The Exchanges

Q Can I ask a tough one, and we are going back to the five factors, but in terms of kind of the scaling, How do you think about scaling that onboarding to the millions of users? How does that look and work?

A So I think one of the biggest misconceptions is that you can't scale one-to-one concierge onboarding to the amount of revenue, let's say, that a venture scale outcome requires. And a little bit of back-of-the-envelope maths shows that simply isn't true. One of the simple questions I always ask myself from my perspective as an angel investor is, Can this potential company get to a hundred million dollars of annual recurring revenue? And there's a few reasons behind that. I think number one, that's the point at which they're a billion dollar company, and then number two, that's the point at which, through revenue, they can go into any other realm of business. And so it's a question that I think about for Superhuman all the time, and because of how efficient the onboarding process is, it turns out you don't need that many onboarding specialists to get to a hundred million dollars Of annual recurring revenue. Let's say that you wanted to get there in two years. Well, in that case, you have to be adding north of fifty million dollars of ARR every single year. Each onboarding specialist can do in the region of 35 to 45 calls per week, and if you do the math, then it turns out that you only need in the region of 60 to 70 onboarding specialists to get to that level of revenue. And as you'll know, that's a much smaller sales team Than the vast majority of companies have. So it actually …

AI assessment note: “you only need in the region of 60 to 70 onboarding specialists”

Q I would love to start with a little bit on you. And for those that maybe missed our first episode, how did you make your way into the world of startups, Rahul? And what was that aha founding moment for you with Superhuman that's really changed the way we think about email?

A Well, to understand the founding moment of Superhuman, we actually have to wind the clock back by about 10 years. So 10 years ago, in 2010, I started a previous company called Reportive, and we built the first Gmail plugin to scale to millions of users. When people emailed you, we showed you what they looked like, where they worked, their recent tweets, and links to their social profiles. And we grew rapidly, and in those two years, we were shortly afterwards acquired by LinkedIn. And across those four years, I developed a very intimate view of email. I could see Gmail getting worse every single year, becoming more cluttered, using more memory, consuming more CPU, slowing down your machine, and still not working properly offline. And on top of this, you might recall, people were installing plugins like ours, Reportive, but also things like Boomerang, Mixmax, Clearbit, you name it, they had it. And each plugin took those problems of clutter, memory, CPU, performance, offline, and made all of them dramatically worse. So we decided it was time for change. We imagined an email experience that is blazingly fast, where searches are instantaneous, where every interaction is a hundred milliseconds or less. An email experience where you never had to touch the mouse, where you could do everything from the keyboard and fly through your inbox. An email experience, of course, that just work…

AI assessment note: “to understand the founding moment of Superhuman, we actually have to wind the clock back”

Q Totally agree with you. I guess my question to you is, can you ever have too much control in a product?

A I don't think you can have too much control, because as business software, we're coming from a bar that is so low, where the controls are so fragile, and so slow. Let's take an example. So let's say I want to email my co-founder, Conrad. In Gmail, the shortcut to compose an email is C. So let's say I type C, and then I type comrade. Now, in Gmail, if I do that at any pace, I end up with two drafts. One to con, and one to rad. And in Superhuman, we had to build our own keyboard handler to ensure that we never lose keystrokes. And in case you think I'm picking on Gmail, this kind of error is status quo for business software. Take Any productivity or any collaboration tool try and drive it hard through the keyboard, and more often than not, you'll end up in a mess. So what I'm really saying is, if you want to build software like it's a game, then you need to create rapid and robust controls.

AI assessment note: “I don't think you can have too much control, because as business software”

Q either get compared to Harry Potter or Benedict Evans, so, uh, I'm clearly winning at life. Tell me, the final one that we spoke about was Flow, and honestly, I didn't fully understand this one, Rahul, so help me out here. First and most importantly, what is Flow? And then I guess second, Now we know what it is, what conditions need to be in place for flow to occur?

A We've all experienced flow at one point or another, and I would imagine that you get into flow when you're in your dark recording studio talking to all of your guests from across the world. Colloquially, we would say that flow is being in the zone, and it turns out to be this intense area of deep psychological research. Technically, flow is a state of mind that has six factors. Number one, Flow is an intense and focused concentration on the present. Number two, flow is so absorbing that we don't think about the future or worry about the past. Number three, flow is so demanding that we don't care what others think about us. Number four, flow is so easy that we always know what to do next. Number five, flow is so powerful that it alters our subjective experience of time. Time can flash by in an instant or stretch out forever. And number six, flow is so rewarding That the activity becomes intrinsically motivating, which, as we know from before, is the most powerful and effective form of motivation. So in short, flow sounds incredible. The question is, how do we create it, and what are those conditions? Well, the conditions for flow are fivefold. Number one, we have to know what to do next. Number two, we have to know how to do it. Number three, we must be free from distractions. Number four, we must get clear and immediate feedback. And number five, and this is the hardest of all,…

AI assessment note: “Technically, flow is a state of mind that has six factors.”

