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

Founder Matthew Rabinowitz opens up about the intensely personal journey that set him on a course to revolutionizing healthcare. A PhD in electrical engineering, he had no background in genetics or biology, but after his sister had a baby with Down syndrome that hadn’t been detected and tragically died after 6 days, Matthew dedicated himself to solving this problem. After overcoming seemingly impossible obstacles, today Natera leverages molecular biology and novel bioinformatics technology to provide prenatal screening in nearly half of U.S. pregnancies, as well as transforming oncology and organ transplants. Hear about Matthew’s vision for the future of computational biology and its profound impact on human health.

Host: Roelof Botha, Sequoia Capital

Featuring: Matthew Rabinowitz, Jonathan Sheena, Steve Chapman, Chitra Kotwaliwale, Sarah Elliot

Tony Xu and Miki Kuusi share insights from building two of the world's most successful delivery platforms—DoorDash and Wolt—which merged in 2022 to create an $80B GOV business operating in 32 countries. In this candid conversation with Sequoia's Alfred Lin live at a Sequoia event in Europe, they discuss the challenges of scaling operational excellence, maintaining culture through hypergrowth and the future of commerce in cities.

Host: Alfred Lin, Sequoia Capital

Featuring: Tony Xu, Miki Kuusi

DoorDash faced skeptics from the start. Grubhub, Delivery.com, and others were already addressing the restaurant delivery market when CEO Tony Xu and his co-founders started in 2013. But after talking to hundreds of local small businesses, they realized there was still an unmet need: None of the competitors solved the problem of delivery with an on-demand workforce, the way Uber had done with drivers. After struggling to raise initial funding, DoorDash found traction. But the next few years would prove tumultuous, with cash scarcity and investor skepticism putting the company perilously close to the brink. The founders’ contrarian decisions, clarity on their commitment to serve small local businesses, and ability to out-operate competitors has turned DoorDash into one the decade’s startup success stories. In this episode, Tony brings us inside their decision-making, and what DoorDash saw that others missed.

Host: Roelof Botha, Sequoia Capital

Featuring: Tony Xu, Keith Yandell, Miki Kuusi, Alfred Lin

The biggest enterprise software company to come out of Europe in the last decade didn’t come from London, Paris, Berlin or Stockholm—but Bucharest, Romania. 

UiPath, founded in 2005 and originally called DeskOver, was a scrappy handful of engineers bootstrapping out of an apartment in Bucharest for about a decade, seeking in vain for product-market fit. When they stumbled upon an opportunity in the nascent enterprise software category of Robotic Process Automation, the company did a hard pivot, changed their name to UiPath, and rocketed from obscurity to the fastest-growing SaaS company ever at the time. After a successful IPO, today they are the global category leader in RPA. The unlikely rise of UiPath is an inspiration and a reminder that you can build something great from anywhere. 

Host: Roelof Botha, Sequoia Capital

Featuring: Daniel Dines, Andra Ciorici-Chelmus, Brandon Deer, Luciana Lixandru 

Reddit is one of the largest and most culturally influential sites on the internet—and its journey is one of the most unusual company stories in internet history. College roommates Steve Huffman and Alexis Ohanian founded Reddit in 2005 and scaled it on a shoestring until Condé Nast acquired it the following year. Struggling for direction under its parent company, the founders left, and Condé Nast ultimately spun it out as an independent company once again. With Reddit buckling under user discontent in 2015, founder Steve Huffman returned as CEO to save the company and navigate the way forward. Over the following nine years, Reddit stabilized and the company’s revenue grew more than 50-fold to a successful IPO 19 years in the making.

Host: Roelof Botha, Sequoia Capital

Featuring: Steve Huffman, Alexis Ohanian, Chris Slowe, Jen Wong, Alfred Lin

MongoDB, founded in 2007, originally aimed to create a platform-as-a-service system with a new database layer. Facing competition from Google, the founders pivoted to focus solely on their database product, MongoDB—a new kind of database built for the scale of the internet era. Founder Dwight Merriman built a product that developers loved, but scaling the company proved challenging until Dev Ittycheria took the reins as CEO in 2014. As cloud computing grew, MongoDB transitioned from on-premise software to Atlas, a fully-managed cloud service. Despite initial skepticism, Atlas now represents 70% of MongoDB's revenue. As Atlas scaled, MongoDB faced another controversial decision: whether to change its open source license model to maintain its commercial moat. These pivotal decisions transformed MongoDB from a niche database to nearly $2 billion in annual revenue.

Host: Roelof Botha, Sequoia Capital

Featuring: Dwight Merriman, Dev Ittycheria and Tom Killalea

Transcript: https://www.sequoiacap.com/podcast/crucible-moments-mongodb/

00:00 - Cold Open

00:19 - Introduction

05:30 - The NoSQL movement

09:52 - Scrapping the platform for the database

14:57 - Launching as MongoDB

19:52 - Moving to the cloud with Atlas

24:52 - Assigning a directly responsible individual

30:15 - How Atlas changed MongoDB

35:03 - Updating the licensing model to avoid “strip mining”

39:50 - Evolving back into a platform

41:26 - Executing on points of leverage