Early Days—Episode 2: Superhuman with Rahul Vohra

Highlights From Transcript

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Intro

Real lessons from real founders, the Early Days podcast. The founder and CEO of everyone's favorite email client, Rahul Vohra, shares his approach to building two successful startups, and how Superhuman first got started.

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Tyler Norwood  00:15

We've got Rahul with us, the co-founder and CEO of Superhuman. Rahul, welcome. Today, we're super excited to hear your story to talk about Superhuman and how you built course. So for anyone who doesn't know, on the call, what Superhuman is, I'd assume people are joining knowing what it is. And you know, every single person that I talk to, who uses Superhuman talks about it, as you know, one of the most life changing things that they've ever adopted, but could you just give us a quick rundown of, how do you think about Superhuman? When someone asks you, you know: what are you the CEO of, Rahul? How do you explain it?

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Rahul Vohra  00:53

Absolutely. Well, as a founder, and as everyone here should have, you need a quick elevator pitch. So the quick elevator pitch for Superhuman is that it is the fastest email experience ever made. Our customers get through their inbox twice as fast as before, reply to that important emails sooner, and many of them see inbox zero for the first time in years.

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Tyler Norwood  01:14

Awesome. And, like I said, so I have to admit to you Rahul, I don't use Superhuman. I'm a bit of a Gmail curmudgeon. I was a huge fan of Rapportive, the company you built before; that was really life changing for me. But almost everybody I know, especially in the venture capital ecosystem, uses Superhuman and sort of lives and dies by it. They can't say enough good things about how much time it saves them and how much it has changed their life. So today, what we really want to focus on is to zoom back and really learn more about you as a founder before Superhuman: how you decided to become an entrepreneur, how you came up with the idea for Superhuman, and to get really laser focused on the first six months of getting Superhuman off the ground. So to kick us off, I would love to hear about your story. And I guess the most interesting question for me is: how did you decide to become an entrepreneur? Like what in your life made you say, "you know what - I'm gonna build companies for a living."

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Rahul Vohra  02:11

I became fascinated with computers before I knew I wanted to be an entrepreneur. So this was from a really early age. And it started, like how I think it starts for many of us, which was a love for video games that has persisted to this day. So video games got me into computers. And then, slowly but surely, I wanted to learn how to program them. And I started to learn how to code when I was just eight years old. So by the time I went to University, where I studied computer science, I was very fortunate to have spent basically every, single evening - from that age of 8 to that age of 18 - programming or coding in some way. I don't know if folks still believe in Malcolm Gladwell 10,000 hours. But again, I was very fortunate to have had 10,000 hours, by the time I went to university. During that period, I would say, about as a teenager, I felt like it would be worth shooting for financial freedom. I could see my parents working really, really hard. They're both doctors, but they were still sort of trapped in this ecosystem, where financial freedom isn't really something that, at least in England, a doctor can achieve. You can obviously live a fantastic life, but not what I think most people would call financially free. So that was one of my initial goals. But then I went to Cambridge, I studied computer science, and I started networking pretty hard. I met lots of people who had achieved financial freedom and many of them didn't actually seem all that happy or fulfilled. And so I learned a very important lesson, I think relatively early - around the ages of 18/19/20 - which is, that's not really enough. It's a great thing to have. And it's a byproduct of success. But at least for me, it wasn't a thing worth aiming for. It eventually becomes pretty hollow. And, of course, the goalposts keep on shifting as one's lifestyle increases. So it very quickly became - I think I remember around the age of 21 - realizing that's not it, what it really is, what the driving force really is, is to create beautiful things that make people smile. And that was the impetus behind Rapportive, and also the driving force behind Superhuman.

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Tyler Norwood  04:39

I mean how lucky to have learned that so early on.

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Rahul Vohra  04:43

I feel blessed that I was able to meet those people at that age.

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Tyler Norwood  04:47

Yeah. So it seems like so you learned how to code, you became an engineer, then you sort of stacked the okay I need to make money doing this. And that's sort of where you arrive at: you make money by building a business. And then you added the final layer on top of it, which is: I don't just care about making money actually want to make things that make people's lives way better.

