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

Summary

This live LaunchFest recording in San Francisco features two in-depth founder interviews. First, Zipline founder Keller Cliffton shares the remarkable story of building the world’s largest commercial autonomous delivery system, which started illegally in the US and launched in Rwanda delivering life-saving blood transfusions. Zipline has now completed over 130 million autonomous miles with zero accidents, reduced maternal mortality by 51% in served regions, and is expanding into consumer deliveries in Dallas with its new quadcopter platform capable of delivering anything from burritos to prescriptions in under five minutes.

The second half features Rahul Vohra, founder of Superhuman, who discusses his entrepreneurial journey from building Rapportive (a Chrome extension with millions of users that was acquired by LinkedIn) to taking on Gmail with a premium email product. Vohra explains the counterintuitive strategy of charging $30/month for email when Gmail is free, the power of concierge onboarding every single user, and the recent acquisition by Grammarly — connecting how the company name “Superhuman” actually came from a chance encounter at a hackathon years before the company existed.

Jason Calacanis moderates both conversations with Rahul Vohra serving as co-interviewer for the Zipline segment, drawing out powerful lessons about finding the right initial customer, persevering through years of skepticism, and why “difficult” founders who pursue non-consensus ideas often create the most valuable companies.

Highlights

”We do this not because it is easy, but because we thought that it would be easy”

“We would talk to investors about this idea and they’d be like, oh, okay, but isn’t this illegal in the US? And we’d be like, yeah, it is. And they’d be like, well, I think we’ll pass.” — Keller Cliffton, 1:20

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51% Reduction in Maternal Mortality

“Every like expert that we spoke to told us this idea was stupid. Most of Zipline’s existing investors told us this idea was stupid… And what’s crazy is that just over the last couple weeks, there’s a new statistic that came out. The University of Pennsylvania did this huge multi-year study of hospitals served by Zipline and found a 51% reduction in maternal mortality.” — Keller Cliffton, 13:23

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130 Million Miles, Zero Accidents

“Zipline just crossed 130 million commercial autonomous miles. It’s now the largest commercial autonomous system on earth. If you were to drive 130 million miles, you would have 600 accidents, 100 injuries, and two fatalities… Zipline has done 130 million commercial autonomous miles, zero accidents, zero injuries, zero fatalities. This is the promise of AI and robotics.” — Keller Cliffton, 12:00

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Blood Delivered to the Roof

“We delivered blood to the roof of a hospital… one of the nurses like climbed up onto the roof, across this like super dangerous roof, got it, brought it downstairs, and they transfused into the patient 10 minutes later.” — Keller Cliffton, 5:18

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Taking on Gmail with Superhuman

“Well, we want to take on Gmail.” — Rahul Vohra, 1:11:18

“I said, ‘Okay, big target, love it. How are you going to beat Gmail?’” — Jason Calacanis, 1:11:22

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Pricing Is the Product

“Not just value for value, like folks pricing is the product as well. It is a flag in the sand that says this is going to be the best goddamn email app you’ve ever used.” — Rahul Vohra, 1:24:20

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Key Points

• Zipline founded in 2011 (0:29) - Keller Cliffton started company a year out of college with the idea of automated logistics serving all people equally
• Started in Rwanda (1:20) - Went to Rwanda because the US wouldn’t grant regulatory permission; focused on blood delivery for postpartum hemorrhaging
• Minister of Health said “just do blood” (3:19) - Rwanda’s Minister of Health focused Zipline on the right use case: blood transfusions for mothers
• Sky Map visualization (7:53) - Real-time map showing 50+ autonomous aircraft flying simultaneously across Rwanda, often mistaken by investors as a simulation
• Individual aircraft flew 1M+ miles (11:07) - Single Zipline aircraft have flown more than a million miles autonomously, lasting longer and costing less than cars
• 130M autonomous miles, zero accidents (12:00) - Zipline is now the largest commercial autonomous system on Earth with a perfect safety record
• 51% reduction in maternal mortality (13:23) - University of Pennsylvania study found hospitals served by Zipline saw a 51% drop in maternal mortality
• Platform 2 quadcopter for US (19:42) - New droid system designed for consumer deliveries in the US, already operating in Dallas
• Dog and “Little Evil Jimmy” challenges (23:01) - Designing delivery systems that can withstand children and animals trying to interfere
• Dallas operations expanding (28:50) - Zipline shifting from Rwanda to US operations, now delivering in Dallas area
• Focus as competitive advantage (40:31) - Keller argues doing one thing well is Zipline’s greatest advantage over diversified competitors
• Rahul Vohra’s Rapportive (48:53) - Built a Chrome extension that grew to millions of users by showing LinkedIn info in Gmail
• Chrome extension as alpha (52:23) - Rahul’s insight: when you see a big product and surrounding dross, you can build the big thing yourself
• LinkedIn acquisition (1:04:28) - Rapportive was acquired by LinkedIn; initial offer was “terrible” but the deal gave Rahul fearlessness
• Superhuman founding (1:07:28) - After selling Rapportive, Rahul somewhat irrationally decided to take on Gmail with a premium email product
• Concierge onboarding every user (1:21:42) - For 2-3 years, Superhuman one-on-one onboarded every single new customer
• Grammarly acquisition (1:30:29) - Superhuman was acquired by Grammarly; the deal started from a chance encounter years earlier

Mentions

Companies

• Zipline (0:00) - Autonomous drone delivery company, largest commercial autonomous system on Earth, $4B+ valuation
• Superhuman (45:57) - Premium email client, acquired by Grammarly
• Grammarly (1:30:29) - Acquired Superhuman; CEO Shishir named Grammarly after meeting Rahul at a hackathon
• LinkedIn (1:04:28) - Acquired Rapportive; Rahul was at LinkedIn for 2 years post-acquisition
• Rapportive (48:53) - Rahul’s first company, Chrome extension showing LinkedIn info in Gmail
• DoorDash (0:29) - Referenced as example of expensive last-mile delivery
• Instagram (13:23) - Referenced as what investors preferred over hardware startups
• Toyota (7:16) - Partner with Zipline in Japan serving the Goto Islands
• Rivian (33:54) - Referenced as example of growth trajectory and valuation challenges
• Coda (1:34:58) - Shishir’s company; Rahul was an angel investor

Products & Technologies

• Platform 1 (7:16) - Zipline’s original fixed-wing delivery aircraft launched in 2016
• Platform 2 (19:42) - Zipline’s new quadcopter/droid system for US consumer deliveries
• Sky Map (7:53) - Real-time visualization of all Zipline autonomous flights
• Chrome Extensions (51:17) - Platform Rahul leveraged for Rapportive; became a theme in his career

People

• Keller Cliffton (0:00) - Founder of Zipline, started company at age 22
• Rahul Vohra (45:57) - Founder of Superhuman, previously built Rapportive
• Alfred Lin (13:23) - Sequoia partner, early Zipline board member who was skeptical of the Africa pivot
• Eric Schmidt (1:15:48) - Former Google CEO; Rahul discussed email strategy with him
• Dharmesh Shah (46:43) - HubSpot co-founder, has deal with Rahul to see ideas first
• Shishir Mehrotra (1:34:58) - CEO of Coda/Grammarly, met Rahul at a hackathon years before the acquisition

Surprising Quotes

“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.” — Keller Cliffton, 1:20

“She was like, ‘Keller, shut up. Just do blood.’” — Keller Cliffton, 3:19

“Your Yelp review was three stars. ‘We got the blood, but we had to risk our lives to get it hanging off the side of the roof.’” — Rahul Vohra, 6:43

“The acquisition gave me an incredible fearlessness. It was like five, six, seven, eight years of me never having to work.” — Rahul Vohra, 1:06:00

“Pricing is the product as well. It is a flag in the sand that says this is going to be the best goddamn email app you’ve ever used.” — Rahul Vohra, 1:24:20

Transcript

Jason Calacanis: 0:00 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. So please join me in welcome, welcoming Keller Cliffton from Zipline.

Rahul Vohra: 0:20 I was just thinking, when did you start? And I know you started in Africa delivering blood and medicine on fixed-wing airplanes, yeah?

Keller Cliffton: 0:29 Yeah, we, I started the company technically in 2011. I was a year out of college. We really started building everything that became Zipline in 2013. 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. We felt like robotics would allow us to build a new kind of logistics system that could be 10 times as fast, half the cost, zero emission. You know, logistics really only serves the golden billion people on Earth well. So, you know, we can afford to pay DoorDash like 15 dollars, basically private taxi for your burrito, private car for your burrito. But 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 have already started their own…

Jason Calacanis: 1:17 100 percent of the room is entrepreneurs.

Keller Cliffton: 1:20 Awesome. Yeah. I mean, you know, I like, you know, we would talk to investors about this idea and they’d be like, oh, okay, but isn’t this illegal in the US? And we’d be like, yeah, it is. And they’d be like, well, I think we’ll pass. You know, and it was not only that, but they were like, well, what is your background in this? Like, do you, you know, do you guys know anything about logistics? Do you know anything about healthcare? 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. And this is definitely like, you know, the definition of Zipline and probably a lot of the, you know, entrepreneurship in these kind of like harder, crazier ideas. It’s like, we were so naive about all the things that were going to be incredibly difficult about building an automated logistics system across Africa, which is where we started. But we needed to go to where we could get regulatory permission quickly. So we went to the country that would give us regulatory permission as a 20-person startup that had no experience, that was Rwanda. We focused on a use case that was like the most important life-saving use case that we could imagine, which was delivering blood transfusions to moms with postpartum hemorrhaging. We, you know, they gave us 20 hospitals and told us to go for it. And that’s what we did in 2016.

Rahul Vohra: 2:33 Yeah, and you think about it. You’ve, you’ve picked an ideal customer who was willing to take the risk because the payoff was so high. Yeah. And that’s really one of the great arts of being an entrepreneur. You have to find a customer who needs your product and it’s life and death. Now when you’re talking about a SaaS product or a marketplace, it’s hyperbolic to say life or death. Yeah. But the stronger the need, the stronger…

Jason Calacanis: 3:00 The more they would be willing to bend the rules or take a chance and you found the ultimate one which was literal life or death and for moms which if you don’t approve this idea you’re literally saying you want moms to die in childbirth it’s like you have no choice but to accept this idea because there’s no other solution.

Keller Cliffton: 3:19 Yeah, maybe and you know I think two things one we weren’t smart enough to find that use case it was actually the customer you know I remember this meeting with the Minister of Health in Rwanda you know I didn’t even like own a suit at the time so I’m like showing up in a hoodie to like meet this Minister of Health and you know I was talking to her about automated logistics and using robotics to deliver and I just remember she was like Keller shut up just do blood. Like she was like look 50 percent of blood transfusions are going to our moms 30 percent are going to our kids we’ll give you 21 hospitals this is like a total nightmare for us managing the blood supply you have you know people think of blood as one thing but you actually have platelets cryoprecipitate plasma packed red blood cells different storage requirements and shelf lives for each of those platelets only last six days for example and and you also have types A B AB and O positive and negative RH factor so it was a really difficult thing for them to do logistically they gave us these 21 hospitals she was the one that kind of like focused us on the right use case. The other idea that I think is very similar to what you’re saying it’s not it wasn’t just critical for us like their level of desperation was high enough that they were willing to accept a very MVP level of our product like when we initially launched it was so painful we had no idea what we were doing we thought we had designed this cool vehicle it turns out the vehicle’s only like 15 percent of the complexity of what we had to figure out like they were handing us all these precious blood commodities where were we going to put them you know how do you maintain inventory I mean we literally got a shipping container we ordered a bunch of Helmer fridges you know we were having to figure out how to build new software to even do inventory management for these critical medical products we had to figure out how to do maintenance on the aircraft scheduled and unscheduled we had to figure out how to get regulatory permission and build an unmanned traffic management system to provide it to the regulator like there was so much of this auxiliary software that Zipline had to build in a totally desperate kind of slapdash way realizing what was required to do it. And I remember you know we would we literally pulled all-nighters for weeks on end it stretched over nine months where we were only serving one hospital because we we weren’t going to roll out more hospitals until we had the first one working and it took us nine months to get that first hospital working reliably and I remember getting woken up in the middle of the night it’s probably like nine or ten months in and it was like Gladys our fulfillment operator and she was like hey I’ve got bad news and I’m like well yeah it’s 2 a.m. my time and she was like we delivered blood to the roof of a hospital it was like this life-saving blood transfusion we were supposed to be delivering and we were always supposed to deliver it very precisely that was a big part of the service like deliver it precisely into their mailbox we’d delivered it onto the roof. And I was like oh my god how’d that happen how could the guidance navigation be off by that much like we’d missed by you know a hundred feet there was a bug in the code we immediately woke up Ryan my co-founder and Eric and like… bunch of others at Zipline and, uh, you know we worked like from 2:00 a.m. to 6:00 a.m. trying to fix it, trying to figure out what had gone wrong, like issue a new software update to the vehicles, got back on the glass, we think we solved the problem. By the way, what happened to the blood?

