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

Welcome to The Peel. I'm your host, Turner Novak, founder of Banana Capital. Today's guest is Rahul Vohra. You might know Rahul as the founder and CEO of Superhuman. It's the premium email client used by busy professionals, including me, to get work done faster. Rahul recently sold his company to Grammarly, which had just acquired Coda, and then rebranded the combined companies to Superhuman, of which he's now the CEO of Superhuman Mail. And I personally love this conversation because Grammarly is one of the original generative AI products, first started in 2009 to help you write better. It's quietly one of the most underrated companies that no one talks about, having grown to over 40 million daily active users and over $700 million in ARR. It's fascinating because they spent years building a backdoor into over a million other products that they're now building more AI products on top of. We talk about Rahul's journey building Superhuman, go inside the acquisition, talk about the grand vision of the new company and all the lessons he's learned from this acquisition, plus selling his first company, Reportive, to LinkedIn in 2014. We also revisit his famous Quantitative Guide to Finding PMF, designing your product like a video game, and why we need more solo founders. A quick thank you to Todd Goldberg, Ed Sim, Sho McGaugh, Ryan Hoover, and Rahul's brother Gaurav for helping brainstorm topics for the conversation. A reminder, I publish new episodes of The Peel every week exploring the world's greatest startup stories just like this one. Check out the back catalog of over 100 episodes and tune in next week for a conversation with Eight Sleep founder Matteo Franceschetti on all things sleep and health optimization. Let's talk to Rahul after a quick word from Hanover Park. Hanover Park vertically integrates fund admin, portfolio management, and the LP experience for finance and investment teams. Most of you have probably interfaced with a fund admin provider in some way. They're a necessary evil for every type of asset manager across not just venture but also private equity and private credit. They provide bookkeeping and accounting so investment firms can report to their investors on a quarterly basis. What's crazy is they charge hundreds of thousands or millions of dollars per year to basically not screw up your accounting. They stitch together third-party software like QuickBooks, Bill.com, Salesforce, and Excel, and then throw a bunch of bodies at you. And that's where Hanover Park comes in. They built their own accounting system from scratch, which ingests all your firm's data and documents, and their AI-native solution automates all the manual work that drives private market investors crazy. Head to hanoverpark.com/turner and try the AI-native ERP for private market funds. That's hanoverpark.com/turner and 10x your fund admin.

Rahul Vohra, welcome to the show.

Hey, thank you for having me.

Yeah, this should be fun. You are fresh off some pretty big news. I guess maybe we're like a month in now. I actually don't know. I don't know how far in we are from this happening, but tell us what happened recently and then we can kind of go behind the scenes of how it all kind of went down.

Of course, yeah. Well, I feel like I'm fresh off two pieces of pretty big news. I'm guessing you're referring to the fact that my company, Superhuman, was acquired by Grammarly. And you were asking me just before the show when that happened, and I was racking my brains 'cause I forgot, I didn't remember the exact date. So this is a good reminder to put it into my permanent memory. It was July 1st this year that we announced the acquisition, although of course we'd been working on it for quite some time before then. And the other piece of news that we're fresh off of is just last week, our parent company Grammarly announced, we announced that we will now be known as Superhuman going forwards, which was quite interesting. We were trending on Twitter. My phone was blowing up, as you can imagine. It's obviously absolutely the right thing for us to do. And the product that I started way back 11 years ago is now known as Superhuman Mail going forwards as we build out the AI productivity suite of choice.

Amazing. So there's a lot of different things I want to talk about based on everything you just said. So I guess the— so the acquisition, you said it was a long time coming. How did it kind of come about?

Yeah, well, I met the CEO of Superhuman, which is Shishir.

That's so crazy to say, like, the CEO of Superhuman, who you were previously the CEO of Superhuman.

I, I know, it's, it's kind of— and usually those kinds of things happen in less than ideal circumstances. I mean, you would have seen this as a VC many times. It's often a founder who's kind of run out of steam, or maybe they're not achieving the results they need to. That's usually the scenario where you have another CEO of the company you founded. This is a weird and unusual situation where we were acquired and the acquired company takes the name. Anyway, I met Shishir many, many years ago, back in 2017. And back then he was the co-founder and CEO of Coda. And we were at a conference, and it was one of those special moments where no one else was around. So, so he and I, we could get into some really deep conversation. And this was the Lobby conference out in Hawaii at the time. David Hornick, who organizes it, he was at August Capital. Of course, now he is at, I think it's Lobby Capital, the conference and the VC fund are now the same. And the team do an absolutely phenomenal job, like just the most incredible set of people that they bring together. And as you know, back then we did only one-on-one VIP concierge onboardings. And we were either early or late, I don't really remember which, but it was just me and Shashir around the pool at this hotel in Hawaii, margaritas in hand. And I asked him, you know, who are you? What do you do? Because the first time I met him, and he told me that he told me his career path and that his first job was actually at Microsoft working on Outlook. And I was like, oh boy, do I have a product for you. I onboarded him right there and then, right by the pool. And as those who've done onboardings with us know, one of the very last steps that we do is we ask you to close Gmail. And when I asked him to close Gmail, his mouse was moving up to his pinned tabs. And another tab caught my eye, which was an app called Krypton. And I asked him, "Hey, what is this Krypton thing?" And Shashir then proceeded to give me the best product demo I'd seen in years. It was a document, it was also a spreadsheet, it was also a database, it was this collaboration tool, it was a mini app builder. And after that conference, we stayed in touch. Shashir invested in Superhuman, I invested in Krypton, Krypton renamed to Coda. And then of course late last year, Grammarly acquired Coda. And in their acquisition announcement, which I think came out middle to late December, I don't remember the exact dates, maybe it was like December.