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Rahul Vohra  05:10

Yes, exactly a little tweak on the end: beautiful things that make people smile. And so that sort of captures a lot of nuance that is very important to me that the, the objet d'art, the thing that is being created, is in itself beautiful. And that's just something I hold to be very valuable. And also that it delights people, that it creates joy, that it brings a little bit of light into people's lives. There's lots of ways you can make people's lives better, that aren't beautiful, that aren't delightful. And I just realized, I'm not interested in those things. But I'm very interested in beautiful things that make people smile.

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Tyler Norwood  05:52

Awesome. And so can you talk me through...so you, you develop this framework, the steps of: obviously, I want to write code, I want to engineer and I want to build things on computers, I want to make money doing it. And then I want to make people smile, I want to bring joy to their life. How did you take that framework and then start applying it to building businesses? So how did you actually bring that to life? We can talk about Rapportive, for example. What was your process of going through and bringing that framework to life and going out and figuring out, what's a problem that I can solve for people that's going to make them smile and bring joy to their life?

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Rahul Vohra  06:28

So Rapportive came out of a very personal problem I was feeling. I had gone through the undergraduate computer science experience at Cambridge, I'd started a PhD in computer science also, and got about one year into that before - and this is cliche - I of course, dropped out because it wasn't really for me, I like to operate in teams, I like to produce products and experiences. And a PhD for anyone who's contemplated or been through one is obviously not that. So I dropped out. And then I was a little bit at a loose end. So I networked my way into the part of the university that helps staff and students create businesses. This is an organization called Cambridge University Entrepreneurs and it's a student run organization. And it's not an exaggeration to say that up until I had taken it over, it had not been particularly well run for a number of years, the previous leaders had run out of all the money and not being successful at raising more. So my first professional job ever was having to raise hundreds of thousands of dollars to fuel this organization, which had essentially become bankrupt over the course of the last year or two. And it was trial by fire. Some folks on this call may have raised money; we all know how hard it is. If we haven't tried to at least we've heard of other people who've tried to do it, some with great success, some of us struggle. But by far the hardest way to do it is for a not for profit enterprise. So we were essentially a charity. We weren't taking equity, we were literally just granting money to teams that wanted to create businesses. That's hard to raise money for, because you're not really selling anything in return, except for the feeling of doing the right thing. And so it was trial by fire, learning fundraising in the best possible way, which is selling not-for-profits. And it was hard. I remember going to events. I'm not particularly great with people: struggling to remember who was who? What's your name? have I actually met you before? I'm also not particularly great with faces. Realizing that software could help solve all of these things. What if, in your email, whenever anybody emailed you over there, on the right hand side, you could see what people look like, where they work, the role that they have, and even things like their recent tweets and a link to their LinkedIn profile. So you can very quickly get up to speed on who they are, so that you can then connect, establish rapport - that's Rapportive - and do your business with them. So I really built it for me. It was a very, sort of solve my own problem, itch to scratch. It took about six weeks to build the first version, and then it kind of blew my expectations away. We had tens of thousands of users sign up over the course of those first few weeks.

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Tyler Norwood  09:31

Yeah, I mean - if you go back to your framework of making people smile and bringing joy to their life - I think when I found Rapportive it changed my life, in terms of how I reached out to people. It changed my life in terms of how contextual I could be when I was emailing someone for the first time - it just gave me so much more information. And so it sounds like very much you were solving your own problem; you were your first customer and you solved that problem. And then it turned out there was a lot of other people out in the world who happened to have that same problem. So let's fast forward: so Rapportive got bought by LinkedIn, and you moved on and ybuilt your next company, Superhuman. Was that also a process of scratching your own itch? Was it your problem that you were trying to solve? Or did you take a different approach to building an email client? I know that I've watched Superhuman for a long time, and I'm sure you've heard this more than anybody in the whole world, but the biggest question in the beginning with Superhuman: was why would you go up against Gmail? Why would you build an email client? Who would ever pay money for an email client when there's free tools out there, etc? So talk me through the process of deciding: you know, okay, building a better email client than what's out there is the problem that I'm going to solve.

