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I regret selling my startup

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Re: I regret selling my startup

#21

Post by redcobra762 »

Munksgaard wrote: post #8
satvikpendem wrote: post #6

All good points here. For those reading just the title, the article asks to critically examine what values you hold and whether selling is compatible with those values. For me, I see selling as just another step to growing the hoard, as you state in the article, but I don't think it becomes draconic in practice. The key in my opinion and experience is making and selling micro projects, not banking on any one taking o…

Perhaps I am unfamiliar with this usage of the word horde, but is it possible that you mean hoard?

Oh come on, you knew he used the wrong word… This isn’t any better, you know. Some people would see this as patronizing.

Re: I regret selling my startup

#22

Post by j7ake »

jongjong wrote: post #13
satvikpendem wrote: post #9

Earlier quoted context omitted.

Why do they have to take VC? The founder in this article bootstrapped their business and sold, they can always do that again.

The odds of succeeding with a bootstrapped software startup are tiny. Though I don't know maybe it's different in the US.

The odds of succeeding with VC is even tinier. It’s just that the media hype up the lottery winners so VC continues to have companies wanting their money.

Re: I regret selling my startup

#23

Post by gnicholas »

neilv wrote: 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…

It massively depends on the person and stage of life. If you have kids whom you are planning to send to college, figure that's roughly $350k per kid. If your nest egg can take that hit and still spin off enough cash for you to comfortably live off of, then perhaps your plan would work. And if you don't have kids (or they're past college), then that definitely makes sense.

Re: I regret selling my startup

#24

Post by jimbob45 »

gnicholas wrote: post #23
neilv wrote: 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…

It massively depends on the person and stage of life. If you have kids whom you are planning to send to college, figure that's roughly $350k per kid. If your nest egg can take that hit and still spin off enough cash for you to comfortably live off of, then perhaps your plan would work. And if you don't have kids (or they're past college), then that definitely makes sense.

$87.5K per year per kid? Has college become that expensive since I went?

Re: I regret selling my startup

#25

Post by gnicholas »

hiAndrewQuinn wrote: post #19
neilv wrote: 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'd put it all in index funds, but I'm still fairly young and my dream has always been to be able to max out my kids' Roth IRAs from birth somehow. (I'm still working on the "how do you get a baby to have taxable income" angle.)

The normal path is to establish a trust fund, into which you and your spouse contribute the maximum annual exclusion amount. By the time they're grown up, they've got a tidy sum. And when they get married, you and your spouse can give the maximum gift amount to each them and their spouse every year.

Re: I regret selling my startup

#26

Post by locallost »

neilv wrote: 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.

Re: I regret selling my startup

#27

Post by neilv »

com2kid wrote: post #20
neilv wrote: 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…

> at least a several-million post-tax windfall,

On the index funds, I'd probably outspend returns.

Re: I regret selling my startup

#28

Post by bhakunikaran »

Out of curiosity, how do you now view the concept of success in entrepreneurship, given your experience? Do you think there's a way for founders to prepare themselves emotionally and mentally for the possibility of selling their business?

Re: I regret selling my startup

#29

Post by gnicholas »

jimbob45 wrote: post #24
gnicholas wrote: post #23

Earlier quoted context omitted.

It massively depends on the person and stage of life. If you have kids whom you are planning to send to college, figure that's roughly $350k per kid. If your nest egg can take that hit and still spin off enough cash for you to comfortably live off of, then perhaps your plan would work. And if you don't have kids (or they're past college), then that definitely makes sense.

$87.5K per year per kid? Has college become that expensive since I went?

Sadly, yes. The school I went to was about $35k/yr back in the early aughts, and is now over $81k. It is not located in an expensive area, and this includes a meal plan. If your kid is in Boston or NYC, figure they're going to spend thousands more on food and going out. Not everyone does, but if daddy's a retired multimillionaire, they'll probably want to...sigh.

Re: I regret selling my startup

#30

Post by jojobas »

neilv wrote: 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…

That's what I think I'd be doing.

Maybe we're both wrong and the more we get the more we want.

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