Pod Insights The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch 20VC: Superhuman’s Rahul Vohra on How 1-1 Customer Onboarding Can Scale Efficiently to $100M ARR, Why Gamification Does Not Work But Game Design Does & What Game Design Means For The Next Generation Of Product Managers About this episode Rahul Vohra is the Founder & CEO @ Superhuman, the startup that has rebuilt the inbox from the ground up creating the fastest email experience ever made. To date, Rahul has raised over $56m with Superhuman from some of the best in the business including a16z, First Round, Box Group and then 2 of my favourites in Jeff Morris Jr @ Chapter One and Ed and Elliot @ Boldstart. Prior to founding Superhuman, Rahul was the Founder @ Rapportive, a company later acquired by LinkedIn in 2014. If that was not enough, Rahul is also an investor having co-founded a new firm with Todd Goldberg just last year. In Today’s Episode You Will Learn: 1.) How Rahul made his way from making the first plugin for Gmail with Rapportive to changing how we think about email today with Superhuman? 2.) Why does Rahul believe game design is worth doing? What is the difference between game design and gamification? What does it take to create a game? What is the truth on game design? 3.) What are the core 5 factors that make up effective game design? How can products incorporate goals to make the user feel emotion when engaging? What emotions does one want the user to feel? How can they be tested? What controls should be placed around the UX? Why are controls so fundamental? 4.) What is the difference between a toy and a game? How can one effectively incorporate toys into their product? How has Superhuman done this effectively to date? Hw can designers create a system of flow in the user experience? What works? What does not work? 5.) Did Rahul intentionally create an entirely new category when it comes to onboarding? Why does Rahul pushback on people that suggest 1-1 onboarding is not scalable? What does the unit economics look like? How does this scale to $100M ARR? Items Mentioned In Today’s Show: Rahul’s Fave Book: The Art of Game Design: A book of lenses As always you can follow Harry and The Twenty Minute VC on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC. Carta simplifies how startups and investors manage equity, track cap tables, and get valuations. Go to carta.com/20vc to get 10% off. More than 800,000 employees and shareholders use Carta to manage hundreds of billions of dollars in equity and Carta now offers Fund Administration so you can see real-time data in the Carta platform and work with Carta’s team of experienced fund accountants. Go to carta.com/20vc to get 10% off.
Transcript Speaker names marked ? are inferred from speaking time and the show’s known hosts — they are not voice-verified.
0:00 Harry Stebbings? Welcome back to the 20 minute VC and founders Friday with me Harry Stebbings and I always love to hear your thoughts and feedback on the show and you can do that on Instagram at H Stebbings 1996 with two Bs. But to our episode today and his episode last year was the most downloaded of the year by far. He's created a product that's changed much of how we work today. And so with that, I'm thrilled to welcome back a friend and phenomenal founder in the form of Rahul Vohra, founder and CEO at Superhuman. The startup that has rebuilt the inbox from the ground up, creating the fastest email experience ever made. Today, Rahul has raised over $54 million with Superhuman from some of the best in the business, including Andreessen Horace, First Round, Box Group, and then two of my favorites in Jeff Morris Jr. At Chapter One and Ed and Elliot at Bold Start.
0:42 Harry Stebbings? And prior to founding Superhuman, Rahul was the founder of Reportive, a company later acquired by LinkedIn in 2014. And if that was not enough, Rahul's also an investor, having co-founded a new firm with Todd Goldberg just last year. But before we move into the show today, I'm sure you've heard about it, but my word, this is a product I love. Carter. Carter simplifies how startups and investors manage equity, track cap tables and get valuations. Go to carta.com/20vc to get 10% off. More than 800,000 employees and shareholders use Carter to manage hundreds of billions of dollars in equity. And Carter now offers fund administration, so you can see real time data in the Carter platform and work with Carter's team of experienced fund accountants. Simply go to carta.com/20vc to get 10% off.
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2:10 Harry Stebbings? They have to be properly equipped and that's where Brex come in. Brex is the company which built a corporate card for startups and who's the fastest company to reach unicorn status in history. Brex founders Henrique and Pedro built a payments business in Brazil, but kept getting rejected for a corporate card in the States. So they built Brex with no personal liability, up to 20 times higher card limits, and huge rewards like 7X points on Uber and Lyft, 4X on Brex Travel and 2X on SaaS software. If you're a VC-backed startup based in the US, see if you qualify for a Brex card today at brex.com and get card fees waived for life by entering the code HARRY during signup. But I'm now very excited to hand over to Rahul Voh, founder and CEO at Superhuman.