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Rahul Vohra  10:53

Great questions. So I think there are two, though we should probably take them separately. The first is how did we find the problem. And the second is this notion of going up against an incumbent, especially in an area where the next best product is really very tough to do, but actually is less crazy than it sounds once you dig into it. So during the two years of running Rapportive of as founder and CEO, and subsequent two years at LinkedIn (where I was also running all of our email integrations) I developed a very intimate view of email, and how professionals do it. I could see Gmail getting worse every single year, becoming more cluttered, using more memory, consuming more CPU, slowing down your machine, still not working properly offline. And on top of this, people were installing plugins like ours, Rapportive. About the time also things like Boomerang, MixMax Clearbit, you name it - they had it. And each plugin took these problems of clutter, of memory, of CPU performance of offline, and made all of them dramatically worse. So that was my experience. And I just decided, it's time for change. We imagined an email experience that's blazingly fast, where search is instantaneous, where every interaction is 100 milliseconds or less -- an email experience where you never actually have to touch the mouse, where you could do everything from the keyboard, fly through your inbox; an email experience that just worked offline, so you could be productive anywhere; and an email experience that had all of the best Gmail plug in functionality that's built in natively. And - despite all of this - was somehow subtle, minimal, and visually gorgeous. So it really came out of a personal, deep understanding of the product environment and actually seeing the products that people were using get worse, not better, every single year. So that's the what. Now, why is it a good idea to go up against an incumbent? Well I'm also - many folks will know - an avid angel investor. With my investing partner, Todd, we've now invested in 100 or so companies. And we love it when folks are going up against incumbents; we love it when the next best product is free. Because it turns out that if you pick the dimensions upon which you compete carefully, it's very difficult - almost next to impossible - for the incumbents to compete back. So take a products like Gmail. Gmail has, if you look at Google's numbers, north of 1 billion users. It is by every way you slice it, a one size fits all tool. And it turns out that the average number of emails that Gmail user receives - that they actually have to do something about - it's about five emails per day. Whereas the average number of emails that a Superhuman user receives that they have to do something about can easily be in the many hundreds of emails. So we did this with a segmentation or a niche strategy. We built Superhuman for the folks for whom email is work and work as email. For the folks where if they don't reply quickly to an email, they damage their reputation, or they block their team, or they miss opportunities. And then we specifically compete on dimensions that incumbents traditionally find hard. And so if you were to go all the way back to the start of Superhuman and look at our strategy, from 2015/2016, you'll see that I'd written down, we would compete on speed and design. And that incumbents struggle to compete on speed, because of a massive scale on an entrenched architecture. And they struggle to compete on design, due to organizational structure and internal politics, as well as having to build a one size fits all solution. So it's far less insane than it sounds.

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Tyler Norwood  14:45

I love the framework. And so with what you've talked about so far, you were at LinkedIn, you had a very intimate view of what email looked like, and a ton of data to support that, and you saw that the current solution and it's getting worse and worse. You broke down and you created a very clear niche of: "this is who has the problem, the worst." So you said, email clients is a problem, Gmail is a problem, Outlook is a problem, etc. And you said, "who's it the most painful for?" Like you said: people for who email is work and work is email. So how far down that process did you get before you wrote a single line of code? Talk me through the process of deciding really specifically what you're going to build versus actually going out and building it? How did that process work? In what order did those things happen really early on in Superhuman?

