Behind the founder: Drew Houston (Dropbox)

(instrumental music) ... people just don't realize the wild journey that you have been on over the past 18 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 100,000 users, 200,500, 500K, a million, 10 million on the ceiling.

Then there's the second era, which is I'll just say everyone's trying to kill you.

(instrumental music) We started getting, uh, all the incumbents, Apple, Microsoft, Google, all of them launched competing products. But weirdly it was sort of like, you see this, 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 2015 was a pivotal year, where things started to shift.

I'd start to hear 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 we 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 narrative completely flipped on the company. Suddenly your employees don't want to wear your T-shirt anymore. Everybody's looking to you as wondering like how the hell did you get us in this situation.

(instrumental music) 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, and also what he's learned about himself throughout the journey. This is a very special episode that I suspect founders will be studying for years to come. A big thank you to Drew for sharing these stories and lessons with us. If you enjoy this podcast, don't forget to subscribe and follow it in your favorite podcasting app or YouTube. It's the best way to avoid missing future episodes and it helps the podcast tremendously. With that, I bring you Drew Houston. This episode is brought to you by Paragon, the integration infrastructure for B2B SaaS companies. Is AI on your 2025 product roadmap? Whether you need to enable RAG with your user's external data like Google Drive files, Gong transcripts, or Jira tickets, or build AI agents that can automate work across your user's other tools, integrations are the foundation. But building all these integrations in-house will cost you years of engineering, time you don't have given the fast pace of AI. That's where Paragon's all-in-one integration platform comes in. Build scalable workflows to ingest all of your user's external data into your RAG pipelines and leverage Action Kit, their latest product, to instantly give your AI agents access to over 100 integrations and thousands of third party actions with a single API call. Leading AI companies like AI21, You.com, 11X and Coffee.ai are already shipping new integrations seven times faster with Paragon, keeping their engineers focused on core product development. Ready to accelerate your AI roadmap this year? Visit useparagon.com/lenny to get a free MVP of your next product integration. This episode is brought to you by Explo, a game changer for customer facing analytics and data reporting. Are your users craving more dashboards, reports, and analytics within your product? Are you tired of trying to build it yourself? As a product leader, you probably have these requests in your roadmap, but the struggle to prioritize them is real. Building analytics from scratch can be time-consuming, expensive, and a really challenging process. Enter Explo. Explo is a fully white-labeled embedded analytics solution designed entirely with your user in mind. Getting started is easy. Explo connects to any relational database or warehouse, and with its low-code functionality you can build and style dashboards in minutes. Once you're ready, simply embed the dashboard or report into your application with a tiny code snippet. The best part? Your end users can use Explo's AI features for their own report and dashboard generation, eliminating customer data requests for your support team. Build and embed a fully white-labeled analytics experience in days. Try it for free at explo.co/lenny. That's E-X-P-L-O.co/lenny. (instrumental music) Drew, thank you so much for being here, and welcome to the podcast.