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

22:57We'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 Incredibly accurately and so you know might seem like a crazy solution But it's really big advantage to keep the main aircraft very high The aircraft is actually staying a football field up. It's a hundred meters and we're lowering the droid a hundred meters to make a delivery The Droid is controlling. It's running. The Droid has its own NVIDIA GPU. It's running its full autonomy stack. Even in really strong weather and crazy wind, rain, snow, that Droid will deliver hyper accurately to wherever you tell us every single time.

23:33Yeah, your co-founder was sharing the wind test and how insane you're doing it. It's insane, yeah. We probably should have brought some on that. Go check out Ryan or my accounts on X. We're always posting. These systems operate in insane hail, insane snow, insane wind. 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 little evil Jimmy grabbing onto that and getting sucked up into the copter and dragged away? Or is that the parents' issue? Well, we only actually picked up a child a couple times, and then we usually return the child 10 minutes later.

24:10So it just hasn't been that big of a legal issue. It's like the start of a Pixar film. As long as we get the kid back to the parents within 15 minutes, it's generally okay. It's worked out. But like, you know, actually the biggest thing is actually not kids. Because the droid actually has cameras on board. And so it basically acts a little bit shy. If there are people right there trying to touch it, it will wait. And it will tell you in the app, like, please give us a little bit of room. The thing is actually dogs have been the main thing. Sometimes droids do come back with chunks bitten out of them.

24:39We assume it's dogs. I hope it's not children. Coyotes. But, yeah, so it's fun. Like, it's an interesting problem. But the serious answer to your question is the droid is easy to be left behind. We don't generally do that, but one in every 10 ,000 flights, something will happen where we leave the droid behind. We have footage of what happened. So if someone was messing with it, we're showing up at your doorstep three minutes later being like, where's our hardware? So most of our customers, but to put it in perspective, just 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 guys who are really into technology.

25:16completely 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, 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.

25:50I 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, stuff goes really wrong. It's the reason Waymo has an advantage, because the Waymo isn't going to sexually assault you. Similar goes for getting logistics delivered by these robotic systems that are highly predictable and 100 % safe is a really big advantage relative to having a stranger come to your door when your 13-year-old daughter is receiving a delivery late at night. So yeah, all of these customers, I would say we've been quite shocked the level of customer love that we've seen.

26:23I mean, there are certain municipalities in Dallas where more than 50 % of homes are Zipline customers. It's like 50 % market penetration. Yeah. What's the requirement to be a Zipline home? Like, how big does my yard need to be? Yeah. Et cetera. So let's actually show the third video. It's a perfect transition. So just to give you the other crazy thing that's happening here is 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. We're launching, you know, just last week we launched Quick Trip and Hawaiian Brothers.

26:56A 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. So it feels pretty wild. It's pretty magical. 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.

27:26So here, yeah, customers 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. You can see all the different awesome brands that are available on the app. You can order whatever you want. Today we can deliver up to 6.5 pounds. We'll be at 10 pounds by the end of this year. So, yeah, I mean, you can deliver basically like 95 % of things that people are ordering via QuickCommerce in this way. Walmart, as our biggest partner today, there are about 100 ,000 SKUs in a Walmart supercenter. We deliver 80 ,000 to 90 ,000 of them.

28:01So people are ordering birthday cakes, rotisserie chickens. We can put two rotisserie chickens in a droid. They'll order an attachment piece for a garden hose. They'll order flowers for Valentine's Day. They'll order a couple sets of Legos. You can literally get everything delivered like this. And because the hybrid, not a quadcopter, but the hybrid bird is up there, the noise is up there, not down here. Yes. I mean, we think that noise is a tremendously important part of the design of these systems. systems, we won't name names, but there is a very big company in Seattle trying to build drone delivery.

28:38They've been spending a billion dollars a year. Not only have they had many, many safety problems with the FAA, where they've sent people to a hospital, they've had crashes, but also noise. 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.

29:15And 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. 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.

29:51I 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 just managing a team and the emotion of a team and your own emotions and making sure you're staying focused and not giving up. 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 uh well we technically did have a power hookup uh over time but like if you're joining the team you're a missionary by definition like we would bring people from google out yeah we 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?