2:57 Speaker 01 You have now arrived at your destination.
3:00 Harry Stebbings? Rahul, I'm so excited for this. As we said before, your episode is the most downloaded founder episode ever with 1.2 million downloads. So huge thank you to that because I'm sure it paid for a lot of my rent and advertising. But thank you so much for joining me today, Rahul.
3:13 Speaker 02 Well, thank you for having me back on the show.
3:14 Harry Stebbings? 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?
3:26 Speaker 02 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.
4:09 Speaker 02 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 worked offline, so you could be productive anywhere, and an email experience that had the best Gmail plugins built in natively
4:51 Speaker 02 and yet somehow was subtle, minimal and visually gorgeous. And so with that, we built Superhuman.
4:57 Harry Stebbings? And I mean, what an incredible journey it's been over the last years to see. In terms of kind of that user experience, I do want to start on really the product mindset that you employ at Superhuman. When we spoke before, you said, "Most companies obsess over what customers want and need. We don't. We obsess over how they feel." So I guess bluntly, Rahul, and before we dive into the granular tactics, why is game design worth doing?
5:18 Speaker 02 Well, today, the vast majority of how a business software feels like work. We have to check our email, we have to submit expense reports, we have to enter data into our CRM. But what I'm asking is, what if we could make software feel less like work and more like play? With game design, we can. Most software companies worry about what users want or what users need, but nobody needs a game to exist. There are no requirements. Because when you make a game, you don't worry about what users want or need, you obsess over how they feel. When your product is a game, people don't just use it, they play it. They'll find it fun, they'll tell their friends, they'll fall in love with it.
5:58 Harry Stebbings? Can I ask, you know, when we think about that and we think about integrating 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?
6:09 Speaker 02 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 nineteen seventies, these 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.
6:52 Speaker 02 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 seventeen percent 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. And that's the problem with rewards. They massively undermine intrinsic motivation. And that is why gamification does not work.
7:37 Speaker 02 When gamification does work, it is because the underlying experience was already a game. And so the real question becomes, how do we design a game?
7:47 Harry Stebbings? In terms of kind of designing the game, then, if we take that as the exact kind of jumping off point. I know it's something that you've been obsessed with for a long, long time. You said yourself, all my life I've obsessed over the question of how do you design a game? So given the many years that you've had to ponder on it, Rahul, where have you landed? And what does it take to create a game within a product today? And what's the truth on game design? Incredibly tough question, I'm sorry for that one.
8:09 Speaker 02 Well, you're absolutely right. I have been obsessed with this question my entire life. As a kid, I learned how to code just so I could make games. And before I was a founder, I worked as a game designer. And as a founder, I've gone deep into the principles of game design. And as it turns out, there is no unifying theory. To create games, we need to draw upon the art and science of psychology, mathematics, storytelling and interaction design. And in doing so, I've found five critical factors, and they are goals, emotion. Controls, toys and this curious thing that we call flow.
8:44 Harry Stebbings? So I do want to unpack those five one by one. And so if we take them in turn, you mentioned goals there. What are the core principles of adding goals to a product? And I guess what makes a good goal?
8:54 Speaker 02 Well, games need goals and as it turns out, goals are a defining feature of games. But we can't just have any goals. We need good goals. And for a game, good goals are concrete, achievable and rewarding.
9:08 Harry Stebbings? 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, integration to the product that people use on a daily basis?
9:19 Speaker 02 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 30 minute 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.
10:00 Speaker 02 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.
10:23 Harry Stebbings? Can I ask Rahul, and this is off schedule, but you know, the onboarding process is so 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?
10:45 Speaker 02 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 on-boardings 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 twenty, thirty minutes. And inevitably, in each case, I would record five to ten bugs that I would insist that we fix before next week.
11:30 Speaker 02 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 on-boardings. And it was exactly the same, and he had also managed to shrink it from a fairly lengthy one- or two-hour affair down to forty-five minutes.
