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I regret selling my startup

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51–60 of 158 posts

Re: I regret selling my startup

#51

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…

Totally, you do you.

I love the movie birdman, on the topic.

Re: I regret selling my startup

#52
post #20

Earlier 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 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 school, then that number drops after the kid is 5, but if you want a private school that is 15k-35k a year.

tl;dr 2 million in the bank isn't enough to raise a single kid w/o supplementary income.

If you retire early you'll have to pay for your own health insurance, a Platinum plan is ~700 a month, not counting any other expenses that you have to pay. 7k a year right there.

Cars cost $ to purchase and maintain. If you retire in Manhattan you can get away with not having a car, maybe Boston if you are lucky. Most other US cities require a car and that is going to average around 10k a year, assuming you have a mid-range car and that somehow you don't need to buy a new car during your retirement.

If all you do is shop at Costco (perfectly doable!) you'll be able to keep food costs down, although you'll have to spend the time and money driving to a Costco.

Outside of Costco, I'm paying around $200-$300 a week for groceries for 3 people. I found this lovely quote

> As far as specific food items go, a dozen eggs and a pound of apples in Seattle costs $3.54 and $2.71, respectively.

Which, while written in August of 2023, is already horribly out of date. (For whatever reason eggs got super expensive recently...)

Figure 1k a month for food, if you never go out to eat, ever. Also no drinking alcohol of any type, that'll blow the budget.

So we are up to 29K a year in expenses so far, just eating and driving around.

No gym membership, no sports or hobbies, no vacations. No streaming services, no cable TV, no internet, no utilities, etc.

Figure another 1k a month for those things and you are now spending 41k a year.

Assuming no kids and a paid off house, 80k is livable, but it'll be somewhat bare bones for a person who "retired with millions in the bank".

Which is kind of messed up, when I graduated college 80k was a really good lifestyle, but inflation did its thing, and so did the rising CoL in Seattle.

[1] The absurd price of college is a huge expense for parents who don't want their kids to be stuck with lots of debt. Having to pony up 30k a year is an obscene necessity driven by the horrid cost of a college degree in America.

Re: I regret selling my startup

#53
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.

It all depends on the multiple. If someone is giving you 3 years of profit up-front, that's probably not worth it. If they're giving you 10 years of profit, that could make sense. You avoid having to work for that period of time, and you avoid the risk that something could go wrong (with the company, the economy, the sector) during that time. It also allows you to diversify your assets.

> If someone is giving you 3 years of profit up-front, that's probably not worth it.

TBH, 3 years of profit upfront is probably worth it if you have no good plans to expand that profit.

Re: I regret selling my startup

#54

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…

> 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 friendly.

As for gridlocked, I can walk to multiple bakeries, grocery stores, and parks. The vast majority of my driving is to places that are less than 15 minutes away.

My rural friends talk about taking a quick trip that's only 90 minutes away. 90 minutes there 90 minutes back, shit, that's 2.5hrs extra spent driving compared to my 30 minute round trip commutes. If I go over the last 5 or 6 months I haven't lost a total of 2.5hrs to gridlock.

> 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?

Why do you think people in the city are soulless? Cities are bastion of art and creativity.

I say high to my neighbors all the time, we get together for drinks and we swap baked goods. This is made all the easier by how close we are together.

Indeed, once I moved into the city, meeting people became easier, and the people around me are friendlier. (And I'm in Seattle, literally the worst city for meeting people in!)

Re: I regret selling my startup

#55

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…

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.

Re: I regret selling my startup

#56
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…

Part of the reason VC's are more comfortable investing in founders who have had exits already is they know the founder will be less tempted to take a $5M acquisition offer because he already has a decent amount of cash. Founders who have already had one liquidity event are more aligned with the VC's goals: swing for the fences — don't play it safe to make sure you can pay off your house.

Re: I regret selling my startup

#57

Earlier quoted context omitted.

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.

Wouldn't those guys inspire some people to spend huge amounts of time researching, stock-picking companies you can understand with moats and good management teams, trying to buy when blood in the water, oddly favor junk food, etc.?

Jack Bogle would have you park it in a balance of broad index funds, and generally don't touch it, nor even think about it:

https://www.bogleheads.org/wiki/Bogleheads%C2%AE_investment_...

Re: I regret selling my startup

#58

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…

I thought it was a refreshingly humble and honest-sounding post, by someone who'd done a lot of reflection.

Of course, not everyone matches the writer's motivations, and he went and told the reader what those motivations are.

Re: I regret selling my startup

#59

Earlier quoted context omitted.

It all depends on the multiple. If someone is giving you 3 years of profit up-front, that's probably not worth it. If they're giving you 10 years of profit, that could make sense. You avoid having to work for that period of time, and you avoid the risk that something could go wrong (with the company, the economy, the sector) during that time. It also allows you to diversify your assets.

> If someone is giving you 3 years of profit up-front, that's probably not worth it. TBH, 3 years of profit upfront is probably worth it if you have no good plans to expand that profit.

Really? IMO 3x profit is a terrible multiplier. Depending on the business, 3x revenue could be worth it, but that's a completely different calculation. Of course, it also depends on how much work you're doing to sustain that profit. If you're working full-time to make this happen, 3x profit is a more attractive proposition than if you're just cashing the checks.

Re: I regret selling my startup

#60
post #52

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…

> Daycare in my area is ~2400 a month

If you are retiring early, why are you paying for daycare?

Many people would love to retire early just to be able to spend time with their children.

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