30:49Where's the meme and ranch? Like, 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 were like up there on a hill, built, you know, designing aircraft, manufacturing them and flying them. So the only people we were going to, 30 hours one way coach to Rwanda, back and forth, back and forth, back and forth, trying to like make the system work. You know, you were only going to do that if you were like super fired up for an insane adventure. Hey, here at my firm, we are AI first, of course. And we're looking for any way to use these new incredible tools to take away the tedious, busy work, all those chores we have to do.

31:24But just taking random chances when a new technology can lead to risks. Now with NetSuite by Oracle, you can put AI to work for your company safely and with confidence. NetSuite is the number one AI cloud enterprise resource planning software, or ERP, and it's already trusted by over 43 ,000 businesses. NetSuite is a unified workspace that brings together every piece of your data into one single easy-to-use interface. And it's the connecting of all this data that makes your AI so much smarter, so much crisper, so much more accurate, so much more valuable. Now you can automate routine tasks and get actionable insights from an AI system that's more like a trusted partner than some isolated chatbot or a bolt-on tool that keeps hallucinating.

32:06And if your revenues are at least in the seven figures, get NetSuite's free business guide, DemystifyingAI at netsuite.com slash twist. The guide is free to you at netsuite.com slash twist. If you were just like wanting a crazy adventure, do something totally different and wild. And so we were recruiting for a 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. You can save lives. It would be so inspiring.

32:40It was important, but not necessarily valuable. Yeah, and I think this is also exactly how SpaceX started in retrospect. And 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 were alive because of what we did. I think the team had this sense of like moral imperative. Nothing was going to stop us. Despite all of the problems and all the shit that we 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 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 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.

33:35You actually turned me down in our seed round. Huge mistake. I was like, I don't know. Seems like kind of a stupid idea. But Jason wasn't alone. I mean, you know, basically 100 % of people turn us down. And, you know, today, I mean. It was really because of hardware. I was like, I don't know. Hardware's so hard. It's hard. It's 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 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. We're going to smash our head against the wall 10 more times in the same pursuit.

34:12And we've got to go to some safety. We've got to go and do the social app. We've got to do the marketplace. We've got to do something safe so that we can 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. Yeah. And even when you think you know, you're like, yeah, this is going to happen. We got this incredible paper markup in year seven. And then the company goes out of business in year nine. And you're just like, or you look at like Rivian, you know, it's like crazy, insane growth all the way through being public company and then$100 billion valuation.

34:46But even so, fucking hard to get hardware to positive gross margins and like a sustainable business. So it's never easy is a DM Jack from Square who just went through some layoffs. And you know, when people are having a hard time, I always reach out. because that's when like everybody goes silent. It's like when you trip and fall, everybody's 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. He's like, enough 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.

35:23And 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, you know, 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. The clays. Yeah, 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, like, I think, for, you know, a check for the first two Model S's to buy them.

35:53Like, you know, I grew up, like, hearing these stories thinking, like, wow, you know, Jason and is like, that's the kind of investor you want to have. So what's crazy is that, like, 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, oh, like, the world just basically reconfigures itself around your vision. You know, ZipLine just raised an$850 million financing round, an$8 billion valuation. Do you want to share your news, or is that going to be a secret for a little while?

36:22I'm going to keep it secret for a little bit longer. Okay, all right. All right, nothing to share. I might make up for past mistakes. And yeah, I think that it's crazy. I think you kind of asked, so how do you do it? I mean, how do you stay motivated? A, it's like you've got to have a mission that is 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 who you really love because you go through really hard shit together and you'll definitely hurt each other along the way.

36:54You have to be able to forgive. 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 redoubling our efforts moving forward well and if you're doing something unique and important part of it is failing and making mistakes and i 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 going to spend a billion dollars on it like better work or else game over yep 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 going to be able to come back and they were like you want to spend what on an e-reader like resell 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?

37:54And he's like, well, here's the thing. 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. And people forget that Amazon tried to make their own phone. And it didn't work. They also tried to make their own Siri, Alexa. They still sell, as we learned yesterday, like 500. They sell some like 500 ,000 units a day or a week or something godly amount. They're selling like insane amounts of Alexis. So 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?