I'm seeing headlines, yeah, December 17th, 2024.

That sounds about right. Yeah, so December 17th, December 18th, 2024, that was announced. And in that blog post, the one that Shishir wrote, at Coda, he said something like, I'm watching how AI changes just about how every tool and service operates. And I drafted my 2025 planning memo, and I titled it the AI Native Productivity Suite. And my jaw hit the floor because if I were to show you our fundraising decks— and we, we should do that at some point— like, I think there's this, especially now that we're acquired, like, there's this fun thing that we can do, or we can go through our fundraising decks over time. And you'll see that we'd, for a long time, we've been pitching that at Superhuman, we're going to build the AI-native productivity and collaboration suite of choice. And so just from that, it was obvious that we had this overlap. And email is a critical part of this suite. It's also a much bigger problem than most people realize. There are roughly 1 billion professionals in the world on average, we spend 3 hours a day in email. That's 3 billion hours every single day. It's north of a trillion hours every single year.

That's insane.

It's crazy. We actually spend more time in email than any other work app. So as soon as I saw this acquisition announcement, I texted him and we jumped on a Zoom. I think it was December 26th that we jumped on a Zoom because we were trying to schedule. And that was literally just before he was about to take his family on vacation. I think they were heading to Brazil or something. And I caught him before he went to the airport. And he pitched me basically what he pitched Grammarly. And apparently, there was this all-hands, and he, you know, he shared his vision with Grammarly. He then shared that deck with me, and then I pitched my deck to him. And it became pretty obvious pretty quickly that we shared the same vision, which is to build AI-native productivity suite of choice. We immediately agreed we should at least have the conversation It was kind of funny because he was like, "Okay, yes, we've announced this acquisition. But here's the problem. I'm technically not CEO until January 10th. And even then, I will just have become CEO. I'm obviously not going to start buying companies immediately." The first day, we're doing a massive acquisition. Exactly. So I was like, "Okay, cool. It's December 26th. You need a break. I need a break. Our respective teams are probably burnt out and need breaks. Let's all take a chill pill and come back in January. And you need to do your listening tour and and let me think about how I want to even proceed with any acquisition scenario. And of course, like, you know, I'm a good founder, I'm gonna find my options, I'm gonna run a wholesome process. And let's just everyone take the time to do this properly. And we came back in January, and then we really got into it.

And so did Shashir, so he was, Coda was acquired by Grammarly, and then he was, as part of that acquisition, they're like, you're going to lead the combined entity? That was, that was kind of the plan?

That was the plan. Yeah, I think the Grammarly team really knew that they wanted a change of guard and a change of leadership. Shashir is one of the all-time greats. And I was very, very lucky to have him as CEO. But it does mean that like this, I was remarking yesterday, to a friend who was asking how it's going. And I said, you know, this is one of the most exciting places I can possibly imagine being. Just a year ago, not only were we not called Superhuman, not only had we not acquired Superhuman, not only was Shashare not the CEO, not only had we not acquired Coda, we were just a completely different company doing something completely different. And all of that has changed in the space of a year. There was just so much change and so much momentum and so much excitement that we have going on.

So I think it might be interesting. I think Grammarly is quietly one of the biggest products that most people don't know of. What is it actually, like the core initial product of Grammarly? And then like how big is kind of the whole umbrella that you guys have gotten to at this point?

Yeah, great question. Grammarly I also had no idea how big it was. I mean, I kind of knew how big it was, right? Like, it's in venture circles, it's kind of talked about, but also very misunderstood. I, you know, bootstrapped primarily for the most of its life.

That's the issue. There was no like VC content marketing machine, like they were reminding everybody about how great it is because there's no— no one was incentivized because no VCs owned it.

Yeah, which, which is a good reminder that when a company quote unquote goes hot, like, how much is it actually a phenomenal business versus the investors are very, very good at helping that story be told in the press? I'm the founders as well. Obviously some founders, the kinds that you and I like to invest in, are phenomenal press machines, which is like good.

Yeah, you like should make a good product, the company should be good, and you should maximize people talking about it. Like, all those things are beautiful when they work together.

I love doing that. Like, I think it's one of the things I can operate at a world-class level in is— I mean, gosh darn it, we went into email, which is a product dominated by incumbents, which are free. And despite everyone before us failing, actually managed to succeed and build a product that people love and pay for. But that requires building momentum, that requires building a brand, it requires telling the story. Yeah, like people just weren't really talking about Grammarly. And I think it's because they didn't really raise funding. I don't remember the exact numbers. But like, I think the first funding raised was hundreds of millions of dollars. It was a fair amount of secondary, some primary, it was definitely growth stage by the time that it happened. And as a result, it's just not part of the normal Silicon Valley like the lore kind of, or like the narrative.

Yeah.