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Rahul Vohra  15:42

The order for Superhuman was very different to the order for Rapportive. So I'll give both, because it really depends on how you can generate some momentum; the number one goal of a founder is to generate momentum. And I like to envisage a huge, ginormous flywheel of the densest material that you can think of; the densest element is osmium. It's twice as dense as lead, if that sort of gives you any indication. And imagine that at the start, it's standing still. And your job is to get it rotating, and you're pushing it. And for the first few months, as you're pushing it, it's barely moving - maybe fractions of a millimeter. But it's your goal to get this thing moving. And the great thing is, especially in SaaS, once this thing starts moving, it's really hard to slow down; it will keep on moving by itself. Now, that's the goal. The goal isn't to write code. The goal  isn't to create a prototype, the goal isn't to raise funding, or build a team or whatever else you might think, actually, is the goal. I used to think it was those things. Before Superhuman and before Rapportive, I tried to start seven companies previously and failed in all kinds of different ways. But the summarization of how I failed was I got to the goal wrong; the goal is to generate momentum. So how do you generate momentum? Well it depends on what you uniquely can do. Another dirty little secret that few people would ever tell you is that at the start of almost every single company, if you take it all the way back to the very beginning, every company is actually started by one person. Sure, there are co-founders. And sure there's a founding team. And of course, it takes a village and then a town or the city to build anything that's noteworthy. But someone, somewhere has to say, "I'm doing this, despite all of the people telling me that I'm crazy and how can you possibly - in this case - sell in email clients and go up against the most well funded company in the world?" Someone has lead it. And then the question is, well, what can that one person uniquely do to generate momentum? Now for Rapportive, I didn't have any money; I didn't have any reputation. I had pretty decent access to very smart people, having come out of the University of Cambridge. And I was also a pretty decent web developer, because I just - for two years - had been the CTO of another failed startup. So this was in the era of Heroku, and Ruby on Rails and jQuery and that era of web technology, and I was pretty proficient in all the things. So I was able to single-handedly stand up Rapportive and built the version that scale to the first 30,000 to 40,000 users. That is awesome if you can do that, because you now have generated momentum. All those potential co-founders who were sitting on the sidelines will think, "oh, this train is leaving the station, I better get on board right now." All the people who you might be considering raising money from, well, guess what? They're going to email you, instead of you having to ping them. And that's what happened at Rapportive; I had no idea how to raise money. But I didn't have to, because of the success that was being generated, everyone reached out to me. Now, the second time around, for Superhuman, it was very different. It was 2014, the Q4 of 2014, as opposed to 2010. So it was four years later. And the goal of Superhuman, it was just so much larger. Rapportive exists as a feature in Superhuman today, and it's probably less than 2% of the product. So the scale of ambition was much, much greater. And I also was no longer a proficient web developer, I'd become a proficient founder and a proficient CEO. So although you might think, well, last time you started with a prototype, therefore, that's what you should do this time. That actually would have been very suboptimal, remembering that the actual goal of a founder is to generate momentum. So the very first thing I did was start to cash in on the goodwill and the returns that I generated for the last company. So Rapportive was a successful acquisition, most investors made 3x to 5x their money. A few very early investors made north of 20x their investment. So I wrote a deck. And I had the initial vision for Superhuman, which hasn't really changed very much to this day, although, of course, it's become a lot larger. And I went back to those folks. And I said, "Hey, this is what I'm going to do, I'm going to build an email experience that's so darn good, people are going to pay for it. And I know that sounds crazy, but this is what I'm here to do." And in that first quarter, Q4 of 2014, I raised about $800,000, almost all of which were from people who'd backed me before. And so despite how crazy the idea is, their point of view was, well, if anyone in the world can pull this off, it's probably Rahul. He has all of the rights pieces laid together. Once I had a little bit of cash in the bank, and this was after about $250,000, I knew that I had to acquire the domain superhuman.com. Well speaking of the name, I'd actually picked the name in June/July earlier that year. And that's like the whole...

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Tyler Norwood  21:12

So that was part of the deck? You knew Superhuman from day one?

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Rahul Vohra  21:16

So, uh, not quite day one. I'd incorporated the company in February of 2014. And I had just come out of LinkedIn in February 2014, but I was super burned out. For anyone who's gone through an acquisition, definitely don't just start your next company immediately afterwards. You really do owe it to yourself to enjoy the proceeds; take some time. I took about six to nine months off after leaving Linkedin. I'd picked the name around the, I think, actually the March/April timeframe. And I'd started fundraising in Q4. And I knew that this was going to be a household brand company. I knew that one of the core growth channels was going to be virality. And that, therefore brand, was going to be exceptionally important. I knew that we were going to use techniques like email signatures which surprise, surprise still works. But today, it has to stand out from the crowd. You can't just be something like, you know, I'm just trying to think - I don't want to pick on any one other email product...But most of them have very boring sounding names, as opposed to a brand that actually stands for something. So I knew that the email signature had to stand out from any other potential email signature that you might see. And so there was this notion that I had to acquire superhuman.com. That was not easy. That was hard. It was hard because the person who owned it had owned it for about seven or eight years, and had rebuffed every single previous attempt from every single previous founder for aquiring it. I similarly went on a mission to get the superhuman Twitter handle and then eventually to get that verified. That took many, many years because it was owned by another startup. So I had to get it off that startup. But over the course of about four or five months, I did eventually acquire superhuman.com. One key trick there is don't try and do this yourself; always hire a broker who knows what they're doing. Because they will be able to put the pressure on the seller in a way that doesn't make it clear who they're representing. And so they'll be able to get that processed.

