Chapter 1: What challenges do founders face in convincing different audiences?
Convincing people of things is possibly the hardest thing we have to do as founders, right? And there are so many different audiences. There's investors, there's future co-founders, there's your earliest users, there's the press, there's... the industry you sell to in general. And I think each one is its own fun little puzzle.
The best, most awesome thing you can do is basically have some form of narrative that sounds like, this train is leaving the station, and if you don't join now, I don't know that you will be able to join. The market doesn't care.
Candidates and investors are looking for the storyline of differentiation, sometimes just for differentiation, because they're in the business of finding different things. Remember, you have the right not to serve. They used to have a survey. We'd be like, what mobile phone do you have? They'd say Android. And I said, well, you can't have superhuman. And people would get confused, like, why?
Isn't it my decision whether or not I buy? And I'm like, no, it's my decision whether or not I sell.
Most founders think product market fit is something you feel. Raoul Vora tried to turn it into a system. Before founding Superhuman, Raoul built Reportive, one of the earliest successful Gmail plugins. But with Superhuman, he approached the problem differently.
Instead of chasing growth immediately, he spent years refining the product, onboarding users manually, charging premium pricing from day one, and obsessing over every interaction. The result was not just a productivity app, but a product that developed a kind of cult following inside Silicon Valley.
In this conversation, Raoul breaks down the frameworks behind that process, from game design principles and onboarding psychology to the product market fit engine that helps superhuman grow.
Raul, as I said, is the founder and CEO of Superhuman, but also previously to that, Reportive. He started out with a CS degree at Cambridge. His LinkedIn still says PhD on leave. Still on. I'm not sure if he's ever plans on going back. He started his career as a game designer working on a game called RuneScape, which was an early MMORPG. Any RuneScape fans in the house here?
Whoa, a lot more than I expected. Love that. He then founded a company called Reportive that was acquired by LinkedIn in 2012. And then after that, founded Superhuman in 2014. Curious, how many people here use Superhuman as their primary email client? Me too. It's a lifesaver and very important to my day-to-day life. I can't live without it.
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Chapter 2: How did Rahul Vohra transition from game design to email productivity software?
Their only job to be done is to entertain you. And so it's an entirely different kind of software design than regular software design. When people think about gamification, they're normally doing things like points and leaderboards and trophies and badges and streaks.
And all of these can kind of push behavior in a certain way, but they don't actually make the underlying thing fun or intrinsically rewarding. So a really great example of this, by the way, is a research study that was done in Stanford in the 1970s.
They took kids who were aged about three to four years old, I believe, or maybe a little bit older, four or five, and they divided them into two groups. And one of these groups was told that they were going to get a reward, like a certificate with a gold ribbon. And the other set of these kids were not told about any reward at all. They were then put into a room, one by one, and asked to draw.
And so afterwards, the kids who were promised a reward, they would get their reward, and the kids who didn't know anything about a reward didn't receive anything. They then observed these children over the next few days to see how much of their time they would spend drawing. The kids who didn't get a reward spent 17% of the next few days drawing.
The kids who did get a reward, they spent 8% of their time drawing. In other words, the presence of the extrinsic motivator reduced the intrinsic motivation. And that actually happens with game design and gamification as well.
So one of the reasons, actually the core reason why gamification didn't work is simply giving your users a reward for something can reduce the intrinsic motivation for them to do that thing. And to actually build things that feel like a game, we actually have to go into the theory of game design, like what is a game, what is play, what is fun, and then build your product around that.
And that's something that we did deeply with Superhuman, now Superhuman Male. I'm curious, like, what are some examples of game design thoughts that go into the core loop, let's call it, of email, which is like the most unfun thing ever? Totally. I was like, how do I make the... And I didn't answer your previous question about why productivity, because it was the least fun thing in my life.
And I was like, how can I make this the most fun thing? Over the years, I came up with multiple principles of game design around... 15 to 20, depending on the day. But they draw upon different areas like psychology and mathematics and storytelling and interaction design and so on. The principles cover areas like goals, emotions, toys, controls, and flow.
Those are like the top five areas I often think about when it comes to how do we make something feel like a game? And I'll give you a specific example, perhaps in the context of toys. So what is a toy and how is it different to a game? The way I would summarize it is actually linguistically. You play with a toy, but you play the game, right? A ball is a toy, but football is a game.
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Chapter 3: What unique strategies did Superhuman implement for onboarding users?
And back then, those onboardings were long. Ours was probably half an hour, but the first ones, they were like two hours each. And I would go to the office. I'd research people ahead of time. Actually, you came to the office. I forgot that. It wasn't a Zoom call. That's right. I remember going to Slack. And we'd probably stopped doing gifting at this point.
But in the early days, it was like, okay, is this guy a whiskey person or a wine person? Or maybe they don't drink. I'm going to bring some tea or something like that. We'd research them. We'd figure out... what they like, bring them a gift for a reason I shall explain shortly, sit down and I would say, okay, show me how you use Gmail or show me how you use, actually back then it was all Gmail.
And I would take notes and then I'd say, okay, this is superhuman. I do a quick demo, get them excited. And then I'd drop the bomb because they weren't expecting this. Okay, now you're going to pay for it. So pull out your credit card. It's $30 a month. By the way, here's a bottle of whiskey. Make it feel a little bit less awkward. Slash deliberately invoking the reciprocity principle.