Yeah, exactly. Which is one of the things that we wanted to change with, of course, this name. Like we are here and we've arrived and like we're on the map and watch out because we're doing some incredible things. So you were talking about like how big is—

Yeah, I'm just curious because like I think I remember seeing something like 70 million active Grammarly users a couple of years ago. I don't know how correct directionally that number is, but Yeah, that's directionally correct.

So I could share that we are north of 40 million daily users of Grammarly, now known as Superhuman, and we make north of $700 million of revenue every single year. And when I heard that, I was like, wait, what? $700 million? 40 million? That's insane. And as we were starting to dig into the acquisition rationale, There were really 3 things that got me. I think first, there was this strong and obvious strategic overlap. Not only is it at scale, it turns out that email sits at the very heart of where Grammarly is used today. For professionals, email is actually the number 1 use case for Grammarly. 3 of the top 10 apps that Grammarly is used in are email apps. And Grammarly helps write more than 50 million emails every single week. That was the first thing. The second thing was the people. Shashir, he's very special. He's actually— I was remarking upon this to my co-founders, who I think you know, Vivek and Conrad. And he's one of the few people that I would actually work with and for. And that is because he's one of the best systems thinkers I know. And I think when you're building a company, and you want to hit, like, $50 billion of market cap, $100 billion plus of market cap, you need like a full stable of the best people in the world, people who are the best at what they do. And in those January meetings, we started discussing the vision. And I said, Cheshire, you are hands down one of the best architects that I know. And I bet that I am one of the best artists that you know. And in order to pull this thing off, We are going to need a bunch of the best architects and a bunch of the best artists. And that really resonates with him. And so far, I've found that everyone at the company has just really been so impressive. I mean, you've seen the rebrand. I don't know if you've been to the website or seen the new identity, but the quality of this thing is incredible. It is one of the best pieces of identity work that I've ever seen. And then, of course, to your point, it was about the upside that we have north of 40 million daily users. We make more than $700 million of revenue a year. And this is a set of people— think about the people who use Grammarly. They've already demonstrated that they are into productivity, that they want tools to make themselves better at what they do. And so there's so much potential value in bringing these users new products, cross-selling, creating this bundle, products that make their lives even better.

So there's $700 million of revenue. Is it as simple as 40 million people that pay X amount per month or year to get the core Grammarly? I think it was kind of like spell checking and then autocomplete and layering in completion generative AI into the keyboard. I think it was a Chrome extension or something if I'm remembering right. I don't know if I explained this right because you're probably way more familiar with it than I am.

The original Grammarly products can be used as a Chrome extension. It can also be used as a native app that I think we confusingly internally refer to as Llama. I was like, what, like Facebook Llama? No, it's not Facebook Llama. It's like a native app that also annotates your screen. Yes, to your point, The core product that Grammarly grew up with is spelling and grammar correction. You know what's really interesting is if you go back 10, 15 years ago, that was AI. Like, that was actually one of the best examples of AI at massive scale was advanced grammar correction. And it's interesting how these goalposts change. And now, of course, what AI is It's still partially that, of course, especially for if you're maybe English as a second language or it's really, really high-stakes communication. And we can, compared to those early days, we can now deliver really interesting and complex insights on what you're writing based on data about who you are and where you work and the kind of people that you're writing to. So I think it is still considered AI, but it's just so interesting how the goalposts shift. So yeah, that. That is the core and the bulk of that revenue. It is primarily a free experience. It is a freemium model for that core business line. And so there's a smaller set of people than the 40 million that pay for Grammarly. And of the overall set of revenue, there's now a fairly substantial part of that that is Superhuman Mail, and then also another big chunk that is, of course, Coda.

Interesting. Okay. And you mentioned that you learned a bunch of lessons on systems thinking from Shashir, or he is one of the best systems thinkers. Can you just kind of explain maybe what you've learned that might be surprising to people or helpful for people?

As founders, we have these grand visions, we have these master plans, we talk about things in terms of Act 1 and Act 2 and Act 3. At Superhuman, independently, of course, we had an Act 1, Act 2, and Act 3. We wouldn't have reached scale or been able to raise money unless we did. And it was extremely and incredibly compelling. And that was the stuff that I was sharing with Shishir, and he was sharing his version of that with me when we were doing our founder dating, so to speak. And I think One of the most palpable things for me, and one of the most exciting and compelling things for me about the acquisition is, as an independent company, you have to do these things in succession. You have to do, okay, act one, we're gonna build the most productive email app ever made. We think we can easily get this to $100 million or plus ARR. By itself, it's gonna be worth billions of dollars. Why? Well, there's a billion people in the world who spend on average 3 hours a day on email. Just 300,000 people paying you $30 a month is $100 million of ARR plus. So that's really not a question of if, it's a question of when and how can we accelerate that. And that then leads us to act 2, which is XYZ, which leads us to act 3, which is this whole ecosystem of applications and agents. It's the AI-native productivity suite of choice. And as an independent company, you have to do these things in sequence. You do act 1, and then you do act 2, and then you do act 3. And if you're lucky, you get to do some things along the way But at the same time, there's so much competition. And I mean, you know, the AI space changes literally every week. The amazing thing at— I have this hyphenated name, Grammarly-Now-Superhuman, GNS. The amazing thing at GNS is that we can legitimately and are actually pursuing these acts in parallel, right? We are pursuing Act 1 at the same time as Act 2, at the same time as the various components of Act 3, at the same time as the agent platform that underlies this whole thing. And when I say systems thinking, I mean the courage and the conviction and the wherewithal and actually the brilliance to sort of zoom out and say, all right, this is the big picture. This is all what we're doing. And marshaling then on top of that, the capital and the resources and the energy really to go after it in a fulsome fashion. It's rare. It's not common. I think part of the reason it's not common is it's a set of instincts that are actually unhelpful for most founding situations. You don't necessarily want your— Yeah, you don't look as a seed founder, Series A founder, to be thinking— If your instinct is build all the things at the same time and we're going to have this, we'll figure out the strategic pathway to do that. You can very easily trip up in product-market fit. I think one of the most interesting things about Shashir as a founder is one of his most formative experiences. And I know this because it's the basis of almost every example. He would not mind me saying that. Is his time as, I think, simultaneously as the chief product officer and the chief technical officer of YouTube. And he saw YouTube and led YouTube's growth through really its most exciting period. Which requires a tremendous ability to handle complexity and to marshal those resources and to operate in, in, inside a larger mothership, which is its own skill altogether. And it's very, very impressive. It is a very, very rare skill. And that's what I call an architect. At the same time, you need artists. I'm not the best person to do that, that piece that I just articulated, but I think I'm really, really good. And I can play at a world-class level when it comes to taking 1, 2, 3, 4, doesn't really matter how many of those products, and then building them and making sure that those products win in markets, even when it's as insane as paid email.

