Drew Houston

Co-founder and CEO of Dropbox, which he started in 2007 after forgetting a thumb drive on a trip to New York. Built Dropbox through Y Combinator (Paul Graham as early backer), raised from Sequoia, and grew it to $4B valuation within four years via viral referral loops and shared folders. Navigated a near-existential competitive period (2015–2019) as Apple, Microsoft, and Google launched competing products, then led a turnaround centred on distributed work and Dropbox Dash (universal AI search). Took Dropbox public in 2018.

Episodes

• Drew Houston on Dropbox, Founder Mode, and the Three Eras of Building — Lenny’s Podcast