38:33Okay, I can walk it back. And understanding the difference, right? Like you're tethered quite literally to your idea here and you can pull yourself back. No big deal. 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 gonna fail. By the way, all of those people like have totally They're the people who are now like oh, we always knew zipline was gonna succeed I'm so proud to have supported them from day one like these people were telling us literally did not do it It's amazing how people will rewrite history in their heads But like I think that 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.

39:20I'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, the fastest growing product. They had this amazing growth team. They were getting ready to go public. It was a$4 billion valuation, which was more money than I could possibly imagine at the time.

39:54And that was the pinnacle of what you could achieve. And it was a file sharing company. And so to think 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. 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.

40:33They're like, okay, 720? And he's like, yeah. or like 1440, whatever the next number is, and 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 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. Did you invest? 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.

41:08And then I was like, oh, wait, maybe I should take some risk, and 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? I mean, Zipline really has this advantage, which is like we're doing one thing, one thing only. we, 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 hyperscale growth that we saw in flight volumes and revenue.

41:49This 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, you know, 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 and Phoenix. We'll soon announce our next like four or five metros. We're going to be launching many more metros every quarter.

42:21That's kind of what the fundraising is about. But if you were to just take, there are about five and a half billion instant deliveries happening in the U.S. 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 U.S. So there's a really provocative thing that we're seeing, which is that 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.

42:53And of course, like today, Uber is 10 times the size of the taxi market in San Francisco. I remember talking to Bill Gurley about it and he's like well you know J. Cal if you know you just think about taxis that's one thing but people also take the BART and then sometimes they also take like uh 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 right because it's just too much trouble to get a cab wound up being correct and I was like yeah Yeah, that makes total sense. And so we just all thought, hmm, we've caught up to taxes already, and it's still growing.

43:29Yeah, Bill's right. It's going to be big. And Travis understood that, because Travis was just building a logistic company, period, full stop. 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. Yeah, Atomic, or Adams. And he'll crush it with that as well. and it was super interesting to watch people get their heads around that. It just, the induced traffic that happens when you add a lane to the 405 or the freeway in Los Angeles, and I watched it happen, like twice when 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.

44:14And then traffic goes right back within three weeks. Then they're like, yeah, we're going to add two more lanes, and they cut another piece of the mountain out, like 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 Hermer, so 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 have Boba. By the way, yes, totally, but also even on that trap point, imagine living in a city like L.A.

44:44where 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 five pound, you know, 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 it 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. Final question, just a practical one.

45:14How do you think about cities and like skyscrapers, Do you have a version three coming? 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... Manhattan is there's a bodega downstairs at every corner, so they don't need you. Exactly. So my point is, like, there are actually almost no cities in the U.S. 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.

45:45but so Zipline, like 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 gonna be tricky. Like, I don't know exactly. By the way, we're 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's really designed for rural locations. Platform two is designed for suburban and city. And then like when you're really talking about Manhattan or downtown Chicago, like that's just not our, focus for the next couple of years.

46:16Tokyo, Shanghai don't have this problem. Your ability to shave minutes there is going to not be as dramatic. Where you're operating now, it's like you can't get what you want. 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. We can serve all of those boroughs. It's perfect for Zipline. I would expect 99 % of addresses in the U.S. are going to be perfect for this kind of delivery. Let's give it up for Keller. Well done. We've got a real treat for you. Raul Vora is here. He is the founder of Superhuman, which was recently acquired by Grammarly, another great company.

46:55Two products I've been paying for since day one when they came out. And I was lucky enough to be an investor in his first company, Reportive. And I will be the first, second, or 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 Raul Vora. How are you doing, brother? Good, good, good, good. We have a deal. Every time Raul starts a company, I get to be the first investor. I don't know about this deal. 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 Raul.

47:37So 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? 2010. So 15 years. 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 at reportive.com. I had a thesis as an angel investor, which was, if I love a product, maybe I should invest in it.

48:23So I emailed this generic email, and I just said, hey, I love this product. Would you ever consider taking angel investing? And you got back to me, and 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 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. 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.