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Tyler Norwood  23:42

So you hired a domain broker to help you go acquire superhuman.com?

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Rahul Vohra  23:47

Exactly. And he's a very good domain broker. And he was able to get him. Folks probably wondering how much it ended up costing; this is question I always get asked. The initial ask was for about $250,000, which I felt was too much. That would have been all of the cash in the company bank accounts at that point. But I got him down to $175,000, which sounds like a lot. But on an interest free...there's a there's a word for this where you, you pay down the loan over time. So interest free page download over time, over seven years. So basically had spread the last 175k over seven years. And I knew that I would raise a Series A within two years and at that point, it would seem nearly free. And so from my point of view, this was an incredibly cheap deal. I was basically leasing it during the seed round period, knowing that as soon as I'd raise the series A, I would pay it off entirely. So that was the rest of Q4. And that was about the first three months so I can continue into the next three months, if you think it's useful or we can go elsewhere.

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Tyler Norwood  24:56

So let's pause there and I want to dig down into a couple of things. I really liked the framework around momentum. And I think that's been talked about quite a lot. I don't think it could be talked about enough. But I love what you've introduced -  the way I kind of think about how you explained it - is this concept of one, I really liked it, one person has to get the thing started. And even when you have co-founding teams, one person was one who came into the room and said, "guys, we're doing this, this is why, etc." But I love how you kind of have...

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Rahul Vohra  25:32

Slight tweak on that: because there's no one to go into a room to. It's one person who just starts doing it, with whatever resources you have. The mistake I had previously made, was looking for that room and looking for the team to say, "Guys, this is what we're doing." Because they'll be like, "Eh I don't like the idea," or "it's going to fail" or whatever. And maybe, hopefully, they're more optimistic than that. But even so they'll be like, "well, why don't we do XYZ?" They'll have their own ideas. There is no better way than simply doing it, showing that it works. And then asking people to join you.

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Tyler Norwood  26:04

Yeah and I love that. So amazing correction, because I think it's...so not only that concept where that train leaving the station, where it's like, "hey - there's legs here, there's something's happening," but also how you described the difference between Rapportive and Superhuman, which is this concept of you as a founder have certain resources at your disposal at different times of your life, right? And so when you started Rapportive, you didn't have all the money in the world, or you didn't have investors you had previously created returns for, you said, "Well, what do I have? Well, I'm a great web programmer, I'm gonna start there." And then with Superhuman, you're like, "Hey, I'm not that great of a web programmer anymore, because I haven't been doing it for a long time. But this time, I have a lot of goodwill that I can tap into, so I can get some money raised and then I can get things moving, etc." I think that's a really phenomenal framework. And I really like - one of the things we all struggle with as founders - is that there's not a checklist, there's especially not a linear order of things that need to be done to get a company off the ground. And I think that's a great way to think about it, where it's like there are things that you have to do in no particular order. But the way you decide what you should do is just ask yourself, "What can I do right now with the resources I have?" And to your point, I think all smart people are looking for flywheels that are already spinning a little bit. Very few people actually want to be the first person to push on the flywheel. And so to your point with Rapportive it's like, "we got 30,000 to 40,000 users." And I'm sure an investor asked you, "how big is your team?" And you're like, "it's literally just me." And they're like, "alright, take my money and we want to invest." So you raise the round for Superhuman and then what next? So your first step in terms of building momentum was "I can get some cash in the bank and we can start investing that cash." The first thing was the domain because brand was very important. How did you then go about...So that was the first three months. How did the next three months pan out? How did you continue to gather resources and build momentum?

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Rahul Vohra  28:13

So getting the domain takes us towards the end of 2014 and the start of 2015. I was very casually raising money all the way through 2014 and 2015. Meaning as and when I was introduced to investors who were potentially interested, I'd go pitch them. But I didn't go out on like a fundraising blitz. I think that's a very important nuance; I didn't try and raise a million dollars before I did anything else. I took the entirety of Q4 to raise about 800,000. And so in the meantime, I was working on other things. I was educating myself; I was reading just catching up on the state of art of startups. For example, there's a book that I would highly recommend to any founder, which is Traction by Gabriel Weinberg and Justin Mez, because I wanted to make sure that I had a concept for the growth of Superhuman built into the company and the product from day one. And then when we get to January, it was actually starting to work on what is this product, like, let's make it real. And the way that I did that, and I love doing it this way - because it really forces you to figure out what's special - is to start writing the copy for the landing page. And not just start writing it, but like finish writing it. This is not too dissimilar to the Bezos notion of start with the PR release. But we're a startup so we don't get to do PR releases. So start with the landing page. And I took it really seriously. This was not something I just busted out in one day. This was a six week, full-time endeavor, meaning...And for context about 1000 words long. If you were to go to superhuman.com today, it is precisely what you see there. Nothing has changed since 2015. In terms of that landing page, it is precisely the same copy.

