I don't think you have to have Fuck You Money to get to this point. Most people eventually become disillusioned with work enough that they reevaluate what matters to them. Getting a very profitable exit is just one way to trigger that experience.
In my experience, a lot of people who get into this state start self-sabotaging hard as a way of rejecting what feels, ironically, like losing control. Sudden freedom can feel foreign and lot like your world got forcibly taken away from you. I'm not surprised the author is turning down opportunities and breaking off with his girlfriend. It's a way of taking back control.
When this happened to me, I pivoted hard from getting satisfaction out of what I built to getting satisfaction out of developing people. Now I take great pride out of the careers I've nurtured...a lot more than what I've built, in most ways. I've heard others express similar ideas in different ways, like "I now enjoy making other people rich."
No matter what, I encourage the author to use this time to build connections instead of destroying them (real connections...not work or SF acquaintances). Something I did not read in this essay is how he grew closer to anyone (in fact, I read the opposite). No path out of this valley involves traveling alone.
Same situation, I truly empathise because it really does seem to take a lot of purpose out of everything. What I’ve found is that you need to replace money/salary/financial success optimisation (assuming you spent a lot of your life and energy to this point focused on these, much like I did) with something else totally unconnected with being measured in that way. For me, I am focused on proving myself as a guitarist in the local jazz and blues scene. These people have no idea how much money I have and wouldn’t give a shit if they did (I didn’t really change my lifestyle after getting lucky so it’s not obvious). So it’s an area I can be creative, grow, and still feel like I’m doing something. At the same time I’m doing part time consulting, mainly for people I worked with in the past who have started companies, just to scratch the tech itch. So far so good but I can’t say yet if it will stick. Maybe for you it’s art, music, going and getting another unrelated degree, or something along those lines? If you have more money than you know what to do with, fundraising and supporting good causes can be really rewarding. Both in terms of giving back something to your local community, and having really nice social elements to it.
One big piece of advice I have is to try to avoid letting others in your social network know exactly how successful you’ve been. Everyone starts wanting to pitch you their investment idea and it can burn down friendships when their ideas are bad. Being a VC to your friends is a path to sadness for everyone.
I think his problem is his identity (founder of Loom) suddenly disappeared.
Now he needs to develop a new identity.
This is especially difficult for single founders without kids (in the sense that people with spouse/kids already derive much of their identity from those 2 things).
Selling a company isn’t all that different from going through a divorce (in the sense that your identity needs to be completely rebuilt from scratch)
- Most people who make a lot of money all at once blow it within seven years. Check out what happens to lottery winners, jocks, and rappers. As a rule of thumb, you can safely spend 4% of your net worth per year. Pay yourself some fixed amount each quarter.
- You don't have to get into complex investments. Half in some bond funds, half in some diversified stock funds will work out OK.
- Any investment where they call you is probably not very good.
Useful reading, although dated: "The Challenges of Wealth", by Domini et. al.
What to do with your life? No idea. What are you good at?
- I was a visiting scholar at Stanford for a while. But it was the "AI Winter" and not much was happening. Did robotics in the 1990s. Held patents on legged running on rough terrain, ragdoll physics. Ran a DARPA Grand Challenge team. Didn't really lead anywhere. Too early. Still programming. A metaverse client I'm writing in Rust is running on another screen.
- Horses have been good for me. Every day, I go out and spend time with a pushy alpha mare who keeps me in shape.
"Riding is the only art which princes learn truly". Horses are not impressed by money. Neither are most riders.
- I've known a few ex-CEOs. One did a lot of reasonable little stuff but never did anything with much impact again.
One founded a charity. Another was really into sailboats, and he just kept on with sailboats, crossing the Atlantic and such. He's lucky in having a wife who is also very into sailboats. One guy bought a nightclub, but it loses money year after year.
Probably not gonna get upvoted but I’m pretty surprised none of the the top comments mentions volunteering or philanthropy. I believe people who get lucky should land a hand in making the world a better place. We are facing huge crises (climate change to name one) and as a wealthy individual you have both the time to spend helping to fix that and the fortune to donate. Being a smart wealthy individual just makes everything more valuable
As a young(ish) man with retirement level wealth personally I don't understand this primarily I suppose because my main passions in life are not profitable.