And so they would, I think only one person ever was like, really? Everyone else was like happily paying for it. They're so invested by this point. And then I would watch them use the product for an hour or two. how much time that would give me. And if you haven't done this, please do this.
And please never stop doing it because even with a mature product, it is incredible how much you will see that maybe even your product engineers or your PMs won't see or your designers. Like you as the founder or you as the CEO are going to see everything. You'll just see every single problem and write them all down bring them back to the team.
And what I did is I said to the team, because they were pushing me to grow faster, right? The team wants to grow as fast as possible. I was always the go slow guy. And I said, no, we're not going to onboard anyone else until we fix these issues. And they say, why? And I said, well, every user has bug fatigue in the sense that they might tell you one bug, they might tell you two or three.
You think they're going to tell you 10 or 20 or 30? Hell no. You think we have less bugs than that? Hell no, we do. So the only way we'll find out about them is if we do the grind and we turn the spigot on very slowly to polish this thing. Like, we just have to keep on doing this polish. So those were the initial motivations. It was...
control the blast radius, make sure every single person became a net promoter, and also use it as a way to build the best possible product, to truly understand what people wanted, to understand about email workflows we didn't understand, of which there are plenty. We built for us, as soon as we hit the market, we started encountering other email workflows. That's fine, that's normal.
We just have to start catering for those workflows and also find all the bugs and fix all the bugs. Then we noticed something really, really weird. which is the metrics for these users were off the charts. Like, the activation was crazy. The retention was crazy. The virality was crazy. The net promoter score was crazy.
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Chapter 4: Why did Superhuman choose a premium pricing model?
So that was the goal. And I was like, okay, how do we do this? So I researched everything that I could possibly find on products market fit. And I don't want to take credit for the question because it's not my question. It's actually Sean Ellis's question. And Sean Ellis was one of the first growth hackers ever. He coined the phrase growth hacking.
He was the first growth marketer at LogMeIn, Eventbrite, Dropbox. And he was the one who came up with the question, how would you feel if you could no longer use the product?
You answer on one of three dimensions, not disappointed, meaning you don't really care, somewhat disappointed, you're like, eh, or very disappointed, meaning you would, you love the product and be very sad if it were to go away.
And so way back in the day, he'd benchmarked this on hundreds of venture-backed startups and found that the companies that grew to product-market fit almost always had more than 40% very disappointed, and the companies that didn't grow to product-market fit almost always had less than 40% very disappointed.
And I thought, aha, well, this is the only research that has ever been done, like ever, on this topic. But it's enough. It's enough to build a process and an algorithm around. So the innovation that we came up with was, How do you turn that into an engine? How do you turn that into a repeatable process that any team, any company can run?
And if you read this, again, it's very hard to poke holes in it. It will reliably make that number go up always. What we did is we added three more questions onto it. So number one is, how would you feel if you could no longer use the product? Number two is, who do you think the product is best for? Number three is, what is the main benefit you get from using the product?
And number four is, how can we improve this product for you? Now, here's why those questions are so important and so powerful. So the second one, who do you think this product is best for? It gets to what founders most forget about products market fit. which is you're allowed to change the market as well as the product.
And it's actually way easier, it turns out, to change the market than the product, because you can just decide, we're changing the market today, guys, product's the same. Okay, let's figure that out. Maybe change your packaging. Oh, by the way, before we ran this analysis, I ran the first question and we had 22% very disappointed. 22, way less than 40.
And you might think, oh, you must have been really bummed out about that. Actually, no, I was excited. I was like, finally, I can explain what I'm feeling to the team in a way that is irreproachable. You can't argue with these metrics. This is what the standard of success says, and we're hard failing. So how do we fix that?
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Chapter 5: What is the significance of product-market fit in Superhuman's growth?
And it won't hover at 58% forever, like Andrew talks about the law of shitty metrics. This will come down for good reason, because hopefully you're expanding industry, you're going to adjacent personas. Those salespeople that we ignored before, we now have to figure out how to build a product that's good for them as well, and so on and so on.
So the number will come down, but that's the art of building great products is you'll keep pushing it back up again. I know that was a lot, and I know it was very long, but I have written this up at length online. So if you Google the superhuman product market fit engine, you can find it. What advice would now Rahul give first-time founder Rahul starting Reportive back in the day?
Oh boy, so much. Let's see if I can do this quick. Know what your strategy is and stick to it. For Reportive, I equivated on strategy constantly, and we were lucky to have a good outcome. but I didn't really know what I was building and who it was for and what the company level thesis was. So have that.
Number two, have as many things as make sense be different and first principled about your company. I think we're living in a golden age where it's now even more possible to do those things than when I was building Superhuman, because you can basically build and do whatever you want. You can decide not to hire for a very, very long time.
So you get to do the blueprints for your company from first principles. That is way more powerful than people realize, and I think a lot of folks take it for granted. I can put it another way, and hopefully your boards will tell you this. Don't just hire a bunch of VPs and do what they say.
Like, literally have your own opinions on everything, because they're probably better than you might think if you have imposter syndrome. And the third really tactical thing is keep increasing prices every year. Stay ahead of the inflation. All right, thanks to Raoul. Thanks so much. It was great.
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