Yeah.

Yeah.

And it's when I think of if I were to go full galaxy brain and like, what is superhuman strategy, you know, like a year ago or 2 years ago, it was probably, oh, you probably want to get into Calendar, which I think you guys did start to add some calendar features. You probably want documents, you probably want like other productivity apps, you're probably gonna make some sort of agents that save me time. And to your point, it's like, okay, well it's all here already. Like I get to do those alongside and like it's all kind of together. Is there, um, is there anything challenging about just like combining these like multiple, like when I think of Grammarly, Coda, Superhuman. Maybe there's more in there, but those are like 3 businesses. Like, you had teams, procedures, motions. Was there anything you've learned about just like, how do you get them all working together? Or maybe you're still figuring it out.

Definitely still figuring it out. I mean, I, I think that it is an ongoing process, and maybe fortunately for Superhuman, the Coda acquisition happened first, and there were a number of things that went really well, but I think there are 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 we'll take all the lessons from this one and apply it to the next one, whatever and whenever that may be. So yeah, there is— there's a strong learning machine here that gets continually applied to everything we do.

You've mentioned a little bit about like the big vision for the company. What is it? Like you've kind of hinted on it, but like 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. It'd been a while since I used it and come back, and it, it's phenomenal. And Grammarly, which is your trusted, always available writing 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.

Oh, I didn't even see that one.

Right, 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, uh, does— is it similar to Grammarly where it kind of embeds, or it looks like it— you like sync it with different things you can integrate with, like calendar? It looks like— look, 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 know, you, you analyze what are you good at, what are you not good at, where are the advantages. And one 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 overstated 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. It's annotating and it's writing and it feels native, like it's a part of those applications. That 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. 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— 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. It's a proto-agent. 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 or I are working together, and let's say we use Slack, and we're talking about a design, maybe where you, 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 we, one or both of us is running Superhuman Go. Let'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 Superhuman Go says, "Hey, it looks like you want to schedule a meeting." As soon as I hover over it, actually inline 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. And 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 assistants that that Grammarly, sorry, that Superhuman Go gives you, becoming increasingly more powerful. And 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.

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 Claude and so on. And they found that more than— if you look at the efficacy of the results, more than, yeah, more than half the efficacy is as a result of how well you are able to prompt the AI. Not the differences between ChatGPT and Claude. In other words, half the battle is knowing how to prompt it. This may sound obvious, but the— 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. And then the third advantage is it's connected. One of the really cool things about the Coda acquisition is we— and 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 lots of 800 different applications and websites. The, 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, we've built this AI superhighway that we could put any agent in. We've built in this one product, we've 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.

Yeah, it sounds like you sort of like the Grammarly has got this almost like backdoor into like every keyboard and you can create some automation experiences using AI any place someone would type to interact with a computer. Like, is that, is that just a super fair way to like really succinctly summarize it?

Definitely fewer words than I've used.

Yeah, yours was way more like elegant. Like, you know, mine was like the most simple, like that's the soundbite, I guess.

But yes, I, I think we would say it's 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, like, because I feel like with Superhuman, people have always loved the product. Like, that's just something 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 4 figures. I guess if it's $30 a month. I had an employee though who used it, so I might, I may have paid you over 4 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 it all the time because they loved using it. How do you think about making an AI product now that people love? Like, are there certain things that you, you're kind of thinking about? It's just like, how do I, I've got this good hit rate. In Superhuman? Like, 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. What made a good, beautiful UI had not really evolved for a very long time. And we have some credit, 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 sort of really bring it to knowledge workers. And then it made its way into Slack and almost every other tool. Figma has it.

Command K was just like you tap Command K and search and you just like, it's like the 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, we all want our tools to be visual and minimal and but somehow at the same time easy to use. We, we want to avoid enshittification, if, if you know what I mean by that, like the, the crud that tends to develop over time. But at the same time, we as, as a company and as product leaders, we, we need to expand our markets, right? We— if we, we started by selling to founders and CEOs, possibly one of the most niche markets you could, could have come up with.

