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I regret selling my startup

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101–110 of 158 posts

Re: I regret selling my startup

#101

Why does ever seller of a business become an angel investor? And the follow up, I wonder how business seller angels perform compared to your normal angel fund...

I'd guess because it is a way to be involved in start ups without the intense work of being a founder?

Re: I regret selling my startup

#103

Earlier quoted context omitted.

I did, doesn't mean people don't make mistakes or sometimes use words incorrectly.

So what did you learn then?

I learned that I used it incorrectly in that instance. Why are you so insistent on a simple grammatical mistake? I don't understand why you care whether someone learned or didn't learn.

Re: I regret selling my startup

#104

Why does ever seller of a business become an angel investor? And the follow up, I wonder how business seller angels perform compared to your normal angel fund...

I'd guess because it is a way to be involved in start ups without the intense work of being a founder?

Ah I guess that is true. Keep some of the fun parts without the bad parts. If you are just throwing out 10-100k angel rounds, depending on how much you sold for it's pretty small.

Wonder if you could do the same thing just offering to be an advisor or on the board for startups without the check?

Re: I regret selling my startup

#105
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…

[deleted]

Re: I regret selling my startup

#106
post #94

Earlier quoted context omitted.

Maybe it's one of those things that is easy to explain but hard to understand if you don't have experiential context. Some people find activities and experiences fulfilling in a non fungible way. That makes them feel alive, more themselves, and more fulfilled than without them. Loving ones job is a powerful source of happiness that's hard to replace, once you've had a taste of it. I can make you smile when you get up…

> Maybe it's one of those things that is easy to explain but hard to understand if you don't have experiential context. Maybe use the word "Ikigai"? It seems to carries the concept very well across cultures. It's doing what you love, what you are good at, what the world needs, and what you can get paid for! https://en.wikipedia.org/wiki/Ikigai A friend told me a life without Ikigai is a life spent waiting for death.…

> because it can just be more opportunities for change/growth/discovery

That was basically going to be my comment, I'm fulfilled by beating the game. Resource acquisition is a Massive Multiplayer game.

I'm fulfilled by the industries I enter to make revenue or sell a company, I'm never doing something grueling and dead end, I feel good about successfully avoiding being in that kind of situation.

I'm fulfilled by enjoying the spoils of success. I'm fulfilled by extending the length of time I can enjoy them. I'm fulfilled by parlaying that into passive income or a nice portfolio, or investing in other high growth assets at my risk or peril.

But making a forever company? Its never appealed to me, and when I look at other's it doesn't make sense to me. There's always something unobjective about it, burdening their family with a reputation to always defend. I dated a woman that grew up on a decently industrial farm, she was interested in Fortune 500 corporate work and excelled at that but having to prove she wasn't an unsophisticated farmer was a common point for her. I asked the father why farming, he said "feeding the people is so fulfilling", it wasn't until I found the grandfather that I got an objective answer. The grandfather was the one with the portfolio of companies and he set one child into the farming one, and another child into the entertainment ones - golf courses specifically. The grandfather was the person I could relate to. Just an example of things I see a lot. Don't get married to a position, don't burden your family with your obsessions.

I am my own lifestyle company.

Re: I regret selling my startup

#107
post #31

Earlier quoted context omitted.

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.

It’s true but it’s still depressing if the market has a bad week and you know that you are down by 6 figures. It bounces back in the end but it’s a source of background stress.

Some people don't think about this, and aren't bothered by it. I'm one of them. If I had a million dollars in index funds, I would check on things maybe once a year.

On the other hand, it's exactly this attitude that's resulted in my spouse handling all of our finances. Maybe she wakes up at 4am fretting about the stock market; if so, she doesn't tell me about it.

Re: I regret selling my startup

#108
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 did this / am doing this. It is indeed nice. However, depending on where you want to live and of course how you want to live, “several million post-tax” after buying 2 homes doesn’t necessarily cut it. I think this is what leads to the “dragon” mindset described. Maths: - 7MM post tax (let’s say) - Less 2MM for 2 houses (rates being what they are you’ll likely not mortgage both properties, or even one; if you do yo…

Can get 8% plus easy in yield on a diversified set of relatively safe REITs and corporate bonds nowadays.

Absolutely would not recommend putting funds in large cap indices if you're planning to retire off portfolio cashflow.

You get close to 4.5% cashflow (interest plus imputed income) on 20y treasury bonds alone, for example.

Why take pricing risk to your income when you can get it directly in dividends/distributions that are very secure?

Re: I regret selling my startup

#109
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 did this / am doing this. It is indeed nice. However, depending on where you want to live and of course how you want to live, “several million post-tax” after buying 2 homes doesn’t necessarily cut it. I think this is what leads to the “dragon” mindset described. Maths: - 7MM post tax (let’s say) - Less 2MM for 2 houses (rates being what they are you’ll likely not mortgage both properties, or even one; if you do yo…

Living mortgage free, 170k post-tax is pretty lavish annual spending almost anywhere in the world.

Re: I regret selling my startup

#110

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…

Maybe this needs an update to the post. I am happy. My life is amazing in terms of health, fitness, diet, family life, where I live, travel etc. But I am also without a driving force. It gives me a new appreciation for the athletes or musician who un-retires.

I don't think it does need an update, it came across quite clearly in the article that you were pretty happy with life in general but felt that selling the company took away a sense of purpose/identity that you hadn't expected.

Was a really interesting read and gave me a lot to think about as a (hopefully) future founder!

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