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The a16z Show
How Superhuman Took Over Silicon Valley Email
00:55:59
Rahul Vorra is the founder and CEO of Superhuman, the premium email client for power users. He previously built the Gmail plug-in Reportive and sold it to LinkedIn. He began somewhere unexpected though, as a game designer on RuneScape. In this conversation, Rahul breaks down why most founders misunderstand product market fit, why premium can actually hurt your business, and how deliberate constraint can become your biggest advantage.
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- [00:01]
A
Convincing people of things is possibly the hardest thing we have to do as founders, right? And there are so many different audiences. There's investors, there's feature co founders, there's your earliest users, there's the press, there's the industry you sell to in general. And I think each one is its own fun little puzzle. The best, most awesome thing you can do is basically have some form of narrative that sounds like this train is leaving the station and if you don't join now, I don't know that you will be able to join. The market doesn't care. Candidates and investors are looking for the storyline of differentiation, sometimes just for differentiation, because they're in the business of finding different things. Remember, you have the right not to serve. They used to have a survey, we'd be like, what mobile phone do you have? They'd say, Android. And I said, well, you can't have Superhuman. And people get confused like, why isn't it my decision whether or not I buy? And I'm like, no, it's my decision whether or not I sell.
- [00:56]
B
Most founders think product market fit is something you feel. Raoul Vora tried to turn it into a system. Before founding Superhuman, Raoul built Rapportive, one of the earliest successful Gmail plugins. But with Superhuman, he approached the problem differently. Instead of chasing growth immediately, he spent years refining the product, onboarding users, manually, charging premium pricing from day one and obsessing over every interaction. The result was not just a productivity app, but a product that developed a kind of cult following inside Silicon Valley. In this conversation, Raul breaks down the frameworks behind that process, from game design principles and onboarding psychology to the product market fit engine that helps Superhuman grow.
- [01:45]
C
Raul, as I said, is the founder and CEO of Superhuman, but also previously to that reportive. He started out with a CS degree at Cambridge LinkedIn. Still says PhD on leave.
- [01:57]
A
Still on leave.
- [01:57]
C
I'm not sure if you ever if he's ever plans on going back. He started his career as a game designer working on a game called RuneScape, which was an early MMORPG. Any RuneScape fans in the house here?
- [02:09]
A
Whoa.
- [02:09]
C
A lot more than I expected. Love that. He then founded a company called Rapportive that was acquired by LinkedIn in 2012 and then after that founded Superhuman in 2014. Curious how many people here use Superhuman as their primary email client.
- [02:26]
A
Me too.
- [02:27]
C
It's a lifesaver and very important to my day to day life. I can't live without it. But in July 2025, Superhuman was acquired by what was then called Grammarly who then renamed the company to Superhuman, where he continues as the head of Superhuman. Mail. Why I'm excited to have Raul here is that Raul is one of the clearest product thinkers that I know. And the story of Superhuman is full of what I would consider highly opinionated and often very contrarian opinions that have now some of them have become sort of standard opinions for how founders think about building zero to one products to start. I'd love to talk a little bit about your start and your start in game design. So you started out as a game designer after studying computer science. I'm curious one just like why that was where you decided to start and how you ended up there. But what is the path from sort of game design to productivity software? And how has that background shaped your vision for Superhuman?
- [03:28]
A
Why game design? I mean, who doesn't like games? That's a good boy.
- [03:32]
C
It's every kid's dream, right?
- [03:34]
A
Every kid's dream. I my first games console was a Super Nintendo. Super Mario World was the first. I see like nod heading here. This is great. And so those were my first games. I learned how to program primarily so I could make games. Both my parents were doctors when they were working and they would pick me up late from school and so I would read the books in the school library. And once I was mostly done with the fiction books, I'd started on the nonfiction books and I found the programming section and I thought, wow, I can use this to make my own games. And so that was at the age of eight or so, which I guess nowadays it would be normal. Back then it was relatively unusual for an eight year old to be programming. So I started programming. I taught myself how to do it and how to make my own games. And that sort of got me on this journey towards not just proficiency with building things, but also I think, as is becoming increasingly important these days, developing our sense of taste. So what actually is fun? Like what is enjoyment? What does it mean to play something versus not play something? And so I went to Cambridge. As Fareed said, I did my undergrad there. I think I remember going around the careers fair and Cambridge is an amazing university, but one thing it doesn't really have much of in terms of technology is the consumer Internet. And so our specialties at Cambridge are things like hardware design, chip design, biotechnology, gene editing, some software, but not that much software. One of the interesting software companies Cambridge has actually produced is a company called Jagex, which is the company behind Runescape. And so of all of the companies at that careers fair, I was like, this is the one, this one's really cool. Also, I'd played World of Warcraft at the time. I hadn't played RuneScape, but I went in for an interview and I was like, wow, there were only 35 people or so at the time. They were having so much fun that I just put all my eggs in that basket and said, hey, hire me, I'm a great computer scientist. I'll create amazing content for you on this gaming platform. And actually to this day, it was one of the most fun jobs I ever had.
- [05:44]
C
Interesting. Did you, sorry to detour from some of the questions that we talked about earlier, but did. Are you. Were you the type that always knew you were going to start a company or did you or. And that was just a chance to sort of learn how to work at a small in a startup or did that come to you over time?
