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I would have taken the 800 million and retired. Would easily be worth 1.5 billion with simple investment. And you would not have needed to work those 17 years.

by retired 2mo ago

ElProlactin 2mo ago
But you're not Drew Houston.
- retired 2mo ago
  Correct. At the 26 years old that he was I would take the millions and just have a chill life. Maybe start collecting rare Lamborghinis.
  - ElProlactin 2mo ago
    And maybe that's why you didn't start Dropbox.
    - retired 2mo ago
      Still started and sold my own company. Quit working. But no, it wasn’t Dropbox.
      - Taikhoom10 2mo ago
        which company?
        sunnybeetroot 2mo ago
        OneDrive
        testdelacc1 2mo ago
        It’s right there in his name. Retired Inc.
- monooso 2mo ago
  The advice isn't for Drew Houston, it's written as general advice for anyone. The point is that different people have different priorities, and retiring in your mid-twenties to enjoy your many millions is a perfectly reasonable choice.
  - somenameforme 2mo ago
    Until one does it and realizes that the concept of retirement is not the same as the reality of such, especially for people who like achieving things, which is going to essentially be 100% of people who end up making millions in their 20s. I think this is why so many billionaires choose to be workaholics even though they have the means to do literally almost anything.
    - monooso 2mo ago
      In which case, fine, return to work, start a new company, start a foundation, whatever. Accepting the aforementioned big fat cheque from Steve Jobs affords you those options.
    - solatic 2mo ago
      There's a very big difference between what you can achieve as an entrepreneur with low net worth and an entrepreneur with a war chest of hundreds of millions of dollars. When you start out with effectively nothing, you are forced to take a day job while you build something out on nights and weekends. The pressure is high to take early investment - and essentially work for your early investors, instead of working for yourself, just so that you can work on your baby full-time. When you have a war chest, then many more capital-intensive opportunities are available to you. Want to build hardware (i.e. without crowdsourcing)? Factories? Pharmaceutical R&D? Training open-weight LLMs? Hell, you want to start an airline? Take your pick, and I'm barely scratching the surface. It's hilarious to think that an $800 million exit would force you to never work again. That's crazy. It only forces you not to work on that company you exited from. The exit enables you to work on almost anything else you can think of. You put $25 million away in close-to-zero-risk investments to let you live off quite an insane amount of interest (even if you only get 2% interest, that's $500k/year) and then have $775 million to work with.
stymaar 2mo ago
If he wanted to “retire” he never had to wor in the first place, he could have hired someone to take his jobs while still keeping his equity. But being the CEO of a well-known startup has a lot of status benefits compared to just being rich. And that's all what matters at this level of wealth. And it gives you a sense of purpose, which we all need.

I would have taken the 800 million and retired. Would easily be worth 1.5 billion with simple investment. And you would not have needed to work those 17 years.

by retired 2mo ago

I would have taken the 800 million and retired. Would easily be worth 1.5 billion with simple investment. And you would not have needed to work those 17 years.

ElProlactin 2mo ago

But you're not Drew Houston.

retired 2mo ago
Correct. At the 26 years old that he was I would take the millions and just have a chill life. Maybe start collecting rare Lamborghinis.
- ElProlactin 2mo ago
  And maybe that's why you didn't start Dropbox.
  - retired 2mo ago
    Still started and sold my own company. Quit working. But no, it wasn’t Dropbox.
    - Taikhoom10 2mo ago
      which company?
      - sunnybeetroot 2mo ago
        OneDrive
      - testdelacc1 2mo ago
        It’s right there in his name. Retired Inc.
monooso 2mo ago
The advice isn't for Drew Houston, it's written as general advice for anyone. The point is that different people have different priorities, and retiring in your mid-twenties to enjoy your many millions is a perfectly reasonable choice.
- somenameforme 2mo ago
  Until one does it and realizes that the concept of retirement is not the same as the reality of such, especially for people who like achieving things, which is going to essentially be 100% of people who end up making millions in their 20s. I think this is why so many billionaires choose to be workaholics even though they have the means to do literally almost anything.
  - monooso 2mo ago
    In which case, fine, return to work, start a new company, start a foundation, whatever. Accepting the aforementioned big fat cheque from Steve Jobs affords you those options.
  - solatic 2mo ago
    There's a very big difference between what you can achieve as an entrepreneur with low net worth and an entrepreneur with a war chest of hundreds of millions of dollars. When you start out with effectively nothing, you are forced to take a day job while you build something out on nights and weekends. The pressure is high to take early investment - and essentially work for your early investors, instead of working for yourself, just so that you can work on your baby full-time. When you have a war chest, then many more capital-intensive opportunities are available to you. Want to build hardware (i.e. without crowdsourcing)? Factories? Pharmaceutical R&D? Training open-weight LLMs? Hell, you want to start an airline? Take your pick, and I'm barely scratching the surface. It's hilarious to think that an $800 million exit would force you to never work again. That's crazy. It only forces you not to work on that company you exited from. The exit enables you to work on almost anything else you can think of. You put $25 million away in close-to-zero-risk investments to let you live off quite an insane amount of interest (even if you only get 2% interest, that's $500k/year) and then have $775 million to work with.

stymaar 2mo ago

If he wanted to “retire” he never had to wor in the first place, he could have hired someone to take his jobs while still keeping his equity. But being the CEO of a well-known startup has a lot of status benefits compared to just being rich. And that's all what matters at this level of wealth. And it gives you a sense of purpose, which we all need.