Jason Calacanis: 6:12 Hmm.

Keller Cliffton: 6:13 And she was like, “What do you mean?”

Jason Calacanis: 6:14 I was like, “What do you mean?”

Keller Cliffton: 6:15 I was like, “Well, like, is it—you know, is it still up there on the roof, like, baking in the sun?” She’s like, “Oh no, no… like, a—one of the nurses like climbed up onto the roof, across this like super dangerous roof, got it, brought it downstairs, and they transfused into the patient 10 minutes later.” And I remember thinking like, “Wow, you know, like we totally fucked up and our customer really met us like more than halfway on this one,” which is like the power of choosing the right use case. It’s like we had, you know, we caught it like—

Rahul Vohra: 6:43 And your Yelp review was three stars. “We got the blood, but we had to risk our lives to get it hanging off the side of the roof.”

Jason Calacanis: 6:52 And you’re like, “Spent the next couple of years trying to get that three-star review on Yelp—”

Keller Cliffton: 6:57 Up to five stars.

Jason Calacanis: 6:58 Up to five stars. But people who maybe haven’t seen it, this was a fixed-wing in—

Keller Cliffton: 7:00 Yeah, let’s show—let’s actually show a video so we—people can quickly see. We have a couple of quick videos.

Jason Calacanis: 7:03 Great.

Keller Cliffton: 7:04 So, you know, first of all, I’ll just show you guys because people always think of drone delivery as this like, “Oh, it’s, you know, it’s science fiction, it’s probably not real, it’s definitely not at scale.” So let me—we’ll just kind of give you guys a sense what the scale looks like.

Jason Calacanis: 7:14 This is the fixed wing in Africa.

Keller Cliffton: 7:16 Yeah, so this is—we call it Platform 1. This is what we launched in 2016. You know, the system operates—we build these distribution centers. They have launchers and recovery systems. This is actually in Japan where you see where we operate serving the Goto Islands with Toyota. And then this is cool. So this is, you know, midnight, middle of the night at one of our distribution centers. You can see how busy the team is. You know, this is now 2:00 a.m. This is fulfillment operations. So what I was describing where you’re packing loading blood, now vaccines, cancer products, infusions, transfusions, everything. Uh, this is the second distribution center in Rwanda. You can see the aircraft there on the launcher. It’s launching, but it’s just happening too fast. Second fulfillment center in Rwanda. You can see it’s now about 7:00 a.m. And this is the cool part. This is the Sky Map. So every one of—this is the entire country that you’re looking at here. Every one of these triangles is a—is an autonomous aircraft flying itself out to deliver to all these different hospitals and health facilities in the country. Every time one of those blue dots appears, that’s like a life-saving emergency order that’s being placed with Zipline. We can typically have a vehicle launched delivering to that site within two or three minutes. You can see at 10:00 a.m. there are 50 aircraft out making deliveries simultaneously throughout the country. Uh, yeah.

Jason Calacanis: 8:24 I—I just saw a blue one zip across wildly. What was that? One went rogue?

Rahul Vohra: 8:29 I—there’s another one right there.

Keller Cliffton: 8:32 Oh, good—good question. Um, so that is our unmanned traffic management system basically recognizing intruder aircraft which the vehicles will look at. So that’s not us, that’s someone else in the airspace.

Rahul Vohra: 8:42 Intruder alert!

Keller Cliffton: 8:43 Hundred percent. But, you know, I took a class like in college about how data travels on the internet. And it was funny, like the first time I saw this Sky Map, I was like, “Wow, like, this is—I mean, we’re creating like a version of the internet, but for real things in the real world.”

Jason Calacanis: 8:54 Yes, these are all Cisco routers moving packets.

Keller Cliffton: 8:57 Exactly. It’s like packets. It’s like packets moving in an automated way. Anyway, the funny thing about this is we would show this to investors like Jason for many of the first years, we’d show them this, and we’d get to the end of the presentation, we’d just show them this sky map and the investors would say like, oh, like the coolest part of your presentation was that simulation of what this could look like one day. And we got so annoyed, it literally so violated people’s concepts of what was possible that they would not believe it. So this is why we now put this CCDV on the right side so people can actually see the teams doing the work, like with the clock, to get a sense for like, this happens in and out. The crazy thing is this video was made about a year ago, we’ve doubled in scale in Rwanda over the last year.

Jason Calacanis: 9:34 Give us an idea of how many miles they’re traveling. I’m watching.

Keller Cliffton: 9:39 So we now have, yeah, this is the, these vehicles will travel, we basically guarantee an 100-mile radius around the distribution center. So these vehicles can fly 100 miles out, 100 miles back, plus we save 100 miles of margin. So if you really wanted to go for it, like, you know, the aircraft in good weather could fly about 300 miles in a round trip, yeah.

Jason Calacanis: 9:57 But these look like these are 50 miles or something on average, 100?

Keller Cliffton: 10:03 Yeah, I think probably on average you’re seeing 50, 70, 80-mile deliveries here.

Keller Cliffton: 11:07 Crazy thing by the way, you know, people also think of these systems as oh, they must be really expensive or they must be very like exquisite, fragile. We have individual aircraft that have flown more than a million miles in their lifetime, fully autonomously. Like I doubt anybody in this room has a car that has driven more than a million miles. You know, it’s kind of counterintuitive, but these systems can actually last a lot longer than cars and they are much more cost-effective.

Jason Calacanis: 11:30 And what would the difference be in Rwanda for driving it? Because they might have backroads that you’re going, they might have mountains. The routes you’re taking are quite literally as the crow flies. So just in terms of some of these missions that are 50 miles away, what would they be in terms of time to drive?

Keller Cliffton: 11:51 Yeah, I mean before, you know, a doctor or nurse at the hospital would typically have to go find a car. If the, so basically there’s a patient who’s having an emergency, they’ll get into a car… drive, find a car hopefully, if there’s a car that’s working or available, they’ll get into that car, drive, you know, an hour to the nearest regional blood transfusion center, wait in line there, fill out a bunch of paperwork, get the product, get back into the car, drive it back. So that’s anywhere from, you know, two to six hours. The roads are often not passable. Rwanda is known as, like, the land of a thousand hills. Just to put like the safety into perspective, you know, Zipline just crossed 130 million commercial autonomous miles. It’s now the largest commercial autonomous system on earth. If you were to drive 130 million miles, you would have 600 accidents, 100 injuries, and two fatalities. That’s, like, on average in the US. In Rwanda, the number would be way higher. And just to, you know, Zipline has done 130 million commercial autonomous miles, zero accidents, zero injuries, zero fatalities. This is the promise of AI and robotics.

Jason Calacanis: 12:54 Amazing, yeah. Let’s give it a round of applause for Zipline. And so you spend half a decade toiling away at this, and then quadcopters become more stable and you say, hey, we’re ready for burritos?

Keller Cliffton: 13:10 Yeah, not quadcopters but like…

Rahul Vohra: 13:16 Wait, quadcopters?

Keller Cliffton: 13:17 One last thing…

Rahul Vohra: 13:21 Some power? What’s that category?

Keller Cliffton: 13:23 Yeah, we call it like a hybrid. Yeah, hybrids. Every like expert that we spoke to told us this idea was stupid. Most of Zipline’s existing investors told us this idea was stupid. You know, I think Alfred Lin, who you know well, has actually kind of like famously said it may have been like, you know, his… so Alfred was already on our board and he stayed on the board, but like, barely, I would say. Like because I think he was like totally not game with this whole new direction of like going to Africa and like focusing on these life-saving use cases. It was so bizarre, it was so confusing, it was so different than anything any other startup at that time. Everyone just wanted to invest in Instagram. So like, what the fuck are you doing in Rwanda, like trying to deliver… none of it made any sense. There was no good analogy for it. And especially we would go talk to experts in global public healthcare or, you know, experts in logistics. Everybody told us there was zero percent chance this would work. You know, we would never get regulatory permission, no one would ever give us a contract, it would never work in the real world, you’d never get the performance we needed, you could never get unit economics to make sense, we would never be able to fly in all weather, you’d never be able to operate 24/7, etc., etc., etc. And even if you could do all those things, like this wasn’t really that big of a problem anyways, is what people would tell us. And what’s crazy is that, you know, just over the last couple weeks, there’s a new statistic that came out. The University of Pennsylvania did this huge multi-year study of hospitals served by Zipline and found a 51% reduction in maternal mortality.

Rahul Vohra: 14:41 Wow, incredible. Yeah.

Jason Calacanis: 14:44 It’s meaningful. And, you know, VCs, and this is no dig to Alfred, but, you know, there is a window in which you have to accomplish tasks, and that gets superimposed upon every founder’s company. And that window is typically 10 years, the life of a fund. And the fund can extend to 12 or 14, but at a certain point, they have LPs they’re servicing, they’re trying to service the founders as well. And you’re on a 20-year timeline for what you’re doing.

Keller Cliffton: 15:10 Yeah.

Jason Calacanis: 15:11 And it’s just, you know, Steve Jurvetson when he did his Future Fund, we had his co-founder here, he decided to tell everybody it’s a 15-year fund and it might go a little bit longer, so full 15. And I think that’s something with real-world tech we’re going to have to get more used to.

Keller Cliffton: 15:27 Totally. I mean, yeah, great point. I mean, you know, I’ve seen all the different stages. I mean, you know, nobody was investing in hardware companies, let alone like robotics companies or autonomous vehicles. I mean, you know, this was like the stupidest thing you could possibly do and uh, you know, but and yet when where from where we sit today, it is so obvious that like the most valuable companies on earth, the companies with the strongest competitive advantages often have these like significant hardware or infrastructure components. You know, you can look at Tesla or SpaceX or, you know, Nvidia, uh, you know, even uh, Google and Microsoft like building massive data centers, they practically like, I mean, they’re spending hundreds of billions of dollars of infrastructure that basically look like, you know, PG&E at this point. It’s crazy. And and it is definitely the case that, you know, I think these hardware companies typically take like a decade. I mean, Tesla and SpaceX case in point, to really get to your first like breakout product that can like hyper-scale. And this is about what Zipline also experienced. But you know, again, like we are right now sitting in this like geo, you know, our parents grew up with the space race. We are now in a new kind of geopolitical race. It is the race for AI and robotics. Every country is trying to leapfrog into the future and be a winner, you know, in this new space. Everybody is going to choose to either build on top of like US technology infrastructure or Chinese technology infrastructure. I think that there is suddenly this incredible, I mean you guys talk about it on the pod all the time, but like there is suddenly this incredibly clear like clarion call in the United States to like we must secure our supply chain, we must build manufacturing capacity, we must be independently able to build all of, you know…

Jason Calacanis: 17:24 Power, compute, applications, robotics, rare earths, logistics, everything. Energy, space, like it is literally democracy versus dictatorships of who can build the most redundant, strongest supply chain. And the idea that, hey, you can mix these two groups together and they would sing in harmony and suddenly the dictators would say, you know what? This is working out so well, we’ll just let people vote.

Keller Cliffton: 17:44 Exactly.

