The

decision to move to Magic Pocket was sort of a transformative from a financial perspective, allowed us to drop our margin significantly and make us a much more attractive company in the public markets. So when the company went public, I think

it was obvious to not just the Magic Pocket team, but to everyone in the company that one of the reasons, one of the big reasons that the IPO was so successful and the company even today is profitable is because of this team. And I would actually say when we went public, the joy, the pride, and the sense of achievement this team had was one of the best. It probably was even more than what they had when they finished the migration, because that was the business impact and the validation that we were working toward for the last four years.

Today, Dropbox has over $2.5 billion in annual revenue, over 18 million paying users, and 500,000 business customers, a scale few imagined possible back in 2007. The company has continued to develop its services for work and collaboration, including products and tools that leverage AI.

What's happening in machine learning and AI is just super exciting. And I've been following it for a long time and engineering is still my first love. I mean, I've been coding since I was a little kid and kind of back to coding like a little kid on weekends. And in a lot of ways, Dropbox is solving the 2024 version of the problem we started with. Because in the beginning, it was, forgot my thumb drive, but the problem I really had is like, I can't find my stuff. I can't organize my stuff. I can't share my stuff. I can't secure my stuff. Kind of funny, you fast forward to today, it's like, you actually have a lot of the same genre of problem. Like I can't find my stuff at work, can't organize it, can't share it, security challenges. So problems are the same. The shape is a little bit different. So a hundred files on your desktop have turned into a hundred tabs in your browser. And for years we've thought about like, why is it easier to search all of human knowledge with Google search than like my company stuff or my own stuff? And Dropbox is really well positioned to solve that problem. And it's a pretty natural evolution for us to go from syncing your files to organizing all your cloud content. And AI and generative AI have opened the door to create some really awesome experiences that I've wanted to build for a long time, but can actually become real. So the first example of that is we have a new product called Dropbox Dash, AI-powered universal search. So it'll search not just your files, but your Google Docs and your email and your Slack and your Salesforce from one place. And I mean, it's a fascinating transition from kind of being this like hyper growth thing to this like profitable, low growth company and then investing for growth again and, you know, reaching top of one S curve, trying to grab onto another. But we're just in the first inning. There aren't very many good things about getting older, but one thing that is good is perspective and having been able to see and kind of ride a bunch of different waves, see a bunch of different cycles. And we're in the most exciting part of these cycles because every 10 years or so, the kind of concrete unfreezes and then, you know, old buildings get knocked down, new franchises get built. Everybody's kind of figuring it out. And that's the kind of thing I love. That's the kind of puzzle I love to solve. I always think about, all right, you know, a year from now, two years from now, five years from now, what will I wish I had been learning today? And some things are pretty tough. Like you're not going to be a great manager or leader in the next two weeks any more than you'll be a great guitar player or a great surgeon. But, over two years, five years, ten years, you can grow a lot. And so I think thinking about that exponential learning rate probably makes a difference between the founders that make it and the ones that don't. There are different ways to keep that learning rate up. I think certainly reading and having a community of people that are going through similar things, having investors, it was really helpful in helping us navigate a lot of these turning points and focusing our attention on the right things. But however you do it, just recognize that's a very primary job and how do you cultivate the judgment and wisdom to keep scaling as your job keeps changing every year in pretty dramatic ways.

This

has been Crucible Moments, a podcast from Sequoia Capital.

Crucible Moments is produced by the Epic Stories and Vox Creative Podcast teams, along with Sequoia Capital. Special thanks to Drew Houston, Arash Ferdowsi, Brian Schreier, Sujay Jaswa, Akhil Gupta, and James Cowling for sharing their stories.