And yeah, venture-backed founders and investors.

Yeah, like, yeah, there's maybe a few thousand people, a few thousand for this, this company. Um, which, by the way, I, I think is a great strategy. I, I love it when, 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, we, 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. What 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, 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. It gives you the commands. 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. People just fell in love with it. Of course, now it is considered table stakes in productivity software of choice. I'm going to 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. So 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 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. And 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. And I think that's the real secret to what we do at Superhuman.

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 Mail, that was definitely the lens that we had, which is make this as fun as a game. Apply the principles 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 1 a couple nights ago. I don't know if you ever played Age of Empires, But with those games, you need to use the keyboard because you're— you like— so what I've been doing is I'll play Age of Empires 1 on hardest difficulty. I don't know if you've ever— like, 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 hotkeys 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, is like, is the shortcuts the hotkeys.

Exactly. 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.

Yeah, I was going to say, you— yeah, so you, you were a game designer for a while, right? Like, so did you get into it like 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 6 or 7 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 a little mini maze or a dungeon on paper. It was 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 jump out to surprise him when he would come home. And it's obviously not a surprise because if that happens every day, it's not surprising.

Yeah, to you as a 6-year-old, you're like, I bet he forgets. He doesn't know I'm here.

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 gonna play a game." And I just drew this maze and I just drew this dungeon and, you know, 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. I worked at Jagex, which, fun fact, people, most 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, and folks will remember that 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. It's not that many, but it is surprising. I can tell you precisely how many people, like 2 or 3 people a year who ping me, who are 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, 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. And 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 5 factors to consider, which are goals, emotions, toys, controls, and flow. And across those things, we then identified about 13 principles of game design. One example 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?

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, the level of the toy and the game itself. Now, in Superhuman Mail, a favorite toy is the time autocompleter, which you use to snooze emails. This is when you hit H and you're then 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. You can type in 2D and it becomes 2 days, 3H becomes 3 hours, 1MO is 1 month. Then people start to indulge in what I call playful exploration. They're thinking, what can it do? Where does it break? How does it work? 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 10th at 10:10 PM. Well, how about a sequence of 2s? Well, that's February 2nd, 2022 at 2:00 PM. 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, timezone math happens without you thinking about it. You can say, hey, send this message 8:00 AM Tokyo time. And it turns out that's 8:00 PM Eastern time. Who's going to stay awake until 8:00 PM Eastern time? And most people are really delighted to find out that if you really want, you can snooze emails until forever. They never come back. You can literally type in H never and the email will never come back. And there's a fun little ASCII shrug emoji, the one that Shrug Ventures has. That's the That's the representation of it. So, yeah, I would say to people interested in game design, think about the features of your product. Do 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.

Interesting. Was this— so your company that you built before Superhuman, it was called? Reportive, was it, was it any, 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 like can't get away.

I know, I, I can tell you exactly why. My— I, 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. And so I learned that about a year in. I, I had a great time. Like, I, I really—

what were you studying?

Uh, machine learning, way before anything worked. So this was 2005 to 2006.

I did like a year, a year and a half So this was like literally if-then statements kind of a thing, like earliest version of it.

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 and It was a different time and very little actually worked. Yeah.

What was the coolest thing you could do?

Automatic scanning of deposited checks and knowing what those numbers were from handwriting. Look, it was 2005, 2006.

That's impressive. Yeah.

Maybe actually no, more impressively than that was large-scale translation and very few companies could do this. Google could could do Google Translate, but like, it was, it was not that impressive. And so I also realized I'm not that— I'm not an AI researcher. I, uh, 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, by being the hype man. Like, I would go to— a lot of these researchers were not good at explaining their ideas, and they not great at writing papers. And I'm like, I'm a pretty good communicator. I can take your idea and 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 it. I would product market the AI research. 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, to help their researchers.

It's kind of not structured that way, but it should be because someone will like write a paper of like, you know, like CRISPR, like we can edit 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 Kleppmann. Well, what do I know? That was two decades ago. For all I know, this is exactly what they do. The 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?

Well, for reportage. You like somehow dropped out of 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 2 teams to go and we would like first money in, right? Pre-pre-pre-pre-seed incorporation money and not huge checks, like in the region £25,000, so call it $30,000, $40,000, $50,000 at the time. So 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 bag and be like, hey, Mr. VC, can you please give us some cash so we can give it to the, give it to the founders and to the, to the staff? And like most student-run organizations, it was in 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 and 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. I 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, Twitter, give me money.

You don't get anything back.

You'd be like, 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, you know, like that's it. So it was a good trial by fire. It, it really taught me how to fundraise in the most hardest circumstances, and it also taught me you know, some of the finer points of BD and like, 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. And 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, this was the product. It was the entire thing. And that is— knowing that 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, like you had a— 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 this was in 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. But I wrote the first line of code January 10th, 2010. And then 6 weeks later, I was done. 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, you know, password unprotected, I applied to Y Combinator and I put in the link. And it was a Friday, I think like 2:00 PM, 3:00 PM. Turner, what do we do in the UK at Friday at 2:00 PM?

Go get a beer.

We went and got a beer.

So, yeah. Wait, was I right?

Yeah, of course. Absolutely. 100%. So 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. And then my phone—

2009.