Q Not at all. I'm very excited, but I do want to start today with a little bit on you. So tell me, how did you make your way into what I call the wonderful world of startups and really come to found the game changer of email that is superhuman?

A Well, I've actually been doing startups for quite a while. I knew from the age of 15 that what I wanted to be was an entrepreneur, and all the way since then, everything that I've done has been towards that goal. Now, I've started any number of companies. I think this is attempt number seven or eight, with only one prior success called Reportive, and really to get to the superhuman, which I started a few years ago, you have to wind the clock back to the previous company. So in 2010, I'd started that company, Reportive, and we built the first Gmail plugin to scale to millions of users. Essentially, when people emailed you, we showed you what they looked like, where they worked, their recent tweets, and links to their social profiles. We grew really rapidly, and roughly two years later, we were acquired by LinkedIn. And during those years, I developed a very intimate perspective of email at LinkedIn. I was running all of our email integrations and just began to understand how professionals do email in really quite a deep way. And 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 now on top of this, people were installing plugins, Reportive, of course, our own, and Boomerang and Mixmax, and later on things like Clearbit. And each plugin took those pro…

AI assessment note: “So we figured at that point that it was time for change.”

Q have one final element to ask you about. And it was one actually that is not on schedule, but one that I spoke to the bold stock guys about. Just before the show, which is why it's not on schedule, and it's your approach to onboarding. It's a very unique and different approach. What is your approach to onboarding, and why do you think it's beneficial to have this approach?

A So our approach to onboarding, and this is considered to be crazy by most people who know about it, is actually to spend half an hour to an hour with each new user. We typically do this over a Zoom call. Now, there are some constraints around that. The constraints are the user has to take a welcome survey, and that pre-qualifies them. That lets Us know whether or not they're likely to be a happy user of superhuman. They have to preauthorize a credit card to show that, you know, they really do mean business and they have an email problem and they're willing to pay for a great solution to that problem. And then we get on that half an hour to one hour zoom call with them. Now on that zoom call, you're paired with an email expert. We have a team of wonderful onboarding specialists. They, they know email better than anybody else in the world. They know our product extremely well, of course. And we're able to ask you what your current habits are and consult on how to do your email faster. And most of our users actually end up getting through their email about twice as fast as in comparison to Gmail. And many of them see inbox zero for the first time in years. And that's kind of the magic with the onboarding. You know, we, on the one hand, filter out the people who either didn't have an email problem or weren't serious about solving it. And on the other hand, we can really focus on de…

AI assessment note: “is actually to spend half an hour to an hour with each new user.”

Q I totally agree, especially on the last one, but when you think about that today, how do you think you've built flow into the product intentionally that's worked specifically very well?

A In order to understand this, I think it's helpful to break the conditions down one by one, and then I'll talk to one or two things inside a superhuman that really push that condition. So the first condition was knowing what to do next. And you can make product decisions that make this dramatically easier for your users. In Gmail, when I archive an email, what do I see? Well, I'm back on the inbox. And now I, the user, have to decide what to do next. And I have to make this decision every single time. And for a high volume emailer, that could be hundreds or potentially even thousands of times per day. This destroys flow. In Superhuman, when I archive an email, I automatically advance to the next email. I don't have to take any decisions at all. That creates flow. So that was knowing what to do next. Condition number two is knowing How to do it. Early on we saw that users would forget our keyboard shortcuts. They knew what they wanted to do, but they didn't know how to do it. So we built superhuman command. Just hit command K and type in what you want to do. It will do it for you and teach you the shortcut for next time. And earlier you'd spoke to the superhuman go-to-market becoming this common, almost widespread thing. Superhuman command Is doing the same. In just the Y Combinator batch, I saw five different companies that had incorporated this into their product, and we have c…

AI assessment note: “In Superhuman, when I archive an email, I automatically advance to the next email.”

Q I would love to start with a little bit on you. And for those that maybe missed our first episode, how did you make your way into the world of startups, Rahul? And what was that aha founding moment for you with Superhuman that's really changed the way we think about email?