Jason Calacanis: 17:45 It’s not going to happen. So it was a beautiful vision for 20 years. They sold us on globalization and then we realized while free markets want to go to the lowest cost place, you have to take a fully baked price. And one of the prices is your own sovereignty, so when a pandemic happens, there’s not somebody who can say, we have all the syringes and masks and the drugs. Like, all right. So let’s…

Keller Cliffton: 17:59 It’s crazy how much the world has changed. change me in in two senses one in you know when I when we were building Zipline 2013 again we were like the you know we’re like the unpopular kid sitting out in the cold in the rain looking in watching everybody else have like big fun you know birthday parties I mean like the social media companies the apps like SaaS companies beloved by investors oh it’s so capital you know it’s so you know capital efficient and like these companies hyper scale and blah blah blah and these companies you know went to the moon now we’re in the middle of like the SaaS apocalypse or whatever you know everybody’s like really struggling AI’s going to replace all of it like it just kind of goes to show I think the most like transformational companies there is no hype cycle for that company like you are a big investor in Tesla and SpaceX when was like the hype cycle to build an electric car or the hype cycle to build a reusable rocket?

Jason Calacanis: 18:44 And I think when the when Tesla started it was considered that Elon was bankrupting himself it was not acting with any degree of logic and that he was I mean essentially a madman and he was going to drive literally the company the companies off a cliff and like literally he built the future he built the future road as he was building the vehicles on it

Rahul Vohra: 19:02 Yeah we’ll look back on that in some ways as a lost entrepreneurial decade but here we are

Jason Calacanis: 19:07 Talk about the US?

Rahul Vohra: 19:08 Well I wanted to see yeah the version 2 intro because because and then and then I guess there’s an entrepreneurial question embedded in it that we’ll ask after number two comes out which is how do you keep the team and yourself motivated to the North Star when you’re doing something that the world thinks is a waste of time? Or that you’re doing it for you know virtue signaling points

Keller Cliffton: 19:29 Yep.

Rahul Vohra: 19:31 which I think some people kind of put you in that box as well oh virtue signaling just wants to you know he wants to speak at TED or Davos Kumbaya

Keller Cliffton: 19:42 You know quick context as we as we put up this second video like Zipline got to this crazy scale we’re operating across eight countries Zipline saves about 17,000 lives a year now we’ve been able to reduce you know we talked about maternal mortality we also have dramatically reduced missed vaccinations for kids we’ve reduced under five childhood mortality due to severe malnutrition by 85% I mean like the statistics go on and on um turns out the experts were fucking wrong a lot of big companies in the US basically started seeing this and started asking us to uh scale in the US and so this is why we built platform 2 which we launched just last year

Keller Cliffton: 21:22 Platform 2 is a hybrid, so the only reason I was like saying like is definitely not a quadcopter. People think of like quadcopters as the little, you know, drone that weighs five pounds, takes pictures. this aircraft weighs, uh, you know, 60 pounds. Um, it, it hovers but it can also fly in fixed-wing flight. This is the infrastructure that we built next to our partners like a Walmart. This is a Walmart infrastructure. You can see the zip undocking, taking off. It’ll fly directly to one of our partners. In this case, it’s a Wendy’s. This Wendy’s restaurant, by the way, Zipline is now more than 50% of all deliveries from that Wendy’s.

Jason Calacanis: 21:52 Wow.

Keller Cliffton: 21:54 So all the other platforms combined are less than 50%. Zipline is more than 50%.

Jason Calacanis: 21:58 Wow.

Keller Cliffton: 22:00 We use what we call a zipping point here, which is basically a mailbox. They just load the mailbox. As soon as it’s loaded, the zip goes, grabs it out of the mailbox, flies directly to a customer home. When we arrive at the customer home, we can deliver it with like dinner plate level accuracy. We’re using this cute little robot called the droid. That’s the thing you see raising and lowering. The droid controls its position in X and Y axis, um, incredibly accurately. And so, you know, might seem like a crazy solution, but it’s a really big advantage to keep the main aircraft very high. The aircraft’s actually staying a football field up. It’s 100 meters. And we’re lowering the droid 100 meters to make a delivery. The droid is controlling—it’s running, you know, the droid has its own Nvidia GPU, it’s running its full autonomy stack. It even in really strong weather and crazy wind, rain, snow, that droid will deliver hyper-accurately, um, to wherever you tell us every single time.

Jason Calacanis: 22:31 Yeah, and your co-founder was sharing the wind test and how insane your—

Keller Cliffton: 22:39 It’s insane, yeah. We probably should have brought some on that. Go check out Ryan or my, you know, accounts on X, like we’re always posting—I mean, like, these systems operate in insane hail, insane snow, insane wind.

Jason Calacanis: 22:51 Yeah, that’s all very impressive, but I noticed little evil Jimmy decided he was going to try to jump up and touch it. So how do you deal with like little evil Jimmy grabbing onto that and getting sucked up into the copter and dragged away, or is that like the parents’ issue?

Keller Cliffton: 23:03 Well, we only actually like actually picked up a child a couple times and then we we usually return the child like 10 minutes later. Um, so it just hasn’t been that big of a legal issue. As long as as long as we get the kid back to the parents within 15 minutes, it’s generally okay. So it’s worked out.

Rahul Vohra: 23:22 It’s sort of a Pixar movie.

Keller Cliffton: 23:26 No, but like, you know, as long as as long as we get the kid back to the parents within 15 minutes, it’s generally okay.

Jason Calacanis: 23:29 It’s all good.

Keller Cliffton: 23:30 Yeah, so it’s worked out. No, but like, you know, actually the biggest thing is actually not kids. Um, because the droid actually has cameras on board and so if it it basically acts a little bit shy. If there are like people right there like trying to touch it, it will wait and it’ll tell you in the app like please give us a little bit of room. Um, the thing is actually dogs have been the main thing. Sometimes droids do come back with like chunks bitten out of them. We assume it’s dogs. I hope it’s not children.

Jason Calacanis: 23:49 Coyotes.

Keller Cliffton: 23:51 Coyotes. Um, but uh, yeah, so it’s fun. Like it’s an interesting problem. But the real answer to your question is the droid is easy to be left behind. Like we don’t generally do that, but one in every like 10,000 flights, something will happen where we leave the droid behind. We have footage of what happened. So if someone was like messing with it, we’re showing up at your doorstep like three minutes later being like, ‘Where’s that hardware?’

Jason Calacanis: 24:19 Hey. Yeah.

Keller Cliffton: 24:21 So most of our customers, I mean, but to put it in perspective, let’s talk about the customers for a sec. First of all, I kind of thought, ‘Oh yeah, it’s probably going to be all these nerdy, you know, guys who are really into technology.’ Completely wrong. All moms and grandmas basically, who are using the service day in and day out. I was hanging out with an 80-year-old grandma a couple weeks ago who’s ordered from Zipline 350 times in the last year. A lot of our customers are ordering every day. Many of our customers order multiple times a day. The service has a Net Promoter Score of 95. If you ask customers, they’re like, ‘I can get whatever I want, delivered whenever I need it,’ at free delivery as long as they meet certain minimum basket sizes. And they don’t have to tip, which they absolutely love. There’s a huge safety aspect to all of this. Like, I think you and I talked about it, but delivery in the same way that a lot of these platforms where you’re using millions of humans, like stuff goes really wrong. You know, it’s the reason Waymo has an advantage because you’re like, the Waymo isn’t going to sexually assault you. Similar goes for, you know, getting logistics delivered by these robotic systems that are highly predictable and 100% safe. It’s a really big advantage relative to like having a stranger come to your door when your 13-year-old daughter is like receiving a delivery late at night.

Jason Calacanis: 25:46 Yeah. And what’s the requirement to be a Zipline home? Like, how big does my yard need to be, etc.?

Keller Cliffton: 25:53 So let’s actually show the third video. It’s a perfect transition. So we just take you to the other crazy thing that’s happening here. All of this is happening through the Zipline app. And so we’ve now added all these amazing partners like Walmart and Chipotle and Buffalo Wild Wings. We just launched Blaze Pizza. Last week we launched QuikTrip and Hawaiian Brothers. A bunch of amazing new brands. HEB is launching in the next couple weeks. And all of this is happening through the Zipline app. So you basically download the app, and the first thing you do is you’ll type in your address. When you type in your address, we will immediately show you a satellite image of your home. And then you get to select wherever you want us to deliver.

Rahul Vohra: 26:18 That feels pretty wild. It’s pretty magical.

Keller Cliffton: 26:21 It also means we can deliver to your backyard, we can deliver to way more secure locations. You don’t have to like get changed out of your pajamas to meet some random human at your front door. So here the customer’s basically getting to pick a couple different areas. Once you set that, then we will always 100% of the time deliver to that exact location. See all the different awesome brands that are available on the app and order whatever you want. Today we can deliver up to six and a half pounds. We’ll be at 10 pounds by the end of this year. Yeah, I mean, you know, that you can deliver basically like 95% of things that are people are ordering via quick commerce in this way. Walmart as our biggest partner today, you know, there are about 100,000 SKUs in a Walmart Supercenter, we deliver 80 to 90,000 of them. So people are ordering birthday cakes, rotisserie chickens, we can put two rotisserie chickens in a droid. They’ll order like an attachment piece for a garden hose, they’ll order flowers for Valentine’s Day, they’ll order like a couple sets of Legos. You can literally get everything delivered like this.

Rahul Vohra: 27:33 And because the hybrid, not a quadcopter but the hybrid bird is up there, the noise is up there, not down here.

Keller Cliffton: 27:41 Yes.

Rahul Vohra: 27:42 Yes.

Keller Cliffton: 27:42 Yeah, I mean, we think that noise is like a tremendously important part of the design of these systems. You know, we won’t name names, but like there is a very big company in Seattle trying to build drone delivery, they’ve been spending a billion dollars a year and you know they are getting like- not only have they had many, many safety problems with the FAA where they’ve sent people to the hospital, they’ve had crashes, but also noise. Like you know, if you build a system that is incredibly annoying and loud, neighbors are going to protest and neighborhoods are going to rise up against you. That is what we are seeing with some of these other technology platforms. When people think of drones, they think of a super freaking annoying sound, like nobody likes the sound of a drone. And so Zipline has a large team of aerodynamicists and aeroacoustics experts who are totally focused on designing the entire powertrain to be as quiet as possible, and then the overall design and that’s like, you know, we design a propeller completely from scratch, we design a motor completely from scratch, we control the vehicle in very specific ways to reduce the amount of noise and then we also keep the vehicle really far away, like a football field away from your house when we’re delivering to make sure that the system is generally like silent, yeah, or as close to quiet as possible.

Jason Calacanis: 28:52 How many years did you spend in Rwanda versus in Dallas, just if you were to, you know, sort of take the two eras of the company, and then how do you keep the team motivated during those years? I mean, obviously, it’s a noble pursuit, but it’s a minor startup doing something interesting in another country, and then now you guys are the bell of the ball, people are like, ‘Oh my God, this is the future and it’s going to change everything in the Western world.’ So take us through like just managing a team and the emotion of a team as a- and your own, like, emotions and making sure you’re staying focused and not giving up.

Keller Cliffton: 29:30 You know, we could only hire a very specific kind of person. Like the people had to be- I mean, we were working from a cow farm at that time. Our offices were like, they were actual construction trailers. Like we had to get our little septic tank where all of our pee and poop was from the bathroom pumped every like five days. It was a crazy setup. Like we had no power, no- well, we technically did have a power hookup over time, but like…

Rahul Vohra: 29:52 So basically, if you’re joining the team, you’re a missionary by definition, no mercenaries, yeah.

Keller Cliffton: 29:58 Yeah, I mean, we would bring people from Google out and they’d be like, ‘Well…’ Wait, where’s the corporate cafeteria and like who’s going to wipe my ass and, you know, all that?

Rahul Vohra: 30:03 Where’s the Neiman Marcus?

Keller Cliffton: 30:04 Yeah, I mean it was so bizarre. Like, you’d be driving out into the middle of nowhere, like on this cow farm and we’re at like up there on a hill, building, you know, designing aircraft, manufacturing them and flying them. So the only people we were 30 hours one way coach to Rwanda back and forth, back and forth, back and forth trying to like make the system work. Uh, you know, you were only going to do that if you were like super fired up for an insane adventure.

Keller Cliffton: 31:37 If you were just like wanting a crazy adventure, do something totally different and wild. And so we were recruiting for very specific kind of talent. Those kinds of people wound up growing by leaps and bounds inside Zipline. I don’t think any of us thought we were building a really valuable company, but we felt like, hey, this would be such an epic thing to do. Like, you can save lives, it could be so inspiring.

Jason Calacanis: 31:54 It was important but not necessarily valuable.

