It always gets worse before it gets better.
I regret selling my startup
41–50 of 158 posts
Re: I regret selling my startup
#42Earlier quoted context omitted.
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.
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.
Re: I regret selling my startup
#43Earlier 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.
But they already did it once, which massively raises the odds the next time around, which might not be so for VC, whose odds anyway is still tinier than bootstrapping, because you can just make enough to live off of and call that successful.
Re: I regret selling my startup
#44I never understood selling of the company unless you've been working in it for 20 years. Like isn't the idea to be your own boss? And why sell it, if you don't have the next idea for the next business up and running? I don't know any tech startup entrepreneurs, but I do have relatives who started their own businesses but always had backup plans and diversity.
Depends on the business. I've co-founded businesses we knew going in was just for the hope of an exit as big as possible as fast as possible, and that we knew we'd walk away from whether we failed or succeeded, and I've founded businesses I'd have liked to have kept if they got to a level I was happy with but sold or left because it became clear the potential wasn't there, or circumstances changed.
It's not at all a given that your goal was/is to be your own boss. Or at least not necessarily in any given company.
Re: I regret selling my startup
#45Earlier 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 do you want to be anywhere near major city if you are retired?
Maybe all your friends are there. I don't know why I'd want to be in the middle of nowhere with no socialization especially with no external force like a job motivating that I do so, as in retirement.
Re: I regret selling my startup
#46Earlier quoted context omitted.
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.
I appreciate the correction, helps me learn something new.
Re: I regret selling my startup
#47Now they are free to do a business with organic growth or anything else they like, that doesn't have the aim of being sold at the end.
Re: I regret selling my startup
#48Earlier 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.
Just listen to a couple hours or Warren buffet and Charlie Munger, it'll cure that and then you can focus on your golf game.
Re: I regret selling my startup
#49Earlier quoted context omitted.
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.
The irony...
I did this. I cashed out in my 20s, bought a $2m home in the middle of nowhere (that goes a long way out here), and live out my days in my workshop surrounded by singing birds, bees, wildlife, trees and gardens, with views across lakes and plains.
And some cosmopolitan wants to tell me, as they cram another million people into gridlocked high-rises in their smoggy grey hellhole, that we in the country are bad for the environment? Or that the soulless crowds you have to navigate through every morning and evening are friendlier than the neighbours and strangers who wave and chat everywhere I go?
If you're able, get out of the cities. Especially if you have children. You have no idea what you're missing.
Re: I regret selling my startup
#50Earlier 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 do you want to be anywhere near major city if you are retired?
Healthcare, family, culture, food, international airports