Hacker News Reader

Comment by ElProlactin | Hacker News Reader

Not sure why this is on the front page but anyway...

> But a lesson from this story is twofold: when Steve Jobs tries to buy you, take it. Economically, the return from a capital efficiency standpoint would be much better. Second, public companies that are truly just a feature never give you great returns.

Dropbox was a private company when Jobs offered to buy it for $800 million in 2009. Drew Houston (the founder) has collected hundreds of millions of dollars in compensation since then and is today worth over $2 billion. He's also on the board of Meta.

So the point about investing in companies that are features might be a decent (if obvious) one for retail investors looking at public equities, but the lesson here isn't "when Steve Jobs tries to buy you, take it".

View on HN

$800M in 2009 Apple stock would be about $24B today!

But $800M in USD is worth only about $1.2B today. Keeping the money invested in Apple is convenient if you're already paid in stock, but beyond the lock-up period we have to keep in mind that it's just one of many things he could have done when accepting the money

Though I think it fair to speculate that if he had taken the deal he would likely have more money today, at the cost of less status

Yeah but who can say Steve Jobs bought their company so early on, the early Dropbox design was so Apple-esque.

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.

But you're not Drew Houston.

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.

And maybe that's why you didn't start Dropbox.

Still started and sold my own company. Quit working. But no, it wasn’t Dropbox.

which company?

OneDrive

It’s right there in his name. Retired Inc.

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.

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.

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.

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.

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.

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.

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?

I can shitpost on HN while walking the Camino de Santiago. There is 5G in Spain.

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.

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 was referring to multiples on invested capital. Plus, it's a bit hurtful when you IPO your company, the stock stays flat if not down, and you step down; I think an Apple acquisition like that is much more of a happy ending IMO.

You're thinking like an investor, not an entrepreneur/founder.

Yes, you're right

Reply on news.ycombinator.com