12:11 Speaker 02 And so then he and I asked ourselves, well, maybe this could be a thing that actually works. At what point does it start to make units economic sense? Can we actually scale this as a go-to-market strategy? And so we hired our first few onboarding specialists, this was phase three of the plan, and they managed to shrink it down from about forty-five minutes to half an hour, without really any sacrifice to the quality of the on-boardings or how well those users did afterwards. And that's how this go-to-market strategy came about.
12:41 Harry Stebbings? Can I ask you a tough one, and we are going back into the five factors there. 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?
12:51 Speaker 02 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 $100 million 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.
13:32 Speaker 02 And because of how efficient the onboarding process is, it turns out you don't need that many onboarding specialists to get to $100 million 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 $50 million 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 turns out to be an incredibly efficient
14:13 Speaker 02 business, not only a way to create delighted customers.
14:18 Harry Stebbings? I'm so glad I asked that question, because then I also think on the backend, obviously it ensures way higher retention and it reduces future customer acquisition, 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 there. And the second that you mentioned was emotion. 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?
14:40 Speaker 02 Well, the best games create strong emotions, because strong emotions are the foundation of our memory. And we must therefore be able to analyse emotion. And to do that, we need vocabulary. Now, there are many models of human emotion, and the most famous is Plotchek'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.
15:22 Speaker 02 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 HUNTO 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 subfacets. 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.
16:05 Speaker 02 You rightly feel like you accomplished something special. And when you do hit inbox zero, we show you stunning and gorgeous imagery. We do this to widen the emotional repertoire beyond joy into love and surprise. We pick images that are peaceful and tranquil, that create a sense of longing and sentimentality, that even amaze and inspire a sense of awe.
16:28 Harry Stebbings? In terms of kind of the incredible emotions that you elicit, I'm sure you've seen a great variety. I guess my question too is, what have been the biggest surprises to you in the emotions that users elicit when engaging with Superhuman today as a product?
16:40 Speaker 02 I think that the most surprising thing has been the breadth and variety of the emotions that we've come across. For example, in these COVID shelter-at-home days, we've been changing the nature of our inbox zero images. And we've added some images that are cozy, stay-at-home images, displaying beautiful homes, the kind of homes that maybe we wish we could be in if we had the opportunity to do so. And it turns out that there is a Danish word that describes that emotion, higger. And it means something like cozy. And secure. And this is an emotion that over the last few weeks, folks have been telling me that they experience through our inbox zero pictures. And it's such a specific emotion,
17:25 Speaker 02 so specific that it's even specific to a particular nation. I never would have thought that Superhuman could evoke the emotion of Higa.
17:33 Harry Stebbings? I love that in terms of the Higa. And I don't know if you know this, but I'm actually half Norwegian, half Danish. So that's fantastic to hear.
17:40 Speaker 02 I did not know that.
17:41 Harry Stebbings? And there we go. Fun fact, the Bosch accent does belie some international variation. But I do want to touch on the third element. And you said controls. Why are controls so crucial in game design? And again, how have you implemented them in a positive way in terms of the user experience with the Superhuman product?
17:58 Speaker 02 Controls can be the main reason why a game succeeds. Let's consider the Wii mote. The Wii sold more than 100 million units, and every single controller since has incorporated motion. But games require much more robust controls than we typically make for business software. Imagine you're playing a game like Street Fighter, let's say. It would be incredibly frustrating if some inputs were dropped, and then your character flopped around and then died. And yet, that is how business software works today.
18:29 Harry Stebbings? Totally agree with you. I guess my question to you is, can you ever have too much control in a product?
18:34 Speaker 02 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 Conrad. 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 one Gmail, this kind of error is status quo for business
19:14 Speaker 02 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, You want to build software like it's a game, then you need to create rapid and robust controls.
19:30 Harry Stebbings? There was one that you said in terms of the factors that did actually surprise me, and it was toys. And so help me out here, Rahul. How do toys differ from games? And how do you think about building toys into a product?
19:41 Speaker 02 This difference turns out to be fascinating because we play with toys, but we play games. A ball is a toy, but football is a game. And as it turns out, the best games are built with toys. Why? Because then they are fun on multiple levels, the level of the toy and of the game itself.
20:02 Harry Stebbings? 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?
