The Drone Company Everyone Thought Was Illegal (Now Worth $4B+) | E2265

The Drone Company Everyone Thought Was Illegal (Now Worth $4B+) | E2265

Author: Jason Calacanis March 21, 2026 Duration: 1:38:38

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Today’s show:

Zipline founder Keller Cliffton started his company with a simple premise: build automated logistics that serve everyone equally. The only problem? It was literally illegal in the US.

In this live recording from LaunchFest in San Francisco, Keller shares how Zipline went from a 20-person team working on a cow farm in Rwanda to operating the largest commercial autonomous system on Earth. They now complete 130 million autonomous miles with zero accidents, while reducing maternal mortality by 51% in the regions they serve.

PLUS we’ve got Rahul Vohra from Superhuman taking us through his entire founder journey, and discussing with Jason why “difficult” founders are often the smartest investments.

Timestamps:

0:00 Intro

1:16 Keller Cliffton starts off the show

3:05 Starting Zipline in Africa

8:40 The magic of sky maps

13:55 Building the drone was just the beginning

15:11 Making a huge difference in maternal mortality

23:48 The threats of Little Evil Jimmy and dogs

29:37 The shift from Rwanda to Dallas

31:14 Netsuite - Get the free business guide Demystifying AI at https://www.netsuite.com/twist

32:28 The moral clarity of the mission

41:17 The challenge of staying focused

46:43 Rahul Vohra of Superhuman joins Jason

49:40 Building Rapportive in Cambridge

51:48 Scaling to millions of users via APIs

1:11:46 How getting acquired made Rahul fearless

1:12:31 The boldness of taking on Gmail

1:22:12 Making everyone pay for the product

1:31:24 Inside the Grammarly-Superhuman deal

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Great TWIST interviews: Will Guidara, Eoghan McCabe, Steve Huffman, Brian Chesky, Bob Moesta, Aaron Levie, Sophia Amoruso, Reid Hoffman, Frank Slootman, Billy McFarland

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Every week, Jason Calacanis dives headfirst into the swirling vortex of Silicon Valley and global tech with This Week in Startups. It’s a direct line to the conversations shaping our digital future, moving far beyond surface-level news. You’ll hear Jason’s unfiltered analysis on everything from market shifts and media trends to the underlying mechanics of building a business, all delivered with a blend of enthusiasm and seasoned skepticism. The core of this podcast, however, lies in the guests. Jason sits down with the very people driving change-founders who have scaled impossible heights, operators managing daily chaos, and investors who spot trends before they become obvious. These conversations are less like formal interviews and more like insider debriefs, pulling back the curtain on real strategies, painful failures, and unexpected successes. For anyone curious about how technology is built, funded, and ultimately changes the world, this series offers a front-row seat. It’s the context behind the headlines, providing a deeper understanding of the forces at play in startups and technology. Tune in for a consistently engaging and insightful look at the ecosystem, straight from someone who lives and breathes it.
Author: Language: en-us Episodes: 100

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