A Well, to understand the founding moment of Superhuman, we actually have to wind the clock back by about 10 years. So 10 years ago, in 2010, I started a previous company called Reportive, and we built the first Gmail plugin to scale to millions of users. When people emailed you, we showed you what they looked like, where they worked, their recent tweets, and links to their social profiles. And we grew rapidly, and in those two years, we were shortly afterwards acquired by LinkedIn. And across those four years, I developed a very intimate view of email. I could see Gmail getting worse every single year, becoming more cluttered, using more memory, consuming more CPU, slowing down your machine, and still not working properly offline. And on top of this, you might recall, people were installing plugins like ours, Reportive, but also things like Boomerang, Mixmax, Clearbit, you name it, they had it. And each plugin took those problems of clutter, memory, CPU, performance, offline, and made all of them dramatically worse. So we decided it was time for change. We imagined an email experience that is blazingly fast, where searches are instantaneous, where every interaction is a hundred milliseconds or less. An email experience where you never had to touch the mouse, where you could do everything from the keyboard and fly through your inbox. An email experience, of course, that just work…

AI assessment note: “I could see Gmail getting worse every single year... So we decided it was time for change.”

Q Okay, absolutely. But if you think about, kind of, determining whether you have that playful side in your product, how do you measure that playful side in your product, and whether you have the toy in, or it's a game? How do you think about that?

A Well, this is best understood by example, so I can talk to an example of a toy in Superhuman, and then share some general questions to help our listeners find their own toys. So in Superhuman, a favorite toy is the time autocompleter, which you use to snooze and set reminders on emails. You type whatever you want, it can be utter gibberish, and it does its best to understand you. For example, two D becomes two days, three H becomes three hours, One MO becomes one month. Now, the time autocompleter is fun because it indulges playful exploration. What can it do? Where does it break? How does it work? And it's not long in onboardings before people start to explore these boundaries. For example, I wonder what happens if I keep on typing 10. Well, it turns out that that's October the 10th at 10:10 p.m. Or how about A sequence of twos. That's February the second, twenty-twenty-two at two p.m. And then we see folks trying more complex inputs, like in a fortnight and a day, and becoming delighted when it works, and it's not long before they find other pleasant surprises. For example, they type in eight a.m. in Tokyo, and they realize that time zone math happens without them ever really having to think about it. So consider the features of your own product. And ask yourself this. Do they indulge playful exploration? Are they fun, even without a goal? And do they create moments of pleasa…

AI assessment note: “ask yourself this. Do they indulge playful exploration? Are they fun, even without a goal?”

Q Yeah, absolutely it is. It's also a very hard thing and a realization to come to as a CEO. I do want to ask my favorite movie, I think, and is aligned to yours. What can we take away, and this sounds bizarre, from Titanic and apply to game design, Rahul?

A Well, this is actually an example that comes from the art of game design by Jesse. There are two kinds of resonance. Resonant fantasy and resonant truth. An experience has resonant fantasy when it resonates with our dreams and desires. For superhuman, it could be the fantasy of having superpowers, and who doesn't want that? It sounds both liberating and exhilarating, but there is something even more powerful than fantasy, and that is truth. And Jesse gives the example of the Titanic. Why is this movie so compelling? It's not the effects, or the execution, or the performances, great though these all are. It is because the movie has a resonant truth that is constantly reinforced, and that is, love is more important than life and stronger than death. Now, most of us don't go around saying this all of the time. That would be strange if we did. But the reason this movie is so compelling It's because most of us actually believe this. It's the kind of belief that we keep buried deep down inside. And so I was inspired to ask the question, what is the resonant truth behind superhuman? What is something we deeply believe, but rarely express? And I think for a product like ours, it would probably involve effort and attainment. So our first attempt was something like this. I am what I do. And it's getting there. But it sounds like our work defines us, which it doesn't really. And so our ne…

AI assessment note: “Jesse gives the example of the Titanic... movie has a resonant truth”

Q How do you think about that when it could be so subjective? So someone's email could be quite easy to get to inbox zero, and then yours or mine or other people's maybe a lot more challenging to get to inbox zero. How do you think about creating challenge when it's so ambiguous dependent on the user?

A Well, superhuman massively increases the skill level for almost Anybody. Whether you are a high volume email user or not, the things that you learn in the onboarding call, the keyboard shortcuts, and the way the product is designed, all contribute to massively increasing your skill level. But I think the question you're asking is, what if your email wasn't that challenging? Let's say it was a lower volume email account, or you were already hyper skilled in the first place. Maybe you were a productivity enthusiast, and you were extremely proficient with keyboard shortcuts. Well, if we don't do anything else, then you still don't end up in flow, and so this is why, and this is going to sound crazy, we increase the challenge level. We provide a challenging goal. Hit inbox zero, but do so without ever touching the mouse. This then rebalances challenge with skill, and across our entire user base, results in flow.

