In today's episode we talk with Drew Houston, founder and CEO of Dropbox. We've known Drew for a long time (YC funded Dropbox in 2007) and he's extremely candid about the many challenges he faced, and overcame, in the journey from building something that solved his own problem to serving as an essential part of the fou

Drew Houston is the co-founder and CEO of Dropbox. Under his leadership, Dropbox has grown from a simple idea to a service used by over 700 million registered users globally, with a valuation exceeding $9 billion. Drew has led Dropbox through multiple phases, from explosive viral growth, to battling all the tech giants

By now, the story is legend. When Drew Houston boarded a bus from Boston to New York and discovered that he had—yet again—forgotten to bring his thumb drive, he was frustrated. So frustrated that he sat down and began writing the first lines of code of what would eventually become Dropbox. After over a decade of changi

Drew Houston has now been CEO of Dropbox for over 17 years. In my latest conversation, he opens up about the pivotal leadership lessons he's learned, the mistakes that shaped the company, and the true challenges of going head-to-head with big tech. We also dive into the highs and lows of fundraising, how valuations can

At the absolute most basic, Dropbox is cloud storage for your stuff — but that puts it at the nexus of a huge number of today’s biggest challenges in tech. As the company that helps you organize your stuff in the cloud itself goes all remote, how do we even deal with the concept of “your stuff?” Today I’m talking with

Block CFO Amrita Ahuja discusses the company’s earnings, cash app growth, and how worked it with regulators about the issues raised in a short seller report around its verification and compliance programs. Plus, Dropbox CEO Drew Houston says AI played a role when it cut 16% of its workforce last week, but warns that “r