- [06:02]
A
I knew pretty darn early, but again, timelines are compressed. Kids these days know very early, right? Turns out, but I remember knowing at 12 or 13 I had this very clear insight that I was going to be a founder or an entrepreneur. And for me it was again seeing my parents who were both doctors and in England, doctors do well. They don't do quite as well as here, but they do pretty well. Not well enough to escape the rat race, right? Like still had a mortgage until their later years, stressed about money, always did well enough to give us a middle class life. And I remember looking at that thinking I want to escape this particular rat race. Now it's a stupid thing to think because it's just rack waist all the way up or down, however you slice it. But my 12 year old self thought, okay, I want to get to the point where I'm financially independent without having to work. And I think that's a reasonable first motivation as a kid. It's actually a terrible motivation as a founder. It's a really bad motivation as an entrepreneur, which became obvious to me over the next ten years after that. But that's when I knew I didn't join Jagex because I wanted startup experience. I joined it just because it seemed fun and so much I think almost every decision I've taken was, oh, this seems like the most fun optimizing decision I could take.
- [07:22]
C
So let's talk about fun for a second because there's this idea of gamifying apps and gamification, but I think a lot of what you talk about is bringing more foundational ideas of game design into product design. What is the difference and how do you think about the difference and how have you brought that into the product?
- [07:41]
A
So again, this is probably dating both of us. If you wind the clock back probably 10, 15 years ago now, gamification was a big thing in the Valley, and it was actually an investment thesis for many venture capital funds. Many founders were setting out to gamify things, and it turns out it didn't really work. And the difference is because of the difference, I should say, between game design and gamification. Game design is when you really make your product like it is a game, and it's much harder than it sounds. If you think about most software versus most games. Games don't need to exist. There are no requirements. Their only job to be done is to entertain you. And so it's an entirely different kind of software design than regular software design. When people think about gamification, they're normally doing things like points and leaderboards and trophies and badges and streaks, and all of these can kind of push behavior in a certain way, but they don't actually make the underlying thing fun or intrinsically rewarding. So a really great example of this, by the way, is a research study that was done in Stanford in the 1970s. They took kids who were aged about three to four years old, I believe, or maybe a little bit older, four or five, and they divided them into two groups. And one of these groups was told that they were going to get a reward, like a certificate with a gold ribbon. And the other set of these kids were not told about any reward at all. They were then put into a room one by one and asked to draw. And so afterwards, the kids who were promised a reward, they would get their reward. And the kids who didn't know anything about a reward didn't receive anything. They then observed these children over the next few days to see how much of their time they would spend drawing. The kids who didn't get a reward spent 17% of the next few days drawing the kids who did get a reward, and they spent 8% of their time drawing. In other words, the presence of the extrinsic motivator reduced the intrinsic motivation. And that actually happens with game design and gamification as well. So one of the reasons, actually the core reason why gamification didn't work is simply giving your users a reward for something can reduce the intrinsic motivation for them to do that thing. And to actually build things that feel like a game. We actually have to go into the theory of game design, like, what is a game, what is play what is fun, and then build your Product around that. And that's something that we did deeply with Superhuman. Now, Superhuman male, I'm curious, what are
- [10:33]
C
some examples of game design thoughts that go into the core loop, let's call it of email, which is the most unfun thing ever.
- [10:44]
A
Totally. I was like, how do I make the. And I didn't answer your previous question about why productiv. Because it was the least fun thing in my life. And I was like, how can I make this the most fun thing? Over the years, I came up with multiple principles of game design, around 15 to 20, depending on the day. But they draw upon different areas, like psychology and mathematics and storytelling and interaction design and so on. The principles cover areas like goals, emotions, toys, controls and flow. Those are like the top five areas I often think about when it comes to how do we make something feel like a game. And I'll give you a specific example, perhaps in the context of toys. So what is a toy and how is it different to a game? The way I would summarize it is actually linguistically, you play with a toy, but you play the game. Right? A ball is a toy, but football is a game. And you can actually use this when you're building products. It turns out that the best products are made with toys because then. Sorry, the best games, I should say, are made with toys because then the games are fun on multiple levels. The level of the toy and the level of the game itself. And an example from Superhuman would be our time autocompleter. This is what happens when you hit H to set a reminder on an email. And I noticed this in onboardings and we ended up deliberately designing for this. But people would start to play with this toy. Once they'd understood how it worked, they'd start to play with it. So if you haven't seen this, you basically hit H. You type in when you want the email to come back, and then it sets a reminder. And so if you type in 2D, it's two days, 3mo is three months, and so on. When people figure out how it works, they start trying to break it. So I saw people type in October 10, 10, 10 10. Like, what does that do? Oh, that's October 10 at 10 10, 10pm or 222. Well, that's like February 2, 2022 or whatever it was. And then people start trying to type in random things like, oh, I wonder if it will handle in a fortnight and a day. And it does. And even had one user type in never. Like, never bring this email back. And we had a Little funny thing over on the right hand side where we have an interpretation of what you typed in in ASCII characters. And we had the shrug emoji guy when you typed in never. Like, little things like that which are fun. And the experience of a toy create these little localized moments of delight. And if you build lots of these in conjunction with each other, you now have a collection of toys that by itself is not a game. You know, Fareed mentioned the word loop. There's the idea of the game loop. You need other things as well. But that's an example of a toy like experience. And so as you're thinking about your own features, I would ask yourself questions like the following. Is this particular feature toy? Like, is it fun just to poke? Does it have what we game designers would call a squishy affordance? Can you like bend it in an analog way and it will react back to you? What's a good example of that? Oh, the jump in Mario. In fact, this is so intuitive, most people don't even realize this happens until I point this out. Let's say you're running in Mario and you hit the A button to jump and you're flying through the air. You're holding down right. When you hold down left, what happens? You go left. That's completely aphysical. Right? So you're flying, you're jumping, and you hold down left and you suddenly start steering left to avoid presumably the big chasm that you just found. But it's fun. That's an example of a squishy affordance that the control system has given you. And controls are a whole other thing. So, yeah, so identify these squishy affordances, Identify these areas where it can respond in an analog way. And ask yourself the question, is it encouraging playful exploration? Because if you can say yes to those things, you've made a toy. It's. And you're well on your way to making a gig in 2014.
