> 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.
I regret selling my startup
31–40 of 158 posts
Re: I regret selling my startup
#32> 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…
Re: I regret selling my startup
#33Re: I regret selling my startup
#34> 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…
Re: I regret selling my startup
#35> 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…
Re: I regret selling my startup
#36> 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…
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
#37Earlier 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.
Re: I regret selling my startup
#38> 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…
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
#39Sometimes 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…
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> 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…