Inside the New Superhuman: $700M ARR, 40M Daily Users with Rahul Vohra

24:01Definitely still figuring it out. I mean, I think that it is an ongoing process. And maybe fortunately for Superhuman, the code acquisition happened first, and there were a number of things that went really well. But I think there were also a number of things that we learned from and have... One of the things I really like about this team, by the way, is sort of the ability to go, okay, that was a mistake. Boom, we're going to fix it and do it better next time, which we then did in the Superhuman acquisition. And I'm sure Or we'll take all the lessons from this one and apply it to the next one, whatever and whenever that may be.

24:35So yeah, there's a strong learning machine here that gets continually applied to everything we do.

24:42Turner Novak:You've mentioned a little bit about the big vision for the company. What is it? You've kind of hinted on it, but what's the big vision for Superhuman 10 years, 20 years in the future? What does it look like? Yeah, my gosh. I mean, it gets me so excited. Okay. So our vision is to give you superpowers everywhere you work. And we're starting by building the AI native productivity suite of choice. And that suite starts with, of course, Superhuman Mail, which you know, it's the most productive email app ever made. It also starts with Coda, which is the all-in-one AI workspace for teams. It's actually an incredible product.

25:21It's been a while since I used it and come back, and it's phenomenal. and Grammarly, which is your trusted, always available, right and partner that works wherever you work. And again, we already talked about it. It's not really a known entity inside of Silicon Valley for most of the knowledge workers here, but this is, oh boy, is this a business at scale that many, many millions of people live and swear by every day. And then of course, a new product that we announced as part of the rebrand last week, which is Superhuman Go. That's a proactive AI companion that works in every app you use.

25:56Turner Novak:Oh, I didn't even see that one. We have big plans for this suite, and our goal with it is to unlock the superhuman potential in everybody. Interesting. I'm looking at Superhuman Go right now because I missed that one. That's really interesting. So it's like, is it similar to Grammarly where it kind of embeds or it looks like you sync it with different things you can integrate with, like calendar, it looks like it syncs with your email. How exactly does that work? Both of those things are true. And this is a good example of systems thinking or strategic thinking. Grammarly, as they were figuring out what the next steps for the company would be, of course, you analyze what are you good at, what are you not good at, where are the advantages.

26:42One of the most strategic assets at Grammarly is that over the last 15 years, the team has done this incredible grind. I mean, it really cannot be over-treated that Grammarly works with over 1 million applications and websites. And it literally plugs into the DOM or if you're using the native app via the accessibility tree, like it feels native. You download the Grammarly app and you're in Microsoft Word or whatever, like Slack, Granola, all these things that we use every day works in Figma as well. These are my daily apps. And it's annotating and it's writing and it feels native, like it's a part of those applications.

27:22That is not easy. That is really, really hard. There is a large contingent of the company that exists to make that work and to keep it incredible. So that's an asset. What can we do with this? Well, this asset is like we've built an AI superhighway, that we have built these rails or this road network across every application and website that people use, But there is only one car that is allowed to drive on this highway, and that is your grammar car or your language car, which isn't, you know, that's kind of nuts. So what the team correctly identified is this is a massive opportunity. This grammar thing you can think of as an agent.

28:07It's a proto agent, one of your first agents, if you will. Relatively limited in terms of skill, but turns out that one agent is an amazing business. What else could we put here? Well, we could actually just build all the superpowers wherever you work, and we could have it be connected to all the tools and applications you already use. So imagine you and I are working together, and let's say we use Slack. And we're talking about a design, maybe where you Slack me a Figma link, and I'm like, yo, this is really cool, but there are some things I want to talk about live. And one of both of us is running SuperHuman Go.

28:46Let's say I'm running it. When I say we should talk about this live, imagine that getting an underline, an annotation inside of Slack. And I hover over it, and SuperhumanGo says, hey, it looks like you want to schedule a meeting. As soon as I hover over it, actually in line in that canvas, I see your calendar and my calendar side to side. This is where we can leverage what we've been building at Superhuman Mail. To your point, we're really, really deep on calendar, very close to an experience that we could pull out as a separate calendar app. Whether or not we do that, we're still debating, but we could do it.

29:21And you can then click. And without leaving, without me leaving Slack, without me breaking flow, without me losing concentration, without me losing focus, I can create a calendar event for you and me. And because Superhuman Go is connected and it can read the screen and it knows what's going on in our apps, it's not just an empty calendar invite. It can pre-populate it with the Figma link that we were discussing and maybe even a summary of the conversation that you and I were having. That's a very, very simple example. But you can imagine these types of assistance that Superhuman Go gives you becoming increasingly more powerful.

30:00And the core strategic advantage here is it's ubiquitous. It works everywhere you work. It's proactive. It works without you having to remember to use it or without you having to know how to prompt AI, which is two big friction points.

30:16Turner Novak:That's a barrier, yeah. Huge barriers, both of them, actually. There's a really interesting study by MIT, I think, that looked at the efficacy of people using mainstream LLMs like ChatGPT and CORD and so on. And they found that more than, if you look at the efficacy of the results, more than half the efficacy is as a result of how well you are able to prompt the AI, not the difference between ChatGPT and CORD. In other words, half the battle is knowing how to prompt it. This may sound obvious. And then the other half of the battle is just remembering to go there. And so if we can fix those problems, that's a really big deal.

31:01And then the third advantage is it's connected. One of the really cool things about the code acquisition is when we say it's the all-in-one AI workspace, it's actually the most connected AI team workspace that exists today. I think it's integrated with 800 different applications and websites. the volume of transactions is the wrong word, automations, the volume of automations that happen through Coda is actually comparable even to Zapier. Like it's really, really high. So a lot of these rails already exist. And so this is a smart application of strategic advantage. Okay, we've built this AI superhighway that we could put any agents in.

31:46We built in this one product, we built this ecosystem of connections in this other product. What we can now build is proactive AI that works wherever you work, that knows what you know, knows what your team knows. And it's really the kind of UI that people haven't experienced yet.

32:01Turner Novak:Yeah, it sounds like Grammarly has got this almost backdoor into every keyboard, and you can create some automation experiences using AI any place someone would type to interact with a computer. Is that just a super fair way to really succinctly summarize it? Definitely fewer words than what I've used. Yeah, yours was way more elegant. Mine was the most simple. That's the sound bite, I guess. Yes, I think we would say it's AI that works wherever you work, that you don't have to remember to use, and which knows what you know. So then, because I feel like with Superhuman, people have always loved the product.

32:46Turner Novak:like that's just something i i would never identify somebody who says oh i love my email provider but i have probably paid superhuman four figures thank you yeah you're welcome actually probably not four figures i guess if it's 30 a month i had an employee though who use it so i might i may have paid you over four figures so and people love the product i mean i think we can maybe talk a little bit about this right afterwards people just talked about all the time because they loved using it. How do you think about making an AI product now that people love? Are there certain things that you're thinking about?

33:25Turner Novak:I've got this good hit rate in Superhuman. How do I keep it going in this new almost interface that people are using? Yeah. In many ways, it has not changed from making a product that people love prior to AI. Of course, the skills change. And the pace of innovation has changed for sure. So what made a good, beautiful UI had not really evolved for a very long time. And we have some credits, I think, to take for changing the way the industry has done certain things. We popularized Command K. We were the first venture-backed app at scale to really bring it to knowledge workers. and then it made its way into Slack and almost every tool, Figma has it.