AI assessment note: “Hit inbox zero, but do so without ever touching the mouse.”

Q Can I ask a tough one, and we are going back to the five factors, but in terms of kind of the scaling, How do you think about scaling that onboarding to the millions of users? How does that look and work?

A So I think one of the biggest misconceptions is that you can't scale one-to-one concierge onboarding to the amount of revenue, let's say, that a venture scale outcome requires. And a little bit of back-of-the-envelope maths shows that simply isn't true. One of the simple questions I always ask myself from my perspective as an angel investor is, Can this potential company get to a hundred million dollars of annual recurring revenue? And there's a few reasons behind that. I think number one, that's the point at which they're a billion dollar company, and then number two, that's the point at which, through revenue, they can go into any other realm of business. And so it's a question that I think about for Superhuman all the time, and because of how efficient the onboarding process is, it turns out you don't need that many onboarding specialists to get to a hundred million dollars Of annual recurring revenue. Let's say that you wanted to get there in two years. Well, in that case, you have to be adding north of fifty million dollars of ARR every single year. Each onboarding specialist can do in the region of 35 to 45 calls per week, and if you do the math, then it turns out that you only need in the region of 60 to 70 onboarding specialists to get to that level of revenue. And as you'll know, that's a much smaller sales team Than the vast majority of companies have. So it actually …

AI assessment note: “you only need in the region of 60 to 70 onboarding specialists”

Q slick and so seamless. You've really been Front and center of creating a whole new category of onboarding. I guess my question is, and it's just out of interest for me, how do you feel about that, and was it intentional to really create an entirely new category of onboarding? I have startups every single day saying, hey, we're doing the superhuman for onboarding. How do you feel about that?

A Well, honestly, it's a little bit flattering, and absolutely was not intentional. I don't think we set out to invent a new go-to-market motion. It really happened organically. You see, in phase one of the company, it was Just myself. I did the first three or four onboardings by myself, and they were very different in nature. They weren't half an hour. They were at least one hour, often two hours long, and I would sit down with the user. I would give them a demo of what we had built. I would do things like a pricing analysis and interview with them. I would, of course, onboard them, and then I would insist on watching them use Superhuman for about 20, 30 minutes. And inevitably, in each case, I would record five to 10 bugs that I would insist that we fix before next week, because it doesn't make sense to have users continuously experience the same issues cohort after cohort. So we did this, and in doing so, we noticed that these users had category-leading metrics. Their churn was industry low. Their retention was industry high. Their net promoter score was off the charts. They were incredibly viral. And I wondered, Whether it was the go-to-market, or maybe it was some kind of founder magic that I was bringing to my table. So I asked our head of growth to do the same thing, and he did the next several hundred onboardings, and it was exactly the same, and he had also managed to sh…

AI assessment note: “honestly, it's a little bit flattering, and absolutely was not intentional.”

Q How does one go from there? What's that subsequent next step? So you have that now, and you have the existing base of would be very disappointed. How do you translate that into the next step, both kind of a product roadmap, but also increasing that kind of very disappointed segment?

A For sure. So yeah, the whole goal here, of course, is to increase the percentage of people who'd be very disappointed without the product. And so the next part is a bit of survey ninjutsu. You essentially take Every single response to your survey and you assign a persona to each one. And, you know, for our very disappointed cohorts, there's a lot of founders, a lot of managers, a lot of executives for our not disappointed cohorts. Let's simplify this example. You might imagine there's perhaps a lot of engineering people who don't necessarily do a lot of email for work. So you take the users who most love your product, you turn those into an HXC, and then you use those to narrow the markets. And what I mean by that is deliberately ignore the responses from customers who don't fit that archetype of people who love your product. So in our case, we focused on founders, on managers, on executives, on BD, and again, I'm just simplifying here. We deliberately ignored sales, customer success, engineers, data scientists, people who don't do email for work, and you just take them out of the survey entirely. Now, what that will do is it will change the The percentage results of each part of the survey. And so for us, just by segmenting our product market fit score jumps by 10% from 22% to 32%. It's a five or a 10 minute exercise. And, you know, in our case, it didn't quite get us past 40%…

AI assessment note: “just by segmenting our product market fit score jumps by 10%”

Q No, I completely agree, and I think it's a massively unspoken element, so I couldn't agree more, and I'm thrilled to hear you say that. Tell me, you've mentioned before about kind of seeing friends of yours in the Valley, kind of the growth expectations. What would you most like to change about Silicon Valley today?

