Behind the founder: Drew Houston (Dropbox)

People just don't realize the wild journey that you have been on over the past eighteen years building this company. It feels like there's almost been these three eras of Dropbox. The first era of you're killing it. For the first several years it was doubling, 10Xing every year, putting like taping user counts that we printed out. to the wall and then running out of space on the wall, having to put it in. Million, ten million. On the ceiling. And there's the second era, which is I'll just say everyone's trying to kill you. We started getting all the incumbents, Apple, Microsoft, Google, all of them launched competing products. But weirdly it was sort of like you see th the videos where there's like the mushroom cloud in the distance, you see it, but you don't hear or notice it. But there is it was also clear that winter was coming. It feels like the year twenty fifteen was a pivotal year where things started to shift. I'd start to hear a kind of a louder set of critics inside and outside the company less than a year later. Google Photos launches.

And not only does it provide a lot of the same value, but they also gave you free unlimited storage for life. And so they just totally nuked our business model. You end up fighting wars on three or four fronts against the big kahunas that have infinite cash and can do whatever they want. So I killed carousel, killed mailbox, went all in on productivity. And I wish I could say Like then everything got better. It was the opposite actually the the the narrative completely flipped on the company. Suddenly your employees don't want to wear your T shirt anymore. Everybody's looking to you is wondering like how the hell did you get us in this situation? Today my guest is Drew Houston. This may be the most interesting and most useful episode of my podcast so far.

Especially if you're a founder, or if you someday want to be a founder. Drew shares the very real talk story of what it's been like to build Dropbox over the past 18 years. Including the ups and especially the downs. He shares stories that he's never shared before, the struggles he's been through that very few people know about, what it's like to compete with big tech. How he's thinking about the future of the company.

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