Crucible Moments

A scrappy upstart taking on hyperscalers in a category with lots of hand-wavers, Dropbox became the canonical example of Silicon Valley viral growth, adding 50 million users in the first years following their 2008 launch and quickly dominating their category. However, as CEO Drew Houston explains, their path from viral sensation to enduring business was filled with daunting obstacles. As giants released competing products and tried to crush them, Dropbox embarked on a set of strategic acquisitions to expand its product line—but failed to find product-market fit with the new offerings. What do you do when your idea for your second act doesn’t work like you hoped? Drew describes the insights that led them to strategically re-focus on work use cases for their core product, and the other moves that would re-ignite growth and turn the company profitable. In a counterintuitive bet, the cloud innovator would end up migrating off of cloud infrastructure to its own servers in order to be more cost-efficient. This engineering feat, called Magic Pocket, became the stuff of Silicon Valley engineering lore. Drew and engineering leaders Akhil Gupta and James Cowling recount the story of how they pulled it off. Host: Roelof Botha Featuring: Drew Houston, Arash Ferdowsi, Sujay Jaswa, Akhil Gupta, James Cowling, Bryan Schreier

Earlier this season we heard the startup story of ServiceNow—from Fred Luddy setting out to reinvent IT workflows as a first-time founder, to Frank Slootman joining as CEO to scale the business to an IPO. Even more remarkable is that ServiceNow has only accelerated as a public company, growing over ten-fold in the last decade. At a recent closed event in Europe, Sequoia partner Pat Grady spoke with ServiceNow’s current CEO Bill McDermott, who took the reins in 2019. This conversation was recorded in September, 2024 when ServiceNow’s market cap was $125B—today that number has grown to $225B. Their conversation sheds light on ServiceNow’s journey to becoming one of the world’s largest software companies, with over $10 billion dollars in annual revenue, and how Bill’s unrelenting focus on elite level execution is key to the company’s continued success. Featuring: Bill McDermott, ServiceNow; Pat Grady, Sequoia Capital

Millions of Americans use their smartphones to invest and manage their finances every day—but before Robinhood started in 2013, finance looked very different. Investing was something for the wealthy, with steep fees charged on every trade, and was done exclusively on computers with arcane trading software. In this episode, co-founder and CEO Vlad Tenev explains why Robinhood set out to democratize access to investing and reinvent it for a new generation, how it overcame immense challenges in that pursuit, and how it reinvented itself amid a market downturn with a holistic suite of customer offerings to mount an historic comeback.    Host: Roelof Botha, Sequoia Capital Featuring: Vlad Tenev, Micky Malka, Andrew Reed, Jason Warnick

This episode takes us back to the earliest days of YouTube, as the founders explain why it was a longshot that succeeded against all odds. When cofounders Steve Chen, Chad Hurley and Jawed Karim left PayPal to start YouTube, it wasn’t even clear that the nascent broadband infrastructure could support playing video in a browser. In a brief period until its acquisition by Google—from its first incarnation as a video dating site to confronting daunting technical and legal challenges—the early story of YouTube is an underdog tale of scrappy upstarts who ended up changing the world.  Host: Roelof Botha, Sequoia Capital Featuring: Steve Chen, Jawed Karim, Zahavah Levine, Colin Corbett, Yu Pan