34:15Turner Novak:Command K was just like you tap Command K and like search and you just like, it's like you can get anything you want, right? Yeah, yeah. Not search in the sense of searching the content of the app. But the idea is, look, we all want our tools to be visual and minimal and but somehow at the same time, easy to use. We want to avoid end shitification, if you know what I mean by that, like the crunch that tends to develop over time. But at the same time, we as a company and as product leaders, we need to expand our markets, right? If we started by selling to founders and CEOs, possibly one of the most niche markets you could have come up with.

34:56Turner Novak:Yeah, venture-backed founders and investors, yeah. Like, yeah, there's maybe a few thousand people, a market of a few thousand for this company. Which, by the way, I think is a great strategy. I love it when founders are like, yeah, my initial market is a few thousand people. Because it lets you solve very, very tightly for their needs and then expand from there. Anyway, of course, we have to keep on expanding. And as you expand, you need to add features. You need to push the product in lots of different directions. How do you keep it visually minimal? And part of our answer to that was Command-K.

35:30What if whenever you needed to do anything, you just hit command K, type in a few characters of the thing you're trying to do. And it's a fuzzy logic match. You can even get the characters in the wrong order. And we had a lot of fun building that. And it gives you the commands. And not only does it give you the commands, it shows you the shortcut for next time. So you don't even have to hit command K. And people just fell in love with it. And of course, now it is considered table stakes in productivity software of choice. And I say of choice because not everyone has implemented it, but if you're a discerning user, then it's the kind of thing that you're going to look for.

36:09So the point I was making was UI, like what good UI was really hasn't changed that much. We pushed the envelope in terms of keyboard shortcuts, in terms of command K, and then I think later on in terms of what does a great onboarding look like. But in terms of making a software that people love, I think it's because we make software like it is a game. Most software companies worry about what users want or what users need, but nobody needs a game to exist. There are no requirements for a game. And when you make a game, you don't worry about what users want or need. You instead obsess over how they feel.

36:48And when your product is a game, people don't just use it, they play it. They find it fun, they tell their friends, they fall in love with it. and game design turns out to be an altogether different kind of product development. I think that's the real secret to what we do at Superhuman.

37:04Turner Novak:Do you think to make a good AI product, it almost has to kind of feel like a game? Look, I mean, there are many ways to skin a cat and there are many roads to success. At Superhuman Male, that was definitely the lens that we had, which is make this as fun as a game. Apply the principle of game design. yeah because i remember i think one of the things i really that got me interested in it and like reason was to use it was the shortcuts if you're if you've used excel if you do any kind of like finance job they're like don't touch the mouse only use the keyboard and then if you go back to like video games like i i was literally playing age of empires one a couple nights ago i don't know if you ever play age of empires but with those games you need to use the keyboard because you're like so what i've been doing is i'll play age of empires one on hardest difficulty i don't know if you've ever but basically they just get unlimited resources yeah they're like cheats at that point yeah they basically get to cheat so you have to figure out my advantage is like i literally just know the hockey's to like quickly create and and move things around as fast as possible so i mean that's that's a gaming like gaming design 101 for like these more advanced games it's like is the shortcuts, the hockey's.

38:22Exactly. Yeah, totally. So, I mean, it turns out there's a lot that goes into great game design and I've actually been obsessed with game design my entire life.

38:32Turner Novak:Yeah, I was going to say, you were a game designer for a while, right? So did you get into it? What was the first game you played? Do you remember? That's a great question. But one of my first experiences as a game designer, I was like six or seven years old and my parents were doctors when they were working. And I remember waiting for my dad to come home and I would have sketched out like a little mini maze or a dungeon on paper. It's a pen and paper game. And I would kind of wait behind the couch apparently with this pen and paper thing. Like hiding? Yeah, I would like jump out to surprise him when he would come home.

39:17and it's obviously not a surprise because if that happens every day, it's not surprising.

39:21Turner Novak:Yeah, to you, as a six-year-old, you're like, I bet he forgets. He doesn't know what he does. I bet he forgets because, boy, I forget everything day to day. So anyway, I did that and then once I had his attention, I'd be like, cool, okay, we're going to play a game. And I just drew this maze and I just drew this dungeon and he would humor me. But that was like my earliest memory of creating a game that someone else would then play. And so really early on, I fell in love with this idea of creating fun gaming experiences for other people. Before I was a founder, I actually worked as a game designer.

39:54I worked at Jagex, which, fun fact, people, I bet no one listening to this will know this, but stands for Java Graphical Extensions. Because back then, online games used to be built in Java. And at the time, we built the world's largest online free massively multiplayer role-playing game in Focus More Room because it was called RuneScape. And I had the really fun job of developing a fair amount of content for that game, including a lot of the southern tropical island. It was the island of Karamja. And I can't tell you how many people, I mean, I can't. It's not that many. But it is surprising. I can tell you precisely how many people, like two or three people a year.

40:39who pinged me, who were like, hey, superhuman, yeah, whatever. But that thing that you made when you were 18, 19, 20 years old, that was like a formative memory for me as a child. I was like, click, click, click, click, all the way through that. And it was so cool. And the quest I made that people really to this day remember and ping me about all the time is Monkey Madness, which was a very, very ambitious quest for the game engine that we made. Anyway, so yes, I did work professionally as a game designer for a while. And during that time, and as a founder, I took the opportunity to go really deep into the principles of game design.

41:19And it turns out there is no unifying theory of game design. To create games, we need to draw upon the art and science of psychology, of mathematics, of storytelling, and interaction design. And at Superhuman, we distilled these down to five factors to consider, which are goals, emotions, toys, controls, and flow. And across those things, we then identified about 13 principles of game design. And one example of principle would be make fun toys and then combine them into games. And so a fun question to consider is, are toys the same as games? It's a philosophical question. What do you think? Are toys the same as games?

42:03Turner Novak:I would say probably not because I think a game is like a system of fun things or designs kind of stitched together and a toy is just one single experience. If that's how I'd maybe define it, yeah. Yeah, I mean, there's no right or wrong answer here, but I think that's right. That there's a level of complexity to games and they're often comprised of toys. There's also a linguistic difference. We play with toys, but we play games. That's an interesting difference. A ball is a toy, but football is a game. And to your point, it turns out that the best games are built with toys. Why? Because then they are fun on both levels.

42:46The level of the toy and the game itself. Now, in Superhuman Mail, a favorite toy is the time auto-completer, which you use to snooze emails when you hit H and you're pushing the email out. and you can type whatever you want. It can be complete gibberish and it still does its best to understand you. And I realized this was fun when in onboardings, I would see people just to start playing with it quite literally, right? Like you can type in 2D and it becomes two days, three H becomes three hours, one MO is one month. And then people start to indulge in what I call playful exploration. They're thinking, what can it do?

43:25Where does it break? How does it work? And it's not long before people start doing this. Hmm, I wonder what happens if I keep typing 10. Well, it turns out that's October the 10th at 10, 10 p.m. Well, how about the sequence of twos? Well, that's February the 2nd, 2022 at 2 p.m. And then I saw people trying to do more complex inputs, like will it get in a fortnight and a day? And then lo and behold, it works. And it's not long before people start finding pleasant surprises. And by the way, pleasant surprise is the fundamental underpinning of joy. the emotion. For example, time zone math happens without you thinking about it.