49:04So 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 not a good combination. And I started it because I thought it would be a great way to start a company.

49:39It 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 film. And so the previous administration had run this one into the ground. The bank account was empty.

50:11There were no more people left. And I was like, aha, I get to be founder. I get to come in and fix this organization. And it was trial by fire. And the first thing I had to do was raise money. And this isn't like, you might think this is easy because, you know, to a wealthy angel like Jason or a Google or a VC fund and say, hey, can I have$100 ,000? I'm going to give it to founders 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?

50:47Best 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 there was something in my email that whenever I email them the next day, 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 original inspiration for my first company, which was Reportive. Yeah. And at that time, email was a bit of a black hole. You would email somebody if you got their email address, and then you'd have to do some sort of research.

51:23But it was such a powerful idea because there were multiple constituents who needed it. If you were working in sales, if you were an investor, if you were doing business development of any kind, it was such an advantage to know what the person's LinkedIn profile was, what the person's Twitter was, what they 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.

52:03I 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 become 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 you 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.

52:54I think the largest one, ad blocker, 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 a 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.

53:37We were literally manipulating the DOM directly. That's what we did. And like Jason has 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. Let's talk about fundraising. It was a different time then. Fundraising back then was, especially with angels, it was a very kind of alchemy, if you will. There was no angel list. 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 Reportive? Well, you were a huge help for this. So like Jason said, we went viral very, very quickly.

54:20And then he emailed kind of out of the blue. And this was, I should share, it 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. 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 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 all the other big VC funds at the time ping me out of the blue.

54:57And 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. 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, Sokka, Sian Bannister, 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 25 or 50K into a company.

55:32At that time, companies only raised 250K, maybe 500. That would be a big seed round. And they were typically at a$5 million valuation. So you'd dilute 5 or 10%, but you would get 5 to 10, 25 to 50K checks. That was kind of the playbook. And I think you were in that playbook. Very much so. I'm trying to remember the other names in that room. There was Sian, yourself, of course, Saka, Manu Kumar, Dave McClure. I think Sherbin may have been there as well. Yeah, Sherbin came in. A lot of the all-time classics. And I remember pitching, and folks were just super interested. So it was actually relatively easy to raise.

56:07By the way, back then, there were no solo GPs. No one really had any micro funds. 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? Yeah, we typically will do$125 ,000 in our accelerator or$250 ,000 from our fund, and then sometimes another$250 ,000 to$750 ,000 from our syndicate. Right, very different times. I was putting together$25 ,000 to$50 ,000 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.

56:42Do you then start learning the playbook of being a Silicon Valley entrepreneur? You move here at some point, yeah? 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.

57:17It was pretty obvious to me that I had to be here, but not immediately so. The original company reported, we were built on the back of another company, co-founded by a friend of ours, Oren Hoffman. He founded this company called Wrapleaf, 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, Reportive was an extremely thin wrapper around this other company called Wrapleaf.

57:57But 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 green room, and apologies, I didn't have time. But that's exactly what you've got to do. You've got to hustle. You've got to show up. And so I hustled. I flew to Silicon Valley. I knocked on the office door of Rap Leaf. I said, hello, can I speak to Orrin Hoffman? And he was like, who are you? Oh, you're the reportive kid.

58:29He then introduces me to Vivek Sodara, 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 just to scale to millions of users very effectively. Each meeting led to another three meetings.

59:02And 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. Yeah, and you learned a couple of Silicon Valley lessons there. You've 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.

59:44And 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. What was the secret to scaling, reportive? And then we'll talk about the acquisition. If you look back on it, there's moments in that curve where it goes up and hits a new high.

1:00:26Maybe 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. Everything we did at Reportive was intuition and by accident, but I'm going to pretend I knew what I was doing and post-rationalize all 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.

1:01:08I 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.

1:01:44There was no account creation. There was no signup. 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 are 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 can we have that picture? Like where are these tweets coming from?

1:02:17Where are these social links? I want that thing. What is that? And then it became a verb. I'm going to reportive that guy. I'm going to check her reportive. 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 I'm a designer, I'm guilty of wanting to perfect things before they're launched. Reportive went viral overnight without my knowing. 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?

