3 ms·

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 you

by 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.
  - mathgeek 2mo ago
    Retirement generally implying “not working” is the disconnect here. For example, a person in poverty who quits their salaried job at 62 and has to go work at Walmart to keep up would be retired for some folks, not for others. Same difference for someone independently wealthy at 25 who pursues new businesses.
- retired 2mo ago
  So exactly what was Drew Houston achieving at Dropbox? They stored your files in 2009. They store your files in 2026. Doesn’t seem like he achieved a lot. It’s not like Tim Cook who launched multiple succesful product lines during his tenure. And you can still achieve things during retirement through adventurous travel or philanthropy.
  - ElProlactin 2mo ago
    So what exactly are you achieving by judging Drew, his life choices and how well you think he compares to the CEO of Apple? You're "retired". Shouldn't you be trekking through Borneo or writing the follow-up to Plato's allegory of the cave while sipping a cocktail on the shores of Fiji?
    - retired 2mo ago
      I can shitpost on HN while walking the Camino de Santiago. There is 5G in Spain.
      - ElProlactin 2mo ago
        Well, I don't want to judge your retirement and what you're achieving by shitposting, but surely you're aware that the Camino de Santiago is a pilgrimage route that for over a millennia has been walked for spiritual growth. I hope you can enjoy it.

by monooso 2mo ago

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.
- mathgeek 2mo ago
  Retirement generally implying “not working” is the disconnect here. For example, a person in poverty who quits their salaried job at 62 and has to go work at Walmart to keep up would be retired for some folks, not for others. Same difference for someone independently wealthy at 25 who pursues new businesses.
retired 2mo ago
So exactly what was Drew Houston achieving at Dropbox? They stored your files in 2009. They store your files in 2026. Doesn’t seem like he achieved a lot. It’s not like Tim Cook who launched multiple succesful product lines during his tenure. And you can still achieve things during retirement through adventurous travel or philanthropy.
- ElProlactin 2mo ago
  So what exactly are you achieving by judging Drew, his life choices and how well you think he compares to the CEO of Apple? You're "retired". Shouldn't you be trekking through Borneo or writing the follow-up to Plato's allegory of the cave while sipping a cocktail on the shores of Fiji?
  - retired 2mo ago
    I can shitpost on HN while walking the Camino de Santiago. There is 5G in Spain.
    - ElProlactin 2mo ago
      Well, I don't want to judge your retirement and what you're achieving by shitposting, but surely you're aware that the Camino de Santiago is a pilgrimage route that for over a millennia has been walked for spiritual growth. I hope you can enjoy it.