20:14 Speaker 02 Well, this is best understood by examples. 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 autocompleteer, 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, 2D becomes two days, 3H becomes three hours, 1MO becomes one month. Now, the time autocompleteer 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 onboarding before people start to explore these boundaries.
20:59 Speaker 02 For example, I wonder what happens if I keep on typing 10. Well, it turns out that that's October the 10th at 10:10pm. Or how about a sequence of twos? That's February the 2nd, 2022 at 2pm. 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 8am in Tokyo and they realise 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?
21:42 Speaker 02 And do they create moments of pleasant surprise? If so, congratulations, for you have a toy and you're on the way to building a great game.
21:51 Harry Stebbings? Can I ask, Rahul, when you talk about this, I do think to Siri, actually. How would you analyse Siri in terms of that playful exploration? In terms of getting the user to test without objective?
22:01 Speaker 02 I think Siri does a remarkably good job for what I understand the state of that part of AI and machine learning to be. When it does understand you, the responses that Siri gives you are more often than not delightful, playful, perhaps even joyful. I think the challenge, though, that we have when we're designing toys is for it not to be a frustrating experience. Because nothing takes you out of the state of mind that a toy can get you to more than frustration. And perhaps it's our British accents, Harry, but at least for me, Siri doesn't understand me anywhere near as much as some of its competitors.
22:40 Harry Stebbings? Oh, it never understands me. I think it's totally the British accents, but I think that's also the audience that struggle with those two. I even get compared to Harry Potter or Benedict Evans, so 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?
23:03 Speaker 02 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.
23:47 Speaker 02 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.
24:28 Speaker 02 And number five, and this is the hardest of all, we must feel a balance between challenge and skill. If the activity feels too hard, we will end up feeling anxious. And if the activity feels too easy, we will end up feeling relaxed, or in the worst case, bored.
24:45 Harry Stebbings? 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.
24:54 Speaker 02 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 of 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.
25:34 Speaker 02 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.
26:12 Speaker 02 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 companies like Linear that have just recently raised from Sequoia that have done the same. And I think it's going to be a sea change. We're going to have this whole generation of products that hyper-invests in not only teaching users what to do next, but also how to do it. And number three, I mentioned freedom from distractions. In Superhuman, you can't see the inbox at the same time as a conversation. And that is a very deliberate decision. It's very contrary to Gmail, whereby default you're multitasking. In Superhuman, you very deliberately can't see what is next or any new email.
26:54 Speaker 02 And anyone can design their interface like this to reduce distraction and to create flow. The fourth condition is clear and immediate feedback. And when you archive a conversation, like I said, we immediately show you the next one. And we have invested hugely in doing this as immediately as possible. Initially, we set out to show the next conversation in 100 milliseconds or less, because that's roughly the threshold at which point user interfaces feel instant. Well, we now have a new renderer that is three times as fast and can do this in 32 milliseconds or less. And the last one, and this is the one that I said was hardest, is matching high-perceived challenge with high-perceived skill.
27:37 Speaker 02 As I said, if the challenge is too easy, your users will be bored. And if the challenge is too hard, your users will be anxious.
27:45 Harry Stebbings? 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?
28:00 Speaker 02 Well, Superhuman massively increases the skill level for almost.
28:05 Speaker 02 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
28:50 Speaker 02 mass. This then rebalances challenge with skill and across our entire user base results in flow.
28:58 Harry Stebbings? I absolutely love that in terms of the ultimate challenge. That's great. I do want to bring them all together though, Rahul, because if we think about the five factors there, you've then said to me before that subsequently, there's kind of seven principles of game design, and this is incredibly hard on me to ask it. It reminds me of almost school tests. But before the quick fire, what are the seven principles of game design?
29:16 Speaker 02 Number one, create concrete, achievable and rewarding goals. Number two, design for nuanced emotion. Number three, create rapid and robust controls. Number four, make fun toys and combine them into games. Number five, make the next action obvious. Number six, give clear and immediate feedback with no distraction. And number seven, and this is the hardest one of them all, balance high-perceived skill with high-perceived challenge. And this may counter intuitively mean making your product harder to use.
29:47 Harry Stebbings? Of those seven, which do you think that most people misunderstand the most?
29:50 Speaker 02 Oh, it's absolutely the last one. You see, we have a whole generation of product managers and product designers who were 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 may 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.
