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I regret selling my startup

nothingeasyaboutthis.com

131–140 of 158 posts

Re: I regret selling my startup

#131

Earlier quoted context omitted.

Yet Person A, who just sold his startup and is sitting on $10M is objectively better off than Person B, who is making $200K a year at a normal job in tech. All other intangible things being equal, Person A's wealth will earn him $2-400K a year just sitting there doing nothing, giving him the choice to go get a normal job if desired, or not, or do anything he wants to do for fun, or not. That startup sale bought him t…

You assume you can buy happiness. Person A is not objectively better off, they're financially better off. Happiness isn't determined solely by bank balance. If what made him tick was a sense of purpose, of seeing the company he founded continue to grow there aren't many options apart from go back to the company, found a new one, or ??? Maybe option 2 is too much work, and without the carrot of a big payoff he'd lack…

Money doesn't buy you happiness, but it _does_ eliminate a set of problems that can impede one's happiness.

Which is not to say that the person with money can't then find additional problems, or use the money such that they reintroduce a class of problems.

Re: I regret selling my startup

#132
post #126

Earlier quoted context omitted.

> because it can just be more opportunities for change/growth/discovery That was basically going to be my comment, I'm fulfilled by beating the game. Resource acquisition is a Massive Multiplayer game. I'm fulfilled by the industries I enter to make revenue or sell a company, I'm never doing something grueling and dead end, I feel good about successfully avoiding being in that kind of situation. I'm fulfilled by enjo…

> I am my own lifestyle company. I love your reply, as it puts the finger on what I felt was missing from this simple answer that was otherwise very compelling! Like there's exploration and exploitation, ikegai is the #2, but something like wanderlust is the #1: the "change/growth/discovery", or what someone else has called "the happy feeling of anticipation of unknowns that comes from a schooltrip/school vacation bu…

but then what indeed, I think the world caters decently to those that have resources. I’ve dabbled in the socialite circuit, its spaced out across the year in a few select major cities, I could do it until I die in between various investing or hands on opportunities. You meet really interesting people that are also dabbling in that lifestyle.

The Winklevoss twins heard about extremely high tech things early on while partying in Ibiza, for example. So have I

I agree with all of your comment

Re: I regret selling my startup

#133
post #94

Earlier quoted context omitted.

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…

> Maybe it's one of those things that is easy to explain but hard to understand if you don't have experiential context. Maybe use the word "Ikigai"? It seems to carries the concept very well across cultures. It's doing what you love, what you are good at, what the world needs, and what you can get paid for! https://en.wikipedia.org/wiki/Ikigai A friend told me a life without Ikigai is a life spent waiting for death.…

Thanks for the word Ikigai. I might actually remember it because it is related to the Japanese word Ikiru, which is the verb to live. Ikiru is also the title of one of Akira Kurosawa's finest films [1], which deals with the life and death of a Tokyo bureaucrat, and more specifically his discovery of meaning and purpose in life. I cant recommend it enough. It is generally ranked in the top 100 films of all time, a personal favorite, and reliably moves me to tears every time I watch it.

The concept of Ikigai seems to be broader than the professional sphere, so it makes sense that some people may have Ikigai, but it is unrelated to their work, or their work is merely a necessity, to support their passion.

I personally believe happiness is a spectrum, so people may have some level of happiness without Ikigai, but it is not qualitatively or quantitatively the same as that with it.

I have personally found great satisfaction and joy in my work at times in my career, and not at other times. In my experience, alignment of work, your skills, and passion is a glorious experience.

Almost like a drug induced euphoria, it can be an eye opening experience, which you can't help but place other experiences into the context of. It makes sense that those who haven't experienced it dont know- how could they.

My professional work isnt currently aligned with my passion, which severly limits my feeling of ikigai, but getting back there is the goal and destination. After getting a taste of it, life without it is certainly lacking.

https://www.imdb.com/title/tt0044741/

Re: I regret selling my startup

#134

Earlier quoted context omitted.

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

And plus, what's the point? Most people work for money. But that's satisfying our needs. If you already have a cash pile though, you actually need to find a way of making a difference again to keep getting out of bed. I think that's much harder. Some people never find their passion.

>Some people never find their passion.

and some people find their passion, and then sell it or lose it.

Re: I regret selling my startup

#135

Earlier quoted context omitted.

Can get 8% plus easy in yield on a diversified set of relatively safe REITs and corporate bonds nowadays. Absolutely would not recommend putting funds in large cap indices if you're planning to retire off portfolio cashflow. You get close to 4.5% cashflow (interest plus imputed income) on 20y treasury bonds alone, for example. Why take pricing risk to your income when you can get it directly in dividends/distribution…

You’d never put your whole nut into treasuries unless you wanted to get killed by inflation. You’re looking at a 50 year retirement if you’re in your 30s. “4%” (Trinity study style I mean) is the pop culture number that accommodates down markets and inflation over 50 years, to a first approximation.

Definitely not, though I was just demonstrating the kind of cashflow you can get from a (default) risk free bond.

The days of buying an index and selling 4%/year being your best strategy are past. At least until/when yields decline again.

If you're strategic and barbell your portfolio somewhat, you can generate around 10% with moderate risk (and this is 10% distributions/dividends, not including any capital gains).

The best outcome for retirees is to build a solid income portfolio and then hope that inflation really does subside and valuation multiples compress again, which would leave you with significant capital gains while portfolio income is preserved.

If inflation resurges or remains moderately high, capital gains will be more limited.

Re: I regret selling my startup

#136
post #127

Earlier quoted context omitted.

Almost all of my problems can be immediately solved with large amounts of money. Those that cannot will certainly be made more bearable by the simple fact that I have a lot less to worry about, and that I will have more mental and emotional resources available to deal with them. Money will _absolutely_ buy happiness. Whoever tells you otherwise is fooling you.

The same thing was said by other famous philosophers, such as A. Grande who publicly declared: "whoever said money can't solve your problems, must not have had enough money to solve them". Yet there seem to be many other things playing a role in happiness. Besides the famous ones like love, I can cite Ikegai, Wanderlust, Ubuntu, Hygge, Wabi-Sabi (...), and it may be foolish to concentrate on just one of them.

Money doesn't bring happiness, but lack of money can bring hardship and lack of happiness.

Money can alleviate hardship and stress, but happiness is more than absence of sadness, hardship, or stress.

Re: I regret selling my startup

#137
> for me it was a personal incompatibility with parts of the business I don’t want to delve into in this post.

Without this, the post was pretty abstract and not very interesting.

Re: I regret selling my startup

#138
post #98
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…

Like any engineer, I know more than a few instant-millionaires. The ones who were capable of being happy before money continue to be capable of being happy. They had sources of self-worth outside of money, social connections outside the office or hanging with their startup bros, and interests that are intrinsically satisfying even if they are not profitable. You don't need all of the above, but you do need at least o…

> Like any engineer, I know more than a few instant-millionaires.

Cries in Europe :(

Re: I regret selling my startup

#139
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 would anyone buy a house in a major city, especially for retirement. You can get something decent for half the price near nature.

I put a lot of effort to get out of my rural farming hometown and into a city, why would I give that up? Especially since I could buy a place on the outskirts right next to a tube station and a nature reserve.

Re: I regret selling my startup

#140
post #83

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…

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.

I grew up in a rural farming town, lived in a few large towns/small cities, and now live in the megalopolis of London.

Cities are great! Cities have people, energy, stuff.

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