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

This Week In Startups is made possible by: Northwest Registered Agent - https://www.northwestregisteredagent.com/twist Circle - https://circle.so/twist Netsuite - https://www.netsuite.com/twist 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 Subscribe to the TWiST500 newsletter: https://ticker.thisweekinstartups.com Check out the TWIST500: https://www.twist500.com Subscribe to This Week in Startups on Apple: https://rb.gy/v19fcp Follow Lon: X: https://x.com/lons Follow Alex: X: https://x.com/alex LinkedIn: ⁠https://www.linkedin.com/in/alexwilhelm Follow Jason: X: https://twitter.com/Jason LinkedIn: https://www.linkedin.com/in/jasoncalacanis Check out all our partner offers: https://partners.launch.co/ Great TWIST interviews: Will Guidara, Eoghan McCabe, Steve Huffman, Brian Chesky, Bob Moesta, Aaron Levie, Sophia Amoruso, Reid Hoffman, Frank Slootman, Billy McFarland Check out Jason's suite of newsletters: https://substack.com/@calacanis Follow TWiST: Twitter: https://twitter.com/TWiStartups YouTube: https://www.youtube.com/thisweekin Instagram: https://www.instagram.com/thisweekinstartups TikTok: https://www.tiktok.com/@thisweekinstartups Substack: https://twistartups.substack.com