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This Week in Startups

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

This Week in Startups

Jason Calacanis

Technology

4.21.4K Ratings

🗓️ 20 March 2026

⏱️ 99 minutes

🧾️ Download transcript

Summary

This Week In Startups is made possible by:

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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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Transcript

Click on a timestamp to play from that location

0:00.0

If you live outside of a city center, you're going to be getting your burritos and your milk and coffee and your Starbucks delivered to you by a quadcopter in under five minutes in all likelihood.

0:12.4

So please join me in welcoming Keller Clifton from Zipline.

0:17.9

All right, I'm a man.

0:26.0

This Week in Startups is brought to you by NetSuite. The business landscape is very chaotic right now.

0:28.9

That's why you need NetSuite by Oracle.

0:31.2

Get the free business guide, demystifying AI at netsuite.com slash twist.

0:36.6

Circle. The easiest way to build a home for your community,

0:39.8

events, and courses, all under your own brand. Twist listeners get $1,000 off the Circle Plus plan by going

0:47.3

to circle.s slash twist and Northwest Registered Agent. Get more when you start your business

0:53.7

with Northwest.

0:54.8

In 10 clicks in 10 minutes, you can form your company and walk away with a real business identity.

1:00.0

Learn more at Northwest Registeredagent.com slash twist.

1:06.5

I was just thinking, when did you start, and I know you started in Africa delivering blood and medicine, on fixed-wing airplanes?

1:14.6

Yeah?

1:15.6

Yeah, we, I started the company technically in 2011. I was a year out of college.

1:20.6

We really started building everything that became Zipline in 2013.

1:23.6

You know, we had this simple idea, which was you should be able to build an automated logistics system that could serve all people equally.

1:29.3

We felt like robotics would allow us to build a new kind of logistics system that could be ten times as fast, half the cost, zero emission.

1:37.3

You know, logistics really only serves the golden billion people on Earth well.

1:41.3

So, you know, we can afford to pay Dordash like $15. You're basically like private taxi for your burrito, private car for your burrito. But, you know, in reality, we always felt like the most exciting thing about automating logistics was to make it something that could be universally accessible, that people could use like multiple times a day no matter where you live. For a lot of people in the room who might be starting their own companies or I've already started their own companies. It's 100% of the room. Okay. Awesome. Yeah. I mean, you know, I like, you know, we would talk to investors about this idea and and they'd be like, oh, okay, but isn't this illegal in the U.S.? And we'd be like, yeah, it is. And they'd be like, I think we'll pass.

2:17.7

And it was not only that, but they were like, well, what is your background in this? Like, do you guys know anything about logistics? Do you know anything about health care? Do you know anything about aviation? And we were like, no, we don't know anything about any of those things. And I have this flag over my desk that says, We do this not because it is easy, but because we thought that it would be easy.

2:37.0

And this is definitely like, you know, the definition of Zipline

...

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