44:00Like you can say, hey, send this message 8 p.m. Tokyo time. And it turns out that's 8 p.m. Eastern time. Who's going to stay awake until 8 p.m. Eastern time? And most people are really delighted to find out that if you really want, you can snooze emails until forever. Like they never come back. You can literally type in H never, and then you will never come back. And there's a fun little Ascii shrug emoji, you know, the one that Niva Shrug Ventures has, like that's the representation of it. So, yeah, I would say to people interested in game design, like think about the features of your product.

44:36Do they indulge playful exploration? Are they fun? Are these features fun even without a goal? And do they create moments of pleasant surprise? Because if so, congratulations, you have a toy and you can use that to build a great game.

44:51Turner Novak:Interesting. So your company that you built before Superhuman, it was called Reportive. Was it anything like, it was kind of email-based, right? Am I remembering right? Like it was like a LinkedIn email overlay or something? Yeah, it turns out I have an email problem. Yeah, you just can't get away. I can tell you exactly why. I went to the University of Cambridge and I started a PhD. Because I had the absurd delusion that a PhD would be a great way to start a company. And it turns out to be one of the worst possible ways to start a company. And the best way is, in fact, just to start a company.

45:37And so I learned that about a year in. I had a great time. Like, I really... What were you studying? Machine learning, way before anything worked. So this was 2005 to 2006. I did like a year, a year and a half.

45:52Turner Novak:So this was like literally if-then statements kind of a thing, like earliest version of it. It was a really interesting point during the state of the art. We'd gone beyond if-then statements. Neural networks were decidedly un-fucking-cool, which today is kind of like, what? But it was a dead technology at the time. It was all Bayesian inference and regression. It was a different time. I'm like very little actually works. Yeah. What was like the coolest thing you could do? Automatic scanning of deposited checks and like knowing what those numbers were from hand-rising. It was 2005, 2006. That's impressive.

46:37Turner Novak:Yeah. Maybe actually more impressively than that was like large scale translation and very few companies could do this. Google could do Google Translate, But it was not that impressive. And so I also realized I'm not an AI researcher. Maybe I could have been, but I'm much more of an entrepreneur. I'm really a designer at heart. And I made a name for myself at the computer laboratory at Cambridge in the UK by being the hype man. A lot of these researchers were not good at explaining their ideas. and they were not great at writing papers. And I'm like, I'm a pretty good communicator. I can take your idea.

47:23And like, you tell me where you want to get it published. I will get the paper published. You know, I'll craft the perfect abstract. I'll think of really, really good examples to market. Basically, product market. I would product market. The AI research. Yeah, yeah, yeah. Yeah. Which, you know, weirdly, now that I think about it, Why isn't that how academia works? Like every department should just hire product marketers to help their researchers. And it's kind of not structured that way. It should be. Because someone will like write a paper of like, you know, like CRISPR, like we can edit

47:56Turner Novak:DNA, we can literally like create anything like we can cure and solve all problems in the world. It's just like no one knows it exists because no one has marketed the paper correctly. Like, I feel like that's probably one of the biggest, the highest ROI unlocks anyone could do. Maybe after post-Superhuman, you go back and you'd be like an academic research hype man again. Maybe, maybe. One of my co-founders did precisely that, and he's made quite the name from reporting, not from Superhuman. He's made quite the name for himself, Martin Kleppman. Well, what do I know? That was two decades ago. For all I know, this is exactly what they do.

48:31The point is, I was not a great academic, and I have completely lost the track. Why am I telling you the story? What was the original question?

48:40Turner Novak:Well, for reportive. So you somehow dropped out your PhD and started the company, right? Yeah. Okay. Here's why. Here's why. I knew I wanted to be an entrepreneur. And I was like, okay, I'm not going to be an academic. How do I be an entrepreneur? I networked my way into the part of the University of Cambridge that helps staff and students create companies. This thing is called Cambridge University Entrepreneurs. We would literally give money to teams to go and we would like first money in, right? Pre-pre-pre-pre-pre-seed incorporation money. And not huge checks, like in the region, 25 ,000 pounds, so call it 30, 40,$50 ,000 at the time.

49:24So it was a kind of a dead organization. It's student run, it's volunteer, it's entirely grant-based. We would come to people like you and like beg and be like, hey, Mr. VC, can you please give us some cash so we can give it to the founders and to the staff? And like most student-run organizations, it was in a complete shambles. Like the previous guy did a terrible job running this. Most people are doing it for resume points. They end up going to work for Goldman Sachs or McKinsey. No one really cares, right? And I did not want to work for a consultancy or a bank. And for me, I really, really cared.

50:03I was like, no, this is my life. I am going to be an entrepreneur. I am going to be a founder. And so I whipped this organization into shape and I started fundraising. No one had ever taught me to fundraise before. I was 21, probably. And this is the hardest kind of fundraising. You know, founders sometimes complain about fundraising, but let me tell you, founders, we get it easy because you're selling equity. I was selling good vibes. I was like, this is grant money. You give me money. And like I say, Turner, give me money. You don't get anything back. What do I get? I'll be like, I'll maybe buy you coffee, although I'll kind of expect you to buy me the coffee.

50:44So it was a good trial by fire. It really taught me how to fundraise in the most harder circumstances. And it also taught me some of the finer points of BD and how do you build relationships? How do you maintain a massive network? and I realized the problem that led me to my last company, Reportive. Now, with Reportive, you could see everything about your contacts right inside your inbox. You could see what people look like, where they're based, where they work, what they do. You could find ways to break the ice, topics, bond over, reasons to get back in touch, and you could learn how to be astute, personal, effective, and ultimately brilliant with people.

51:29And by the way, this feature is built into superhuman mail. It's awesome. It's pretty unique. It's one of the reasons people love the product. But back then that this was the product, it was the entire thing. And that is that knowing that it would like a product like this just had to exist. I came to that realization through running this organization, Cambridge University Entrepreneurs. And it got like pretty big if I'm remembering, right?

51:57Turner Novak:Like you had, I forget, I actually have never seen like an actual number. I just know that it got pretty big, but what was like the scale of this? And then what happened? Like ultimate, ultimate outcome of the business? Yeah. Yeah. We scaled initially super rapidly at the time. I mean, these, these numbers will seem quaint in retrospect, but. But this was in like 20, 2009, right? 2010 ish. Yeah, I started writing the first line of code. This was a single founder company to begin with. Actually, so was Superhuman. By the way, I think that's the best way for companies to start. We can talk more about that in a bit.

52:32But I wrote the first line of code January 10, 2010. And then six weeks later, I was done. Like it is, it was such a simple product. And I'd applied to Y Combinator. Now, if you've applied to Y Combinator, you would know this, that one of the fields is please give us the link to your demo if you have one so we can play with it. Actually, I don't know if they still have that, but they did at the time. And I didn't want to create any unnecessary friction, so just password unprotected, I applied to Y Combinator and I put in the link. And it was a Friday, I think, like 2 p.m., 3 p.m., Turner, what do we do in the UK on Friday at 2 p.m.?