30:30 Harry Stebbings? Yeah, that is, I couldn't agree with you more in terms of that generation of product managers. It's focused minutely on reducing clicks to the most minimum that can be possible. So totally aligned there. I do want to move into my favourite element though, which is the quickfire round, as you know. So I say a short statement, Rahul, and then you give me your immediate thoughts. Are you ready to dive in?
30:47 Speaker 02 Let's do it.
30:47 Harry Stebbings? Okay, so I promised I would read more this year. Even in quarantine, I'm not stopping reading more. Tell me, what's your favourite book and why?
30:54 Speaker 02 Well, of course, it would be remiss if I did not mention The Art of Game Design by Jesse Shell. Of all of the books ever written on game design, I think if you were to read only one, this would be the one. And it covers much of what we've talked about here, as well as a whole lot more. So for any of our listeners, founders, product managers, designers, people who want to make business software that feels and plays like a game, I'd wholeheartedly recommend The Art of Game Design.
31:20 Harry Stebbings? Can I ask, you also invest now as an angel, and this is just to entreat. You invest as an angel obviously with Todd. Do you dig deep on how founders think about game design today when meeting them and assessing their companies?
31:31 Speaker 02 I actually don't ask specific questions oriented around game design, or at least it's not obvious that I'm doing so. What Todd and I are looking for is, actually, as you know, quite a number of things. One of those things is, is there someone on the team, ideally the CEO, who is an incredible product designer? And for me, the definition of incredible product designer in its wraps up a lot of the perhaps counterintuitive things that we've discussed. They'll have an intuitive understanding of how to create flow. They'll have a gut sense feel for what emotions their product creates. They'll enjoy the craftsmanship of sort of intensely
32:15 Speaker 02 lasering over the little details of the application or the experience that they're making. They may not necessarily know that they're doing game design, but they'll be doing the action. That contribute towards making a well-designed game. I just so happen to know that what we're actually practicing here is game design. And it's a very neat way to package that up and to share this with other people. So much so, in fact, that when new folks join Superhuman, I actually buy them a copy of The Art of Game Design. And then we go through this presentation, we go through all of the things that I've learned over the years on how to make business software that feels like a game.
32:53 Harry Stebbings? I love that in terms of the onboarding and I didn't actually know that. In terms of kind of those little intricacies there, what do you know now, Rahul, that you wish you'd known at the beginning of your founding of Superhuman?
33:02 Speaker 02 Before products market fit, the CEO's job is to find product market fit. And we talked a tremendous amount about that in our last episode. After product market fit, the CEO's job changes. It becomes to continually put themselves out of their job by hiring the best people in the world for every part of the company.
33:21 Harry Stebbings? Yeah, absolutely it is. It's also a very hard thing and a realisation come to as a CEO. I do want to ask, my favourite 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?
33:34 Speaker 02 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.
34:19 Speaker 02 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 is 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.
35:03 Speaker 02 And so our next attempt was something like this, I deserve to succeed. It has some of the right vibes, like striving for success, but some of the wrong ones, like success should come to us all. I don't think any of us deeply believe that. And so maybe it's about deserving the chance to be successful. And then we stumbled upon this, if I work hard enough, I can achieve anything. And there we have it. This would never come out in a user study. But it is a powerful truth that all of our users deeply believe. It's the kind of statement that in the right conditions can send a chill down your spine. And if you're looking to create a piece of art, whether it's a game or a movie
35:43 Speaker 02 or anything else that truly moves people, the advice is to find your resonant truth.
35:49 Harry Stebbings? 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 with Superhuman. What would you most like to change about Silicon Valley today?
36:02 Speaker 02 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.
36:45 Speaker 02 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.
36:53 Harry Stebbings? Yeah, no, I couldn't agree more. And absolutely, for those referencing the date, it is April the 10th. So there we go. Tell me, investor value add is something that is commonly discussed on Let Me Know How I Can Be Helpful on Twitter. What is the most valuable thing an investor can do for you, Rahul, other than the capital providing?