Great, so now I don't have to profitmax every single thing and can rely on my investments. That means I can study pottery, languages, learn about cars, guns, travel, spend time with my old mum, family, start a small business, whatever it is, without care for whether it contributes to the bottom line.
It kind of seems to me as if the poster here has some sort of savior complex - like they can't just be well off and enjoy it, they have to somehow change the world. That's not necessarily a bad thing, but at some point why not take time for you and yours?
I do however identify with the "it's not relatable" thing. If you live off of investments then suddenly you are, well, seperate, from people who can't, in a way that you can try to hide but it leaks out, you can't explain away being able to travel wherever whenever you want, etc.
I can't imagine a world where I wouldn't know what to do.
There is diarrhea on my building, trash in the street, people needing medical help in the alley, and potholes in the street.
Just walk out your front door and start doing things.
My recent triumph was getting a building owner on my street to finally repair the hole in front of their building. Imagine what I could do with a backhoe.
Start small, think big. Help people who deserve it in real, honest (typically not through the computer) ways.
I'd much rather be less wealthy in that way to be rich in this way.
Therapy. Wealth and success is one of the most massive crutches there is. It can make it almost impossible to be truly in touch with your insecurities and pain because its simply too easy to hide in your victory. Your toughest challenge now is to, despite your wealth, find a way to contact the pain that drove you to your hunger for success. As the bible said, it's easier for a camel to get through the head of a needle than for a rich man to go to heaven. I interpret that metaphorically.
I can definitely sympathize with this guy. I imagine selling your company, coming into immense wealth, and losing your identity of ~10 years can really mess up an individual.
But at the same time... this seems rich coming from the dude who co-founded Loom. Calling his ex-coworkers NPCs and believing he's qualified to streamline the US government - all because he built a glorified screen recorder? Have some humility LOL.
"Before enlightenment, chop wood, carry water. After enlightenment, chop wood, carry water"
You do what you were enjoying before, just now you don't need to get paid in money for it. May be you will get paid in fame, noble prize, smiles of people whose life you impact etc. The money you have can't buy those directly but only when you put effort.
I suppose "the author can go fuck himself" is a frowned-upon response on Hacker News
Like what an incredibly egocentric, condescending, deplorable way to talk about other human beings with their own rich inner lives, desires, needs, relationships, etc.
"No, they're just pre-programmed, unthinking bots following basic algorithms."
Perhaps I missed something, but from what I saw none of his attempts to do something new seemed to involve any kind of genuine efforts to improve the lives of others...
Bit amazing that wasn't even something he would consider.
Don’t feel guilty if you don’t know what you want to do with your life. The most interesting people I know didn’t know at 22 what they wanted to do with their lives. Some of the most interesting 40-year-olds I know still don’t.
I'm not sure if Mary Schmich (who did write it) takes pride in her words being frequently credited to an esteemed writer, or if it rankles. Later Baz Luhrmann made the words into a #1.
Anyway, I agree. You don't need to know where to go next, just be curious and find things as you investigate. Sometimes a project will call to you. Don't be concerned if it hasn't yet.
Your project does not have to be a business. If you wanted to embark on a Dwarf Fortress kind of project you could happily work at it for the rest of your life without needing it to be a money making venture. Your Dwarf Fortress might be A database of the world's cheese or a castle built entirely from synthetic diamonds you produce one at a time from your own machine. It doesn't have to be easy or even possible to complete. I don't think you can decide on something and go do it. I think your thing will tell you when it is ready.
Sounds a lot like the guy who said I have 23 gold medals and have no idea what to do (Michael Phelps). Although it isn't a DSM recognized condition, psychologists often refer to the depression of people who obtain the pinnacle of success as “post-gold medal depression.” Here is an article about it. [0]
"What shall we ever do?" -- T.S. Eliot - The Wasteland
"What SHOULD we do?" -- Dr. Seuss - The Cat in the Hat
Regarding the part of breaking up with girlfriend shortly after a winning startup exit, I'm reminded of a friend. (Different situation, but something to think about.)
She saw her bf through the difficult process of a developing a creative work, and eventually he completed it, won a prestigious reward... and he broke up with her.
He got invited to the White House because of the award, and I think missing out on that recognition and experience, where she could've attended as the partner, was symbolic for her.
It wasn't that he was upgrading, since she was an all-around catch, including probably being fabulous at whatever kind of cocktail party circles he entered.
It did seem like awkward timing, to decide that a relationship wasn't going to work out, after all.
