have a pile of money, you turn into a dragon. The goal becomes to sit on the pile of money and make sure it doesn't get smaller, and ideally grows on its own. Is this universal? If I had at least a several-million post-tax windfall, I think I'd buy a nice home and maybe a little beach house, put the rest in index funds, and spend my time being healthy, and building particular op…

How many million are we talking about? Because if you cash out for 4 million, 2 million of that is a decent new house in a major city, and not some water front property, but a cookie cutter above average new build. Now you have 2 million left, which, to be honest, if you are just living off of index fund earnings, isn't all that much. Figure 7% growth per year, and you need to set aside 3% of that to grow the fund, y…

Why do you need substantially more than 80k to live if your house is paid down in cash? Earning 200k is usually about spending half of your net income on mortgages etc.

Not that 80k is the lifestyle of a king, but it is plenty to get by with if all you are buying is insurance, food and entertainment.

Re: I regret selling my startup

#37
post #20

Earlier quoted context omitted.

How many million are we talking about? Because if you cash out for 4 million, 2 million of that is a decent new house in a major city, and not some water front property, but a cookie cutter above average new build. Now you have 2 million left, which, to be honest, if you are just living off of index fund earnings, isn't all that much. Figure 7% growth per year, and you need to set aside 3% of that to grow the fund, y…

Why would anyone buy a house in a major city, especially for retirement. You can get something decent for half the price near nature.

Bad for environment. No friends around. Pluses and minuses so it’s not obvious.

Re: I regret selling my startup

#38
post #20
post #17

> What you don't know is that when you have a pile of money, you turn into a dragon. The goal becomes to sit on the pile of money and make sure it doesn't get smaller, and ideally grows on its own. Is this universal? If I had at least a several-million post-tax windfall, I think I'd buy a nice home and maybe a little beach house, put the rest in index funds, and spend my time being healthy, and building particular op…

How many million are we talking about? Because if you cash out for 4 million, 2 million of that is a decent new house in a major city, and not some water front property, but a cookie cutter above average new build. Now you have 2 million left, which, to be honest, if you are just living off of index fund earnings, isn't all that much. Figure 7% growth per year, and you need to set aside 3% of that to grow the fund, y…

It's easily into the 'diminishing returns' category in terms of lifestyle.

You can buy a lovely house, support a family, 80k is still a full salary for most people and will certainly support 'standard day-to-day' living, and if you want a little more money for your holiday in the Caribbean you can always take on some cushy exec/advisory work a couple of days a week.

Re: I regret selling my startup

#39
post #2

Sometimes I feel like people who sell their startup for a modest sum (hundreds of thousands to low millions) get put in a box of 'not ambitious enough' and this makes it hard to get new opportunities later as investors are seemingly all looking for unicorn founders who want to become billionaires and then achieve world domination... I feel like any signal that you are a rational human being with well-defined, limited…

You just have to frame it accordingly. If you go to a VC and boast about an exit of hundreds of thousands as if it's be a success to the., that may give a VC pause, because it's be a failure to them. Failure doesn't bother VCs so much as failure to understand that an exit that size isn't what success looks like to them. It's fine to say it was success to you at that point.

But if that is what you want this time too, a VC is wrong for you. If you want a VC investment, you need them to understand you want a big exit this time.

I used to work at a VC, and one of the most frequent reasons we didn't take pitches forward was founders who presented a great pitch that fit what you described.

We rejected them because while it'd be entirely rational for them to want to take an exit that'd make them happy, those goals are fundamentally incompatible with a VC funds risk profile.

Consider that most VC funds invest in high risk startups, and so most of their investments fail. For that reason you need a portion of the survivors to give massive returns. Then it's irrational to cap your potential upside return from the companies that become successful enough to have a shot at providing those returns.

This isn't just greed, but survival: most VCs fail to raise a second fund because they either fail to even return the capital or return too low returns to be worth it. You set yourself up for failure if you put your money in a high risk startups where the founder promises you that your best possible return will be, say, 5x.

And so if you as a founder want "well defined, limited", VC capital isn't for you, and that's fine. There are other investors.

Re: I regret selling my startup

#40
post #20
post #17

> What you don't know is that when you have a pile of money, you turn into a dragon. The goal becomes to sit on the pile of money and make sure it doesn't get smaller, and ideally grows on its own. Is this universal? If I had at least a several-million post-tax windfall, I think I'd buy a nice home and maybe a little beach house, put the rest in index funds, and spend my time being healthy, and building particular op…

How many million are we talking about? Because if you cash out for 4 million, 2 million of that is a decent new house in a major city, and not some water front property, but a cookie cutter above average new build. Now you have 2 million left, which, to be honest, if you are just living off of index fund earnings, isn't all that much. Figure 7% growth per year, and you need to set aside 3% of that to grow the fund, y…

Why do you want to be anywhere near major city if you are retired?
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