A I would like to see a more heterogeneous economy, one that, that doesn't just rely on startups as the main driver of the economy, number one. And number two, I'd like to see faster housing policy. So as I'm no doubt sure that, that you know, that San Francisco is an extremely expensive place to live. It is in fact the most Costly city in America now. Salaries are skyrocketing every single year. House prices are skyrocketing still, depending on the, the segments of the housing market that you look at. And I don't think it, it does us any favors if what we as an industry in Silicon Valley are trying to do is build world changing companies. Because now it turns out what the rational thing to do is, is headquarter here, be here, raise money here because capital is relatively abundant and Valuations are high. It's a very founder-friendly place to be, but it isn't rational to spend money here. The rational thing to do is to go and spend the money elsewhere, perhaps in Seattle, where there's less taxation, or perhaps in Canada, where there's R&D credits, the government will literally give you money back to set up an R&D office there, or perhaps even in London, where you are, so one can arbitrage the currencies. And as someone who lives here, I wish that wasn't the case. I wish we could build organizations right here, but it's becoming increasingly less rational to do so.

AI assessment note: “I would like to see a more heterogeneous economy... number two, faster housing policy.”

Q And so what did you uncover from yours then?

A Well, so we gave our highest expectation customer a name. She's Nicole. Now, Nicole is a hardworking professional. She deals with many people. She might be an executive, a founder, a manager, or in business development. She works really quite long hours, and often into the weekend. She considers herself very busy and wishes she had more time. She does feel she's productive, and she's self-aware enough to realize she could do better, and she'll occasionally investigate ways to improve. And she spends a lot of her day in her inbox, of course. On a typical day, she'll read up to 200 emails. She'll send 50. On a very busy day, she might send as much as a hundred. And critically, She considers it part of her job to be responsive, and she prides herself on being so because she knows that if she's unresponsive, she might block her team, damage her reputation, or cause missed opportunities. Now, generally, she has a growth mindset. She's open-minded about new products. She keeps up to date with technology, but she may have a fixed mindset about email. Whilst she's open to new email clients and experiences, she is skeptical that one could make her go faster.

AI assessment note: “we gave our highest expectation customer a name. She's Nicole.”

Q What do you know now, Rahul, that you wish you'd known at the beginning?

A That it's a marathon, and to take care of both body and mind. In Reportive, I worked so hard and let myself get so stressed that I actually ended up hospitalizing myself. My body just gave up on me. I couldn't eat, move, walk. This thing that was carrying my mind around just basically said, all right, I'm done, I'm out. And I was actually in hospital for a week, and it took me two weeks of recovery afterwards. It was a pretty serious outage. And at the start of superhuman, I started taking much better care of my body, but I wasn't taking care of my mind, and that resulted in some breakdowns as well. And so now I take good care of both. I exercise regularly, and I also work on my mental well-being. I see both therapists as well as two executive coaches, and so there's this team of people that work with me to keep me in tip-top condition, and I wish I'd known that at the beginning.

AI assessment note: “That it's a marathon, and to take care of both body and mind.”

Q Not at all. I'm very excited, but I do want to start today with a little bit on you. So tell me, how did you make your way into what I call the wonderful world of startups and really come to found the game changer of email that is superhuman?

A Well, I've actually been doing startups for quite a while. I knew from the age of 15 that what I wanted to be was an entrepreneur, and all the way since then, everything that I've done has been towards that goal. Now, I've started any number of companies. I think this is attempt number seven or eight, with only one prior success called Reportive, and really to get to the superhuman, which I started a few years ago, you have to wind the clock back to the previous company. So in 2010, I'd started that company, Reportive, and we built the first Gmail plugin to scale to millions of users. Essentially, when people emailed you, we showed you what they looked like, where they worked, their recent tweets, and links to their social profiles. We grew really rapidly, and roughly two years later, we were acquired by LinkedIn. And during those years, I developed a very intimate perspective of email at LinkedIn. I was running all of our email integrations and just began to understand how professionals do email in really quite a deep way. And 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 now on top of this, people were installing plugins, Reportive, of course, our own, and Boomerang and Mixmax, and later on things like Clearbit. And each plugin took those pro…

AI assessment note: “to get to the superhuman, which I started a few years ago”

Q And so what did you uncover from yours then?