- [15:02]
C
Pitching a piece of email software. Just talking to people about this, how you convinced anyone that email. But we thought about it in a fun way. I'm curious how you came to decide that that's the company you wanted to build. And also like how you convinced anyone that they should build it with you, you know, as partners, as investors, as anything. Because it is kind of like completely opposite the way people were building software, especially productivity or B2B software.
- [15:32]
A
Yeah, totally. So convincing people of things is possibly the hardest thing we have to do as founders. Right? And there are so many different audiences, there's investors there's future co founders, there's your earliest users, there's the press, there's the industry you sell to in general. And I think each one is its own fun little puzzle for investors. I was fortunate to had sold a previous company. I'd sold my last company, rapportive, to LinkedIn. By the way, Rapportive was also in the email space. We built the first Gmail plugin to scale to millions of users. Basically on the right hand side of Gmail, we showed you what people look like, where they worked, their recent tweets, and that is now a feature inside of Superhuman Mail. I had some track record as a founder, which is a useful thing, especially when you have a crazy sounding idea. And so I went to all the people I'd made money for and I was like, hey, listen, I have this new idea, I think it's a great idea. It's probably going to sound crazy and I can pitch it to you, but I think you're going to want to invest in it just because it's me as opposed to the specific idea. And if you have a set of people who believe in you like that, then that's great, you should just go do that thing, right? And I think that's how I raised the first million or 2 million. I'd already raised a million for Rapportive and we ended up giving all this money back. And basically my pitch was like, can I have the million back again? And plus, plus I want to do something great with it. When it came to call that a pre seed round, when it came to the real seed round or the Series A or the series B, obviously that doesn't work. I mean it can maybe work if you're a well known enough founder. But I needed to tell a real story. And the thing that was really going for me with email is, and every VC knows this because every VC is drowning in email. It is just this absolutely ginormous market. And my pitch basically boiled down to, I bet you this is the biggest market you will see for the next four weeks in your Monday morning partnership pitches. And let me show you the math. We have a billion professionals on average. This is still the average number we spend three hours a day reading and writing email. That's 3 billion hours every single day that go into reading and writing an email. That's north of a trillion hours a year that go into reading and writing email. And yet before Superhuman, we still had only a one size fits all solution, which was Gmail and Outlook. And by the way, those things are Nearly free. And they don't solve the problem. For the people who do the most email, you find a more dislocated market than that. And this is just the start of what we're trying to build. We're actually building the productivity and collaboration suite of choice. Email, it turns out, is the best place to start because of all of these things. It's the most open ecosystem you can literally even at a Fortune 500, just bring your own email clients and there you are, your past security. So we can use that as a way to grow and expand. And so that's a lot more of a strategic pitch that's just like, okay, what do VCs respond the most to? Actually, every VC is different, but the core thing is market size. So pitch that and then figure out what unique things on top of that they're going to respond to. And it's funny that you mentioned the whole feelings over wants and needs. And maybe this was timing or maybe this is a good example of founder market product fit. Especially with my game design background, the investors who got the most excited and I think for our series B we had like seven term sheets. They all wrapped themselves around that idea. Some were like, oh wow, kind of slack came out of a game design background founder. Could this be like that again? Or consumer VCs who were doing their first SaaS deal. Or SaaS VCs who saw the returns that consumer partners were getting and thinking maybe this could be like that. Maybe this isn't just your average buy boring B2B SaaS company. And it's certainly like we never pitched it that way. In fact, we capitalized on that storyline by saying this is absolutely not your average B2B boring SaaS company. Because we have this B2C motion. We're building a 100 year brand. This brand will be here for a very, very long time. As you know, that is so much more true now than back then. So it was a question of figuring out what storyline would most resonate with each particular partner and vc and then telling that story when it came to co founders, which was the other part of your question, it's actually quite different. Right. With co founders, it was a single founder company for about a year before I brought on board co founders. The pitch is very different. The thing that would resonate the most I found is momentum, which is actually ultimately the job that we have as founders is to create momentum. And there's always cool stuff happening at other companies. Just got a raise or I need to see through the next vesting Cliff or my company just went public and I need to hang around for a while. There are always these excuses, right? But you need to get those people with you right now. The best, most awesome thing you can do is basically have some form of narrative that sounds like this train is leaving the station and if you don't join now, I don't know that you will be able to join. And so for me, the ways I did, and I didn't even write any code, but it was stuff like the very first thing we did was buy superhuman.com, which was kind of insane, by the way, because I raised $250,000 first check into the company and I immediately spent 175,000 on it on the domain. But I knew that's momentum, like the un serious about building this company. And again, I was speaking to like five or six potential co founders. They're all watching this momentum take place. Then it was hiring one of the best design agencies out there and then it was producing great designs and then it was writing the landing page for Superhuman, which is more or less actually still the copy that we have today. Like really obsessing over that and making sure we're telling that narrative. Then it was continuing to raise more and more and more money. So over the period of about nine months to a year, my potential co founders were seeing all of this happen. And by the time I had one or two million dollars raised, the main name in place, the landing page in place, the storyline there, the first designs done both to wireframe and high fidelity concept, I think it was just very obvious to them this was going to be a very exciting thing and I wasn't messing around. And that's how we built the mobile.
