Stubbornness Carried Zipline Into an $8B Era

Keller Cliffton and Jason Calacanis discuss investor doubt, hardware pain, bold decisions, rewriting history, and Zipline's recent fundraising momentum.

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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