A Well, so we gave our highest expectation customer a name. She's Nicole. Now, Nicole is a hardworking professional. She deals with many people. She might be an executive, a founder, a manager, or in business development. She works really quite long hours, and often into the weekend. She considers herself very busy and wishes she had more time. She does feel she's productive, and she's self-aware enough to realize she could do better, and she'll occasionally investigate ways to improve. And she spends a lot of her day in her inbox, of course. On a typical day, she'll read up to 200 emails. She'll send 50. On a very busy day, she might send as much as a hundred. And critically, She considers it part of her job to be responsive, and she prides herself on being so because she knows that if she's unresponsive, she might block her team, damage her reputation, or cause missed opportunities. Now, generally, she has a growth mindset. She's open-minded about new products. She keeps up to date with technology, but she may have a fixed mindset about email. Whilst she's open to new email clients and experiences, she is skeptical that one could make her go faster.

AI assessment note: “we gave our highest expectation customer a name. She's Nicole.”

Q What do you know now, Rahul, that you wish you'd known at the beginning?

A That it's a marathon, and to take care of both body and mind. In Reportive, I worked so hard and let myself get so stressed that I actually ended up hospitalizing myself. My body just gave up on me. I couldn't eat, move, walk. This thing that was carrying my mind around just basically said, all right, I'm done, I'm out. And I was actually in hospital for a week, and it took me two weeks of recovery afterwards. It was a pretty serious outage. And at the start of superhuman, I started taking much better care of my body, but I wasn't taking care of my mind, and that resulted in some breakdowns as well. And so now I take good care of both. I exercise regularly, and I also work on my mental well-being. I see both therapists as well as two executive coaches, and so there's this team of people that work with me to keep me in tip-top condition, and I wish I'd known that at the beginning.

AI assessment note: “That it's a marathon, and to take care of both body and mind.”

Q So, okay, if you think about how you then integrate that thinking into the product today at Superhuman, what do you think you've done in terms of goal setting, integrated into the product that people use on a daily basis?

A Well, in Superhuman, we set a very concrete goal. Get to inbox zero. And good goals must be achievable. This is one of the reasons why we onboard users. In fact, it's the main reason why we onboard users. For each new user, we do a live concierge onboarding. This is a One-to-one video call with one of our wonderful onboarding specialists, and in that call, we teach faster workflows to get to inbox zero. We teach powerful shortcuts so you never have to touch the mouse, and if you're very far away, we wipe the slate clean so that you are within a stone's throw of inbox zero, thus making the goal more achievable. So we have concrete, we have achievable, and finally, the goal should be rewarding. When you hit inbox zero, You feel triumph over your email, a previously rare and incredibly rewarding feeling. Now, most business software does not have clear goals, and if there are goals, they are often unachievable and unrewarding. If you want to build software like it's a game, then we have to create goals that are concrete, achievable, and rewarding.

AI assessment note: “we set a very concrete goal. Get to inbox zero.”

Q Of those seven, which you think that most people misunderstand the most?

A Oh, it's absolutely the last one. You see, we have a whole generation of product managers and product designers who are brought up on this notion of Make the product easy to learn. Make the product easy to use. And what I'm saying is if you actually study some of the theories behind game design, and you go into flow, which takes you back into intrinsic motivation, and why we choose to do things, and what makes activities inherently interesting and satisfying, it's actually those activities which have high perceived challenge, as well as high perceived skill. And I think we've gone too far when it comes to designing our business software. We have In a sense, made them too easy to use.

AI assessment note: “Oh, it's absolutely the last one.”

Q I love that description of kind of your fundraising journey. You said to me before, actually, that you always be raising, but never raise actively. Can I ask Rahul, what did you mean by this? I didn't dive into it with you at the time, but I'm too intrigued now.

A This is Sort of an allergic response to my experience at Reportive, as well as a response to what I see happen, my friends here in Silicon Valley. Now, a lot of people can spend way too much time fundraising. Even for good to great companies, these things don't just necessarily fall into place. You know, you sometimes hear of rounds completing in a week, pitching a few firms. Those are the exceptions, not the rules, generally speaking. So I have seen, and I myself did this in my last company, many, many founders, Waste a tremendous amount of time on fundraising, and that's because they're running an active process. They are going out to markets with a story and trying to close that in a hopefully a short amount of time and then get back to work. I have found for superhuman, and we've been executing it this way, that it is actually, if you can pull it off, much, much, much more efficient to not do that and to let the market come to you. So to be always sufficiently well capitalized ahead of your needs so that you At the right time, the right seed investor will come to you. The right series A investor will come to you. The right series B investor will come to you, and they'll preempt your next round. So always be open to that idea, and I'm always open to it both from lead investors as well as from individual angel investors, and never be out actively trying to chase capital. That…

AI assessment note: “never be out actively trying to chase capital. That's really what I meant by that.”