- [22:10]
C
The way to build a collaboration tool was give it, make it freemium, put it out there for free, allow people to just sign up for it, try it, get going with it, make it really, really simple to get started on. But there's a lot of things about Superhuman that are actually the opposite of that. So one is this human touch onboarding. I'm curious how you decided to do this because now it's pretty commonplace. I suspect a lot of you are doing a process like this, but in a lot of ways I think it was unique for a product like this at the time. I would love to hear some of the motivations for why you did that. Was it about discovery? Was it about activation and customer success? Was it about your price point? Like, what are the things that fit into deciding to take like a very different worldview on how to get people going on product.
- [23:03]
A
So interestingly, when, when we started the company for a few years, I thought we would do it the quote unquote normal way. Again, if you wind the clock back 10, 20 years ago, 20 years ago freemium was considered a big deal because it was a novel business model back then. Now it's sort of brain dead obvious and I think over time it came into fashion, then it fell out of fashion. Then we all realized what it really was, which is actually a relatively expensive way potentially of financing your marketing. And there are certain specific cases where it works really, really well. Slack is a great example. The product is multiplayer or collaborative by default. Like that is the primary use case. Obviously true for Slack and where in using the product you build up a retentive moat. Everything from the habit of going back to Slack every day in the morning to the data that you're actually putting into the product, right? Those are all things that of course you want to treat it like give it away for free because once people start using it, it'll be so difficult for them to stop using it. But email doesn't actually check those boxes. Email is now there is collaboration in Superhuman, but even today it's still primarily a single player experience. 20% of the use case perhaps is collaborative and multiplayer. And because of that you don't have the pull of other people bringing you back. There are some pulls, right? Your reminders are not going to manifest in quite the same way in Gmail. Back then we didn't have split inbox, but things like split inbox are now a reason to come back. Things like the AI and the calendar, those are all now reasons to come back. But in those early days we didn't have those things. Except for the search was fast, it was really pretty, has keyboard shortcuts. The feel would pull you back. But if you were a lazy user or we hadn't quite sold you yet, then you'd be back in Gmail. I took all of this in and at the same time I saw how easy it was becoming to get an initial set of users to try your product. It is not hard for any one of us to throw something out there and with a little bit of grit get 10,000 people to sign up. Right? That is used to be impressive, super not impressive. These days you can get 10, 20, 30,000 people to sign up for basically anything. The problem is getting those people to stick around. And more importantly than that even what do they say about you to all of their friends and to the people that Matter now, it was obvious to me with Superhuman, partially because I lucked onto it with Rapportive. Rapportive, Just kind of like massive success all by itself. Good product, perfect timing, very lucky. Became a cult product. So I looked onto making a cult product, and I was like, can I recreate the conditions to create a cult product? And it turns out the answer is you absolutely can. You just have to be very strategic about how you do that. One of the most important things, if that's your goal, is to have as few people saying anything bad about your products as possible. So how do you control for that? Well, just make sure everybody is deliriously happy. Well, how do you achieve that? The way you achieve anything as a founder is just maniacal control over every single detail. And so I insisted that we would only onboard five people a week, that I would onboard all of those five people. And back then, those onboardings were long hours, was probably half an hour. But the first ones, they were like two hours each. And I would go to the office, I'd research people ahead of time.
- [26:41]
C
Actually, you came to the office. I forgot that it wasn't a zoom call.