53:19Turner Novak:Go get a beer. We went and got a beer. Yeah. Wait, was I right? Yeah, of course. Absolutely. 100%. So it cycled from the office where I was squatting to the local pub, which was called the Golden Hind. And I had a pint of beer. We were just hanging out with a bunch of other founders, and we were chit-chatting. This was 2009. Oh, you did have a phone, I was going to say. I did have your phone. Okay. So this is like barely iPhone is like just kind of out. Yeah. But yeah, I was like an iPhone 3G. Yes, I think. Yeah, I think so. And I had a phone and great industrial design, by the way. Like it starts buzzing.

54:03And I'm like, oh, notifications are coming in for this app. Nozumi. Nozumi was an app for Heroku. And I was like, what the heck is going on here? And it's like sign up, sign up, sign up, sign up, sign up, sign up. and I open the app on the phone, the terminal, and I type in user.count and I hit enter. By the way, I had 10 users when I left the office and it was like 500. I do up and enter and it's like 1 ,000. Up and enter, it was like 2 ,000. I'm like, oh, oh shit. I literally said, here, hold my beer. I cycle back to the office. And it turns out that this good friend of mine Peter had shared the link, leaked the link with the Next Web.

54:51And the editor at the time, Zee McCain, the Next Web used to be like this really, really big, still is, used to be this really big deal. Blog Online had written about it, written an article, and it was like a glowing recommendation, a glowing review. And over the first 24 hours, we had like 10 ,000 downloads. Over the next two or three days, we got like 32 ,000 users. And again, now, like whatever, these numbers. That's child's play. But at the time, it was like, I mean, like Sequoia reached out and like Jason Calacanis reached out and like all these people randomly reached out to this dude in Cambridge, UK, because at the time, that was very, very unlikely and very rare.

55:34And so, First of all, I'm eternally grateful to Pete for leaking that link. That's what a good friend does is he tips off the press and doesn't tell you. The next thing you know, it goes super viral. Secondly, it's exactly what you want when you're applying to Y Combinator. I think my application sucked. But as soon as that happened, they were like, yeah, okay, you're in. You've clearly hacked the system. You want to do fine and good job. Good job, you're in. it was a little bit weird because we ended up having to have the YC interview 30 days before the actual YC interviews, which they do only very rarely.

56:13I don't know if they do this anymore, but they do very rarely. They did very rarely if there were extreme circumstances. So I remember being on a Skype call, that era, on a Skype call with PG and he was kind of pacing around. So we We could only really see his T-shirt and his shorts. He was pacing around. They're like, are you there? He does this interview remotely. His head was above the screen. We saw Jessica's face. Okay. It was above the screen. It was actually really funny. He just got an interview, and we get in. And he said afterwards, that was risky, because the acceptance rate for those interviews was apparently way lower than the normal course of interview.

56:55But we get in. And yeah, that's the story of how Reportive took off. The reason the acquisition came about is we scaled to millions of users and we managed to acquire all of LinkedIn's daily active users at the time, 2012, into one app, like 2 million-ish users. Which is weirdly high and weirdly low, right? But the specific users that we had were a very valuable set of users.

57:22Turner Novak:Yeah, you just think of like who were LinkedIn power users in 2012. It's probably just like sales people and like recruiters and someone who would want that's the bar in their email to just say like, hey, Rahul just did this. You should slide in and, you know, suggest this or. It was a lot of Silicon Valley, a lot of CEOs, a lot of founders, a lot of executives. I would say like that's like half of it. And then, yeah, sales and recruiters. At LinkedIn, we used to say, hire, market, sell. So recruiters, marketers, salespeople. Okay. And then so they got to the point where LinkedIn was like, hey, there's something here.

58:02Turner Novak:We want it. Come join the company. If only acquisitions were that easy. The superhuman one was six months of intense efforts. The LinkedIn reportive one was a bit different. And again, I think there are multiple ways to sell a company. But the reportive LinkedIn one was a bit more traditional. It was the direct result of a business development relationship, an API integration relationship. To begin with, we didn't work with LinkedIn directly at all. Because as you can imagine, LinkedIn did not want people taking LinkedIn profiles and sticking it inside of Gmail. You might think, well, that's good for LinkedIn.

58:46this is the classic platform API protectionism debate. Yeah, it is good for LinkedIn, I guess, but in a way, if they control it, it would be better, right? Like, and if one of their businesses is monetizing search on both sides for people looking for jobs and people looking to hire for jobs, then does this get in the way? Like, there are some big philosophical questions there. So historically, LinkedIn has never had a public look up people by email address API. So what we did is we bought the data, and historically there have always been companies that scrape LinkedIn and sell the data. We bought the data of one of the first companies to do that, which was a company called Rapleaf.

59:27Rapleaf founded by Oren Hoffman and a bunch of other people, including Vivek Sodera, who became one of my co-founders for Superhuman. Fun story about Vivek is he was the very first person I ever met in San Francisco. Okay. Early in the course of reportive, I was like, I need access to some data. It was basically a small data play. Give me a profile. I'm going to render it in Gmail. Who sells the data? There was really only one company that was doing this well, and they were called Rapleaf. And I learned through my mentors, from my mentors in Cambridge, what were blessed with a lot of successful entrepreneurs around the University of Cambridge.

1:00:08A very clear lesson was there is no substitute for simply turning up. And so I just got on the plane and I landed in San Francisco and I emailed Orrin Hoffman, the CEO of Rapleaf. I was like, yo, this is me. This is what I'm building. You may have seen we went viral yesterday or two days ago. We're interviewing with YC and just got in. Can I please come and hang out at your office? And also, by the way, can I have your data? By the way, I don't have any money. Can I have it for free? And to my great surprise, he, but again, like if you don't ask, You're not going to get it, right? Got to shoot your shot.

1:00:43To my great surprise, he said, sure, come swing by the office. We'll take good care of you. As I think you might do, you know, like this young child is like, hey, could I have your attention? He's like, yeah, yeah, cool. Have some attention. And he pawned me off to Vivek. I was like, Vivek, you are our startup guy. This appears to be a startup. Maybe please take care of whatever this is. And so I get to the office and I meet with Orin. He gives me like 15 minutes. I give him the pitch. He's like, cool, if you're investing, if you're raising money, I'll invest 10K. And he then handed me off to Vivek.

1:01:24And Vivek was like, so I guess he was the second person I ever met in San Francisco. And he then brokered the deal with me. And he was like, yeah, we'll give you like 4 million lookups a month, which at the time was, I was like, because you can cache these lookups and the data doesn't change very frequently. I was like, wow, that's like way more than we'll need for a very long time. And then after that, it was going to be a few cents per lookup. We negotiated the cost and I went my merry way. And that was that. We didn't really talk that much thereafter, except for YC Demo Day. And I do the YC Demo Day pitch.

1:02:02And it was a very weird pitch because we'd already raised our seed round by then. So my pitch for YC Demo Day was like, I've already raised money, but let me tell you what we're doing anyway. And if you'd like to stay in touch with Series A, then let's talk. The person who came up to me after that YC Demo Day is a person we both know, Emily Choi. Who has this massive role at Coinbase now, right? And at the time, she was running corp dev for LinkedIn. And she said, hey, this is really cool. This is really interesting. Would you be down to come like hang out at LinkedIn and speak to, I think our head of products at the time, who was Adam Nash, who runs Daffy right now.