37:09 Speaker 02 I think it's a twofer, a combination of two things. Number one, being highly available for those, hopefully, rare moments when you just need a quick piece of advice or a second opinion on something. And then number two, having that advice be highly nuanced and well backed by experience. And in particular, the outcome that I'm always looking for is to see around corners and help prevent mistakes before they happen. Another thing about products market fit is once you've hit it, you want to avoid as many first time mistakes as possible because you're now in a race, you're now in a race to hold that tiger by the tail as it's shooting off.
37:51 Speaker 02 And one of the best ways to do that is to avoid as many mistakes as possible.
37:55 Harry Stebbings? I would obviously never single out any single one of your investors, but Ed Sim is my absolute favourite. So I totally agree with you in terms of him having all those qualities. So that's great to hear. Tell me, Rahul, next five years for you and for Superhuman, paint that vision for just how big this can be.
38:09 Speaker 02 In five years' time, we'll be a billion dollar company and I think we'll have multiple product lines. My challenge is to become the kind of CEO who can scale to lead an organisation through the many transformations that occur on that kind of journey. And I think the next major challenge for me, as it will be for many CEOs, will unfortunately be an upcoming recession. It now seems inevitable. We are headed into a recession. I think this is going to require a different kind of company building to before.
38:40 Harry Stebbings? 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 Horace's peacetime wartime. And obviously with Andreessen behind you, how do you think about that peacetime versus wartime?
38:51 Speaker 02 I think I directionally agree with the piece. 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 is 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.
39:37 Speaker 02 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.
39:44 Harry Stebbings? No, absolutely, we are. And Rahul, as always, I just love having you on the show. I always so enjoy our discussions. So thank you so much for joining me today and I can't wait to see the next five years ahead for Superhuman.
39:53 Speaker 02 Well, thank you for having me back.
39:57 Harry Stebbings? He really is just such a special founder and thinker. And if you'd like to see more from Rahul, you can find him on Twitter at Rahul Vohra. Likewise, it'd be great to welcome you behind the scenes here. You can do so on Instagram at H Stebbings 1996 with two Bs. I'd love to see you there. But before we leave you today, I'm sure you've heard about it, but my word, this is a product I love, Carter. Carter simplifies how startups and investors manage equity, track cap tables and get valuations. Go to carta.com forward slash two zero VC to get 10% off. More than 800,000 employees and shareholders use Carter to manage hundreds of billions of dollars in equity. And Carter now offers fund administration, so you can see real time data in the Carter platform and work with Carter's team of experienced fund accountants.
40:39 Harry Stebbings? Simply go to carta.com forward slash two zero VC to get 10% off. And speaking of equity for amazing team members, you have to check out Switch, a great startup initiative to send laid off talent amid the coronavirus crisis directly to vetted top startups still hungry to hire. Switch is free for all parties. It's just here to help. It's a free platform by the team behind Wanted. The big idea was to create a shortcut between companies firing and the startups that are still really hungry. to hire, so companies can upload their laid off list for other startups to hire them on the spot. And VCs play a crucial role by letting their portfolio companies know of Switch. Hence, we're featuring them on the podcast. Switch has now over 10,000 talent. It's supported by over 100 VCs and 300 startups. You really must check it out. That is switch dot help.
41:23 Harry Stebbings? And once you get that incredible talent through Wanted, they have to be properly equipped. And that's where Brex come in. Brex is the company which built the corporate card for startups and who's the fastest company to reach unicorn status in history. Brex founders Henrique and Pedro built a payments business in Brazil, but kept getting rejected for a corporate card in the States. So they built Brex with no personal liability, up to 20 times higher card limits, and huge rewards like 7X points on Uber and Lyft, 4X on Brex Travel, and 2X on SaaS software. If you're a VC backed startup based in the US, see if you qualify for a Brex card today at brex.com and get card fees waived for life by entering the code HARRY during signup. As always, I so appreciate all your support and I can't wait to bring you another fantastic set of episodes next week.
Previous 20VC: Upfront’s Mark Suster on COVID Redefining What A Great Company Looks Like and What Valuations Look Like, Why Pay-To-Play Is Back On The Table & Why We Will See The Death of Party Rounds Next 20VC: Airtable's Howie Liu on Potential Consolidation In The Collaboration Tools Market, The Transition From Peacetime To Wartime CEO & How To Make The Move To Remote Work Successful; The Process Beyond The Tools Page updated October 26, 2026 · transcript and summary are machine-generated