- [26:44]
A
That's right. I remember going to slack. And we'd probably stop doing gifting at this point. But in the early days, it was like, okay, is this guy a whiskey person or a wine person? Or maybe they don't drink. I'm going to bring some tea or something like that. We'd research them, we'd figure out what they like. Bring them a gift for a reason. I shall explain shortly. Sit down. And I would say, okay, show me how you use Gmail. Or show me how you use. Actually, back then, it was all Gmail. And I would take notes, and then I'd say, okay, this is superhuman. I'd do a quick demo, get them excited, and then I drop the bomb. Because they weren't expecting this, okay, now you're going to pay for it. So pull out your credit card. It's $30, by the way. Here's a bottle of whiskey. Make it feel a little bit less awkward. Deliberately invoking the reciprocity principle. And so they would. I think only one person ever was, like, really? Everyone else was, like, happily paying for it. They're so invested by this point. And then I would watch them use the product for an hour or two, however much time they would give me. And if you haven't done this, please do this, and please never stop doing it. Because even with a mature product, it. It is incredible how much you will see that maybe Even your product engineers or your PMs won't see, or your designers, like you as the founder or you as the CEO, are going to see everything. You'll just see every single problem and write them all down, bring them back to the team. And what I did is I said to the team, because they were pushing me to grow faster, the team wants to grow as fast as possible. I was always the go slow guy. And I said, no, we're not going to onboard anyone else until we fix these issues. And they say, why? And I said, well, every user has bug fatigue in the sense that they might tell you one bug, they might tell you two or three. You think they're going to tell you 10 or 20 or 30? Hell no. You think we have less bugs than that? Hell no, we do. So the only way we'll find out about them is if we do the grind and we turn the spigoton very slowly to polish this thing. Like, we just have to keep on doing this polish. So those were the initial motivations. It was control the blast radius, make sure every single person became a Net promoter, and also use it as a way to build the best possible product to truly understand what people wanted to understand about email workflows we didn't understand, of which there were plenty. Like, we built for us. As soon as we hit the market, we started encountering other email workflows. That's fine, that's normal. We just have to start catering for those workflows and also find all the bugs and fix all the bugs. Then we noticed something really, really weird, which is the metrics for these users were off the charts. Like, the activation was crazy, the retention was crazy, the virality was crazy, the Net promoter score was crazy. Our ARR was just sort of like going up without coming down in any way. Like, the churn was surprisingly low. And so I looked at that and I was like, huh? Am I just that compelling? People love it so much. So my brother used to work for the company. He was our head of growth at the time. I was like, why don't you go do this? Just let's just disambiguate whether it's me or the process. Yeah. And he did it. He was actually even better than I was. I was like, huh? Okay, good reality check. Also, it's probably the process. So that's when I had this light bulb moment. This was just before A16Z invested back in late 2018, early 2019, where I was like, what if we hired a team of people to do this round the clock over Zoom. 40 calls a week. Why has no one ever done this? Like, why has no one run this play? And I start googling it. The closest I could find is what Jason Lemkin on Sasta called like call to close. Like these companies that have so much top of funnel volume that they're just set up a round robin of people on a phone call to basically show you the product and take your credit card number. This is a little bit harder than that because you have to watch the user in Gmail figure out their workflow, replicate that in Superhuman and then obviously fill the funnel. So that was the idea. I then had my brother hire two people to be the first test onboarding specialists. We came up with the name of this role onboarding specialist to figure this out, to disambiguate whether or not it was him. Could we. The next test was could we hire a smart person off the street and have them do it. And so we hired two. You always want to do this in pairs so you don't have the failure mode of you just hired a bad person. Also it's nice if there's a bit of competition. They did, and they did exceptionally well as well. And then I was like, okay, this is it, we're scaling this up. And by the way, VCs love this if you have a. Because VCs are always looking for the alpha, they're looking for the edge. And we had like six or seven different aspects to our storyline. Whether it was me personally or my game design background or this feelings over user requirements or the onboarding process or the price point or our product market fit approach which we haven't talked about yet. All of those together made it so the Series B, it was actually really easy. It was like a week long process. And even just the storyline alone was like, wow, there's enough going on in this company that is sufficiently different and thought through from scratch that that alone was interesting to the Bally's best VCs. So yeah, we scaled that team and then the limit, the net detractor aspect continued to be important for many, many, many years because it took us a long time to get to an Android app, it took us a long time to get to an Outlook integration, it took us a long time to build our sales features and our salesforce integration and our pipedrive integration and so on and so on. Because this stuff just takes time, especially back then to build to a high degree of quality. And so what I didn't want was people signing up saying oh, you don't have an Android app. And it turns out that, guess what? I need a mobile email app to do my email. You guys suck. Remember, you have the right not to serve. I'm going to say that again. You have the right not to serve any customer. Founders, forget this. So people would sign up and say, and we used to have a survey, we'd be like, what mobile phone do you have? They'd say, Android. And I said, well, you can't have Superhuman. And people get confused like, why isn't it my decision whether or not I buy? And I'm like, no, it's my decision whether or not I sell.
- [33:29]
C
Yeah, it's interesting how these sort of different things, the dots connect. It's like one by asking for money up front, it's sort of like, okay, I'm committed to going through this process with you. By having a human there, I am going to walk through this sort of complicated set of use cases and be able to personalize towards an aha moment that, that drives really high retention, it drives ARR growth. But this piece about the net promoters is a really interesting one, which is if I got through all of that, I'm probably going to tell my friends about it, but not just because it was a great experience, but because it was different that it was contrarian or different from what other people are doing. It seems like almost like by making very focused, strange decisions that kind of fit together. There's, there's, there's something new there or something.