Q given the virality that people are so impressed with. So I totally see that working, and I'm so glad that we did dive into that. I do want to go back to the five factors, though, and the second that you mentioned was emotions. Talk to me about this. How do you think about the integration of product and emotion, and what emotion do you want to elicit with superhuman?

A Well, the best games create strong emotions, because strong emotions are the foundation of our memory, and we must therefore be able to analyze emotion. And to do that, we need vocabulary. Now, there are many models of human emotion, and the most famous is Plutchik's wheel. He identified eight core emotions, joy, surprise, Anger, and so on. Opposite emotions are across from each other. For example, joy is the opposite of grief. And on his wheel, this is really interesting, you can blend adjacent emotions to create more complex feelings. For example, when you combine joy and anticipation, you get optimism. And when you combine joy and trust, you get love. But as game designers, we need richer vocabulary than academia provides. Because the emotions that we are aiming for Are much more nuanced. The most useful model I have found is the Emotion Wheel by the Junto Institute. It contains the subtleties that we need to think about. And you asked, what kind of emotions do we design for at Superhuman? Well, we care deeply about joy, and joy has many sub-facets. We design for enthusiasm and excitement. Our users come to us super excited. We design for optimism and hopefulness. Our users want Superhuman to dramatically improve their lives. We design for pride and triumph for when you hit Inbox Zero, especially if it's the first time in years, you rightly feel like you accomplished somethi…

AI assessment note: “And you asked, what kind of emotions do we design for at Superhuman? Well, we care deeply about joy”

Q Can I ask, you know, when we think about that, and we think about integrating it into a product today, we see levels, we see points, we see leaderboards, you name it. I guess my question is, how does gamification differ from game design?

A Well, I would start by saying this. Gamification does not really work. Game design works, but game design is not gamification. It isn't simply taking your product and adding As you said, points, levels, trophies, or badges. And to understand why gamification does not work, we have to understand human motivation. And there's a very interesting study from Stanford that demonstrates the difference perfectly. In the 19 seventies, the Stanford researchers recruited children aged around three to four years old. And all of these kids were generally interested in drawing. Now, some kids were told they would get a reward. A certificate with a gold seal and a ribbon. Some kids were not told about any reward, and so they did not expect one or even know of one. And each child was invited into a separate room to draw for six minutes, and then afterwards they would either get the reward or not. And over the next few days, the children were observed to see how much they would continue to draw by themselves. Here's the thing. The children with no reward spent 17% of their time drawing. But the children who expected a reward, they only spent Eight percent of their time drawing. The reward had halved their motivation. So what's happening here? Well, researchers differentiate intrinsic and extrinsic motivation. With intrinsic motivation, we do things to earn rewards and achieve external goals. An…

AI assessment note: “game design is not gamification. It isn't simply taking your product and adding”

Q Can I ask, do you think you're transitioning into a wartime CEO? I know that's a really tough question to end on, but I always think back to Ben Horowitz's I think I directionally agree with the piece.

A I don't see myself as the kind of person who acts in the way that the wartime CEO is described in that post, but I definitely perform better in wartime. I definitely perform better when there's a crisis, when we need to rally quickly, when we need to urgently move, and when our existence It's something that we actually have to talk about, and it's something that every single company in the valley right now is talking about. Again, maybe for those who are listening from outside of the valley or they're looking inwards, just in the last week or two, I've seen furloughing, I've seen layoffs, like I mentioned, I've seen term sheets being pulled. Folks on Twitter have been saying that the new three times valuation is the flat round. I don't think it's quite as bad as that, but we're just seeing this dramatic change to how technology feels. In Silicon Valley.

AI assessment note: “I don't see myself as the kind of person who acts in the way”

Q finding that product marketplace. And you've said before on your quest to reverse engineer a process to getting to product market fit. So if we take it from the very top and before we dive into the granular, can you kind of unpack what you said being the first step as anchoring amount around a metric? What did you really mean here? And what was that revealing moment for you?