1:02:49Great products executive, great angel investor. Really great guy all around. He was like, she was like, yeah, yeah. Can you come hang out with Adam? So I was like, yeah, I don't have anything to lose. Sure. I'll come hang out at LinkedIn. Why not? So I hang out with Adam, and he's super lovely. He's like, hey, listen, so Rapleaf is stealing our data. Oh, no. Your product is really, really great. And we just really don't... He was trying to find the words without saying, you've got to stop doing what you're doing. But we're going to... And he basically said without saying, we're going to sue the hell out of Rapleaf.

1:03:26They're going to die. They're going to go. Go on. He didn't say that literally, but that was the intimation. What was that? This behavior is not okay, but we like your use case. And I was like... Negotiating on the fly here, like a light bulb went off. I was like, oh, this is it. This is my one shot. This meeting, honestly, probably makes or breaks the company. I figured out the right set of things to say. I don't remember exactly what it was because it was in an adrenaline blur where I pitched him what we were building. I pitched him where we were trying to go. I was trying to be as friendly and as polite and as collaborative as possible.

1:04:07and he was like, you seem like a good guy and you seem like you have really, this I remember the basing, you have really great product instincts. Let's work together. I'll give you the API, but don't fuck it up. And I was like, okay, all right. I promise I won't. We leave and then, you know, he connects me to the API team and we get access to this API, which by the way, I think at peak, 21 companies ever had. And then like the other companies were real companies, you know, like Dialpad as the telephony solution and a bunch of other CRM type things. And then randomly reported because of this one meeting.

1:04:47And with this API, we could give LinkedIn email address and they would give us a profile and we'd put that profile in the right hand side of Gmail.

1:04:55Turner Novak:It was all in the name of like giving more information to people and like making it more useful. Right? Yes, yes, yes, yes. So we ended up like, that advantage became such a huge advantage. So like Reportive, like Superhuman, like any company to get traction, like that gets traction, attracted a silly number of imitators. I mean, I think there were like five or six companies that tried to build Reportive and were like, yeah, we can build this better than you can. The thing is, they just never, ever had the data because we were the chosen company by LinkedIn, that they were only going to give it to one startup because I guess they wanted to limit their exposure.

1:05:36They trusted me as a founder. We treated their data with super high integrity and we always protected it. By the way, people would try and scrape it via us. And we promised them that, like, okay, you put your alarm bells on, and we're going to put our alarm bells on. If either of us notice scraping, then let the other know, and we'll fix it. But every month, people would figure out how to scrape the data from Reportive, and we would fix it. So this is a classic BD situation. We now have a very privileged integration partnership with LinkedIn. And of course, as part of that, we would meet with the corporate development team every three to six months.

1:06:22And of course, what's happening is two things. A, they want to make sure you're not abusing the, or three things, you're not abusing the API. B, you're not headed in a direction that's going to be competitive and that you're still like within the parameters of what the API is designed for. And C, because of course they're talking about this. I didn't quite realize it at the time, but this is clearly important enough to them that they want to see it exist, but not quite important enough that they want to resource it internally. But has it become important enough that they want to now own it? And when it became clear that we had all their daily active users, which had I known at the time, I think I would have sold it for a lot more money.

1:07:01Turner Novak:Really? Okay. Yeah. They were like, hey, how do you feel about doing this at LinkedIn? Now, in reality, it was a lot more complicated. I can tell the story if you're interested. But the very short version is we were pitching Greylock for our series A, and we were pitching Reid and David C. And Reid came back, and he was like, there are two ways we can do this. We can write you a term sheet from Greylock. Or here's another idea. Bear with me. What do you think about doing this at LinkedIn? And we talked a little bit about what that might look like. And I'm like, you know what? These are both interesting.

1:07:34Let's parallel track these and see where these conversations go.

1:07:37Turner Novak:Interesting. Okay. Do you, do you, so you feel like, I guess kind of summarize the story. It sounds like you had unique product. You had access to some kind of unique thing that like no one else had. You were positioned in a way where it was like not important to LinkedIn originally. Like they just were kind of like, yeah, whatever. We don't want to build this. like we'll work with this 21-year-old kid and whatever. But it became so well-performing that they're like, maybe we do kind of want this. And then you kind of hit a point where you did have almost like multiple bidders in a way to the point where you maybe had a little bit of leverage, even though you didn't even know maybe the true leverage you might have actually had with how many people were actually using it.

1:08:26Yeah, sort of. So initial momentum, like we built a product that people love based on Wrapped Leaf data. and it took six weeks to build, started going viral. Boom, every investor in the Valley is contacting me. I then leveraged that to get into YC. I then leveraged YC to close a funding round actually ahead of Demo Day, which was unusual at the time. We were the first party round that YC ever saw. PG wrote, yeah, PG wrote his estate, well, specifically high resolution funding, I think is the name of the estate. He wrote that after we did what we did, kind of in response to the pattern that we had.

1:09:00we then leveraged YC Demo Day to get a meeting with LinkedIn. We then leveraged the meeting with LinkedIn and their desire to put that aspect of rapidly founded business to get the direct API. We then just kept building good products and kept growing. We then leveraged, and then to your point, it performed well. We sort of attracted most of our daily active users into one platform. And I think just as they were growing, that they were just post IPO, they were starting to figure out what application services do they want to own. Email is this perennially strategic thing that, you know, it became strategic for a lot of companies at the end of last year as well.

1:09:38That's how I knew it was one of the right times to sell Superhuman. And so it became perennially strategic in 2012 when we sold Reportive. We ended up getting offers from LinkedIn, from Twitter, from Salesforce, I believe. And each with different theses, right? Like with LinkedIn, in, it's we're going to put LinkedIn profiles in Gmail and Outlook. And with Twitter, it's going to, we used to show tweets before Elon killed the API.

1:10:05Turner Novak:Oh, yeah, you did. Yeah, I remember that. Yeah. And with Salesforce, it's the obvious use case of like, what if you could see and update your CRM right from your email like that? That'd be awesome. Yeah. Yeah, it exists. We've done it for Salesforce, HubSpot, and Pipedrive. So very obvious reason, And we spoke with Google as well. Very obvious reasons for all these companies to own Reportive. And, you know, again, we ran a process, which was insane and crazy. I ended up going to hospital. LinkedIn signed a term sheet. They ended up walking away from a signed term sheet. All kinds of drama. Wait, so hospital?

1:10:43Turner Novak:How did you end up in the hospital? I was working so hard and living so badly as a, I think I was 20, 25 at the time, maybe. I just not taking care of myself that like I burned out mentally and physically. And that happened in the middle of our series C fundraise and in and around the acquisition process. But I will tell you this. I, let's see, I'm trying to summarize this. So I was hospitalized for about a week. Long story short, I ended up, we had an office for a report of 588 Brandon, I think it is, across from Tres Agave, the Mexican place. And I was walking to the McDonald's that used to be near 4th and King.

1:11:42and I remember walking every single step being more and more painful like this sharp shooting pain of my leg and it was getting worse and worse and worse until by the time I get to the McDonald's I'm like I just can't walk anymore and I end up collapsing on the roadside and there's this because it's San Francisco so next to this homeless guy he looks at me he was like hey buddy you don't look so good. I'm thinking, wow, how did my life get to this point? Like, what happened? Then I collapsed outside the McDonald's and the home of the sky is telling me I don't look great. And so I pull out my iPhone 3GS and I text one of my teammates, Lee.