1:02:52You know the answer. Go to bed early or drink beer? It's one or the other. What do they do? read a book? It sounds really boring. 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. 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.

1:03:32And 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 Reportive, 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 had 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. They don't want to be slowed down, it makes sense. So I did that.

1:04:09I 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 NextWeb. And he was like, I know what's better for Rahul than what Rahul thinks is better for Rahul. And he did, it turned out. And the NextWeb grabbed ahold 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 Rolof Botha reached out. And they were like, this kind of...

1:04:43By the way, nowadays, super easy. That's very common. But back then, very uncommon. Yeah. And Roloff, 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 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? Two others. Two others. And, hey, you started to get offers. there was what I considered an absolutely terrible offer from LinkedIn.

1:05:19But 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. So it was a good outcome, not ridiculous, 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? Yeah, there were a few things. So I think one, like you mentioned, is my co-founders were just done. Like we'd gone through a grueling, this is going to sound weak when I say it, but a grueling 20 months.

1:05:53It was like not even two years. And I think 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 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's so long ago, I don't think anyone will care, but we basically sold for about$15 million and so personally I ended up making several million dollars and that's a big deal.

1:06:33When you're 20, 26, 27. Yeah, at the time that was the dream. That's the dream, right? That was the dream because getting an apartment here was a million dollars, not seven. Yeah. I mean, I would never invest in San Francisco real estate, but 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 require 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.

1:07:19Because it just means that your second go-around or your third go-around, maybe one day I'll have a third go-around, I'll be even more fearless. It just means you're going to do something extra special. I had the same experience when I saw Weblogs, Inc. It was a very similar amount of money,$30 million. I had a partner. and Mark Cuban was our only investor, but you get that first$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.

1:07:59I 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 Reportive, with maybe even Post with LinkedIn, but you didn't do it. Yeah, we can talk about it. So like we discussed, I sold Reportive 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 it could have been a billion-dollar company. Who knows? Let's say this. It was certainly beloved. If you were in Silicon Valley at the time, you used that product.

1:08:41We, 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 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.

1:09:20And so it's funny, actually, that this all comes full circle. There was a launch event that you did in the Palace of Fine Arts, I think it was. Yes, I remember, yeah. Remember you had Jason, sorry, not Jason, Jeff Wiener on stage? I did, yeah. It was one of the keynotes. He was running LinkedIn at the time, yeah. Yeah, so he was the CEO of LinkedIn at the time. And I'm going to 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 he's 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.

1:09:51I'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, reportive. I'd like to buy it back. I think it would look good for you. I think it would be great for me. Let's figure out the 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. Reid likes you. Reid Houghton'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.

1:10:29I 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 were 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. Trendsuit was in the room. We talked about this deal. And for that reason, we decided to walk away. Yeah, superhuman. I remember it like it was yesterday. You text me because I said, listen, I'm totally fine signing off on the deal with the reportive deal to LinkedIn.

1:11:09Whenever 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. pay for a vacation. I want to go on his vacations. Yeah, whatever. It was okay, but you've got to remember at that point I had 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 Raul.

1:11:44He 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 three years ago. I think you lasted three years at LinkedIn. So I get the bagels. He comes over the place. We're sitting on the deck having some bagels. I said, what's the idea? And he says, well, we want to take on Gmail. I said, okay, big target, love it. How are you going to beat Gmail? Merle says, we're going to be faster. 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.

1:12:28Love 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, a dollar a day. I said, okay, you're going to beat the largest company in the world. You've 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, which they are given unlimited for free access to Gmail.

1:13:03Yeah. Can you explain the idea? I said, I'm in. And I wrote the largest check out of the fund, which I think was 500K? That's right. 500K out of a$10 million fund, which has paid off greatly for us. Thank you. It will be the biggest winner in that second launch fund. And 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. We made an all-in bet with maybe close to 10 % of the fund. Long story short, the idea was killer.