Oh, you did have a phone. I was going to say. I did have a phone. Okay. So this is like barely iPhone was like just kind of out. Yeah.

Yeah. I was like, I had an iPhone 3GS, I think. I may have. Yeah, I think so. And I had a phone and great industrial design, by the way. Like it starts buzzing and I'm like, oh, notifications are coming in for this app, Nezumi. Nezumi 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. And I cycled 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. And the editor at the time, Zima Kane— 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. Over the first 24 hours, we had 10,000 downloads. Over the next 2 or 3 days, we got to 32,000 users. Again, now, whatever, these numbers—

That's child's play.

But at the time, it was like— I mean, Sequoia reached out and Jason Calacanis reached out and all these people randomly reached out to this dude in Cambridge, UK, because at the time, that was very, very unlikely and very rare. And so, so first of all, I'm eternally grateful to Pete for like 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 kind of sucked, but as soon as that happened, they were like, yeah, okay, you're in. Like, this is exactly, you know, You clearly hacked the system. You're going to do fine. And good job. Good job, Jørgen. 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. I 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 pacing around. We could only really see his t-shirt and his shorts. He was pacing around. They're like, "Are you there?" You couldn't see his face?

It was like— His head was above the screen.

We saw Jessica's face. It was actually really funny. He just did an interview, and we get in. He said afterwards, that was risky because the acceptance rate for those interviews was apparently way lower than the, the normal course of interview. But we get in, and yeah, that, that's the story of how Reportive took off. The, the reason the acquisition came about is we, you know, we, 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. And which is weirdly high and weirdly low, right? But this, the specific users that we had were a very valuable set of users.

Yeah, you just think of like, who were LinkedIn power users in 2012? It's probably just like salespeople and like recruiters, and someone who would want that, that 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, like we want it, come join the company.

If only acquisitions were that easy. The Superhuman one was 6 months of intense efforts. The, 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. This is the classic platform API protectionism debate. Uh, 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 lookup 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 off one of the first companies to do that, which was a company called Rapleaf. Rapleaf, founded by Oren Hoffman and a bunch of other people, including Vivek Sodhara, 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. Early in the course of Reportive, I was like, I need access to some data. I need like the— 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 we're blessed with, a lot of successful entrepreneurs around the University of Cambridge. A 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 Oren 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 2 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? You got to shoot your shot. To 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. It 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 back office and I meet with Rahul Vohra and 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. And 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 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. And 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, haha, 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 during or after that YC Demo Day is this 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 product at the time was Adam Nash, who runs Daffy right now. Great product 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, hey, 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 Rapley for 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 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 Rapley. They're going to die. 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, like a light bulb went off. I was like, oh, this is it. Like, this is my one shot. Like, I either— this, this meeting, honestly, probably makes or breaks the company. And I figured out the right set of things to say. I don't remember exactly what it was, because it was in like an adrenaline blur, where I pitched him what we were building, I pitched him where we're trying to go. I was trying to be as friendly and as polite and as collaborative as possible. And he was like, "You seem like a good guy. And you seem like you have really—" This I remember verbatim. "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 Reportive because of this one meeting. And with this API, we could give LinkedIn an email address and they would give us a profile and we'd put that profile in the right-hand side of Gmail.

It was all in the name of like giving more information to people and making it more useful, right?

Yes. That advantage became such a huge advantage. So Reportive, like Superhuman, like any company to get traction, that gets traction, attracted a silly number of imitators. I think there were like 5 or 6 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, I guess they want to— wanted to limit their exposure. They trusted me as a founder. We, we treated their data with super high integrity and like the— 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, we're gonna put our alarm bells on. If either of us notice scraping, then let the other know and like, we'll fix it. But like every month, people would figure out how to scrape the data from Reportive and we would fix it. So that's— 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 3 to 6 months. And 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 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 internally. But has it become important enough that they want to now own it? Right? 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.

Really? Okay.

Yeah, they were like, hey, how do you feel about doing this at LinkedIn? Uh, you know, in reality it was a lot more complicated. I can tell the story if you're interested, but the, the very short version is we were pitching Greylock for our Series A, and we were pitching Reid and David Sze. 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. I'm like, you know what, these are both interesting. Let's parallel track these and see where these conversations go.

Interesting. Okay. Do you, do you feel, so you feel like, I guess to kind of summarize it, 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, to, to LinkedIn originally. Like they just were kind of like, yeah, whatever, we don't wanna 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 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.

Yeah, sort of. So initial momentum, we built a product that people love based on Rapleaf data. And it took 6 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 essay. Well, specifically, High Resolution Funding, I think is the name of the essay. He wrote that after we did what we did, kind of in response to the patent. That we had. We then leveraged YC Demo Day to get a meeting with LinkedIn. We then leveraged the meeting with LinkedIn and their, their desire to put that aspect of Ramply out of business to get the direct API. We then just kept building good products and kept growing. We then leveraged— and, 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. It, you know, it became strategic for a lot of companies at the end of last year as well. That'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 Reported. We ended up getting offers from LinkedIn, from Twitter, from Salesforce, I believe. And each with different theses, right? Like with LinkedIn, 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. Oh yeah, you did. 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, to own Reportive. And, you know, we again, we ran a process which is, which was insane and crazy. I ended up going to hospital. LinkedIn signed the term sheet, they ended up walking away from a signed term sheet. All kinds of drama. Wait, so Hospital?