1:12:28And I'm like, yo, Lee, I think I might be dying next to McDonald's. Can you please come rescue me? And he comes racing out of the office. He finds me and then he picks me up and he hoists me over his shoulder and I'm like onwards to Safeway. He kind of just like drags me the next two blocks to Safeway. I buy some medicine because I'm having this major acid reflux episode. So I buy some antacids. And like an idiot, I go back to the office and I keep on working. And I work the rest of the day and I wake up again at three o 'clock in the morning with this major intense abdominal pain, like really, really bad, lower left abdominal pain.

1:13:07And by the way, if anyone's ever feeling that, you should be worried. This may be appendicitis. Like that is a go to the hospital situation, right? So I called my dad, who is a doctor. And he was like, this may be appendicitis. You should go to the hospital. So we're new to the US. Me and my two co-founders, we're all British. I didn't know how any of this works. I'm like, do I even have insurance? I think I have insurance. I wake up my COVID, like, we need to go to the hospital. We could barely afford an Uber. Taking an Uber was considered extreme for us. We would always take public transport.

1:13:41But we splurged for an Uber. We get to St. Francis Memorial Hospital. And I remember the nurse interrogating me. She was like, okay, so can you describe your day? And I was like, well, like, what do you do? I'm like, well, I'm a founder. She's like, how's it going? And I'm like, oh, yeah, it's fine. We're crushing it. Remember that time when was Gary Vaynerchuk crushing it? We were definitely crushing it. And she was like, no, really. And I'm like, well, honestly, it's pretty stressful. And she ticks something on her clipboard. And she was like, do you do any exercise? And I was like, I think I exercised sometime when I was 15.

1:14:23She was like, what do you eat? Do you have a good diet? And I was like, well, for lunch, I have a bagel and a brownie. And then as a team, we go out for dinner every night. And she was like, you have a bagel and a brownie every lunch. And I was like, yeah, I've had that for the last two years. She was like, OK, so what do you what do you have for dinner? It was like, you know, we will have a pizza or a burger. We'll go to 21st Amendment. We'll have some beers. And she sighed and like tick. And then she had another question that I don't remember. And she said, OK, so here's the thing. You have a hiatal hernia.

1:15:03It's a hernia right here, right? Amongst other things that are probably going wrong. And that is irreparable, short of surgery, which actually doesn't really work. And that explains the acid reflux. We don't really know what's going on with the rest of you. but your insides are basically way older than your outsides. And you need to stop living like this or you will die quickly. And I know that that might be harsh to hear, but like that is just the truth.

1:15:31Turner Novak:I mean, you're going to die if you don't. You need to hear that. Yeah, I know. I know. But you know, like, and I now say this, I have given this story so many times to younger founders and sadly to not so younger founders. I know people doing this in their 30s as well. I'm kind of honestly I'm a little worried about this whole 996 thing because you know what if it works out freaking great cool you make a hundred million dollars and you sail off into the sunset and that's good for you but if it doesn't you might die early you might get a hiatal hernia like you might have these irreparable life problems now I'm at least glad that the younger generation is drinking alcohol way less but like you know they're doing other stuff.

1:16:15And we don't know what that other stuff is, what the long-term implications of those things are going to be.

1:16:22Anyway, why am I telling you the story? This all happened simultaneously with the LinkedIn acquisition. And I will tell you, coming out of that experience, I was in hospital for a week. I was in recovery for about four weeks. My aunt and uncle very lovingly took care of me at that place in Sunnyvale. And I was like, I had to learn how to eat again. I was like eating little tiny bowls of rice every day, liquids only. And then slowly my, like, I think the level of system shock was just all basically everything shut down. I had to learn how to move again and walk again and eat again. And like, it gave me this profound appreciation for my health and for my body and for my level of stress.

1:17:09And that is a superpower. That is a true superpower when you don't give a in fundraising situations or in M &A situations. Because just a few months before, when the Series A investors were mistreating me, which they did, not Greylock, but the other firms, or when the potential acquirers were mistreating me, which they did, I used to get really wound up about it. I used to get super stressed about it. It felt existential. It felt like my entire life was at stake here. But something changed. It really just felt like a change in aura. I literally stopped caring. I just did not care anymore. Zero fucks left to give.

1:17:55And I was in those meetings. And the moment I sensed BS, I was like, cool. We'll be in touch. Nice conversation. And you know what? that changed the dynamic of every single conversation I was in. They could feel it. They could sense it. And suddenly everyone started chasing us. It is weird how much aura plays a part in fundraising and M &A, but it does.

1:18:17Turner Novak:So you almost died and almost dying completely just changed your, really like your, just like mindset and your perception to the point where you just like didn't give a shit about the material work, like immaterial material things like, oh, what term sheet do we get? Whatever. Just like I almost died. Like, I don't give a shit. Whatever you can throw at me. Like I I've seen the worst of this. I've seen. Yeah, exactly. I was reminded what actually mattered. And, you know, I still cared about making the company successful. And here's a crazy fact. We sold the company with two weeks of runway left.

1:18:54Two weeks. You can imagine that at a premium is a great exit. Some of our investors made 20x their money. Most of them made three to five X their money, two weeks left. And at the end of that, I was just like, I was like Zen mode. And there was just something about the aura where I just didn't care anymore. Like I knew it was going to work. And my reaction was, I'm going to make this work no matter what. And the thing that I lost patience for was being mistreated. And so when people would mistreat me and give me BS answers or the runaround or ghost me, I was like, yeah, I'm not dealing with it.

1:19:30Yeah.

1:19:31Turner Novak:So you mentioned two other things. LinkedIn pulled a term sheet or something with the acquisition and then also the two weeks of runway before you landed this. Tell me about those two things. Yeah, we signed a term sheet with LinkedIn on December the 11th of 2011. And there are two ways you can do M &A at the small scale. I mean, at the small scale is often like an acquisition of talent as just as it is roadmap and future roadmap. And for us, it's kind of a mixture of all of those things because we were only five people, including me. And so you have a choice of doing the interviews before signing a term sheet or after.

1:20:13And there are pros and cons either way, of course. Interviews, this is when they meet the team. Meet the team. And for a team of five, they're going to meet the whole team. For superhuman, male, I think they met maybe, I want to say, five, 10, 15 people, max, more like 10 people. But for reported, it was the entire company because we were only five people. And so they are going to meet the people at some point, sooner or later. Any acquirer is going to want to peek under the hood and do the due diligence and say, okay, every founder says they have the best team in the world. are they actually?

1:20:53Way more due diligence happens here, by the way, than VCs do. VCs, I found, just generally roll with it. They'll meet your co-founder. Maybe they'll come to the office, but that's very rare these days.

1:21:01Turner Novak:Some of them don't even meet the co-founder. They're just like, ah, Rahul seems great. The chart's going up. Which is shocking. Most VCs do not meet the CTO. It's kind of crazy. I mean, I've changed my initial decision based on meeting other co-founders. Whether it's I actually do end up investing or I don't based on meeting other people on the team. And it's usually not like I met the CEO, I hated them, but then like the CTO was great and I invested. It was more of like, man, maybe there's something here. I just always meet both the co-founders and you meet the CTO and like, oh, this person's a really good engineer or like really, there's definitely something here.

1:21:42And then you go back to the CEO and you're like, okay, now I kind of get this.

