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I made several million dollars in Silicon Valley and retired at age 40. Now I travel perpetually but I have a couple of "home bases". Every day, I'm thankful

I made several million dollars in Silicon Valley and retired at age 40. Now I travel perpetually but I have a couple of "home bases". Every day, I'm thankful that I have my health and a full day to do whatever I want. Time is finite, and living off investment income gives me freedom from having to sell my time for money. I own 100% of my own time now. I saw a sign once that said, "My hope is to die in a staff meeting: that way, the transition from life to death will be subtle." I understood the sentiment 100%. Even by Silicon Valley terms, I had a great income and a good career. But I will never return to it.

ryandrake 9y ago
You're living the dream, man, congratulations. If I ever were to have enough to "draw down until death" I'd do it in a heartbeat. I don't understand these people who have millions of dollars and still get up, go in to work and sit in their 9:30 TPS report review meetings every day, when they have the means to simply not do it. I guess, at some point, for some people, compensation becomes not a means of survival but some kind of grotesque "life scorecard." Screw that.
- peteretep 9y ago
  It's easy to build a lifestyle that you feel is "essential" while spending almost any amount of cash. Some people continue to sit in those meetings so they can continue paying for a very expensive lifestyle.
  - siberianbear 9y ago
    One of the things that was interesting about reaching this level of wealth is having personal relationships with people at these companies before they became rich, and then seeing what they did after they became rich. A few, many in senior management, live for the thrill of the hunt. They want to find their competitor, beat the crap of them, watch them slowly die, bury them, and then dig up the corpse and do it again just to make sure their competitor is really dead. I get why these people stay in the game. Getting a metric ton of money is just a by-product of the hunt. They reminded me of this Conan [1] clip. Some of them, like me, just decided that they had enough and wandered off the ranch and did their own thing. Some of them, as you point out, just have a lifestyle expectation that requires a large amount of income. This prevents them from accumulating the capital to become financially independent. This describes a lot of the people I know. They were dealt cards that would have allowed them to escape the matrix, but didn’t care about escape or didn’t understand the game. I think a few just wouldn’t know what to do if they left the ranch. One guy I knew who was in the first twenty or so employees at one of my employers that made it big, who is probably worth $50M or more, just keeps going back to his cube every day writing software. He drives a Volkswagen and lives in a modest house. Why he’s still there is beyond my capacity to understand. [1] https://www.youtube.com/watch?v=Oo9buo9Mtos https://www.youtube.com/watch?v=Oo9buo9Mtos
- amingilani 9y ago
  As an alternative point of view, even if I netted the $25m at which point my quality of life peaks, I wouldn't stop working. I love what I do. Money is nice and all but I'm an inventer at heart and all the money in the world isn't worth the rush you get by building something and getting people to use it. I plan to make a lot more than my fuck-you-money goal of $25m because then I'll be able to do more insane things.
- Bakary 9y ago
  They perhaps garner a sense of usefulness and productivity from working, even if it is illusory? The periods in my life where I was the most idle were also the most miserable as your mind can turn against you.
shubhamjain 9y ago
I keep reading about similar successes and I don't imagine there is a better deal than spending your whole day doing whatever the fuck you want. If you have a family, is there a greater relief than knowing you have enough time for them? But also recognise that success of this kind is rare. How many HNers might be living a similar dream? I would be surprised if it's more than 100-200 and mind you, HN is a place where a good fraction are smart people who potentially can build a valuable business.
marinacalado 9y ago
Damn, I wanna have your life when I grow up! :) That is so amazing and inspiring!

ryandrake 9y ago

You're living the dream, man, congratulations. If I ever were to have enough to "draw down until death" I'd do it in a heartbeat. I don't understand these people who have millions of dollars and still get up, go in to work and sit in their 9:30 TPS report review meetings every day, when they have the means to simply not do it. I guess, at some point, for some people, compensation becomes not a means of survival but some kind of grotesque "life scorecard." Screw that.

peteretep 9y ago
It's easy to build a lifestyle that you feel is "essential" while spending almost any amount of cash. Some people continue to sit in those meetings so they can continue paying for a very expensive lifestyle.
- siberianbear 9y ago
  One of the things that was interesting about reaching this level of wealth is having personal relationships with people at these companies before they became rich, and then seeing what they did after they became rich. A few, many in senior management, live for the thrill of the hunt. They want to find their competitor, beat the crap of them, watch them slowly die, bury them, and then dig up the corpse and do it again just to make sure their competitor is really dead. I get why these people stay in the game. Getting a metric ton of money is just a by-product of the hunt. They reminded me of this Conan [1] clip. Some of them, like me, just decided that they had enough and wandered off the ranch and did their own thing. Some of them, as you point out, just have a lifestyle expectation that requires a large amount of income. This prevents them from accumulating the capital to become financially independent. This describes a lot of the people I know. They were dealt cards that would have allowed them to escape the matrix, but didn’t care about escape or didn’t understand the game. I think a few just wouldn’t know what to do if they left the ranch. One guy I knew who was in the first twenty or so employees at one of my employers that made it big, who is probably worth $50M or more, just keeps going back to his cube every day writing software. He drives a Volkswagen and lives in a modest house. Why he’s still there is beyond my capacity to understand. [1] https://www.youtube.com/watch?v=Oo9buo9Mtos https://www.youtube.com/watch?v=Oo9buo9Mtos
amingilani 9y ago
As an alternative point of view, even if I netted the $25m at which point my quality of life peaks, I wouldn't stop working. I love what I do. Money is nice and all but I'm an inventer at heart and all the money in the world isn't worth the rush you get by building something and getting people to use it. I plan to make a lot more than my fuck-you-money goal of $25m because then I'll be able to do more insane things.
Bakary 9y ago
They perhaps garner a sense of usefulness and productivity from working, even if it is illusory? The periods in my life where I was the most idle were also the most miserable as your mind can turn against you.

shubhamjain 9y ago

I keep reading about similar successes and I don't imagine there is a better deal than spending your whole day doing whatever the fuck you want. If you have a family, is there a greater relief than knowing you have enough time for them? But also recognise that success of this kind is rare. How many HNers might be living a similar dream? I would be surprised if it's more than 100-200 and mind you, HN is a place where a good fraction are smart people who potentially can build a valuable business.

marinacalado 9y ago

Damn, I wanna have your life when I grow up! :) That is so amazing and inspiring!