Keller Cliffton: 31:58 Yeah. And I think, I mean I think this is also exactly how SpaceX, you know, started in retrospect. And, um, during those times once we got started, once the team got that first taste of like, wow, I mean we were meeting moms and kids who are alive because of what we did, I think the team had this sense of like moral imperative. Nothing was going to stop us, uh, despite all of the problems and all the shit that went wrong and plenty of stuff went wrong during those 10 years that we were—well, yeah, basically—I would say like the first era was really like seven or eight years of just operating exclusively in Africa. Um, it was never an option to back out because, like, people were relying on us with their lives and the moral clarity of the mission was so clear we had to figure it out. Um, you know, it flips, like now we are—it’s almost today it’s almost in some sense just as hard, just in different ways. Then no one believed in us. We couldn’t get investors to give us any money. You actually turned me down in our seed round.

Jason Calacanis: 32:52 Huge mistake. I was like, ah, I don’t know.

Keller Cliffton: 32:56 Seems like kind of a stupid idea. But Jason wasn’t alone. I mean, he, you know— 100% of people turned us down. And, and you know, today it means…

Jason Calacanis: 33:03 It was really because of hardware. I was like, ah, I don’t know, hardware’s so hard. I’ve just been so burnt. This is like actually, it’s a good thing to pause on. It’s so hard to be an investor because you wind up getting your ass kicked and you’re like, I don’t know if I can stay in business. And I don’t know if I could sell to my LPs and my team like we’re going to smash our head against the wall 10 more times in the same pursuit. And like we got to go to some safety. We got to go to and do the social app. We got to do the marketplace. We got to do something safe so that we could stay in business. It really is a very weird business. And also you don’t know if you’re good at it and if that fund’s going to work until years 8, 9, 10, 11, 12. And even when you think you know, you’re like, yeah, this is going to happen, we got this incredible paper markup in year 7 and then the company goes out of business in year 9 and you’re just like,

Rahul Vohra: 33:54 Or you look at like Rivian, you know, it’s like crazy insane growth all the way through being a public company and then 100 billion dollar valuation but even so, fucking hard to get hardware to positive gross margins and like a sustainable business.

Jason Calacanis: 34:06 So you know, it’s never easy is a memo from Jack from Square who just went through some layoffs. And you know, and when people are having a hard time I always reach out because that’s when like everybody goes silent is like when you trip and fall everybody like looks away. And he had done his layoffs and I just sent him a note, it’s never easy. And he wrote back, yep. And he’s like, nuff said, right? But I just wanted to make sure he got the message like I recognize how hard his week, month or year has been just to deal with that one decision of like oh my god.

Keller Cliffton: 34:40 And hardware companies I think like you have these existential crises every time you launch a new product. Like you can look even Tesla had been profitable, Model 3 nearly kills the company, you know. And I grew up the reason I was always admiring Jason is like I had grown up kind of reading all these stories like the lore of like you meeting with Elon and him showing you the like, you know, the picture of the Model S being like oh man…

Jason Calacanis: 34:59 The clays.

Keller Cliffton: 34:59 …the clays of like oh this could have been, you know, but the company’s probably going out of business and like you writing him I think for, you know, a check for the first two Model S’s to buy them like, you know, I grew up like hearing these stories thinking like wow, you know, Jason is like that’s the kind of investor you want to have. So what’s crazy is that like all, you know, it is funny how you basically beat your head against a dam for like 13 years and there’s like zero cracks in the dam, you’re making no progress, no one believes in you and then suddenly it’s like, oops, like the world just basically reconfigures itself around your vision. Zipline just raised an 850 million dollar financing round at an 8 billion dollar valuation.

Jason Calacanis: 35:46 Incredible. Do you want to share your news or is that going to be secret for a little while?

Keller Cliffton: 35:50 I’ll keep it secret for a little bit longer.

Jason Calacanis: 35:51 Alright, alright, nothing to share. I might make up for past mistakes.

Keller Cliffton: 35:54 And yeah, I think that um, you know, it’s… it’s crazy. Like, I think you kind of asked, like, so how do you do it? I mean, how do you stay motivated? I mean, A, it’s like you gotta have a mission that is like so important to you that you will put up with a giant amount of pain for a long time while everybody’s telling you you’re an idiot. Two is I think you have to be surrounded by people… people who you really love because like you go through really hard shit together and you’ll definitely like hurt each other along the way. Um you have to be able to forgive and just like put shit in the past like all right that was fucked up that was not good that was a huge mistake all right like re-doubling our efforts moving forward.

Jason Calacanis: 36:16 Well, and if you’re doing something unique and important part of it is failing and making mistakes and I just heard an interview where somebody was talking about their time with Bezos and I mentioned I think yesterday there are one-way doors and there are two-way doors and like a one-way door is like we’re building a factory and we’re gonna spend a billion dollars on it like better work or else game over.

Keller Cliffton: 36:37 Yep.

Jason Calacanis: 36:38 And then there are two-way ones like hey we’re gonna launch Amazon Prime and give people a hundred dollar a year two day guarantee for unlimited deliveries and he said almost universally every single time he did a hard decision the entire company fought him on it and he had to explain this is a two-way we’re gonna be able to come back and they were like you want to spend what on

Rahul Vohra: 36:51 Yep.

Jason Calacanis: 36:52 an e-reader like we sell books brother like you want to make a digital thing like that’s Sony’s business you want to take on Sony with a Kindle and he’s like well here’s the thing I you know I was thinking this and then they were like you want to make the fire phone and he’s like yeah we’ll make a phone.

Rahul Vohra: 37:13 Yep.

Jason Calacanis: 37:14 And people forget that Amazon tried to make their own phone.

Keller Cliffton: 37:17 Yep.

Jason Calacanis: 37:18 And it didn’t work. They also tried to make their own Siri Alexa they still sell as we learned yesterday like 500 they they sell some like 500,000 units a day or a week or some godly amount they’re selling like insane amounts of Alexas so.

Rahul Vohra: 37:40 Yep.

Jason Calacanis: 37:41 Number one nobody knows and paralysis is what kills company and boldness is what makes companies but boldness while you’re watching okay did I just run off a cliff? Okay I can walk it back and understanding the difference right like you’re tethered literally like to your idea here and you can pull yourself back no big deal.

Rahul Vohra: 37:51 Yeah exactly.

Jason Calacanis: 37:54 Yeah exactly.

Keller Cliffton: 37:55 Yeah, exactly. And I think a third part of it is probably just like stubbornness ability to like ignore all of these people who hate you and think you’re going to fail. By the way all of those people like have totally you know they’re the people who are now like oh we always knew Zipline was going to succeed I’m so proud to have supported them from day one like these people were telling us literally not to do it. It’s amazing how people will rewrite history in their head but like I think that um you know one one thing you know just gets me really pumped when you think about and maybe you I don’t think we’ve talked about this but like you know I graduated from college moved straight to the Bay Area was really inspired by like Tony and Alfred I’d read like Delivering Happiness you know Tony Hsieh was our first investor Alfred was our second they had been in the same dorm that I lived in just like 15 years ahead of me. I didn’t even know entrepreneurship was a thing you could do but I reflect like when I moved to the Bay Area in 2013 like the hottest company in the entire Bay Area was Dropbox. That was like the height of what I could imagine it was possible to do in entrepreneurship they had like the best people.

Rahul Vohra: 39:00 the fastest growing product that this amazing growth team, they were getting ready to go public. It was a 4 billion dollar valuation which was more money than I could possibly imagine at the time. And like that was the pinnacle of what you could achieve. And it was a file sharing company. And so to think like just 12 years later the scope and scale of human ambition in Silicon Valley has extended to building artificial general intelligence, life extension, colonizing Mars, you know, nuclear fusion, automated logistics, humanoid robots, you know, DNA computers like the list goes on and on and on.

Jason Calacanis: 39:41 Compounding success can make you dangerous. Like as you rack up the success you’re like what next? Let’s increase the degree of difficulty. You see it with extreme athletes. They’re like okay, Tony Hawk’s like I did a 360, they’re like okay, 720? And he’s like yeah, or like 1440, whatever the next number is and it’s just just keep pushing it. And Dropbox actually launched at Launch festival all those years ago. I remember when Drew showed it to me with his partner and it it didn’t work. And he’s like what advice do you have for us? I was like well if it worked that would be good.

Rahul Vohra: 39:59 Did you invest?

Jason Calacanis: 40:00 I did not. I wasn’t investing at the time. I didn’t have any money, well I did have a little bit of money but I was like everybody told me to don’t take any risk with your first sale, so just save that money, don’t ever invest it. And then I was like oh wait, maybe I should take some risk when I started investing. Now you’re getting pulled in 10 different directions, 20 different directions. How do you stay focused? And what matters today as a leader? How do you keep the troops focused and not drowning in opportunity?

Keller Cliffton: 40:31 I mean Zipline really has this advantage which is like we’re doing one thing, one thing only. If you take the demand that we observe in Dallas right now, so yeah just to make it clear, like we went super tall in Dallas last year. The service grew 15% week over week for most of last year. So insane kind of hyper scale growth that we saw in flight volumes and revenue. This year we’re expecting to grow by another 15X. We will by the end of this year be the largest part 135 certified operator in the US. In fact we expect to be bigger than all other airlines combined. So it’s very rapidly like the FAA is going to spend most of its time managing autonomous vehicles, not even human vehicles, you know, piloted aircraft. If you were to just extend the customer demand that we see in Dallas today, we’re just now launching Houston, Phoenix, will soon announce our next like four or five metros, we’re going to be launching many more metros every quarter. That’s kind of what the fundraising is about. But if you were to just take, there are about 5 and a half billion instant deliveries happening in the US every day being done by all the platforms that you guys all know and love. If you were to just extend the buying behavior that we observe in Dallas right now to the rest of those metros, there would be 50 billion instant deliveries in the US. So there’s a really provocative thing that we’re seeing which is, I think it’s a good analogy would be Uber in San Francisco. If you remember where they were always like, oh, Uber can only be this big because even if they capture like 50% of the taxi market, it’ll only be a $15 billion company. And of course, like today Uber is 10 times the size of the taxi market in San Francisco.

Jason Calacanis: 42:11 I remember talking to Bill Gurley about it and he’s like, ‘Well, you know, J-Cal, if you just think about taxis, that’s one thing, but people also take the BART, and then sometimes they also take, like, you know, they drive themselves or they take a bicycle, some people walk, and then of course sometimes they don’t even go out at all cause it’s just too much trouble to get a cab.’

Keller Cliffton: 42:30 Wound up being correct.

Jason Calacanis: 42:35 And I was like, yeah, that makes total sense. And so we just all thought, hmm, we’ve caught up to taxis already and it’s still growing. Yeah, Bill’s right. It’s gonna be big.

Keller Cliffton: 42:46 And Travis understood that because Travis was just building a logistics company, period full stop. Like he didn’t care what moved, what was moving, who was moving, where they were going, if it was a burrito or a person. Now also starting to focus on autonomous logistics with his recent announcement.

Jason Calacanis: 43:03 Yeah, Atomic, or Atoms.

Keller Cliffton: 43:05 Yeah, Atomic, or Atoms, and he’s, he’ll crush it with that as well. And it’s super interesting to watch people get their heads around that.

Rahul Vohra: 43:08 The induced traffic that happens when you add a lane to the 405 or the freeway in San Francisco and I watched it happen, like twice on living there. They had just opened a lane on the 405 going through the Sepulveda pass and they cut a little piece of the mountain off and then it was like, it’s going to change everything. And then traffic goes right back…

Jason Calacanis: 43:31 Within two weeks.

Rahul Vohra: 43:32 Yeah. And they’re like, ‘yeah, we’re going to add two more lanes,’ and they cut another piece of the mountain out and even a service road. And it just gets filled. And you’re like, ‘what’s happening?’ It’s like, oh, people realize the traffic isn’t as bad so they go to Hermosa, you know they go to Laguna or they take a job further away because it’s bigger. It doesn’t matter. Like here, you’re going to lower the cost, it’s going to induce so many people to be like, ‘yeah, we should, we should have boba.’