1:21:45Turner Novak:So I think that's really so important, just meeting everybody, as many as you can. Yeah, I couldn't agree more. So LinkedIn met everybody, and we disagreed about this. There's perverse incentives here, because the company is always trying to acquire you for less. And I think people are literally incentivized on that. I think there are people in the organization whose job it is to acquire you for less. and we thought that you know we signed we agreed a price at the term sheet this is me and my my naivete i thought cool end of negotiation that's bs that is not the end of the year that is like the first 10 or 15 and so there's going to be a bunch of retrades and reprices all along and do not be surprised if you end up anywhere from like 50 of what you thought you're going to sell up to like, you know, maybe you trade at a heck at 10, 15 % below whatever that price was.

1:22:43Right. And, but I didn't know that. And they met the team and there were two or three people where they were like, they were like, okay, some of your engineers, fantastic. Some, you know, we, we don't think they've, they've met the bar that you've sold us. And I was like, that's BS. These people are fantastic. They are great. You don't know them. And they actually are phenomenal and went on to have incredible careers at LinkedIn. So like LinkedIn was wrong. I was right. But we got into this disagreement about this and they wanted to retrade on the basis of interviewing the team. And then stuff happened internally and our executive sponsor went on like a six week vacation and this, that, the other.

1:23:20And they pulled the term sheet because they wanted to retrade on price and we couldn't agree on the retrader price. I felt like it was just like completely not within the spirit of how we were engaging. But of course they did end up buying the company three months later.

1:23:38Turner Novak:Yeah, because that is pretty common where they'll say like, oh, you owe like back taxes or, you know, we incurred all these costs and like you have to pay the costs and we're going to like back it out of the price. And then you and then also it's like you might have had you might have had other conversations that you like drop out of and they know you're like the only option or they they know that they are now the only person you're talking to. So you want to make sure I've had that with with portfolio companies before is like all those things I just mentioned have been things where they've like, there's kind of gotchas where, yeah, the price is like 30 % lower than you initially thought.

1:24:12Turner Novak:And you have a month of runway and you just have to do the deal. Yeah. I mean, there are ways you can protect against this. And I'm by no means an expert, but I think we handled this very well at Superhuman. We worked with, and I'm going to give a shout out to my new favorite M &A advisory bank, Axom, AXOM. They did phenomenal work, incredible work here. They're all ex-catalyst, which means they have the catalyst playbook, the precision, the Rolodex, the contacts, the whole thing. It's really, really, really great work. And I don't remember the term sheet exactly, but it's things like, look, we both agree there will be no material retrates.

1:24:53Now, what is material? We didn't define what material is, but at least there's something to point to that we can start to have a conversation around if and when we need to. And we agree the topics that we will retrade over. Sales tax is a class of class. And that's super normal, like actually happens, is happening in our case because like most startups don't pay sales tax in certain states. Like it's just not something that you set up. And that also isn't a risk most acquirers can take on. So when an acquisition happens, it is expected that those states will come knocking and say, hey, you owe us.

1:25:31It's usually not a bunch of money, but you owe us some sales tax, right? And to mitigate that, you'll create these escrow funds or a holdback or things along those lines. That's all completely normal. But you know what? 26-year-old me did not appreciate the extent of the retrade that that LinkedIn wanted to do.

1:25:49Turner Novak:Yep. And I actually have to give a shout out for speaking of sales tax. One of the sponsors of the show, Numeral, they're probably the best way to figure out your sales tax if you're a founder. Just plug it in, start using it. They'll figure that stuff out for you just as you go. The worst thing you want is to owe like 10 grand, 20 grand in a bunch of different states and you just weren't keeping track of it. So they're a good way to get around that. You still have to pay it. But one thing you can do is you can actually, Usually your customers will pay it. If you're just like, hey, 4 % sales tax on the invoice.

1:26:22Turner Novak:You can generally tack it on. You just got to do it. Because a year later, you can't really go back to your customers and be like, hey, by the way. Yeah, it was getting right. Just thinking through. So when you first started Superhuman, you had alluded to earlier, you did this personal onboarding. Can you just explain what that was? I feel like there's a superhuman onboarding was like a thing that people started to do. Can you just explain it and how it worked? Yeah, I've seen a lot of companies, especially in the productivity space, get this wrong. And I no longer believe in the traditional launch.

1:26:58Let's say you've built a new email app or a new task manager or a new calendar app. Now, the surface area of these products is absolutely massive. It's bigger than almost any domain you could think of, which means you also get a massive service area for bugs, as well as massive variability in how users want to use the product. Most companies would launch their app, and because the demand for these products is so high, you quickly get tens of thousands of users. As we talked about, that's not harder these days. But guess what? Those users will very quickly find thousands of bugs, and any company would very quickly get overwhelmed.

1:27:31And they would simply not be able to fix those issues fast enough. And so those users then become disappointed, they churn out, and they tell everybody about their experience. And that is the very definition of a net detractor. And in my experience, it's significantly better to do what we did, which is onboard customers at a measured pace every week. And that way you have the bandwidth to fix any issues they find and you can focus on making them especially and particularly happy. So yeah, that's what we did.

1:28:00Turner Novak:And you have this sort of quantifiable product market fit framework. is that, does it fit in with that at all? And then I'm curious, like really quick, what is it? And have you made any changes to it over the past couple of years? Because I feel like people are probably pretty familiar with it, but maybe have you had any changes in kind of how you think about it? So I think we're talking about the product market fit engine that we built at Superhuman, which I believe is still one of the most shared entrepreneurship posts of all time and on first round reviews. So if you want to find it, search for superhuman products market fit engine.

1:28:37It gives you a way to define products market fit. It gives you a metric to measure products market fit. And it gives you a methodology to systematically increase it. The crazy thing is it can even generate your roadmap for you. And guaranteed, this will make sense when you read it, guaranteed that roadmap will take you to products market fit as measured by this metric over time. And it's a very thorough process, which is definitely more than a 15 minute conversation. But it basically revolves around one core question, which is how would you feel if you couldn't use the product? Three possible answers.

1:29:09Very disappointed, meaning they would love it. They'd love the product. Exactly. Somewhat disappointed or not disappointed. And you measure the percentage that say very disappointed. And there's a whole process for figuring out what to build to get more and more and more people saying very disappointed. And yes, we still use it to this day.

1:29:27Turner Novak:Interesting. And it's basically if I think it's 40 % of people are very disappointed, then you have product market fit. Am I remembering that right? Yes. Although the caveat with all of these metrics and supplies to NPS and everything else is the number changing over time is just as if not more important than the absolute number because there's going to be some form of systematic bias in however you measure this. And we do it by email. I'm sure we'd get different numbers if we texted people, right? But the question is, how is it changing over time? Interesting. Okay. And it's why products do like email might be a product that people naturally hate or love versus it might be another category that people, people like love this, even if it's a bad product, just generally speaking, like the category.

1:30:08Turner Novak:So I guess you could be biased there too. But that's an interesting point of just like, do people over time get more and more disappointed if you were to no longer be able to use the product? Or as you add new and new personas, are you able to maintain the high score that you have? It's usually how we think about it. when it comes to sort of like building the superhuman brand? I know we talked about earlier, you literally rebranded the top company around the superhuman brand that you had kind of built. Maybe it was just a coincidence because the name is a great name. Maybe that's all it is. But like, how do you think about just building a good brand?