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Tyler Norwood  30:16

So you nailed the vision.

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Rahul Vohra  30:19

Yeah, we actually got it right from the get go, which is very lucky, it doesn't always happen. But the vision was correct from day one. And, to be clear, we need to change the website. I'm not saying it's the right website for today, but it was the right website for back then. And I spent six weeks writing that copy, researching other email application websites, finding the words that I liked, figuring out the tone and the voice. I literally rewrote every single sentence north of five to 10 times. I should probably actually make this a blog post. I think it might be interesting for folks to see the process, but subjected the higher landing page to a very intense copywriting process. And that took about four to six weeks. Now, as I was doing this, I was updating my deck; I was continuing to improve my pitch. Remember, I'm casually meeting investors all along the way. And all along this way, I'm also attempting to recruit a founding team. So would be co-founders. I ultimately ended up with two co-founders, Conrad Irwin and the Vivek Sodera. Conrad is still with the company today; Vivek ended up leaving Superhuman towards the end of last year. But my goal was to find co founders. I would never recommend that anyone truly be a single founder. It is a very hard and lonely journey. And you do need folks who are going to build this with you. But those folks, to your point, anyone smart is going to want to see momentum. And so in the same way that it's wise to send out investor updates to your investors during the good and bad and not just to go back to them when things are going bad. It's wise to drip feed progress to your would be co-founders and your would be candidates so that they really feel the pulse and the beats of this project. And so they get the sense that actually this is no longer a project. This is a company and it's going to happen. So I was building this copy out and sending it to would be co-founders. Once I had the copy done, I then started on the wireframes. So what actually is this product going to look like? And how will it work, not high fidelity, this was low fidelity using Balsamiq. And I ended up creating - probably over the course of another three to four weeks - about 50 to 60 different screens, modeled after what the best email applications were at that time. With the enhancements that I thought I would make them significantly better. And I definitely got some things wrong. So at that time, we had a three pane layout, meaning we had a sidebar, a preview pane, and a contextual sidebar. So the list of threads, your inbox, so to speak, was in one very narrow view, which is how Mail app does it on native macOS. But it's not how most people who have a very high volume of email like to see their inbox, they'd like to see it full screen like Gmail does it, as a simple example of something that I got wrong. So that was the next three to four weeks. And then this sort of brings us to March, April, May, it was finding a design partner to turn those wireframes into really high fidelity designs, pixel perfect designs. Now, I'm not a great visual designer. I'm a good creative director; I can direct a visual design to very high quality. But I don't personally have the skillsets to push every pixel myself. And so this was what I recognized at that time. And so I found this amazing organization, Ueno (U-e-n-o), that had previously, or was at that time, working with Uber and Airbnb, run by this chap called Hallie, an amazing designer. And we were one of his very first clients. And so I said to him, "Hey, this is the vision. This is my fundraising deck. These are the wireframes. This is my mood board." I'd assembled images that sort of conveyed the brand that we were trying to achieve. I'd love to work with you on high fidelity designs. And the reason for that is probably not what folks are thinking. It's not because these were the designs that we ended up making. But it was because I wanted to get everything to the next level of realism. This was another way to generate momentum. These were ultimately throwaway designs, but they helped me get my founding team on board. They helped me get the next set of investors on board. They helped me find out what product questions and what design questions I hadn't yet answered. And so that roughly takes me to May or June of 2015, by which point I had probably one or two and a half million dollars in the bank; we had superhuman.com; we had all the wireframes. We had the landing page copy ready, and we were designing the actual landing page itself. I had two co-founders, Conrad Irwin and Vivek Sodera, and we also had our first engineer, Vivesh Kakadu, who Vivek had brought over from his previous startup that had wound down previously. So we were off to the races.