- [34:20]
A
It wasn't being strange or different for the sake of it. Like I genuinely thought all of these things were the right thing to do for their own reasons. The market doesn't care. Like candidates and investors are looking for, for the storyline of differentiation, sometimes just for differentiation because they're in the business of finding different things.
- [34:41]
C
So let's talk about the pia, the product market fit engine. Because we talked a little bit about Net promoter scores and about having people who wanna talk about it and drive word of mouth. But another sort of what looks in retrospect like a great decision but odd decision is you spent almost three years working on the product before you launched it broadly. And so I want to start with how you would advise founders to think about their decision of when to launch a product versus continuing to iterate and improve with a small set of users.
- [35:15]
A
Well, it was a different world back then. Everything took 100 times longer and I didn't feel like the market was moving at all. Yes, email clients are a dime a dozen and they come and go, but they're also all terrible. And so I'd just be like, there was never going to be an email app that would ever displace us. I think if we were to fail, we'd either have to like Paul Graham says it would be a self inflicted wound. It would be running out of cash, hope or what's the other one? He says, oh, co founder breakups. Those are the top three reasons you run out of money, you run out of hope, or your co founder partnership falls apart. So I always thought that's the risk here. It's not competition. I think what I would do if I was starting something right now, I would have a crystal clear set of ideas as to why the company strategy would succeed. And this is one thing I used to be really bad at strategy for my first company, Reportive had zero strategy, just cool product, great, good go. And then I think as I've grown Superhuman over the years I've gotten better at strategy. It's still something I'm very actively working on. I think it's one of the last skills most of us acquire as founders and as product people. But I would have a very crystal clear strategy that articulates why the sequence of steps that we intend to take, we think will actually work and why they stand up in the face of competition. I'll give the example of Superhuman. I knew how hard it was to build and I didn't think that anyone else would be as crazy about it. And by that I mean raise as much money and be as patient over it and spend three years building the thing eventually. And I realize this will sound like survivor bias, but eventually the amount of time you spent building something can be the moat, right? If you've come out of a three to four year build, everyone else is looking at that thinking, am I going to start an email client company?
- [37:32]
C
Bad.
- [37:32]
A
I want to do something else. I think that's kind of what happened with Superhuman Mail. Occasionally people have started email out companies but like they don't go anywhere and like one or two people and they are unable to raise any money for it. Generally speaking. Slack obviously did that to the chat space. There's this notion of taking the oxygen out of the room. And so I felt like we could get to that point with mail and that was part of our strategy with charging for it upfront. That was also a very deliberate part of the strategy. So we talked about why not freemium. We haven't talked about why a premium price point. And that goes, was it $30 a month when you started it? Was 29. 29 for like six months. And then I was. Then I had a conversation with a pricing expert who was like, 30 sounds more premium than 29 and it's basically the same. And I was like, you're absolutely 100% right. So we made it 30 and then we only changed it two years ago and now we have 30 and 40 to pay for the extra AI costs, which was a mistake, by the way. So one quick aside on that mistake, we should have been changing pricing all along the way. And if I were to go back in time, I think we'd have 30% more AR. Now you can basically charge me whatever
- [38:49]
C
you want, I'll keep paying it.
- [38:50]
A
Write that down. I had a very clear thesis around pricing, which was one thing we didn't talk about with onboarding, was it wasn't just five random people a week, it was the five most influential people a week I could find. Because there is this thing that I think we'll talk about called the highest expectation customer, which is most of your customers actually aspire to be like somebody. If you can figure out who they aspire to be like and get those people to love your product. Well, now you've just started to build virality that doesn't rely on viral mechanics. It's what virality really is, which is just word of mouth. And so the five most influential people I could find, how could I price it such that it spoke to how those people think about themselves? And how those people think about themselves is, if you haven't noticed, because you all probably are those people as well. Email is kind of part of the ego, right? It's like, oh, yeah, I get this many emails a week. This is how much time I spend on email. Or this is how much time I don't spend on email because of how many emails I get a week. It's funny how the ego can go in both ways. Like the amount of work and the pressure was part of the ego. And I was like, well, if that's the case, you know what's going to make you feel good about it? Spending a lot of money on fixing that problem. So that's part of how we priced it at 30. And then that was my initial psychological analysis. And then I took kind of a step back and I was like, wait a minute, there's actually a bigger trend line here. There's a bigger story here, which is the idea of the prosumerization of the enterprise. This is roughly when 2019, when David Ilovich made the investment for a 16Z. So we'd just seen the consumerization of the enterprise. We all know what that is. Basically, enterprise software sucks. What if it had the sensibilities of consumer software? And I was like, well, consumers are really, really wide buckets. And it turns out that the people who do email for a living, they're not consumers, they're prosumers. What's a prosumer? A prosumer is a power user, but with none of the time of the power user and all of the economic agency of the power user. They have all the money to spend, but they don't have any time to figure things out. That's a prosumer. Generally speaking, what is the prosumerization of the enterprise? And could we do that which is actually part of what we're still building now, but at the wider superhuman company in many, many different areas, in many products verticals. And so I had this idea that that could also be part of our strategy. And there's a bunch of other things as well, like this positioning and how we thought about customer support and so on and so on. But all of these are laddered up to. Short of the entire world changing this strategy feels like it would be basically unassailable. It would have to be one of the three PG things which is you run out of time, hope, slash, patience, or something goes wrong with the co founders that would break the company.