1:13:44where did the idea come from that you would beat them on speed elegance with luxury software great question and by the way i remember the other thing rofer and rofo writer first refusal and writer first offer never give those away okay oh yeah rofo yeah right sorry mind blank oh my gosh the the strategy vis-a-vis gmail what a great question and this is actually one of one of the our investment theses by the way i also invest 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.

1:14:19And 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 if I were to describe would make a ton of sense. I'm not gonna 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 thing that we spend more time on, which is sleeping.

1:14:53And 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 the epiphany really hit me when it when I was commuting from speaking of Uber from LinkedIn to 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 as folks like Jason and Gary Vee have long 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 absolutely huge and here I was an email founder that had made investors money that had built a cult beloved product 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 enough about and I think was very much aligned in our case.

1:16:06And 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? Yes. Yeah. So I had the opportunity to talk to Eric Schmidt about this. He was at a Summit at Sea event. Summit, great organization. They used to throw these huge boat parties and they got all these incredible people to come.

1:16:46One time, Eric was there and speaking of bagels, he was just having a bagel at the buffet. And again, you got a hustle. So I just turn up. 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. 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.

1:17:32He said, in that room, we have, and he just kind of like pointed in AOL, a giant old machine spewing chemicals and dust and everything. and it prints$100 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 every hour, like a one carat diamond comes out. And it's the most amazing machine. But nobody's going to appreciate it, but I do. Because that machine is slowing down. Nobody can notice it because there's$100 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.

1:18:24So 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. Wow, 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 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 wasn't a thing. And they were spending$300,$400 per web page. And we were spending seven. He said, we've never seen anything like it.

1:19:01And 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 gladiator who was willing to defend your little fiefdom. But when you went out and talked to investors with this crazy idea, I know a couple of investors said yes, but some might have said no. 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? Definitely not 10 for 10. 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 was at Charles River Ventures, long said that their best ever deals, which include companies like Twitter, where they, I think they did a passing on that or sort of got in via audio.

1:19:44They 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.

1:20:21Pivot. You're a startup. You can do something adjacent. Maybe you sell to Facebook at that point. Maybe you do something different. So, like, that's totally okay. 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. Regardless of the stage of your career, you just move on. But use it as an opportunity to hone your pitching skills. You did the hard work. You're in the conversation. They're not going to leave early. Even Alfred Lynn from Sequoia or whoever is going to do the half hour.

1:20:59They'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. Hone your craft. Really make sure that you can do the objections backwards and forwards. But in my mind, if I sensed hesitation, I just immediately wrote it off. Let's talk about the launch 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, I remember design came up. And remember thinking from first principles came up. What if we charge$0 a trade? What would that do in the market?

1:21:37You had this incredible idea. Would people pay$1 a day for this? It wound up being a little bit less, maybe. I don't know if you bought the year. But you also had an 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, this is 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. And many startups since have said, oh, we're doing what Raul did on episode whatever of This Week in Startups.

1:22:13He 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. Okay. So, 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 400 or 500. And the first several hundred I did in person. And this took a while. 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, a bottle of wine, whiskey.

1:22:54If 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. I didn't onboard them yet. Then I would onboard them. And 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 forgot a very important piece. Before doing that, I would ask them to put in their credit card. And a lot of people would be like, what?

1:23:27I'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. He did this to me at Cyclast. I'm sitting there with Cyclast. He says, I'm ready to show you the product. I'm like, okay. He gets to the work. And he goes, okay, and then this is the point in the signup 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, Raul. I was like, well played.

1:23:58And, you know, I always admonish investors for ever taking free product, right? Like pay for the product. I literally had somebody who had been in the syndicate for Calm.com, which was a$4.5 million investment, which had hit at that time a billion-dollar valuation. We had sold a little bit, and so he had, 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, and he put$5 ,000 in, and it was worth 300 times that. And he said, like$1.5 million, and he said, I don't have a subscription to com.

1:24:39Can you email Alex and Michael to give me a free subscription to com? I said, you've made$1.5 million, and you're asking me to email the founders for a$100 a year subscription to com. I just want to make sure we have that right. And he wrote back, I'm sorry, and I'm an idiot. Every time I see the same individual, he comes up, I'm the idiot. I'm like, you asked for free com. He said, yes. It's our little joke. But this was key because you were establishing that there was value for value. Not just value for value. 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.

