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I regret selling my startup

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Re: I regret selling my startup

#71

Post by bberenberg »

locallost wrote: post #33

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.

Re: I regret selling my startup

#72

Post by Gyrantula2 »

com2kid wrote: post #54
Gyrantula2 wrote: post #49

Earlier quoted context omitted.

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 ar…

> 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? Uh yes, if you shove a million people out in the middle of nowhere, you have to cut down all the nature, remove the wetlands, pave a bunch of really wide roads, and now all of a sudden your paradise is a bland soulless sub-urban hellscape that is no longer environmentally…

If anyone proposed housing a million migrants here, we'd sooner build gallows for the genius with that idea than to break ground on high density housing. It's a wildly controversial idea, but you could just stop letting so many people into your city...

Cruising through the countryside at top speed to a larger town with the windows down and the radio up for an hour on the rare occasion I need something urgently is a pleasure compared to sitting in bumper-to-bumper traffic to and from work, or crammed into a train with everything around me being suspiciously sticky and slightly smelly twice per day. We have what we need. You'd be surprised how little you miss the overwhelming number of choices and conveniences you have in the city. Anyway, I'm not that remote - I do most of my shopping online so everything is delivered to the door (albeit a day or two later than for you).

It's the look in their eye, or their nature and priorities implicit in their choices. Cities are utterly bereft of soul, spirit, meaning, purpose, culture, etc. Whatever they do have in these respects seems to me like a cynical parody of their true form. They will convene a meeting for consultants to identify an urban area in need of beautification, commission an agendered hippie to plonk some monstrous perverted multicolour sculpture there for millions of dollars and boast about it like this isn't an insult to everything pure, and decent, and good in this world.

The baked goods trading sounds really wholesome, I'm genuinely glad you have that.

Still, there's a good reason city-folk come out here for rest and relaxation while I dread going into the big smoke and get the hell out as soon as I'm done doing what I need to do.

Re: I regret selling my startup

#73

Post by cornel_io »

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…

Re: building again...

For some people, they don't have the same drive once they've done it once and were successful. I've got friends who were incredible operators for their first N companies, because they were hungry, but then after a big cashout they started to suck at their N+1st attempts. They make mistakes like being unwilling to start small, feeling like they should be Respected(TM) and that getting in the way of their relationships with potential partners, not being frugal with runway, being too precious about repeating exactly what worked before, etc. I've also seen some completely unable to ever fall in love with an idea the way they did pre-exit, and just bounce around doing projects forever without ever committing to anything.

On the other hand some people get better, much better, on their later tries. So YMMV, probably depending on your personality.

Re: I regret selling my startup

#74

Post by outcoldman »

Gyrantula2 wrote: post #49
renewiltord wrote: post #37

Earlier quoted context omitted.

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 ar…

Just want to say, appreciate the discussion about the environment. Never actually thought about what is better towns (rural areas) vs cities.

And I am sure the answer is not as simple as it sounds. But my guess, there are too many people in the world, and living in the house in that sense is a privilege.

Re: I regret selling my startup

#75

Post by outcoldman »

I am kind of, have the same flow of thoughts. I have never worked on the project for more than 4 years. Now I have a product that I have built and live on, for the last 7 years. I don't have that much passion about this product anymore. But at the same time it allows me right now to work only 4 hours a week on average, and spend 2 months a year to build new versions of the product. I am making good Google Principal Software Total compensation.

Selling a company means I can probably get 4-6x of my annual income. But I am afraid to become that dragon on the pile of money. Draining money will be terrifying for me. And I am not good with managing money.

At the same time, I am afraid that company can slowly disappear, customers choose alternatives. And maybe 4-6 years that is how much I can get from it. But at the same time I will have opportunity to fix things, adjust my life based on the income.

Re: I regret selling my startup

#76

Post by horns4lyfe »

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…

If it takes 2 million to get you a “decent” house, you’re already playing the status games that will have you chasing money forever.

Re: I regret selling my startup

#77

Post by earthling8118 »

vidarh wrote: post #39
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…

You just have to frame it accordingly. If you go to a VC and boast about an exit of hundreds of thousands as if it's be a success to the., that may give a VC pause, because it's be a failure to them. Failure doesn't bother VCs so much as failure to understand that an exit that size isn't what success looks like to them. It's fine to say it was success to you at that point. But if that is what you want this time too,…

So they choose to invest in high risk scenarios and as a result it becomes a matter of survival, and you're claiming that greed isn't involved? Is that not the reason to invest in high risk as opposed to low risk?

Re: I regret selling my startup

#78

Post by DiggyJohnson »

Gyrantula2 wrote: post #72
com2kid wrote: post #54

Earlier quoted context omitted.

> 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? Uh yes, if you shove a million people out in the middle of nowhere, you have to cut down all the nature, remove the wetlands, pave a bunch of really wide roads, and now all of a sudden your paradise is a bland soulless sub-urban hellscape that is no longer environmentally…

If anyone proposed housing a million migrants here, we'd sooner build gallows for the genius with that idea than to break ground on high density housing. It's a wildly controversial idea, but you could just stop letting so many people into your city... Cruising through the countryside at top speed to a larger town with the windows down and the radio up for an hour on the rare occasion I need something urgently is a p…

What's interesting to me in so many of these discussions is how the core issue turns out to be the commute, more than any other factor. Here we see this happen in a conversation about pros and cons of city living. We also see it in WFH discussions: many staunch WFH proponents focus on doing away with their miserable commute.

All of this is kinda foreign to me, because I've never had a "bad" commute. Right now I'm 14 minutes from work one-way, no traffic in my direction.

This is rambly, and I think you're both making a solid points about something that is fundamentally subjective. So I'll just say that I feel sorry for all of you guys that are hating life during your commute.

Re: I regret selling my startup

#79

Post by toomuchtodo »

com2kid wrote: post #52
olivermuty wrote: post #36

Earlier quoted context omitted.

Why do you need substantially more than 80k to live if your house is paid down in cash? Earning 200k is usually about spending half of your net income on mortgages etc. 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.

We are talking early retirement here, so presumably young enough to still have a family. Daycare in my area is ~2400 a month (not the super fancy daycares either, they are over 3k a month). If you want to fully fund a 529 college fund, that is 30k a year for 15 years[1]. So right off the bat we have 50k a year in expenses for having a single kid, not counting feeding them and other activities. If you choose public sc…

This isn’t a wealth problem, this is an expectations problem.
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