- [41:47]
C
So let's talk about the product market fit engineering. This is a product framework that I think you popularized called, I would call it the product market Fit Score. I think a lot of people here call it the Superhuman question. Now can you walk through what that is, why you developed it and sort of the story around getting to a more scientific approach to measuring product market fit, which to this point I feel like is always like, you know it when you see it, but you built sort of a system around developing and understanding a product market fit. And I would love you to walk through that a little bit and just sort of give the 2 minute version, 1 minute version of what it is and then sort of how to operationalize that for founders building and trying to get there.
- [42:34]
A
It was about April 2017 and we were two, three years in the team were pushing really, really hard to launch. No one wants to work on something that hasn't launched. No one wants to not have user feedback. But I believed deep down inside that this thing would just flop on first launch if we threw it out there. I believe that we did not have products market fit. But I couldn't just say that to the team that is not an inspiring thing to hear from your CEO. Yeah, we don't have products market fit. Keep working is not a good plan. Instead it doesn't work with investors either. Doesn't work. We don't have products market fit. Please invest. Yeah, don't do that pitch bad pitch. Instead I wanted to come up with a really. And if you haven't been able to tell, I love unassailable stories. Like a narrative that no matter how you poke this, no matter how you peel it apart, it hangs together so coherently, both logically and emotionally that people are just incredibly compelled. And so that was actually part of. People don't realize this. The goal wasn't necessarily to get to product to market fit. That was the side effect. The goal was to inspire the team in a way that would be long lasting and basically forever. And as a really crazy side effect, it is now the most viral entrepreneurship article, I think of all time. It's the most shared article on first round review. So that was the goal. And I was like, okay, how do we do this? So I researched everything that I could possibly find on products market fit. And I don't want to take credit for the question because it's not my question, it's actually Sean Ellis's question. And Sean Ellis was one of the first growth hackers ever. He coined the phrase growth hacking. He was the first growth marketer at LogMeIn, Eventbrite, Dropbox and he was the one who came up with the question, how would you feel if you could no longer use the product? You answer on one of three dimensions. Not disappointed, meaning you don't really care, somewhat disappointed, you're like eh or very disappointed, meaning you love the product and be very sad if it were to go away. And so way back in the day he'd benchmarked this on hundreds of venture backed startups and found that the companies that grew to product market fit almost always had more than 40% very disappointed. And the companies that didn't grow to products market fit almost always had less than 40% very disappointed. And I thought, aha. Well this is the only research that has ever been done like ever on this topic. But it's enough, it's enough to build a process and an algorithm around. So the innovation that we came up with was how do you turn that into an engine? How do you turn that into a repeatable process that any team, any company can run? And if you read this again, it's very hard to poke holes in will reliably make that number go up Always what we did is we added three more questions onto it. So number one is, how would you feel if you could no longer use the product? Number two is, who do you think the product is best for? Number three is, what is the main benefits you get from using the product? And number four is, how can we improve this product for you? Now, here's why those questions are so important and so powerful. So the second one, who do you think this product is best for? It gets to what founders most forget about products. Market fit, which is you're allowed to change the market as well as the product. And it's actually way easier, it turns out, to change the market than the product, because you can just decide, we're changing the market today, guys. Product's the same. Okay, let's figure that out. Maybe change your packaging. Oh, by the way, before we ran this analysis, I ran the first question and we had 22% very disappointed. 22. Way less than 40. And you might think, oh, you must have been really bummed out about that. Actually, no, I was excited. I was like, finally, I can explain what I'm feeling to the team in a way that is irreproachable. Like, you can't argue with these metrics. This is what the standard of success says. And we're hard failing. So how do we fix that? Well, it turns out that the easiest thing you can do is change the market. So I was looking at all of the survey responses from like the first hundred, 200 people using superhuman, and I was like, I really want this number to be more than 40. How do I make this number more than 40? I'm just going to select a bunch of people where it goes more than 40. It turns out I'm segmenting the market. And I was like, what set of people makes this number be more than 40? And it turned out that if I just dropped Data Science, Sales and engineering, but kept VC, CEO, founder BD, it was like 10 percentage points higher. It was 32%. That was as close as I could get it by doing literally zero work. So that's just the right to not serve. I could be like, and we did this. We deliberately didn't serve people who were in adjacent Personas to the core Persona to begin with. So that's the power of that second question. So we were surveying these people, we were getting these four questions back. The very first thing we did was change the market. And so we got from 22% to 32%. Then the question is, okay, what do you build to systematically get to 40% per plus. And this is where I like to ask the question, who do you think the product is best for? And it turns out this is a very powerful question because it turns out that your happiest users will almost always answer that question by describing themselves using the words that matter most to them. This is like product marketing ninja skills. You literally get your product marketing copy and your positioning directly from your happiest users. If you just act on the feedback from your users, you will end up building a confused, muddy mess. I mean, back then we didn't even have the engineering cycles to act on all the feedback we do now, right? All of us can build, we can vibe code whatever we want. But that makes taste and discernment even more important now than it was back then. So you need to figure out who to listen to and