(Don't worry, she's OK now: highly accomplished in her own career and creative side, and is also raising a family with a better match.)
I stopped working over twenty years ago and it was the best thing to ever happen to me. I spent thousands of days with my children, paid off my house, we drove brand new cars for the first time ever.
Over time, I’ve just found things to do with my time. I try project Euler problems and I’m pretty interested in meteorology. The rest of the time, I just participate in things my kids are interested in or involved in, though it’s not as easy as when I was young.
Routine is key, and being honestly and wholeheartedly engaged is key. You gotta do the time, don’t let the time do you.
"Working at DOGE" for 4 weeks reminds be of "Teach for America"... maybe it's fairly smart people with decent intentions [1] but not what's needed - not people taking a break from getting rich to do some charity work - rather what's needed is dedicated professionals devoting their careers to teaching / governance.
[1] for the record, I don't think that DOGE has good intentions. A lot of the tweets are nonsensical and I think just a rebranding for typical Republican cuts to health and retirement spending in exchange for more tax breaks at the top.
I think that a lot of people with money need to be reminded that having wealth is a social responsibility in itself. If you can live just from passive income maybe you should just gift interesting people the excess money and have them accomplish their goals.
Talk to a bunch of people and realize what you want to support. If some of them need 10k to start a business just give it to them. Or, if you want some equity, put it in a non-profit that reinvest its earnings. Go to a film school, organize a contest and fund the movie of the most promising students.
I was never rich like the author, yet I once gave a bookbinder that I had hired to make a cool leather-bound book the starting capital he needed to make his own shop just because it turned out so well and he was so passionate about it. Looking back, it still feels great to have helped someone like this.
Humans need activities that produce meaningful outcomes, they don't need careers or work.
I read the blog post and many of the comments and can’t help but think… how is it you guys are so smart you can create enormous amounts of wealth with no idea what to use it on?
There are millions of people struggling to survive and you have amassed a pile of resources you’ve determined the best thing to do with is bury?
I felt similar when I finished my PhD. It was the singular “thing” in my life to the exclusion of all others. Luckily I was 150k in debt so I didn’t have the luxury of acting like a buffoon for months.
Man if I was rich I’d donate half, invest half, and go back to stocking a small family owned grocery store like when I was in high school. I really enjoyed that job.
It’s a weird post. Part cry for help, part not-so-humble brag, and 100% not something any close friend, significant other, or therapist would recommend you hit send on. Feels a little strung-out, to be honest.
“Rich guy is bored, you’ll never believe what happens next”
despite the title..i read this post as an exhaustion with SV culture. everything starting with the personality types that are elevated (ie some flavor of antisocial personality disorder) and ending with the activities that earn you social capital (ie identifying the next anti-consensus big industry).
i've seen this happen with people that have had much much smaller financial success in the industry..or even ones that haven't had any at all. you are either naturally inclined to identify with the culture or you trick yourselves into it so that you may belong.
<insert paragraph about social desire to be connected and how we construct an image of ourselves through others>
the culture of SV today is an amalgamation of Taylorist ideas, Randian objectivism, Utilitarianism etc etc. there is a lot of social capital to be earned by embodying the values of these currents. DOGE is a quintessential representation of this. it is not surprising at all that author had such a visceral reaction to it.
its important to emphasize that there have been very successful companies that have gone against the current (ie Apple), with an emphasis on craftsmanship, obsession with the process, taste-driven vs data-driven decisions and appreciation for things that are outside of profit maximization.
Some comments were deferred for faster rendering.
madrox|1 year ago
In my experience, a lot of people who get into this state start self-sabotaging hard as a way of rejecting what feels, ironically, like losing control. Sudden freedom can feel foreign and lot like your world got forcibly taken away from you. I'm not surprised the author is turning down opportunities and breaking off with his girlfriend. It's a way of taking back control.
When this happened to me, I pivoted hard from getting satisfaction out of what I built to getting satisfaction out of developing people. Now I take great pride out of the careers I've nurtured...a lot more than what I've built, in most ways. I've heard others express similar ideas in different ways, like "I now enjoy making other people rich."