How did you get—

how'd 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, I burned out mentally and physically. Hmm. And that happened in the middle of our Series C fundraise and in and around the 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 Reportive, 588 Brandon, I think it is, across from Trey's Agave, the Mexican place, and I was walking to the McDonald's that used to be near 4th and King. And I remember walking, every single step being more and more painful, like this sharp shooting pain up 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? That I collapsed outside the McDonald's and the homeless guy's telling me I don't look great. And so I pull out my iPhone 3GS and I text one of my, one of my teammates, Lee, and 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 and he finds me and then he picks me up and he hoists me over his shoulder and I'm like, onwards to Safeway. And he kind of just like drags me the next 2 blocks to Safeway. I buy some medicine because I'm having this major acid reflux episode. So I buy some antacids. 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 3:00 in the morning with this major intense abdominal pain. Like really, really bad lower left abdominal pain. And 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 call my dad, who is a doctor, and he was like, this may be appendicitis. You should go to the hospital. So we were new to the US, me and my two co-founders. We were 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 co-founders like, we need to go to the hospital. We could barely afford an Uber. Like, taking an Uber was considered extreme for us. We would always take public transport, but we splurged for an Uber. We, we get to St. Francis Memorial Hospital and I remember the nurse interrogating me. She was like, okay, so can you, 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 it was Gary Vaynerchuk crushing it? We were definitely crushing it. And, and she was like, no, really? And I'm like, well, honestly, it's pretty stressful. And she like 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. She 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 2 years. She was like, okay, so what do you have for dinner? I 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, okay, so here's the thing. You have a hiatal hernia. So it'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, 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, that is just the truth.

I mean, you're gonna die if you don't. You need to hear that.

Like, 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 $100 million 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. You might have these irreparable life problems. Now, I'm at least glad that the younger generation is drinking alcohol way less, but they're doing other stuff and we don't know what that other stuff is, what the long-term implications of those things are going to be. Anyway, why am I telling you this 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 4 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 basically everything shut down. I had to learn how to move again and walk again and eat again. And like, it, it gave me this profound appreciation for my health and for my body and for my level of stress. And that is a superpower. That is a true superpower when you don't give a fuck 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 was like, I can't— it really just felt like a change in aura. I literally stopped caring. I just did not care anymore. Zero fucks left to give. And I was in those meetings. And the moment I sensed BS, I was like, cool, right? 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.

So you almost died, and almost dying completely just changed your, really, like, you're just like a mindset and your perception to the point where you just like didn't give a shit about the material, 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'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 2 weeks of runway left. 2 weeks. You can imagine that. At a premium. It was a great exit. Some of our investors made 20x their money. Most of them made 3 to 5x their money. 2 weeks left. And I, 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.

Yeah, so you, so you mentioned two other things. LinkedIn pulled a term sheet or something with the acquisition, and then also the two, two weeks of runway before you landed this. Uh, tell me about those two things.

Yeah, we signed a term sheet with LinkedIn in this on December 11th, 2011, and there are two ways you can do M&A at a small scale. I mean, at the small scale is often like an acquisition of talent, as just as it, as it is roadmap and future roadmap. And for us, it was kind of a mixture of all of those things because we were only 5 people, including me. And so you have a choice of doing the interviews before signing a term sheet or after, and there are pros and cons either way, of course.

Interviews— this is when they like meet the team.

Meet the team. And for a team of 5, they're going to meet the whole team. Right, for Superhuman, male, I think they met maybe, I want to say, 5, 10, 15 people max, more like 10 people. But for, but for Reportive, it was the entire company because we were only 5 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 So, okay, every founder says they have the best team in the world. Are they actually? Way 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. 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 have, I've changed my initial decision based on meeting other co-founders, like 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 you're like, oh, this person's they're a really good engineer, or like, really, there's definitely something here. And then you go back to the CEO, you're like, okay, now I kind of get this. So I think that's really— it's so important, just meeting everybody, as many as you can. Yeah, I couldn't agree more.

So LinkedIn met everybody, and they— we all, you know, we disagreed about this. Uh, there's perverse incentives here because the the company is always trying to acquire you for less. And I think people are 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 it, we agreed a price at the term sheet. This is me and my naivete. I thought, cool, end of negotiation. That's BS. That is not the end of the negotiation. It's still getting started. 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 were going to sell up to like, you know, maybe you trade a haircut 10, 15% below whatever that price was. Right. And but I didn't know that. And they met the team and there were 2 or 3 people where they were like, they were like, okay, some of your engineers, fantastic. Some, you know, we, we don't think 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 6-week vacation, and this, that, the other. And the— they, they pulled the term sheet because they wanted to retrade on price, and we couldn't agree on the retrade of 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 3 months later.

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 gonna 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 this kind of gotchas where, yeah, the price is like 30% lower than you initially thought, 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 an I want to give a shout out to my new favorite M&A advisory bank, Axom, A-X-O-M. They did phenomenal work, incredible work here. They're all Ax 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 sheets exactly, but it's things like, look, we both agree there will be no material retrades now. What is material? We didn't define what material is, but at least there's something to point to that, 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 classic one. 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, when an acquisition happens, it is expected that those states will come knocking and say, hey, you owe us— it's usually not a bunch of money, but like, you owe us some sales tax, right? And to mitigate that, you'll create these escrow funds or a holdback or, or things along those lines. That's all completely normal. But you know what, 26-year-old me did not appreciate the, the extent of the retrade that LinkedIn wanted too. Yep.

