It would have been easy to second-guess, but once we made the call to switch, we locked arms. That level of rigor, understanding that getting it right was more important than cost-it took a lot of patience in the boardroom. Sometimes, we missed a milestone and had to reset the clock.

There was a period of time where we were essentially paying double. I think it was the right strategy, but it was a big investment. The team invested a tremendous amount of time in developing validation in different layers of the stack and in other processes. We knew we couldn’t lose a single piece of data, so we rebuilt large portions of AWS and mirrored everything across the cloud and our own infrastructure. That makes it easy to get behind them 100 percent. But Drew and Arash are the full package-deeply technical, incredible insight, excellent leadership skills. We believed they could make it a success. Ultimately, it came down to the caliber of the Dropbox teams who owned the project. Our leadership team had to take a leap of faith, and so did the board. They helped us see around the corners, and they understood the best companies make these big investments. Why screw that up?” Bryan and Sequoia encouraged us to think long-term. DrewĪnother investor might have said, “You’re cash-flow positive. Buying the hardware was a lot of money up front. We did a fair amount of financial modeling, but it was a risky decision. The bet was we would be more efficient on our own and save money over time. Eventually, though, as Dropbox grew and as Amazon became more of a competitor, we decided to leave AWS. It helped them build an infrastructure-intensive company with a low burn rate they were cash flow positive a couple of years in. We just had a slightly bigger check to write each month. We didn’t have to worry about any of that. We’d heard all these stories about people hauling servers around in the trunks of their cars. Drew and Arash were among the first to get to scale on Amazon Web Services (AWS). Before Dropbox, everyone rented their own servers.

Founder dropbox