No matter what, I encourage the author to use this time to build connections instead of destroying them (real connections...not work or SF acquaintances). Something I did not read in this essay is how he grew closer to anyone (in fact, I read the opposite). No path out of this valley involves traveling alone.
j4coh|1 year ago
One big piece of advice I have is to try to avoid letting others in your social network know exactly how successful you’ve been. Everyone starts wanting to pitch you their investment idea and it can burn down friendships when their ideas are bad. Being a VC to your friends is a path to sadness for everyone.
cj|1 year ago
I think his problem is his identity (founder of Loom) suddenly disappeared.
Now he needs to develop a new identity.
This is especially difficult for single founders without kids (in the sense that people with spouse/kids already derive much of their identity from those 2 things).
Selling a company isn’t all that different from going through a divorce (in the sense that your identity needs to be completely rebuilt from scratch)
Animats|1 year ago
General comments:
- Most people who make a lot of money all at once blow it within seven years. Check out what happens to lottery winners, jocks, and rappers. As a rule of thumb, you can safely spend 4% of your net worth per year. Pay yourself some fixed amount each quarter.
- You don't have to get into complex investments. Half in some bond funds, half in some diversified stock funds will work out OK.
- Any investment where they call you is probably not very good.
Useful reading, although dated: "The Challenges of Wealth", by Domini et. al.
What to do with your life? No idea. What are you good at?
- I was a visiting scholar at Stanford for a while. But it was the "AI Winter" and not much was happening. Did robotics in the 1990s. Held patents on legged running on rough terrain, ragdoll physics. Ran a DARPA Grand Challenge team. Didn't really lead anywhere. Too early. Still programming. A metaverse client I'm writing in Rust is running on another screen.
- Horses have been good for me. Every day, I go out and spend time with a pushy alpha mare who keeps me in shape. "Riding is the only art which princes learn truly". Horses are not impressed by money. Neither are most riders.
- I've known a few ex-CEOs. One did a lot of reasonable little stuff but never did anything with much impact again. One founded a charity. Another was really into sailboats, and he just kept on with sailboats, crossing the Atlantic and such. He's lucky in having a wife who is also very into sailboats. One guy bought a nightclub, but it loses money year after year.
iddan|1 year ago
naming_the_user|1 year ago
Great, so now I don't have to profitmax every single thing and can rely on my investments. That means I can study pottery, languages, learn about cars, guns, travel, spend time with my old mum, family, start a small business, whatever it is, without care for whether it contributes to the bottom line.
It kind of seems to me as if the poster here has some sort of savior complex - like they can't just be well off and enjoy it, they have to somehow change the world. That's not necessarily a bad thing, but at some point why not take time for you and yours?
I do however identify with the "it's not relatable" thing. If you live off of investments then suddenly you are, well, seperate, from people who can't, in a way that you can try to hide but it leaks out, you can't explain away being able to travel wherever whenever you want, etc.
iancmceachern|1 year ago
There is diarrhea on my building, trash in the street, people needing medical help in the alley, and potholes in the street.
Just walk out your front door and start doing things.
My recent triumph was getting a building owner on my street to finally repair the hole in front of their building. Imagine what I could do with a backhoe.
Start small, think big. Help people who deserve it in real, honest (typically not through the computer) ways.
I'd much rather be less wealthy in that way to be rich in this way.
smokedetector1|1 year ago
crakhamster01|1 year ago
But at the same time... this seems rich coming from the dude who co-founded Loom. Calling his ex-coworkers NPCs and believing he's qualified to streamline the US government - all because he built a glorified screen recorder? Have some humility LOL.
vimgrinder|1 year ago
You do what you were enjoying before, just now you don't need to get paid in money for it. May be you will get paid in fame, noble prize, smiles of people whose life you impact etc. The money you have can't buy those directly but only when you put effort.
imgabe|1 year ago
KPGv2|1 year ago
I suppose "the author can go fuck himself" is a frowned-upon response on Hacker News
Like what an incredibly egocentric, condescending, deplorable way to talk about other human beings with their own rich inner lives, desires, needs, relationships, etc.
"No, they're just pre-programmed, unthinking bots following basic algorithms."
JansjoFromIkea|1 year ago
Bit amazing that wasn't even something he would consider.
Lerc|1 year ago
Don’t feel guilty if you don’t know what you want to do with your life. The most interesting people I know didn’t know at 22 what they wanted to do with their lives. Some of the most interesting 40-year-olds I know still don’t.