And I actually have to give a shout out for— and 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 $10,000, $20,000 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, like, usually your customers will pay it if you're just like, hey, 4% sales tax, like on the invoice. Like you can, you can generally tack it on. You just gotta do it and not, you know, cuz like a year later you can't really go back to your customers and be like, hey, by the way.

So yeah, it's worth getting right. Just thinking through.

So when you first started Superhuman, you had kind of alluded to earlier, you did this personal onboarding. Could you just explain what that was? I feel like there was a, like, 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. Let's say you've built a new email app or a new task manager or a new calendar app. Now the surface area for these products is absolutely massive. It's bigger than almost any domain you could think of. Which means you also get a massive surface 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 hard these days. But guess what? Those users will very quickly find thousands of bugs, and any company would very quickly get overwhelmed. And 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. 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. 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 years? 'Cause 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 Product Market Fit Engine. It gives you a way to define product market fit. It gives you a metric to measure product 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 product-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, like, one core question, which is, how would you feel if you couldn't use the product? 3 possible answers: very disappointed, meaning they would love it, they 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.

Interesting. And it's basically, if I think it's 40— if 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 this applies 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 that'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. So I guess you could be biased there too. But that's, 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? Is 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, the, 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 just, maybe that's all it is. But like, how do you think about just building a good brand?

Well, 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, you'd be like, hey, what is this? Superhuman thing. What does it mean to be sent by a superhuman? 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— and it still feels surreal because it just happened last week— I think will happen. I think that we are going to build this 100-year company and this this dream that we had when we founded Superhuman all the way back 11 years ago is going to still come to pass.

And, and that is incredible. Do you have any, like, like a personal productivity stack? I don't know if it's just use all the, the Superhuman suite of products, but like, what do you do you think that's kind of unique in terms of like being more productive? I'm assuming you gotta have some, some tricks up your sleeve.

I do. And of course, the superhuman products are amazing, but the spirit 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. So 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 screenshot the screen in and around your dictation. So if there's a particularly hard-to-spell name or A project codename 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. Interesting.

Okay. I've heard of people use that. I've never actually tried it. And is that— 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 ChatGPT grinding away in Pro mode. So, you know, buy the most expensive ChatGPT I can. I think I'm just going to always— like, if they had a $10,000 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 $10,000.

Yeah, well, I hope maybe it replaces an actual human assistant at that point. But I just have it constantly grinding away. I turned 42, 2 weeks ago, 2, 3 weeks ago. And so I have very middle-aged dinners. My dinners are like, so peptides, cancer screening, full-body MRI. That's the thing that gets discussed.

Like, my back is kind of sore and my knee is like, yeah, that's terrible for a long time.

And, 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 non-stop— I'm sure I cost OpenAI more money than, than I pay them— I've had ChatGPT grinding away on coming up with a personalized health plan for me and, and for my wife that, that's going to be, you know, like this, this executive program, and then this kind of like peptide protocol over here and like this other protocol over there. And it's— 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. So that's, that's what I'm doing to— it's, it's not more productive. 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.

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 ChatGPT can just like summarize it. Exactly.

Yeah, I'm just like, tell me what to do. And I obviously, I double-check. I mean, this is my health, but, um, 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+ startups now. Uh, check size is typically $300K to $500K. We're investing out of Fund 3. 7 unicorns. So we have Zip, Supabase, Hitouch, Mercury, Writer, NexHealth, 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. So they're not a unicorn yet? I would have sworn. No comment. Celine's company's comment, right? Okay, fair. They received FDA efficacy approval in February, making them the first company in the history of forever to receive FDA approval for lifespan extension. And people are sleeping on this. Do 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 compound, like longevity has become mainstream. We were just talking about it. GLP-1s are normalized. The, 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.

Yeah. And I was talking about Celine. She's a— she was a solo founder. You mentioned you think there should be more solo founders. I— because I feel like general consensus is like, you get a bunch of people, everyone's good at different things. Like, it's not as hard because you have, you have help. Like, 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 effort and the wherewithal and the momentum, and usually also often the idea to say, like, yeah, we're gonna go do this thing. And they start marshaling the resources, they probably start putting in 12, 13, 14-hour days. And not everyone's doing that to begin with, and nor should they. The, the other thing I found is, because I've started— tried to start many companies— two 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, and 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 Reportive case, I did that for, for 3 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 9 months and raised the first million dollars of capital by myself, bought superhuman.com by myself, built the first mocks, 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 Sudhara, who was my operations co-founder, and Conrad Owen, my CTO.

Yeah, it sounds like there's a lot more that goes into it than people might think for that kind of stuff. Well, this is a lot of fun. Thanks for coming on the show. This is awesome. Yeah, absolutely.

Thanks for having me. Great conversation.

And thank you for listening. Thanks again to Hanover Park for supporting this episode. Head to hanoverpark.com/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 Gaybrick 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 Eight Sleep founder Matteo Franceschetti for a deep dive on personal health and how he built a hardware company. If you like this conversation, please like, comment, subscribe, and share this with a friend. If you don't wanna 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.