Keller Cliffton: 43:53 By the way, yes, totally, but also like even on that traffic point, imagine living in a city like LA where traffic is so gnarly and so many people are spending so much of their lives sitting in traffic, like idling engines, where it’s like how should we solve the problem of getting a 5-pound delivery of food to you? We’re going to use a 4,000-pound gas combustion vehicle driven by a human to go sit in that same traffic and cause it. It’s actually pretty insane when you consider like, hey, if you could just remove 20 or 30% of that traffic, do it with a 60-pound vehicle that is autonomous and electric. This is, yeah, the obvious future.

Jason Calacanis: 44:29 Incredible. Final question, just a practical one. How do you think about cities and like skyscrapers? Do you have a version 3 coming?

Keller Cliffton: 44:35 So it’s funny, you know, people always ask about cities, and I always know that whenever someone says ‘city,’ what they actually mean is Manhattan. The reality is there are actually almost no cities in the US that look like Manhattan or downtown Chicago. Like most cities look like Phoenix, which is where I grew up, or Dallas, or Denver, or Houston, or San Antonio, or Seattle, or like the list goes on and on, Atlanta, Tampa.

Jason Calacanis: 44:59 Got it.

Keller Cliffton: 45:00 Um, so Zipline in Dallas we serve basically 100% of the city. We expect to serve 100% of all those other cities I just mentioned. Like skyscrapers are sort of like the one place where you just, you know, yeah it’s going to be tricky, like I don’t know exactly… By the way, for a lot of really tall apartment buildings we just deliver to the roof. As long as they have roof access you can deliver to the roof, that’s actually a much safer place to deliver. Zipline platform one is really designed for rural locations, platform two is designed for suburban and city and then like where when you’re really talking about Manhattan or downtown Chicago like that that’s just not our focused right now.

Jason Calacanis: 45:29 Tokyo, Shanghai don’t have this problem. Like your ability to shave minutes there is going to not be as dramatic because in the… where you’re operating now it’s like you can’t get what you want.

Keller Cliffton: 45:41 Yeah. But even when you talk about New York City, where most people live in New York City, it’s not Manhattan, it’s the boroughs and we can serve all of those boroughs. It’s like perfect for Zipline. So just, you know, I would expect like 99% of addresses in the US are going to be perfect for this kind of delivery.

Jason Calacanis: 45:57 All right, let’s give it up for Keller, well done! [Applause] We’ve got a real treat for you. Rahul Vohra is here. He is the founder of Superhuman which was recently acquired in by Grammarly, another great company, two products I’ve been paying for since day one when they came out. And, um, I was lucky enough to be an investor in his first company Reportive and um, I will be the first, second, third, or fourth if I have to be that far behind in his next two or three companies which I’m sure he’ll do someday. Please welcome Rahul Vohra. How you doing, brother?

Rahul Vohra: 46:32 Doing good, good to see you.

Jason Calacanis: 46:33 We have a deal. Every time Rahul starts a company, I get to be the first investor.

Rahul Vohra: 46:41 I don’t know about this deal.

Jason Calacanis: 46:43 It’s a deal when he says I’ll come to you with the idea first. But then the co-founder of HubSpot Dharmesh has the same deal with Rahul. So we fight on X about who was the first investor in Superhuman and Reportive, but you just sold and I thought we would go through a little bit of a structured conversation here. I thought we’d go through a structured discussion about the journey of inception to acquisition because you’ve now done it twice over a decade or so of you and I working together. How long has it been? 12 years? 10?

Rahul Vohra: 47:21 2010. So 15 years.

Jason Calacanis: 47:24 It’s been 15 years of working together, yeah. And what a great time we’ve had. I want to go back to when you and I met. I emailed info@reportive.com. I had a thesis as an angel investor which was if I love a product, maybe I should invest in it. So I emailed this generic email and I just said hey I love this product would you ever consider taking angel investment and you got back to me. You had seen this week in startups which I think was on episode 10 at the time. But what was the inspiration for Reportive, how did you get product market fit and just tell me about that first early inspiration?

Keller Cliffton: 48:00 And iteration to get product market fit. In the audience, about half the audience… it’s all founders. Half the audience is first-time founders, half probably on their second idea.

Rahul Vohra: 48:10 So, there are a lot of ways to do this. The way that I like the most is just to solve my own problem, which I think has gone a little bit out of vogue in recent years. So I’m keen to be doing this. I think more of us should be solving our own problems. The reason, by the way, it’s gone out of vogue is sometimes the things that we build don’t appear to have large markets, right? Both companies, in fact, that I’ve started, unless you start really poking at them, they don’t seem like they’re going to have very big markets. So in this case, I had… it’s 2005. I started a PhD in computer science, computer vision actually, machine learning, but before machine learning worked. It was neural networks before we had compute, which is… is not a good combination. And I started it because I thought it would be… it’d be a great way to start a company. It turns out, it is a terrible way to start a company. The best way is, in fact, just to start. So I ended up dropping out of the PhD one and a half years in, and I networked my way into the part of the University of Cambridge, which is where I was at, that helps staff and students create companies. This is an organization called Cambridge University Entrepreneurs. Now, this is a student-run organization, and if you’ve ever been involved in any student-run organization, you probably know that they’re generally a shit show. And so the previous administration had run this one into the ground. The bank account was empty, there were no more people left, and I was like, ‘Aha! I… I get to be founder. I get to come in and fix this organization.’ And it was trial by fire. The first thing I had to do was raise money. And this isn’t like… you might think this is easy because you know, you go to a wealthy angel like Jason or a Google or a VC fund and say, ‘Hey, can I have a hundred thousand dollars? I’m going to give it to founders who at Cambridge who are going to build the next big thing.’ That sounds easy, but we weren’t taking equity. This was literally grant money. So I was selling good vibes. I’d be like, ‘You know this is the right thing to do, right?’ Best way to learn fundraising for anyone. And it was the very first job I ever had, and I’m not a great person with people. I was like, ‘I wish that there was something in my email that whenever I emailed them the next day and I… I could see their picture. I could tell whether or not I met them before. I could see where they work, what their job title is, their recent tweets, links to their social posts on LinkedIn, Facebook, and so on.’ And so that became the… the original inspiration for my first company, which was Rapportive.

Jason Calacanis: 50:30 Yeah, and at that time email was a bit of a black hole. You’d email somebody, if you got their email address, and then you’d have to do some sort of research. But it was such a powerful idea because there were multiple constituents who needed it. Um, if you were working in sales, if you were an investor, um, if you were doing business development of any kind, it was such a… advantage to know what the person’s LinkedIn profile was, what the… Twitter was, what the…

Keller Cliffton: 51:00 were tweeting about and even to see the history and you had found an interesting thing, there was a platform that came out around that time that you were able to ride, which was Chrome extensions. So maybe a little bit about when you launch a new product, the impact of different platforms and the timing there.

Rahul Vohra: 51:17 I think it’s key to find edges of all different kinds. In this particular case, it was the Chrome extension platform. So if you cast your minds back to 2010, Chrome was the hot new thing. Gmail had actually only been out for four or five years and people were migrating off Firefox, which had a very vibrant add-on ecosystem, to Chrome and also from Internet Explorer, of course, in droves. It suddenly becomes the platform that everyone was using. And so I thought, aha, this could be a new way to build the kind of product that no one has seen before. And if we were to go to the Chrome web store or the gallery as it was called back then and look at what people were using, there was really only one extension type that had any large number of users, and it was an ad blocker. I think the largest one, Adblock, had something like 50 million users at the time. But there was nothing else. Like literally nothing else. It was all crappy little things that didn’t seem like they could be real businesses. But that’s alpha. When you see something like that, you see one big thing and a bunch of dross, well maybe you can also build the big thing. That’s like the iPhone App Store when it first came out. So it seemed crazy at the time that I would go raise money for a business and try and build a really big thing by writing, by hand at that point of course, megabytes of JavaScript and trying to stuff that into somebody else’s website, which was Gmail, when there was no API, there was no integration points, we were literally manipulating the DOM directly. But that’s what we did. And like listeners probably said in the past many times, like these ideas seem a little crazy to begin with. So that’s an example of finding a platform.

Jason Calacanis: 53:05 Let’s talk about fundraising. It was a different time then. Fundraising back then was, especially with angels, it was very kind of alchemy, if you will. There was no AngelList, it was Venture Hacks, there was no way to actually reach angels. So how did you raise money being in England at the time for Rapportive?

Rahul Vohra: 53:31 Well, you were a huge help for this, so just like Jason said, we went viral very, very quickly and then he emailed kind of out of the blue. And this was, I should share, might be helpful for folks to know, this was like attempt number five or six for me as a startup. People often say, oh great, you’re two for two. And I’m like, yeah, but remember the five startups before those two that completely failed and went nowhere. And so I was used to talking to business angels, I was used to sort of building things and having them fail, and it all… It always felt like pushing water uphill and then suddenly this thing explodes and Jason pings me and Sequoia pings me and a bunch of all the other big VC funds at the time ping me out of the blue and I’m like, huh, maybe this is what it’s meant to feel like. So I think you invite me out to California, I think I fly out, it was either you or a friend hosted a dinner.

Jason Calacanis: 54:21 Yeah, Open Angel Forum, it was a little event I used to do because nobody, none of us knew who the angels were, but I knew like six or seven of them and then there were a couple of us who were new to it, myself, Saka, Cyan Banister, Naval Ravikant. We were all kind of like the punk rock kids trying to get our names out there so we would get deal flow and because we kind of thought it was dope to put the first 25k or 50k into a company. And at that time, companies only raised 250k, maybe 500, that would be a big, you know, seed round. And they were typically at a five million dollar valuation so you’d dilute five or ten percent but you’d get five to ten, 25 to 50k checks. That was kind of the playbook. And I think you were in that playbook.

Rahul Vohra: 54:53 Very much so. I’m trying to remember the other names in that room, so there was Cyan, yourself of course, Saka, Manu Kumar, Dave McClure, I think Shervin may have been there as well.

Keller Cliffton: 55:13 Yeah, Shervin came in.

Rahul Vohra: 55:14 A lot of the old-time classics. And I remember pitching and folks were just super interested. So it was actually relatively easy to raise. By the way, back then, there were no solo GPs, no one really had any microfunds. I mean, these days, when you raise from Launch or other funds like that, you’re going to get I assume half a million to a million, something like that?

Jason Calacanis: 55:31 Yeah, yeah, we typically will do 125k in our accelerator or 250 from our fund and then sometimes another 250 to 750 from our syndicate.

Rahul Vohra: 55:43 Right, very different times. I was putting together 25 to 50k checks and so my goal was like, hmm, maybe I can find 30 really nice people who are going to take a bet on some random kid from Cambridge. So that’s how we went about fundraising.

Jason Calacanis: 55:58 So you then start learning the playbook of being a Silicon Valley entrepreneur, you move here at some point, yeah?

Rahul Vohra: 56:07 It was very obvious that we had to move here. So we were based in Cambridge at the time, we came out here, we do this fundraising. We also at the same time get into Y Combinator and we were the first YC company ever to have fully concluded its fundraising several weeks before demo day. And so PG was like, what are you going to do? I’m like, I don’t know, I’m just going to pitch anyway, which by the way, turned out to be very valuable because I met the head of Corp Dev for LinkedIn. It was pretty obvious to me that I had to be here, but not immediately so. The original company Rapportive, we were built on the back of another company, co-founded by a friend of ours, Oren Hoffman, he founded this company called RapLeaf and he built an API company. And so the idea was you could give Oren an email address and he would, somewhat controversially, go and scrape the entire web finding everything about that email address and give you a JSON payload back. And so it’s funny in this realm of people criticizing thin wrappers, Rapportive was an extremely thin wrapper around this other company called RapLeaf. But we were also the best consumer use case that they ever had. Anyway, I’d learned through hanging around with a lot of entrepreneurs in Cambridge that there is no substitute for just turning up and knocking on the door. So props to Aditya, I think that’s your name, whoever tried to find me in the greenroom, and apologies I didn’t have time. But that’s exactly what you got to do. You got to hustle. You got to show up. And so I hustled. I flew to Silicon Valley. I knocked on the office door of RapLeaf. I said hello, can I speak to Oren Hoffman? And he was like, who are you? Oh, you’re the Rapportive kid. He then introduces me to Vivek Sodera, who is one of his co-founders, who then later on became the co-founder for Superhuman. And I was like, can I have your API, but for free? And they were like, what? This is our business, like we sell this. And I was like, yeah, but I don’t have any money and I don’t think this app is going to make money, but it’s a great advert for your company. Can I have it but for free? And they were like, okay, we’ll give it to you for free, which ended up becoming our secret weapon, so we were able to just scale to millions of users very effectively. Each meeting led to another three meetings. And so I came to Silicon Valley with an empty calendar. By Thursday or Friday, I was like doing 15 hour days, completely back-to-back. And I remember sitting on a Friday evening on a couch in Engine Yard, if you remember that, with my co-founders thinking, wow, we just got to move here. We got more done in a week than in four weeks of trying to email from Cambridge.

