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I regret selling my startup

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Re: I regret selling my startup

#11

Post by satvikpendem »

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?

Yes, sorry, hoard, not horde.

Re: I regret selling my startup

#12

Post by chris-orgmenta »

chris-orgmenta wrote: post #4

This seems a little 'grass is greener' to me. Not sure if this is glib, but: You can build the business again from scratch (ok, maybe you have a non compete for a while...) But you can't magic the $ you just got, out of thin air. So he's been paid for the hard work he has done, and now if he so chooses he can do the same again, or different. So seems like Boris is standing on the greener grass right now, to me at lea…

Or to put it another way:

It looks like Boris created, nurtured and sold something (to safe, loving hands), with nice closure. That to me sounds like something to be very proud of, and something that you can cherish and reflect back on with positive (not bitter-sweet) emotion, and keep in contact with the friends made along the way.

And the freedom and opportunities ahead are also something that might be harnessable? That power... You can generate a 'bubbly school-holidays' emotion from something like that. Apprehension + Excitement + Unknowing + Freedom?... I don't know, 'bubbly school holiday feeling' is what I always come back to in order to describe it.

Re: I regret selling my startup

#13

Post by jongjong »

satvikpendem wrote: post #9
jongjong wrote: 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…

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.

Re: I regret selling my startup

#14

Post by Subdivide8452 »

gnicholas wrote: post #3

When I see or hear advice, I try to understand what the person's context was. Here, I feel like I don't know enough about the founder's situation to know whether any of this would be relevant to me. For example, does he have a family? How old is he? Roughly how much money did he sell for? How much profit was the business generating beforehand, and what was its trajectory? Without knowing things like this, I can't rea…

He gives reasons why it didn’t work for him. He gives 10 pillars of his personality, 4 of these pillars were standing due to his company ownership. You don’t need to have the exact same pillars, but you need to project it upon your own life and see how selling the company would effect your personality. Then consider it for yourself if it’s worth it.

Re: I regret selling my startup

#15

Post by yieldcrv »

farmdve wrote: post #5

I 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.

and I never understood people that want a forever company. Never get married to a position.

The shares I purchase in my brokerage account and the shares I make up on a sheet of paper are treated the same to me.

Why make your identity around running a company. Sell the company and live life. My quickest creation and flip was 3 months and went to party for the next 12. Why not do that

Re: I regret selling my startup

#16

Post by gnicholas »

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 bar for success is much lower. VCs want a big multiple, so they want you to take risks. If the risks pay off, everyone wins big. But when you're bootstrapping, it can be a 'win' to make a couple hundred grand a year, working part-time. Most people consider that to be a pretty good gig.

Re: I regret selling my startup

#17

Post by neilv »

> 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 open source software and hardware.

(Building things without résumé keywords being a consideration; it's almost unimaginable, now.)

Re: I regret selling my startup

#19

Post by hiAndrewQuinn »

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.)

Re: I regret selling my startup

#20

Post by com2kid »

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, you are stuck with 80k a year left to live off of, in a major city, and this is all ignoring taxes.

10 million in the bank and you can start to "be secure".

Though it all depends on what QoL you want in retirement. I know a guy who retired early and happily spends 70% of his time playing video games. He avoids bougie foods and goes on a couple of nice trips every year.

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