1:30:47Well, I think there are two pieces to this. Number one, build something people love. And then number two, build something memorable. And even if you don't love Superhuman, the product, you can't help but remember it. Like, it's just one of those names that it kind of piques interest. It's intriguing. If you didn't know it was a mail app, like, hey, what is this Superhuman thing? What does it mean to be sent by a Superhuman? Like, what actually is that? So there was that. And the other piece of this was I was deliberately back solving for a 100-year iconic generational brand, which it still feels surreal because it just happened last week, I think will happen.

1:31:27I think that we are going to build this 100-year company. And this dream that we had when we founded Superhuman all the way back 11 years ago is going to still come to pass. And that is incredible.

1:31:42Turner Novak:Do you have any, like a personal productivity stack? I don't know if it just use all the superhuman suite of products, but what do you do you think that's unique in terms of being more productive? I'm assuming you've got to have some tricks up your sleeve. I do. Of course, the superhuman products are amazing, but this birth of the question isn't that. Outside of the superhuman products, I am typing so much less than I used to. More than half of my input is now voice. I use this app, Whisper Flow. It is incredible. I just hold down function. I just say what I want. They do things where they like screenshot the screen in and around your dictation.

1:32:22So if there's a particularly hard to spell name or like a project code name that's weird or unique, they'll even get that. And I mean, as you can tell, I speak pretty fast. I speak even faster when I'm dictating. And it gets it right. And not only does it save me time, I'm less tired at the end of the day because I haven't been tippy-tap typing all day long.

1:32:43Turner Novak:Interesting. Okay. I've heard of people use that. I've never actually tried it. and is that any other any other tricks that you feel like you do or is that probably the biggest one that is the biggest one oh the other one that's huge but this is just obvious i constantly have chat gpt grinding away in pro mode so you know buy the most expensive chat gpt i can i i think i'm just gonna always like if they had a ten thousand dollar a month thing i'd probably buy it i don't know what it would do but yeah hopefully it's good if it's ten thousand dollars yeah Well, I hope maybe it replaces an actual human assistant at that point.

1:33:19But I just have it constantly grinding away. I turned 42 two weeks ago, two, three weeks ago. And so I have very middle-aged dinners. You know, my dinners are like, so peptides, cancer screening, rail, full body MRI. Like that's the thing that gets discussed.

1:33:40Turner Novak:Like my back is kind of sore and like my knee is like terrible for a long time. And so I'm like, okay, I have to take this stuff seriously now. Like, but I'm not an expert. So for the last week, basically nonstop, I'm sure I cost open AI more money than I pay them. I've had chat GPT grinding away on coming up with a personalized health plan for me and for my wife that that's going to be, you know, like this executive program. and then this peptide protocol over here, like this other protocol over there. And I'm constantly refining and generating the plan. Like, honestly, the kind of thing where I feel like I'm working full-time with a person.

1:34:20So that's what I'm doing to... It's not more product... In a way, it's more productivity, but it's, I think, common to a lot of what we see with AI. It's simply work I wouldn't do otherwise. Like, it's not giving me more time, but it is letting me do something I previously would not be able to do.

1:34:37Turner Novak:Yeah, because it's just like it's completing a job like it's doing some digital labor for you like I'm sure you would love to have done all this research, but like you would have had to search around and Read some things and now chat you can just like summarize it and exactly. Yeah I'm just like tell me what to do and I Obviously I double check. I mean, this is my health, but Yeah, it does a remarkably good job Yeah, and I know you do a little bit of angel investing too with my friend Todd. What's kind of what do you guys like investing in? Yeah, yes, we do a whole bunch. We've invested in 120 plus startups now.

1:35:13Check size is typically 300K to 500K. We're investing out of fund three. Seven unicorns. So we have Zip, Superbase, High Touch, Mercury, Ryter, NextHealth, Placer. So that's a 6 %-ish unicorn rate. As of today, we have many, many more to come. One that we're particularly excited about right now is Loyal. Loyal makes longevity drugs for dogs. You probably saw this. Celine's actually a prior guest of the show. I love Celine. She's awesome. I didn't know that. Yeah. I mean, she's a force of... They're not a unicorn yet? I would have sworn. No comment. Celine's comment, right? Okay. They received FDA efficacy approval in February, making them the first company in the history of forever to receive FDA approval for lifespan extension.

1:36:03And people are sleeping on this. Like, you know how big that is. That means the government believes and agrees that their drug is going to extend the lifespan of older, larger dogs. And they have many tailwinds that will continue to pound, like longevity has become mainstream. We were just talking about it. GLP-1s are normalized. The veterinary market is consolidating with private equity. So that's one of many examples that we're currently very, very excited by. But yeah, it's really fun to invest in startups alongside Todd. And I think it makes me a better executor of technology and a better operator.

1:36:42Turner Novak:Yeah. And talking about Celine, she was a solo founder. You mentioned you think there should be more solo founders. Because I feel like general consensus is like, you get a bunch of people, everyone's good at different things. It's not as hard because you have help. Why should there be more solo founders? It's a question of timing. I have this thesis that if you double click enough on any co-founding story that you might come up with, it really was every single company, a solo founding journey. Like one person had the vast majority of the efforts and the wherewithal and the momentum, and usually also often the idea to say like, yeah, we're going to go do this thing.

1:37:23And they start marshalling the resources. They probably start putting in 12, 13, 14 hour days. Not everyone's doing that to begin with, and nor should they. The other thing I found is, because I've started, tried to start many companies to have worked. It is very easy when you have a group of co-founders and you don't know what you're doing. You don't have an idea that you're all agreed upon, or you're operating in a bit more of consensus mode. Like, do we all agree that this is the idea? I have never made that work and I've never seen it successful. What I've seen to be successful and what I've experienced is me, like the guy at the start saying, this is the idea.

1:38:01And like, I'm going to will this thing into existence. And it may sound crazy, but here I go. And I do that for like in the report of case, I did that for the three months until we got into YC. And that was the point where I recruited co-founders. And in Superhuman's case, I did it for nine months and raised the first million dollars the capital by myself, bought superhuman.com by myself, built the first MOX landing page, knew exactly what we were going to build, hired a design agency, started creating concepts. And I used that momentum to bring on board Vivek Sudara, who was my operations co-founder and Conrad Owen, my CTO.

1:38:37Yeah, it sounds like there's a lot more that goes into it than people might

1:38:41Turner Novak:think for that kind of stuff. Well, this is a lot of fun. Thanks for coming on the show. This is awesome. Yeah, absolutely. Thank you for having me. Great conversation. And thank you for listening. Thanks again to Hanover Park for supporting this episode. Head to HanoverPark.com slash Turner to upgrade your fund admin to the 21st century. If you missed it, make sure to check out last week's episode with Will Gaber at Stripe, where we go inside their stablecoin strategy, how they use AI, and if they'll ever go public. Tune in next week for 8sleep founder, Matteo Franceschetti, for a deep dive on personal health and how he built a hardware company.

1:39:14Turner Novak:If you like this conversation, please like, comment, subscribe, and share this with a friend. If you don't want to miss a future episode, subscribe to my newsletter, The Split, linked in the description to get each episode plus the transcripts emailed directly to your inbox every week. Thanks again for listening. See you next time.