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I regret selling my startup

nothingeasyaboutthis.com

81–90 of 158 posts

Re: I regret selling my startup

#81
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 your monthly burn is so much higher it comes out in the wash). - 4% because you read about FIRE - 200k pre-tax (you tax burden should be low, maybe 15%) - 170k post tax for your family. If you live anywhere higher than average COL you might find yourself feeling a bit like a large reptile at times.

Re: I regret selling my startup

#82
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…

> Is this universal?

You tell me, we live in the same world. Humans universally have serious issues with greed, selfishness, and all manner of other ugly things. We are not basically good, we are basically evil.

A twisted man has a sort of twisted Midas touch, so that even if he has natural abilities in managing wealth things become tainted. He may even realize he's a dragon (speaking as a fellow twisted man). C.S. Lewis had some things to say about people who suddenly realize they are dragons in "The Voyage of the Dawn Treader."

The problem isn't wealth, it is our hearts.

Re: I regret selling my startup

#83
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…

I couldn’t agree more.

The saying ‘concrete jungle’ is so far off the mark. There’s no similarity between a city and a real jungle.

Once you’ve been out for a while, cities are clearly concrete zoos.

Re: I regret selling my startup

#84

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…

Eh, I grew up in one of the most rural parts of the UK. It's overrated. The scenary is nice and it's a safe, quiet place to grow up, but if you had ambitions beyond local teacher it's a maddening place. And it's the filtering effect - the kind of people I get along with don't move to random farming villages in the middle of nowhere, so while I had friends, I never had that uber-close "I get you" thing. Since moving to London, it's happened a lot more.

Re: I regret selling my startup

#85

Earlier quoted context omitted.

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…

Funny thing is I live so much closer to friends in a city than I did in my rural upbringing. I can walk to at least half a dozen friend's places inside 10 minutes right now - in my rural hometown, it was a 20 minute walk to the nearest, and anyone else needed a car.

Re: I regret selling my startup

#86
post #55

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…

Some people, like me, prefer the stimulation of cities to the quietness of the countryside. And city dwellers have a lower environmental footprint than rural people (in the West), because of efficiency in transport, recycling/treatment and land use. It's not a mystery, you can find dozens of sources in a second work your favourite search engine.

[dead]

Re: I regret selling my startup

#87

Earlier quoted context omitted.

Why do you want to be anywhere near major city if you are retired?

Healthcare, family, culture, food, international airports

Young people. I live in a semi-rural area in the UK and it's starting to feel like the last stop off point before the crematorium. The consensus view seems to be to move further out as you age but I'm starting to wonder if the opposite would be better.

Re: I regret selling my startup

#88

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…

It is also hard, and can take a mental and physical toll on you.

Re: I regret selling my startup

#89
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…

> If anyone proposed housing a million migrants here,

I never said migrants, I was talking about what happens if a million city dwellers take your advice and decide to move to the country. It'd be an environmental nightmare!

> compared to sitting in bumper-to-bumper traffic to and from work

Again, I rarely have bumper to bumper traffic, when I do, it is for a handful of minutes.

> You'd be surprised how little you miss the overwhelming number of choices and conveniences you have in the city.

In a given week, all less than a 15 minute drive:

Gym class with my son Swimming classes with my son BJJ classes Weekly library visit Weekly shopping trips with my son

Weekend choices are the Zoo (15 minutes away) Aquarium (an entire 20 minutes away!), or parks (plenty to choose from in walking distance). Heck there is now an indoor ice skating rink (less than 20 minutes away).

All of these are things I do every week. (Except for ice skating, I'd fall on my arse).

Of course there is plenty more. Just because I'm in a city doesn't mean I'm stuck in the city, in under a 2 hours drive I can reach the following:

1. Multiple ski resorts 2. An almost uncountable number of incredible camp sites 3. Countless small ocean side towns 4. Multiple amazing mountain day hikes

A bit further away there is an actual honest to goodness rain forest (3.5hrs) or I can go play on an active volcano (3.5hrs)

Lake Washington is just a handful miles away, everything from renting a boat for the day to seasonal hydroplane races to lake side picnics.

If I'm bored, I can go down to a local comedy club, hit up a poetry reading, multiple books clubs, or just go see a live concert. Seattle of course also has a huge sports scene, not my style, but between Football, Soccer, Baseball, and Ice Hockey, people who do like sports are pretty well entertained.

I was not expecting any of this when I moved to the city. I did not realize how pleasant live is here. I'm not living in Manhattan or London. The city isn't smog covered. If you ever fly into Seattle you can look out the airplane window and see how green everything is.

> Cities are utterly bereft of soul, spirit, meaning, purpose, culture, etc.

I mean, grunge, punk, and even multiple sub-genres of EDM, all sprung from cities. If you want to be incredibly elitist, plenty of classical music (and art, and paintings!) came from urban areas as well.

Saying cities don't have purpose or spirit is silly. I've travelled to multiple world cities, and each one has a completely different spirit. You may not like the spirit of a given city, and that is OK, but saying they don't have spirit isn't being honest. Given the site we are on, we can likely agree that the spirit of the Bay Area is technology at any cost, hustling and selling your ideas and trying to go big or die trying. Someone can say that spirit sucks, but no one can deny that it exists!

> 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.

So ignore the civic stuff? The problem with public art pieces is that they have to not offend anyone, so after every interest group in the world has filed their objections, the artwork often ends up being super boring.

Meanwhile, plenty of cities have entire blocks set aside for street artists to make incredible murals. Local artists have open workshop days where you can come in and talk to them about what they are making. Guerrilla art exists. One time some friends and I stumbled across a tiny gallery hidden in an unlabeled building that was open at 10pm! Just, walking around, boom, art gallery.

> 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.

If you are going to the downtown part of a city, yeah, it is stressful and it sucks. Likewise, if I go into a rural area and head to a rendering plant, or a tire factory, that also sucks, but it wouldn't be fair for me to highlight the worst part of rural living with the best part of rural living!

Meanwhile one of my most memorable experiences in London was just walking around and just randomly stumbling onto Columbia Flower Road ( https://en.wikipedia.org/wiki/Columbia_Road_Flower_Market).

Or the time I was staying in a NYC AirBnB and I woke up one morning to a food festival outside my door.

The amazing and talented buskers in Mexico City.

The great street food that is available almost everyplace except in American cities (ugh).

And to be with all of this, I'm not saying rural living has no advantages. As a child I used to spend every summer down with family by the Russian River in California, and even to this day I have friends in rural places that I go to visit, dropping in for a day or sometimes a week.

I totally understand what the nice parts of that are, but I didn't understand the nice parts of city living until I moved from suburbia into a city.

Re: I regret selling my startup

#90
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

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 in the morning excited to start the day, and then you have the pleasure of doing it as long as you can. It can be a way to live life, not an alternative to it

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