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Tyler Norwood  35:39

It's awesome. I mean, just starting from that little grain of sand in the very beginning of the goodwill you had from Rapportive. So you went through this whole process, I guess, the last thing I'm curious about, and you know, we love talking to our founders about this. So you gathered a lot of information from LinkedIn about how people were using Gmail. You chose this niche of people who do a lot of email for work. When was the very first time you talked to prospective customers? And put something in front of them? When did you loop them into the process of building Superhuman?

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Rahul Vohra  36:16

I've always believed in picking a product area where I am a perfect example of a prospective customer. That was true for Rapportive. It's true for Superhuman. If I ever do another company, it's almost certainly going to be true for that also.  Because it gives you such an unfair advantage. I can have that internal dialogue with myself constantly, all the time, every day. And that's what I did. So the answer to your question is from day zero, I was just asking myself is this something that would make my life better. And then because of the unique type of products that Superhuman is because investors happen to be high volume emailers, they were also all prospective customers, they also intimately felt the problem, so I could ask them. During the course of Rapportive, I'd made many friends who were founders, all of whom are also very high volume emailers. And so I could also ask them. So just through my social connections, I was able to sanity test the idea for Superhuman as we went. However, that's what I call operating in low gear. Soon you have to wrap this up to the next level. And we did this around May or June when we started to get the landing page live. That first landing page was not great. It was essentially just a paragraph and a little box where you could put your email address in. But nevertheless, people were finding it. Slow to begin with, 10, 20, 30 per day. But this is a number that has just increased since then. And this is a simple hack, but one of the most powerful hacks is to constantly interview users all the time. So from that time, whenever anybody would sign up, they would receive an automated email from me. And that email would say, Hi, this is Rahul. Thank you for signing up for Superhuman. Can't wait to show you what we're working on. Before we jump in, I have two quick questions. Number one, what do you use for email today? Number two, what do you hate about it? Thanks, Rahul. Bye. That's it. That was literally all my email. I don't know what the response rate was; I never tracked that number. But enough people replied to that email, that it soon became a full time job just staying on top of those emails back and forth. And initially, it was me, then eventually it was our head of growth. But we stayed on top of these emails. And the trick is is not just to sort of log it away. But as soon as you get a response to quickly and rapidly reply in a very authentic manner, and just keep on asking why. So people would say, for example, "I use Gmail and I use boomerang and what I hate about it is how clunky and slow everything is." And then I would reply back and be like, "Well, why is it clunky? Why is it slow? What features in boomerang are you using?" And they might say, "Well, I'm using a reminder of people to reply, and I'm using send later." And then I would reply back again. And I would say, "Well, which one of those is more important? Is it reminders if people don't reply, or is it scheduled sending?" And of course, they reply back and say, "It's reminders if people don't reply." A d then I'll keep on digging. I'll be like, "Well, okay, is it reminders if people don't reply, do you ever use reminders regardless." And I'm starting to collect data. Now this isn't being tagged or triaged any anywhere. Not at this point in the company today, we take that very seriously. But it was it was being logged in my mind. And it was developing a mental model and intuition of what people were looking for. And through that methods, we actually interviewed 700 customers, if actually not more, over the course of that first year of Superhuman. So on average more than two, but...

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Tyler Norwood  40:10

Wow. And I mean, it's incredibly impressive. And I sort of chuckled to myself, because you say "the email from Rahul" and you know, I think everyone's so familiar with the messages from you. Even today, we get new feature launches and all that stuff and that's still a big part of the company. So at that stage, so you set up this incredible feedback loop from your customers. How did you manage that? So really, really nailing the products, kind of building out this mental product roadmap of I've got a really good intuition and understanding of the features that our customers want. How did you balance that with scale? So when did you sort of shift gears from, okay, we're going to keep this small, we're gonna try to talk to every single customer in depth, the process is inherently not scalable, like you're kind of logging this in your head, etc. When did you feel like, okay, let's start really putting our foot on the gas? So that happened naturally, or was it a conscious decision?