Keller Cliffton: 58:40 Yeah, and you learned a couple of Silicon Valley lessons there. You got to be in the mix. And you don’t need to ask for permission. And you can ask for something outrageous. And if it’s outrageous enough to make sense, there’s somebody who might say yes. And that, I think, is very important for founders. We had Vlad here yesterday, another 14, 15-year relationship I’ve had with a founder, and he just came up with the most outlandish idea ever. We’re going after a TAM that equals zero. Millennials don’t trade stocks. We’re going to try to manifest that into existence, which very much is related to the Superhuman story, which we’ll get to in a moment. But let’s talk about scaling.

Jason Calacanis: 59:30 What was the secret to scaling Rapportive, and then we’ll talk about the acquisition? If you look back on it, you know, there’s moments, you know, in that curve where it goes up and hits a new high, maybe it comes down a little bit, the downloads, but you’re at a new plateau. I’ve seen that in every podcast I’ve ever done, I’ve seen it in many different investments, little spikes that get you to a new plateau in terms of growth and trajectory.

Rahul Vohra: 59:53 Everything we did at Rapportive was intuition and by accident, but I’m going to pretend I knew what I was doing and post-rationalize. I sought the lessons for you. So the first thing was this Chrome extension platform. And it’s one of my favorite kinds of software. It’s the kind of software that you don’t have to remember to use. So as soon as you’ve installed a Chrome extension, then it kind of doesn’t matter whether or not you see value on day one, or day seven, or day 14, or day 30. I know eventually, you’re going to have a life-changing moment in your email as a result, and we’ve got you forever, like you’re never going to uninstall that thing. As soon as we help you make a hire, or close a deal, or raise some money that you otherwise would not have been able to do, you’re like, holy shit, this thing is awesome. So we’ve got you. And that’s really colored how I think about software since then. The most powerful software is software that you don’t have to remember to use. Some other things: it’s really, really fast to onboard. All we had to do was get you to click a button, the Add to Chrome button. There was no account creation, there was no sign up, there was no indexing, there was no configuration. It was just one click and done. The other thing is it was incredibly viral. People spend three hours a day in their email. And at least back then, everyone was in offices. So for three hours a day, people were just kind of, you know, looking over everyone else’s shoulders and by the way, there was no Slack, people weren’t really chatting at that time, people were in their email, and what do they see? Well, someone’s Gmail looks better than my Gmail. How come you have that picture? Where are these tweets coming from? Where are these social links? I want that thing, what is that? And then it became a verb. I’m going to Rapportive that guy, I’m going to check her Rapportive. Right, when you can make your thing a verb, you know you’re onto something. And then I think perhaps the most interesting thing and, you know, I’m a designer, I’m guilty of wanting to perfect things before they’re launched. Rapportive went viral overnight without my know- sorry, not overnight, over an afternoon without my knowing, and then again overnight. So again, I was in Cambridge, it was a Friday afternoon, Jason, what do people in Cambridge in the UK do on a Friday afternoon?

Jason Calacanis: 1:02:11 They… you know the answer. Go to bed early or drink beer? It’s one of the other.

Keller Cliffton: 1:02:15 What do they do, read a book? That sounds really boring.

Rahul Vohra: 1:02:17 Yes, some people read a book. It was a beautiful summer’s day Friday afternoon, a bunch of us are working in the incubator, we look around and we go, ‘is it beer o’clock? It’s beer o’clock.’

Jason Calacanis: 1:02:22 Yes.

Rahul Vohra: 1:02:23 So we go to the pub, I’m like two pints deep, our thing is hosted on Heroku, I’m using a mobile app to control Heroku, and suddenly my phone is blowing up. I’m like, what is happening here? And I’m running out of credits, so I log in on my phone, I type in user.count and we had 10 users at the time, but instead it said 400. And I type in up and I press enter and it’s like 1,000. I type up and enter and it says 2,000. I’m like, what the fuck is going on? And so I Google Rapportive and it turns out that we are headline news on A media property called The Next Web, which at the time was one of the largest tech blogs. I’m like, how did this happen? And here’s what happened. As many of us probably know, when you apply for YC—I think they still do this—but they had this input field that was like, ‘Put a link to your demo and do not password protect it,’ because they don’t want to be slowed down. It makes sense. So I did that. I put a link to the thing. I had 10 users. I didn’t tell anybody about this and I just assumed, pretty rationally, that no one would find this. But my best friend at the time had tipped off The Next Web, and he was like, ‘I know what’s better for Rahul than what Rahul thinks is better for Rahul.’ And he did, it turns out. And The Next Web grabbed a hold of this, tried it, installed it, wrote it up, and was like, ‘Guys, this is the best product to have launched all year.’ And we got 30,000 users overnight. That’s when you reached out. That’s when Roelof Botha reached out and they were like, ‘This kind of—’ By the way, nowadays, super easy, that’s very common, but back then, very uncommon.

Jason Calacanis: 1:04:03 Yeah. And Roelof, for people who don’t know, was the person who created the scouts program. And so I’m guessing what happened was, I said ‘I’m going to scout this’ and then I said it to him and he reached out because the idea was, well, what if we could find more startups and Sequoia could get an early warning system? You then, you had, I believe you had four co-founders, you plus three?

Rahul Vohra: 1:04:27 Two others.

Jason Calacanis: 1:04:28 Two others. And, hey, you started to get offers. There was what I considered an absolutely terrible offer from LinkedIn. But you had co-founders and I was like, ‘Oh my god, this is a billion-dollar company, please don’t sell it!’ And you explained to me you had co-founders and, you know, hey, the team was kind of done, and you wound up selling to LinkedIn. It was a good outcome, not a ridiculous one, but, you know, hey, any outcome’s great. Take us through making that decision, because I do kind of remember you struggling with it, yeah?

Rahul Vohra: 1:04:58 Yeah, there were a few things. So I think one, like you mentioned, is my co-founders were just done. Like we’d—we’d gone through a grueling—this is going to sound weak when I say it—but a grueling 20 months. It was like not even two years. And you know, I think I—I could have kept on going. I mean, I’ve been an entrepreneur my entire life. But I convinced two other people to not be an academic and not be a software engineer and to be co-founders of this company with me. And it was hard. And I think they—they were looking for a notch on the belt, a feather in the cap, and to lock in some early wins and move on. And by the way, there is absolutely nothing wrong with that. From—we—I mean, it—it’s so long ago, I don’t think anyone will care. We basically sold for about $15 million. And so personally, I ended up making several million dollars. And that’s a big deal when you’re 26, 27.

Keller Cliffton: 1:05:51 Yeah, at the time, that was the dream.

Rahul Vohra: 1:05:53 That was the dream, right? That was the dream because, you know, getting an apartment here was a million dollars, not seven.

Jason Calacanis: 1:05:58 Yeah. I mean, I would never invest in San Francisco—

Rahul Vohra: 1:06:00 It was like five, six, seven, eight years of me never having to work. And more importantly than not having to work, it just gave me an incredible fearlessness. Like, I just didn’t give a fuck. I could do stupid ideas like Superhuman, which also requires several years to actually get off the ground. And by the way, investors can tell when you’re fearless. So my strong recommendation is, if you have an opportunity, whether it’s secondary or selling your company, to lock in that kind of money, if it’s life-changing for you, then you should definitely do it, because it just means that your second go-round, or your third go-round—maybe one day I’ll have a third go-round, I’ll be even more fearless—that it just means you’re going to do something extra special.

Jason Calacanis: 1:06:44 I had the same experience when I sold Weblogs Inc. There’s a very similar amount of money, $30 million. I had a partner and Mark Cuban was our only investor. But you get that first, you know, $10 million wire, $5 million wire, whatever it winds up being. Well, now you don’t have to work for money. And now any idea you have, you can work on for a year or two, and you can put the first 250k up. You can maybe push out the pre-seed round or the friends and family round and you become dangerous.

Keller Cliffton: 1:07:13 I was like, ooh, you had an idea, which I don’t know if we’re allowed to talk about, but of getting into the Gmail kind of business, getting into the email business with Rapportive, with maybe even post with LinkedIn, but you didn’t do it.

Rahul Vohra: 1:07:28 Yeah, yeah, we can talk about it. So, like we discussed, I sold Rapportive to LinkedIn and at the start of Superhuman, I think somewhat irrationally, I wanted that baby back because, you know, to your point Jason, it could have probably, maybe could have been a billion-dollar company, who knows. It was, let’s say this, it was certainly beloved. If you were in Silicon Valley at the time, you used that product. We, it turns out, had I known this, we would have sold for a lot more money. We basically had every single daily active user of LinkedIn on that product, and that’s actually one of the reasons why they acquired the company. And they also when I left, they just didn’t particularly care about it. This is very common with acquisitions. Acquisitions are hard to make go well. And I mean we were just talking backstage, I’m so glad this is my second one because I know all the kinds of things that can go wrong, and we’re preventing all of those things because I can see around the corners. But back then, I couldn’t, and things were challenging and I wanted to do right by the users and by the company. And so it was funny, actually, this all comes full circle. There was a launch event that you did in the Palace of Fine Arts, I think it was.

Jason Calacanis: 1:08:44 Yes, I remember. Yeah.

Rahul Vohra: 1:08:47 Do you remember you had Jason—sorry, not Jason, Jeff Weiner on stage?

Jason Calacanis: 1:08:48 I did, yeah. It was one of the keynotes.

Rahul Vohra: 1:08:50 So he was running LinkedIn at the time.

Keller Cliffton: 1:08:51 Yeah. Yeah, he was the CEO of LinkedIn at the time.

Rahul Vohra: 1:08:54 Yeah, and I’m gonna go back to our boy Aditya, who for reference, when I was in the green room just before this, he comes to the back and… Like hi, I’m Aditya, I’m 16 years old. Can I pitch you my startup? And I’m like, I’m really sorry, not right now. I’m dealing with an emergency, but I respect the hustle. In the Palace of Fine Arts, Jeff Weiner was there, and I grab him after your conversation with him, and this was after I’d left. I’m like, ‘You’re Jeff. Rapportive. I’d like to buy it back. I think it would look good for you. I think it’d be great for me. Let’s figure out a deal that works good for the both of us.’ And to my great—I mean, you know, I hustle, I always turn up—to my great surprise, he was like, ‘All right, I like you. We like you. Reid Hoffman’s one of the founders of LinkedIn. Let’s figure this out.’ And so over the course of the next few months, we start negotiating this, and we almost get to a deal that is signable. I think they wanted 5% of the company, which I was—it’s expensive, but like, you know, when you stack it up against YC and other things, it’s not that expensive. And if it weren’t for that, I would have said yes, but they also wanted an option to buy the company first if anyone else was going to try. And that’s basically a poison pill. Like, that can depress your acquisition multiple by several. So, you were in the room, Bill Trenchard was in the room, we talked about this deal, and for that reason, we decided to walk away.

Jason Calacanis: 1:10:12 Yeah. Superhuman. I remember it like it was yesterday, you text me because I had said, ‘Listen, I’m totally fine signing off on the deal with the Rapportive deal to LinkedIn.’ Whenever you sell a company, it’s always best practice to get unanimous consent from your investors even if you don’t need it. You can drag some people along. But I’m like, ‘Yeah, of course, yeah, my blessing. Whatever, seven times my money. I’m cool with it. It’s nice. Paid for a vacation.’

Rahul Vohra: 1:10:42 I want to go on his vacations, damn.