I'm not sure if Mary Schmich (who did write it) takes pride in her words being frequently credited to an esteemed writer, or if it rankles. Later Baz Luhrmann made the words into a #1.
Anyway, I agree. You don't need to know where to go next, just be curious and find things as you investigate. Sometimes a project will call to you. Don't be concerned if it hasn't yet.
Your project does not have to be a business. If you wanted to embark on a Dwarf Fortress kind of project you could happily work at it for the rest of your life without needing it to be a money making venture. Your Dwarf Fortress might be A database of the world's cheese or a castle built entirely from synthetic diamonds you produce one at a time from your own machine. It doesn't have to be easy or even possible to complete. I don't think you can decide on something and go do it. I think your thing will tell you when it is ready.
dataviz1000|1 year ago
"What shall we ever do?" -- T.S. Eliot - The Wasteland
"What SHOULD we do?" -- Dr. Seuss - The Cat in the Hat
"What should we do?" -- Shakespeare - Hamlet
When I'm bored I like to read poetry.
[0] https://www.npr.org/sections/thetorch/2016/09/08/493111873/a...
tiffanyh|1 year ago
If the insights are correct, each cofounder netted ~$56M [1]
[0] https://vinay.sh
[1] https://www.cbinsights.com/research/loom-valuation-investor-...
neilv|1 year ago
She saw her bf through the difficult process of a developing a creative work, and eventually he completed it, won a prestigious reward... and he broke up with her.
He got invited to the White House because of the award, and I think missing out on that recognition and experience, where she could've attended as the partner, was symbolic for her.
It wasn't that he was upgrading, since she was an all-around catch, including probably being fabulous at whatever kind of cocktail party circles he entered.
It did seem like awkward timing, to decide that a relationship wasn't going to work out, after all.
(Don't worry, she's OK now: highly accomplished in her own career and creative side, and is also raising a family with a better match.)
thunkingdeep|1 year ago
Over time, I’ve just found things to do with my time. I try project Euler problems and I’m pretty interested in meteorology. The rest of the time, I just participate in things my kids are interested in or involved in, though it’s not as easy as when I was young.
Routine is key, and being honestly and wholeheartedly engaged is key. You gotta do the time, don’t let the time do you.
This worked for me anyways.
ks2048|1 year ago
[1] for the record, I don't think that DOGE has good intentions. A lot of the tweets are nonsensical and I think just a rebranding for typical Republican cuts to health and retirement spending in exchange for more tax breaks at the top.
mihaic|1 year ago
Talk to a bunch of people and realize what you want to support. If some of them need 10k to start a business just give it to them. Or, if you want some equity, put it in a non-profit that reinvest its earnings. Go to a film school, organize a contest and fund the movie of the most promising students.
I was never rich like the author, yet I once gave a bookbinder that I had hired to make a cool leather-bound book the starting capital he needed to make his own shop just because it turned out so well and he was so passionate about it. Looking back, it still feels great to have helped someone like this.
Humans need activities that produce meaningful outcomes, they don't need careers or work.
nooneevencares|1 year ago
There are millions of people struggling to survive and you have amassed a pile of resources you’ve determined the best thing to do with is bury?
joshcsimmons|1 year ago
I felt similar when I finished my PhD. It was the singular “thing” in my life to the exclusion of all others. Luckily I was 150k in debt so I didn’t have the luxury of acting like a buffoon for months.
Man if I was rich I’d donate half, invest half, and go back to stocking a small family owned grocery store like when I was in high school. I really enjoyed that job.
cmckn|1 year ago
“Rich guy is bored, you’ll never believe what happens next”
nibab|1 year ago
i've seen this happen with people that have had much much smaller financial success in the industry..or even ones that haven't had any at all. you are either naturally inclined to identify with the culture or you trick yourselves into it so that you may belong.
<insert paragraph about social desire to be connected and how we construct an image of ourselves through others>
the culture of SV today is an amalgamation of Taylorist ideas, Randian objectivism, Utilitarianism etc etc. there is a lot of social capital to be earned by embodying the values of these currents. DOGE is a quintessential representation of this. it is not surprising at all that author had such a visceral reaction to it.
its important to emphasize that there have been very successful companies that have gone against the current (ie Apple), with an emphasis on craftsmanship, obsession with the process, taste-driven vs data-driven decisions and appreciation for things that are outside of profit maximization.
mmoustafa|1 year ago
And that is your internal struggle my friend