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Rahul Vohra  41:10

It was about two to two and a half years later. And by the way, it is scalable to talk to every user even as you scale. We we do so today; we heavily invest in that. And we tag and triage every single thing that we've heard. I think at this point, we've tagged over 85,000 verbatim phrases from our customers in different ways, which gives us a real edge when it comes to building the product. But the answer to your question, how did we know when we could scale, this is where it gets to the Superhuman Product-Market Fit engine. And so it was clear to me in that first one or two years, that we didn't have product-market fit. And I also knew that product-market fit is the number one reason why startups succeed. And the lack of it is the number one reason why startups fail. And so, therefore, we had to get to that point. But I didn't know how to measure product-market fit, I didn't have a methodology for iterating and for developing it. And many people on the call are probably familiar with this now. It's one of the most widely read introductions to the topic. But I ended up coming up with a methodology not just to measure product-market fit, but to iterate and develop it over time, and a way to systematically increase your degree of product-market fit over time. So I came up with that engine, then we ran that engine. And when our product-market fit was consistently north of 40% and rising; and when our NPS was consistently north of 50; and when our engagement was high; and when our churn was low or equivalently, our retention was high. That was when it was more obvious that we had something that was going to be amazing and we step on the gas. And you can sequence those things, not all of those things are going to be true on day one. The very first thing to look out for is, is your product market fit score 40% or more.

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Tyler Norwood  43:06

And that was when you knew it's time to shift gears time to go.

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Rahul Vohra  43:10

Well, that's when you start looking at other measures. It's necessary, but it's not sufficient. So you start looking at NPS; you start looking at engagement rates - which is a leading indicator of survey results; you start looking at dollar churn and dollar retention. You can have high product-market fit score, but still have not a great business, for example, if you're not retaining enough of your users by the end of the year, so you do want to make sure that you have a lot of things in place. But the very first thing is the product-market fit score.  

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Tyler Norwood  43:45

Awesome. And I think so would you think about product-market fit as a reflection of the amount of value that you're bringing to the customer base?

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Rahul Vohra  43:55

So the way that we measure it is "how would you feel if you could no longer use Superhuman?" And you get to answer on three different ways. Not disappointed, meaning you wouldn't care, somewhat disappointed you kind of care. And very disappointed. You would care considerably if the products were to disappear. Now, what does that actually measure? Sure, it could be value. It could be dependence; it could be emotional connection. There's a lot of things wrapped up in one. It specifically doesn't ask, "how valuable is Superhuman to you?" It specifically doesn't ask, "do you need this product?" It's just, "how would you feel if it were to go away?" And the question is deliberately vague in that way. Because there are multiple ways to create something that people would be very disappointed if they were to stop using. But ultimately, that's that's what we're trying to get to whether it's through being entertaining, or through being useful, they're both viable ways to create good products that has Product-Market Fit.

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Tyler Norwood  45:01

Incredible. Well Rahul, this has been incredibly insightful. It's been awesome having you on. I think we've got a lot of great nuggets here, a ton of amazing learnings, kind of looking under the hood of your personal process and the story of Superhuman. So a few people want to know, just in closing, what's next for Superhuman? So I think a lot of people have asked, you know, Superhuman 2.0? And with the next generation Gen Z coming into the field and using the internet in such different ways, where's Superhuman heading?

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Rahul Vohra  45:35

Well, we have a lot of incredibly exciting things in the works, some of which I can talk to; some of which, obviously, I can't. What you might expect over the coming weeks is a very exciting calendar feature. So the foundation for calendar features to come, we're building a full week calendar view. And that's going to be tremendously useful. I've personally stopped going to Google Calendar. There's no need for me, because it's built into Superhuman now. And that's going to come shortly, on a slightly longer timescale, on timescale of three to five months Superhuman for Outlook. The Google workspace ecosystem is only about 11% of the overall productivity ecosystem. So we're going to massively expand our markets by bringing Superhuman to Office 365. That's going to happen this year as well. And then, for after that, I will say wait and see. It's gonna be exciting.

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Tyler Norwood  46:33

Well, awesome. Well, two awesome things to look forward to. I saw your tweet on your how painful would it be for your Outlook users test and it seems like you guys are in a great position to crack that piece of the market. Obviously, the calendar integration is incredibly exciting. That's the other huge piece for everybody. So for anyone who's on or listening that doesn't use Superhuman or hasn't tested it out, I would definitely recommend going and testing it out and becoming part of the Superhuman team. And Rahul, I have to thank you again, this has been incredible it's really, really useful for founders all over the world to hear, you know, human stories like this about how something was actually started. So I've got to thank you once again.

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47:15

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