In 2014, Keller Cliffton made an audacious pivot: shut down his robotic toy company and rebuild it as an autonomous drone delivery system for life-saving medical supplies. Investors were skeptical: The team knew nothing about drones, healthcare, or logistics. But they pushed forward anyway. This is the story of Zipline's journey from near-death to delivering blood to remote hospitals in Rwanda, battling volatile weather and regulatory hurdles, and eventually becoming a global leader in autonomous delivery: This year Zipline began delivering household items directly to front doors with its new Platform 2 in the US for the likes of Walmart and Chipotle. From fixing broken launchers at 3 AM before the Rwandan president's visit to winning unprecedented FAA approval, Zipline's founders bet everything—multiple times—on their vision.

Their story proves that if you just keep going, even when everyone's written you off, you can build something truly transformational.

Host: Roelof Botha, Sequoia Capital

Featuring: Keller Cliffton, Keenan Wyrobek, Ryan Oxenhorn, Maggie Jim, Alfred Lin

Previously on Crucible Moments, we explored the inflection points that shaped some of the most significant names in technology. Now, we're returning for a brand new season. Join us as leaders from Stripe, Zipline, Palo Alto Networks, Klarna, Supercell and more share what it's actually like to navigate the make-or-break decisions, early stumbles and leaps that turn scrappy startups into market defining forces.

Hosted by: Roelof Botha, Sequoia Capital

When Nubank started 10 years ago, a few big banks in Brazil had a stranglehold on the largest economy in Latin America: they controlled nearly all the market share, and imposed some of the highest fees and worst banking terms in the world. David Vélez was an unlikely character to challenge the system: an outsider from Colombia and Costa Rica with a Stanford MBA, David was working at Sequoia with the goal of investing in Latin American companies. When the realization struck that they couldn’t find any companies they wanted to invest in, David set out to start one himself. What followed is a literal David vs. Goliath story of epic proportions. David and co-founders Cristina Junqueira and Edward Wible explain how Nubank survived competitors' attempts to crush them, and became the largest Latin American neobank, with over 100 million customers across three countries.

Host: Roelof Botha

Featuring: David Vélez, Cristina Junqueira, Edward Wible, Doug Leone

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