Jason Calacanis: 1:10:44 Yeah, whatever, it was okay. But you got to remember at that point I’d done Uber and Thumbtack and I was… oh, I said, ‘Just promise me when you have your next idea, you’ll just text me. I don’t care what time of day it is.’ So it’s a Sunday, I’m at my place in Cow Hollow, and I get the text from Rahul. He says, ‘Hey, are you around?’ And I said, ‘Yes, I’ll go get bagels, can’t wait to hear your new idea. Here’s the address.’ And he goes, ‘How do you know I have a new idea?’ I said, ‘I remember four years ago, I think you lasted three years at LinkedIn.’ So I get the bagels, he comes over to the place, we’re sitting on the deck, having some bagels. I said, ‘What’s the idea?’ And he says…

Rahul Vohra: 1:11:18 Well, we want to take on Gmail.

Jason Calacanis: 1:11:21 Okay. I said, ‘Okay, big target, love it. How are you going to beat Gmail?’

Rahul Vohra: 1:11:29 We’re going to be faster.

Jason Calacanis: 1:11:31 I said, ‘Okay, so faster than the largest compute cluster ever built globally with the largest number of engineers who have built the fastest server-level data delivery system in the world. Love it. That’s crazy.’ And he had a reason for why he would beat them and it was a really good one. And then I said, ‘Hit me with the business model.’ And he said…

Rahul Vohra: 1:11:50 A dollar a day.

Jason Calacanis: 1:11:52 I said, ‘Okay, you’re going to beat the largest company in the world…’ You got to remember at that point in time Google was the company everybody said— You can’t beat Google, like what if they launch a product? So you’re going up against the unbeatable company of the moment. It would be like going up against Nvidia today or Tesla. So you’re going to go up against them and you’re going to beat them by charging a dollar a day for which they are given unlimited for free access to Gmail. Yeah. You explain the idea, I said, “I’m in.” And I wrote the largest check out of the fund, which I think was 500k out of a 10 million dollar fund, which has paid off greatly for us. Thank you.

Rahul Vohra: 1:12:24 That’s right.

Jason Calacanis: 1:12:25 It will be the biggest winner in that second launch fund. And like, literally, we have one bet we make out of every fund, which is the all-in bet. You were that all-in bet for that fund. And the only other people who have had the all-in bet would be Travis for Cloud Kitchens, which was our third fund where we made an all-in bet with maybe close to 10% of the fund. Long story short, the idea was killer. Where did the idea come from that you would beat them on speed, elegance with luxury software?

Keller Cliffton: 1:13:03 Great question. And by the way, I remember the other thing. ROFO and ROFO. Right of first refusal and right of first offer. Never give those away.

Jason Calacanis: 1:13:12 Oh yeah, ROFO. Yeah, you’re right.

Rahul Vohra: 1:13:14 Sorry, mind blank. Oh my gosh, the strategy vis-a-vis Gmail. What a great question. And this is actually one of our investment theses, by the way, I also invest, so let me know if you want to chat. And I love companies that go up against incumbents. Because the thing is with incumbents, yeah they look scary, but they’ve got so much shit to do. And if you look at how dysfunctional they are inside, there is so much room to maneuver. And I had a whole theory of a plan to attack and segment Gmail that, you know, if I were to describe would make a ton of sense. I’m not going to do the whole thing because we’d run out of time. But when it comes to things like Gmail, there’s a billion professionals in the world. On average we spend three hours a day. That’s three billion hours every single day. That’s north of a trillion hours every single year. I literally couldn’t imagine a thing that we spend more time on. In fact, there’s only one thing that we spend more time on, which is sleeping, and I wish we could fix that. I suffer from sleep apnea, I really wish we could improve that, but I had no idea how. The next biggest thing that we spend time on was, and still is, email. And the epiphany really hit me when I was commuting from, speaking of Uber, from LinkedIn to San Francisco, from Mountain View to San Francisco. It’s like roughly an hour-long ride and I was in the back of an Uber and I got so much done on that one ride. And I realized the magic of Uber, as folks like Jason and Gary Bee have long since said, it’s not about transportation, it’s about time, right? The magic of Uber is you get back time. And so I started looking for ways to give people back time. And there is no better way than to make you go twice as fast through your email. Like in terms of maximum market size, it’s absolutely huge. And here I was, an email founder that had made investors money, that had built a cult… beloved products that knew all the people that could easily go and raise money to do it again. So it really felt like a perfect coming together of all the resources. People talk a lot about product market fit, but there’s also founder market fit that we don’t talk quite as much about, and I think was very much aligned in our case. And then there were all the things about, Jason, you mentioned luxury software, just the core idea is incumbents can’t afford to make a product for everybody. We mentioned NVIDIA, there’s probably a whole set of companies that even NVIDIA can’t afford to make a product for because it does not make sense at their scale. And to me, the craziest example of this is, do you remember Inbox by Google?

Jason Calacanis: 1:15:47 Yeah.

Rahul Vohra: 1:15:48 Yeah. So, I had the opportunity to talk to Eric Schmidt about this. He was at a summit at Sea Island Summit, a great organization. They used to throw these huge boat parties and they got all these incredible people to come. One time Eric was there and, speaking of bagels, he was just having a bagel at the buffet. And again, you’ve got to hustle, so I just turned up and I’m like, “Hello, I’m the founder of Superhuman. We make an email app that is better than Gmail, no shade. Why did you shut down Inbox?” And he said, “The derivative of the derivative of the growth rate was too slow.” And I was like, “But you had 500 million users. Any other startup would like be worth $10 billion at that point.” He was like, “It’s just not Google scale.” And that is why you can go after incumbents.

Jason Calacanis: 1:16:36 Yeah, it’s such a brilliant insight. When I sold Weblogs, Inc., which did Engadget and Autoblog, all those things to AOL, Ted Leonsis took me aside. He said, “In that room, we have,” and he just kind of like pointed, “a giant old machine spewing chemicals and dust and everything, and it prints hundred-dollar bills at the rate of like 10,000 a second. They’re just piling up, and we have dump trucks coming in and taking all those and putting them in the bank. And you have this little machine called Weblogs, Inc., and you know, every hour, like a one-carat diamond comes out. And it’s the most amazing machine, and but nobody’s going to appreciate it, but I do. Because that machine is slowing down. Nobody can notice because there’s hundred-dollar bills everywhere, we can’t pick them up fast enough, but people are stopping paying for dial-up access. And your machine is the future, and your machine will someday put out 10-carat diamonds every minute and it will just keep growing. So we have to protect it. We’re going to protect it. We’re going to give you this money because you can produce content that beats our content, and it cost you, at the time, an average blog post for us cost $7 to write.”

Rahul Vohra: 1:17:51 Wow.

Jason Calacanis: 1:17:52 Fully baked. Because we were paying people per post, $2.50, and then we made it $5, then we made it like $7. And writers thought we were idiots because—

Rahul Vohra: 1:18:00 they were making four of them an hour and making $28 an hour in 2005, which for a writer was like to work from home, work from home was another thing. And they were spending 300, 400 dollars per web page, and we were spending seven. He said he’d never seen anything like it.

Jason Calacanis: 1:18:15 And that was the challenge of being inside of a big company. You needed to have a rabbi, you needed to have a protector, you needed to have some, you know, gladiator who was willing to defend your little fiefdom. But when you went out and talked to investors with this crazy idea…

Keller Cliffton: 1:18:32 I know a couple of investors said yes, but some might have said no. What when they said no, what didn’t they get and how did you deal with the rejection? Or was it just all 10 for 10?

Rahul Vohra: 1:18:41 Oh, definitely not 10 for 10. I, you know what, I think if you have a 10 for 10 idea, it’s probably too consensus. Exactly. Our other good friend George Zachary, who’s at Charles River Ventures, long said that their best ever deals, which include companies like Twitter, where they, I think they ended up passing on that or sort of got in via Odeo. They were always the ones that split the partnership the most, like the most controversial deals. So how did I deal with rejection and what were people’s complaints? I mean, yeah, sometimes investors would be like, well, what if Google does this? That’s not a smart investor. I mean, come on, seriously. If someone’s asking what if an incumbent does this, that applies to every single other product and the right answer is the one that I just gave. In fact, those are the ideas that you probably want to move towards. And the answer is simple, if for some reason Zuck suddenly decides to be the 800-pound gorilla in your space, that’s fine. Pivot. You’re a startup. You can do something adjacent, maybe you sell to Facebook at that point, maybe you or maybe you do something different. So like, that’s totally okay.

Keller Cliffton: 1:19:46 Do you try to convince the investor they’re wrong at that stage in your career or do you just move on? They don’t get it, it’s not for them, I have other people on the list.

Rahul Vohra: 1:19:58 Regardless of the stage of your career, you just move on. But, use it as an opportunity to hone your pitching skills, right? You did the hard work, you’re in the conversation, they’re not going to leave early. Like, you know, even Alfred Lin from Sequoia or whoever is going to, they’re going to do the half hour, they’re going to do the hour with you and you’re with one of the smartest human beings on the planet. So have the goddamn debate. Like, hone your craft. Really make sure that you can do the objections backwards and forwards. But in my mind it was an im- if I sensed hesitation, I just immediately wrote it off.

Keller Cliffton: 1:20:30 Let’s talk about the launch, um, and then catching fire. You have always been a first-principles thinker and an incredible designer. And I think when we had the discussion with Vlad yesterday, remember design came up? And remember thinking from first principles came up. What if we charged zero dollars to trade? What would that do in the market? You had this incredible idea, would people pay a dollar a day for this? Wound up being a little bit less maybe, I don’t know, if you bought the year. But you also had an…

Jason Calacanis: 1:21:00 Idea that when you told it to me, I was immediately concerned for three minutes. And when you explained to me your reasoning, I said, ‘Oh my god, it’s one of the most brilliant things I’ve ever heard,’ which was: you said no to customers and you onboarded them and they had to go to an onboarding. Nobody had ever done that before in many startups since have said, ‘Oh, we’re doing what Rahul did on episode whatever of This Week in Startups,’ he explained. We force people to do an onboarding. Explain to the founders here how you came up with that idea, why you came up with it, what the resistance was internally to it, and then what made it work so well.

Rahul Vohra: 1:21:42 Okay. So for folks that don’t know, in the early days of Superhuman, for about two or three years, we one-on-one concierge onboarded every single new customer. I actually personally did the first four or five hundred. And the first several hundred I did in person. And this took while, like it took an hour or two per person. I would go to their office, I would bring a gift. If they drank alcohol, I would research it, bottle of wine, whiskey; if they didn’t, it would be something else. And it would be roughly as follows: we would sit down, I would say, ‘Hey, can you show me how you do your Gmail?’ and they’d be like, ‘Okay.’ I’d watch them for 20 minutes and then I would do a demo of Superhuman. I would show them all the cool things, but I didn’t onboard them yet. Then I would onboard them. Then I said, ‘I’m going to watch you do your email and I’m going to help you get to inbox zero.’ And at the end, I sorry, I forgot a very important piece. Before doing that, I would ask them to put in their credit card. And a lot of people be like, ‘What? I’m doing you the favor here and you’re asking me for the credit card?’ and I’m like, ‘No, I’m giving you the best product you’re going to use this year. I would like your credit card, please.’ And so not even our investors did not get to pay.

Jason Calacanis: 1:22:52 You did this to me at Cyclops. I’m sitting there with Cyclops. He says, ‘I’m ready to show you the product.’ I’m like, ‘Okay.’ He gets to the workflow and he goes, ‘Okay, and then this is the point in the sign-up where we put your credit card in.’ And I was like, ‘All right, great.’ And he’s like, ‘May I have your credit card?’ and I was like, ‘Well played, Rahul.’ I was like, ‘Well played.’ And you know, I always admonish investors for ever taking free product, right? Um, like pay for the product. I literally had somebody who had been in the syndicate for calm.com which was a 4.5 million dollar investment, which had hit at that time a billion dollar valuation. Um, we had sold a little bit and so he had a, I think a 100x return already with still the majority of his shares still in play. And he emailed me and said, ‘Hey, I’m one of the investors, you know, whatever, I need to put $5,000 in and it was worth 300 times that,’ uh, at 1.5 million, and he said, uh, like 1.5 million, and he said, ‘I don’t have a subscription to Calm. Can you email Alex and Michael to give me a free subscription to Calm?’ I said, ‘You’ve made 1.5 million dollars and you’re asking me to email the founders to give you a free subscription? Pay for the subscription!’