A Sure. So if you go back to that LinkedIn experience, that was around. The weird initial fundraising ahead of traction, et cetera, that was towards the end of And it was really the start of 20 15 when we began to get that core team together. So in the summer of 2015, we set up our office, and we started to write code. And in the summer of 2016, we were still coding. And in the summer of 2017, team much bigger at this point, we were still coding. And I felt this intense pressure to launch, both from the team and also from within myself. Because after all, Reportive had launched, scaled, and been acquired in less time. Yet here we were, two years in, And we still had not passed go, but I knew as a product founder with some wisdom and some experience that no matter how intense the pressure, a launch would go really badly. I did not believe we had product market fit, but I couldn't just tell the team how I felt. You know, these are super ambitious, hyper-intelligent engineers. They poured their hearts and souls into the product. It's not what they wanted to hear. And so like many founders, I turned to some of the more classical definitions of Product market fits, you know, really anywhere I could look the people that over my career I'd looked up to. So I started with Paul Graham, you know, what would Paul Graham have to say about something like this? He would say, well, you have pro…

AI assessment note: “I did not believe we had product market fit, but I couldn't just tell”

Q Rahul, having been through such a painstaking and long journey with the team itself, what were the biggest takeaways for you? Actually, first question is, where did the very disappointed score end and is at today? That's the first question, but then secondly is, kind of, what are those cool takeaways for you, having been through this painstaking process, that you'd advise founders, maybe, and invest Pondering the same journey.

A My advice to those two different groups would be very different. My suggestion to the investment community, especially the investment community that advises early stage teams, would be to stop pushing for premature growth, especially premature growth at a product market fit. I think as an industry, we all already know that this ends in disaster. You know, I see this with my friends and my peer group, that the pressure for premature growth is still all too common. It is much more Rational in the medium and the longterm, I think, to iterate using a process like the one I've just described to find product market fits and then launch in the right way. And then on the other hand, for founders, I would say once you're in this iterative process, know when to flip the switch. So when you're past the 40% threshold and that number is sustaining, even as you're adding more users, the metric isn't going down. That's when you want to push Pedal to metal. That's when you want to grow as fast as you can. As an entrepreneur who's just passed this threshold myself over the course of the last year, I can say it's not particularly easy, especially if you've spent years in the wilderness, conserving capital, hiring slowly, iterating, constantly optimizing. It is a huge mindset shift to suddenly say, okay, we're now going to deploy all the capital. We're going to raise all the capital. We're going …

AI assessment note: “My advice to those two different groups would be very different.”

Q finding that product marketplace. And you've said before on your quest to reverse engineer a process to getting to product market fit. So if we take it from the very top and before we dive into the granular, can you kind of unpack what you said being the first step as anchoring amount around a metric? What did you really mean here? And what was that revealing moment for you?

A Sure. So if you go back to that LinkedIn experience, that was around. The weird initial fundraising ahead of traction, et cetera, that was towards the end of And it was really the start of 20 15 when we began to get that core team together. So in the summer of 2015, we set up our office, and we started to write code. And in the summer of 2016, we were still coding. And in the summer of 2017, team much bigger at this point, we were still coding. And I felt this intense pressure to launch, both from the team and also from within myself. Because after all, Reportive had launched, scaled, and been acquired in less time. Yet here we were, two years in, And we still had not passed go, but I knew as a product founder with some wisdom and some experience that no matter how intense the pressure, a launch would go really badly. I did not believe we had product market fit, but I couldn't just tell the team how I felt. You know, these are super ambitious, hyper-intelligent engineers. They poured their hearts and souls into the product. It's not what they wanted to hear. And so like many founders, I turned to some of the more classical definitions of Product market fits, you know, really anywhere I could look the people that over my career I'd looked up to. So I started with Paul Graham, you know, what would Paul Graham have to say about something like this? He would say, well, you have pro…

AI assessment note: “I turned to some of the more classical definitions of Product market fits”

Q Listen, anything that relates back to Titanic has a massive thumbs up from me, Rahul, so I absolutely love that in terms of the resonant truth. Tell me, you've been in the Valley now for a number of years, and really at the epicenter, obviously, today was superhuman. What would you most like to change about Silicon Valley today?

A I think a tremendous amount is about to change, and it's not clear how far the ramifications will go. For our listeners, we're recording this at just over a month into shelter in place, and unfortunately, a recession now seems very likely. And just in the technology ecosystem alone, I've seen early stage valuations drop by about 20 to 30%, and I've even seen some term sheets being pulled from deals, behavior that was honestly unthinkable as recently as just a few months ago. And so as we go through this, I think it's really important for us to remember at all times that we are going through it together, and that we should help those in need. So for example, at Superhuman, one of the small things we've been doing is just providing Superhuman for free to those whose jobs have been affected by COVID, or who are helping to fight on the front lines.

AI assessment note: “I think a tremendous amount is about to change”