1:25:28May I have your credit card? And it is very effective. No one ever said no. And also, it kind of, you know, like, 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, 400 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 MPS, the lowest churn, the highest activation and engagement rates, the highest product market fit score, which is this whole other thing that we can talk about.

1:26:09And 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 20 people to do this round the clock, 40 calls per week. This is roughly when Andreessen Horowitz invested, and it became the superhuman onboarding. Yeah, it was so brilliant, like a lot of the non-consensus ideas. And what's truly brilliant about it is you're going to connect on two or three things that that person really appreciates.

1:26:45So now they can explain to the next person. It relates in a way to net promoter score, which is, you know, if you're an advocate of the product, you'll say, how likely are you to recommend superhuman to another, to a friend? You know, if they say 9 or 10, they're an advocate. They're going to go out in the world and they're going to not shut up about it. If they say 7 or 8, they're just indifferent. They're not actually going to ever do it. And then if it's 6 or under, they're in all likelihood a detractor. tractor 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 amman 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 amman hotel yeah uh one in india one in india amman hotel created a new category it's like four star and then they made five star and then like they're like six star they define a totally different category uh 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 uh sodas with the marble in it there's a person playing this incredible uh japanese uh 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 your room it takes time and I was like well I just want to get to my fucking room you know like and get on with it but now I can tell you all the features of the Amman 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 university I was like guys I have to stop by the Amman and they were like why do you have to stop by the Amman I'm like I got to 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.

1:28:46And I literally go buy four of those every year and that's my shampoo. It's that level of obsession that's 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. Oh man, totally. It's all about... So we'll circle back to that random anecdote that you reminded me of. So I got married one and a half years ago at the Leela Palace in Udaypur. Like in Amman, 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 just reminds us of our wedding.

1:29:26So every single time that we go through India, we also pick up these shampoos and these body lotions because it is so meaningful for us. This is an interesting point, and I'll bring it full circle back to design. And by the way, scent triggers memory. 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 1 ,500 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.

1:30:05although 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? Here's the font. Tell me about the spacing. It's like, it's the standard spacing.

1:30:40Okay. And tell me about the height, the kerning, the weight. And we designed all of those things for superhuman. Right. And it's so funny when I talk to my team, I'm like, we were 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 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 codified into a heuristic. Let's talk about selling. You had lots of opportunities.

1:31:18There were a lot of people who coveted what you built with Superhuman. And there was 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. 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.

1:31:56There is no other choice. the pendulum between point solutions and bundles swings back and forth roughly every five ten 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.

1:32:34Why isn't all of this connected? So there's 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. I'm going to wind the clock back to 2017. 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, Rattleleaf Vivek, was like, you should go. I'm like, I don't want to go. Like, we don't have fucking time.

1:33:09I've got to build this. We ought to hit products 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 to 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 get to talking and he's like this gem of a human being, super nice and we start asking each other what we do.

1:33:50Our careers now, our journey. I tell him about Reportive, LinkedIn. He was like, oh cool. I used to work at Microsoft. I said, what on? He said, Outlook. I was like, well 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 Margarita's in hand, these two productivity nerds nerding out at the pool. I do the whole credit card trick thing with him.

1:34:26He 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 okay, 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.

1:35:07That 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, Shashia, 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 diehard fan for the last eight years. Yeah, that is super helpful. And that's Shashir. And he not only loved the product, he loved the name so much that, yeah, he named the combined company and is working towards a new product, which combines them all, just called Superhuman.

1:36:01Yeah. How did that come up? How did we change the name? Yeah. Did it come up during the acquisition? Did it come up after the acquisition? You 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 became the future? Well, Shashir 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.

1:36:37I 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 upon a Zoom call a few days later. And he immediately told me, he was like, by the way, the Grammarly name, good for a single product company, not good for what we're trying to do. Do you have any ideas for names? 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.

1:37:11This 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, 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 rates and quality of the team and other synergies.

1:37:49At 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. Man, it's great to know you Raul 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, Raul.

1:38:24So 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. Thank you so much. You love me, Ben.