Keller Cliffton: 1:24:00 for a $100 a year subscription to come. Just want to make sure we have that right. Anyway back, I’m sorry I’m an idiot.

Jason Calacanis: 1:24:07 Every time I see the same individual, he comes up, I’m the idiot. I’m like you asked for free Cal? He says yes. It’s our little joke.

Keller Cliffton: 1:24:14 But this was key because you were establishing that there was value for value.

Rahul Vohra: 1:24:20 Not just value for value, like folks pricing is the product as well. It is a flag in the sand that says this is going to be the best goddamn email application you have ever used and will ever use and I am personally staking my reputation on that and I’m going to look you in the eye and say all of those things, this is true, may I have your credit card. And it’s very effective. No one ever said no. And also, it kind of you know like it for better or for worse it tied up my ego with the thing. Like I would not let that fail having personally looked the top two, three, four hundred CEOs and founders in the Valley in the eye and said yeah I’m going to build that thing and I would like your money for it please. So it then later on turned out that these customers were the most viral we’ve ever seen in the category. They had the highest NPS, the lowest churn, the highest activation and engagement rates, the highest product market fit score which which is this whole other thing that we can talk about. And I was like huh is this just me maybe I’m just very effective in person. So I had my brother do the same thing. He had the same if not better metrics. And we looked at this and we were like well maybe we should just staff a team of people to do this over Zoom. So we ended up hiring twenty people to do this around the clock forty calls per week. This is roughly when Andreessen Horowitz invested and it became the Superhuman onboarding.

Keller Cliffton: 1:25:44 Yeah, it was so brilliant, like a lot of the non-consensus ideas. Um and what’s truly brilliant about it is you’re going to connect on two or three things that that person really appreciates so now they can explain to the next person. It relates in a way to net promoter score which is um you know if you’re an advocate of the pro product you’ll say um how likely are you to recommend Superhuman to another to a friend you know if they say nine or ten they’re an advocate they’re going to go out in the world and they’re going not shut up about it. If they say seven or eight they’re just indifferent they’re not actually going to ever do it and then if it’s six or under they’re in all likelihood a detractor they’re going to say bad things about you and cost you and you do a little formula to figure out your net promoter score some of the greatest ones in history were the Model S, the iPhone, etc. Um but I was um I went to the Aman Hotel in Tokyo a couple years ago when I was on book tour and it was around the same time you were doing this I had the have you been to an Aman hotel?

Rahul Vohra: 1:26:49 Yeah, uh one in India.

Keller Cliffton: 1:26:52 One in India. Aman Hotel created a new category that’s like four star and then they made five star and then like they’re like six star. They define it totally.

Jason Calacanis: 1:27:00 different category. And when you go in, like two people greet you, they bring you to reception, and then they open a folio and in Japan, they give you one of those sodas with the marble in it. There’s a person playing this incredible Japanese instrument and they walk you through everything at the hotel, and then they walk you to your room. They show you the spa, they show you your room. It takes time. And I was like, well, I just want to get to my fucking room, you know, and get on with it. But now I can tell you all the features of the Aman hotel. I can tell you about the pool on the 44th floor and its view, I can tell you about the breakfast, I can tell you about the room, I can tell you about the shampoo. And in fact, every time I go to Japan, and I was there with Will and Amanda just recently for our founding anniversary, I was like, guys, I have to stop by the Aman. And they’re like, why do you have to stop by the Aman? I’m like, I gotta go to the spa and buy the shampoo. Because when I use that shampoo, I just smell the countryside of Japan and it makes me happy. And I literally go buy four of those every year and that’s my shampoo. It’s that level of obsession that is just so rare in the world, and in a world of AI slop, I think you would agree, like, that’s going to be the thing.

Rahul Vohra: 1:28:17 Amen, totally. It’s all about… so to circle back to this random anecdote that you reminded me of. So I got married one and a half years ago at the Leela Palace in Udaipur. Like an Aman, they just dial every detail to 11 out of 10. And there is a scent that they designed for that hotel, and every Leela has a different scent. And so my wife and I, obviously it just reminds us of our wedding. So every single time that we go through India, we also pick up these shampoos and these body lotions because it just is so meaningful for us. This is an interesting point, and I’ll bring it full circle back to design.

Jason Calacanis: 1:28:25 By the way, scent triggers memory.

Rahul Vohra: 1:28:27 It really does. It really does. What is design? I recently gave a talk on this topic at Superhuman, the big Superhuman, which is now one and a half thousand people. And my answer was really simple. It is design is simply the number of conscious decisions that you take. It’s not about visuals, although it can be. It’s not about scent, although it can be. It’s not about narrative, although it can be. It is simply how many conscious decisions that you take. And what separates a world-class designer from someone who’s just starting on their design career is simply the number of decisions. And so when I’m in design review, which is actually how I spend most of my week, I have an amazing job, it is simply pointing out how many different things that the more junior designers are doing subconsciously and they’re taking for granted. And I’m just asking, well, what if you made that decision deliberately, what would you then choose?

Jason Calacanis: 1:29:51 Here’s the font, tell me about the spacing.

Rahul Vohra: 1:29:54 And it’s like, it’s the standard spacing.

Jason Calacanis: 1:29:55 Okay, and tell me about the height, the kerning, the weight.

Rahul Vohra: 1:29:58 And we design all of those.

Keller Cliffton: 1:30:00 Thanks for Superhuman.

Jason Calacanis: 1:30:01 Right. And it’s…

Keller Cliffton: 1:30:02 it’s so funny when I talk to my team, I’m like, what… we’ve been designing a logo recently for this week in AI and I was like, tell me the decision making behind it. But I didn’t have it formed like how many decisions did you make? This is why I love talking to you because we always, we always hit on some things that make me expand my thinking about subjects and a lot of times the intuition just hasn’t been formed into a phrase or a… codified into a heuristic.

Jason Calacanis: 1:30:29 Let’s talk about selling. You had lots of opportunities where a lot of people who coveted what you built with Superhuman, and there’s this great company doing Grammarly that had bought Coda. And they coveted Superhuman, why? And how did this deal go down? Because you could have kept raising money, you had a large number… you had a lot of revenue. I don’t know if you were profitable at the time, but you could have easily been.

Rahul Vohra: 1:30:54 Yeah. Yeah, we easily could have been profitable, but like most venture-backed startups, we were investing in our growth. The reason to sell was actually really simple. In most spaces, and especially productivity and collaboration, you either become the platform or you sell to a platform. There is no other choice. The pendulum between point solutions and bundles swings back and forth roughly every five, 10 years. I think the cycle will go a little bit faster now, but it was very obvious to me that the pendulum was swinging hard back towards bundles. AI was accelerating that. Obviously with AI, what matters more and more is the data that you have. You want your email app to be able to take your meeting notes and write follow-up emails automatically. You want it to connect to your document system, to Coda, so everything is automatically generating everything else. Think about Grammarly, which helps you write more confidently and more accurately. Why isn’t all of this connected? So there was the opportunity to create a really incredible bundle. And this is another example of just getting out there and hustling. Let’s talk about how this happened, and we’ll wind the clock back…

Jason Calacanis: 1:31:56 …back to 2017.

Rahul Vohra: 1:32:00 We were grinding away in our small, tiny office here in San Francisco for Superhuman Mail. And I was… you know, we hadn’t even launched. But there was this conference called The Lobby Enterprise put on at that time by August Capital. My co-founder Vivek, Vivek, was like, ‘You should go.’ And I’m like, ‘I don’t want to go. Like, we don’t have fucking time. I gotta build this, we gotta hit product-market fit. I’m not going to take out a week just to go drink tequila next to a pool in Hawaii.’ And he was like, ‘Trust me, something good will come out of this. I don’t know what it is, but something good will happen.’ And I’m like, ‘Fine. This is why I hired you, is to make me uncomfortable and to push me into things that I don’t want to do. I trust you. I will go have this mandatory vacation.’ So I turn up and I’m a little bit early and there’s this other brown dude who’s also early sitting by the pool, a little bit older than me and we… we get to talking and he’s like this gem of a human being… super nice and we start asking each other what we do. Our careers now, our journey. I tell him about Rapportive, LinkedIn. He was like, oh cool, I used to work at Microsoft. I said what on? He said Outlook. I was like oh do I have a product for you. And so I pull out my laptop and I just start demonstrating Superhuman. And it turns out that he’d also previously been the chief product officer and the chief technology officer of YouTube at Google, was a Gmail fanboy, and I was like, can I onboard you right now? And he was like yes please do. So we margaritas in hand, these two product-y nerds nerding out at the pool, I do the whole credit card trick thing with him, he loves it. And as the last part of the onboarding is, now as we wrap I’m going to ask you to close Gmail. So as his mouse is moving over to the Gmail tab and he’s about to click, next to it I see another tab with a fav icon that I don’t recognize. It’s a capital K. I say what is that? He was like, oh it’s my startup, Krypton. I’m like what the heck is Krypton? Can you do me a demo? And he proceeds to do the best product demo I’ve seen that whole year. It is a document editor, it is a spreadsheet, it is an application builder, it is a database, it is collaborative. I’m like holy shit, you have blown my mind on what I even thought collaboration and productivity was. That thing then became Coda and Coda became this product that is now used by millions of people, 50,000 plus companies, and was acquired by Grammarly. And now that person Shishir is the CEO of Grammarly. And he had used the product Superhuman Mail, my product, for the last eight years. And let me tell you this, there is no better position to be in when you’re thinking about maybe selling the company when the CEO of the company that should probably most buy yours has been a die-hard fan for the last eight years.

Keller Cliffton: 1:34:58 Yeah, that is super helpful and that’s Shishir and he, uh, he not only loved the product, he loved the name so much that, uh, yeah, he, uh, named the combined company and is working towards a, uh, new product which combines them all just called Superhuman, yeah.

Jason Calacanis: 1:35:16 How did that come about?

Rahul Vohra: 1:35:19 How did we change the name?

Jason Calacanis: 1:35:22 Yeah, did it come up during the acquisition? Did it come up after the acquisition? He said, hey by the way, I’m going to rename the entire company. When did you find out that that would be the brand that, you know, was becoming the future?

Rahul Vohra: 1:35:34 Well, Shishir and I had stayed in touch over the eight years. I was an angel investor in Coda, he was an angel investor in Superhuman. By the way, you should all angel invest in each other’s companies, there’s going to be several billion-dollar companies just from this room, so have at it. And I texted him the day they announced the Coda acquisition. I was like, yo, congratulations. By the way, we should definitely hang out because I think there’s a much bigger story here. And we ended up on a Zoom call a few …days later. And he immediately told me, he was like, “By the way, the Groundly name, good for a single-product company, not good for what we’re trying to do. Do you have any ideas for names?” And I was like, “Ha, ha, ha. I think I have the best name of all time for this product space.” And I was joking because this was like one day into what was a six-month conversation to maybe sell the company. I then go to the Coda acquisition party, which was at Press Club here in San Francisco. This was like January 18th. He’d only been the CEO for eight days and he was testing some names with me, which I won’t share because they weren’t particularly good. I was like, “Shishir, these are bad names. These are really bad names. But you know, I have a really good name. I’m just going to throw that out there.” And internally, I think he was running the right playbook, which was, look, we’re going to assess Superhuman on its own merits, name absent. Like, we’re not going to take the name of this company into account. We should assess this acquisition on things like revenue and growth rate and quality of the team and other synergies. At the same time, the company had just hired a branding agency. And that branding agency, you know what the number one name that they’d recommended was? Superhuman. And they did not know that we were in acquisition talks. And so at that point, the writing was kind of on the wall and it just made the rest of everything so much easier.

Keller Cliffton: 1:37:22 Man, it’s great to know you, Rahul, and it’s been just wonderful to be on the journey with you over all these years. I can’t believe it’s 15. And anytime I ask you to show up for me and talk to founders, whether it’s 10 or 400, you show up, which just means the world to me, Rahul. So I just want to thank you personally. And let’s give a big round of applause to one of the great product designers and entrepreneurs of this generation. Rahul Vohra.

Rahul Vohra: 1:37:40 Fantastic. Thank you so much. Thank you so much.

Keller Cliffton: 1:37:53 Alright.