who not to listen to. So remember, we have a pie with three segments. We have the very disappointed segment, we have the somewhat disappointed segment, and the not disappointed segment. By re segmenting, I'd got the superhuman segment from 22 to 32%. We want to make that more than 40. So the question is, how do we grow the size of that pie? Well, we can't play with segmenting the market anymore. We already did that. So now the next optimization is trying to get people who are in the other 2 segments into the segment that we want. There are 2 possible segments, the somewhat disappointed segment and the not disappointed segment. And you might think, well, let's go to the not disappointed segment and see if we can convince those people to fall in love with our product. But the problem with those people is they are so far removed from loving your products that no matter what you build, there is literally nothing that you can build them that they would fall in love with your products on a short enough timescale. So don't tell them this, but just politely disregard. Ignore all their feedback. That leaves the other segment, which is the somewhat disappointed users. I didn't mention this question yet, but we've previously asked another question, which is, what is the main benefit of the product for you? This is a super important question. Back then, for Superhuman Mail, it would have been things like focus, flow, speed, keyboard, shortcuts. It's really, really, really fast. Today. It's a lot more about AI and stuff, but that's what it was back then. You go to your somewhat disappointed segment and you subdivide it into two groups. Group one, the group for whom the main benefit does not resonate. They may have written down, for example, for us, oh, it works offline or I like your mobile app or I like read receipts or whatever it is. And then the set of people for whom the main benefit did resonate. These are the people who said I love the speed, I love the keyboard shortcuts. Politely disregard group one. And the reason is even if you built everything that they asked for, fixed every bug that they report, the main benefit of your product still does not resonate with them. So they will end up falling in love with your product for quote unquote the wrong reason. And this is where founders and founding teams can get a little bit distracted and pulled into the wrong markets or building the right thing for the wrong reasons or the wrong thing for the right reasons. Instead go to group two, which is the somewhat disappointed users for whom the main benefit did resonate. Because only a few things I would wager it's only a stone's throw, a stone's gap is holding them back from falling in love with your product. And just systematically work down that list. And then the final piece of this is because I promised it can basically generate a roadmap that will take you to products market fit. Vision driven teams tend to focus just on the list of things for what do you love about this product? Data driven teams tend to focus on just the complaints that are coming in. I like to start each planning cycle with half our energy going into building more of what users love already. In our case making it even faster, even more beautiful, even more keyboard driven stuff. Nowadays it would be something like integrating OpenCore into mail so it works with your agent ecosystem, that kind of stuff. And half the time just working down all the boring complaints that people have about the product. If you only work down all the boring complaints, someone's going to out innovate you. If you only do the innovation, you're not and this is more obvious when you sit down and think about it really hard. But you're not going to grow the size of the pie that is very disappointed without your product. You do both of these things and you will. And the results from Superhuman were we went from 22% to 32% just in a few minutes, just by segmenting. And then the quarter after we were at 46%. The quarter after that we were at 56%. The quarter after that we were At 58%. And it won't hover at 58% forever. Like Andrew talks about the law of shitty metrics. This will come down for good reason because hopefully you're expanding industry, you're going to adjacent Personas those salespeople that we ignored before, we now have to figure out how to build a product that's good for them as well. And so on and so on. So the number will come down. But that's the art of building great products is you'll keep pushing it back up again. I know that was a lot and I know it was very long, but I have written this up at length. So if you Google the Superhuman product market fit engine you can find it.
- [53:34]
C
What advice would now Rahul give? First time founder Rahul starting Rapportiv back
- [53:41]
A
in the day oh boy, so much. Let's see if I can do this quick. Know what your strategy is and stick to it. For Rapportiv, I equivated on strategy constantly and we were lucky to have a good outcome, but I didn't really know what I was building and who it was for and what the company level thesis was. So have that number two. Have as many things as make sense, be different and first principled about your company. I think we're living in a golden age where it's now even more possible to do those things than when I was building Superhuman because you can basically build and do whatever you want. You can decide not to hire for a very, very long time. So you get to do the blueprints for your company from first principles. That is way more powerful than people realize and I think a lot of folks take it for granted. Put another way, and hopefully your boards will tell you this, don't just hire a bunch of VPs and do what they say. Like literally have your own opinions on everything because they're probably better than you might think if you have imposter syndrome. And the third really tactical thing is keep increasing prices every year. Stay ahead on inflation.
- [54:48]
C
All right, thanks to Raul. Thanks so much. It was great.
- [54:56]
B
Thanks for listening to this episode of the A16Z podcast. If you like this episode, be sure to like, comment, subscribe, leave us a rating or review and share it with your friends and family. For more episodes go to YouTube, Apple Podcasts and Spotify. Follow us on x16z and subscribe to our substack@a16z.substack.com thanks again for listening and I'll see you in the next episode. As a reminder, the content here is for informational purposes only, should not be taken as legal, business, tax or investment advice, or be used to evaluate any investment or security, and is not directed at any investors or potential investors in any A16Z fund. Please note that A16Z and its affiliates may also maintain investments in the company companies discussed in this podcast. For more details, including a link to our investments, please see a16z.com disclosures.