Superhuman's secret to success: Ignoring most customer feedback, manually onboarding every new user, obsessing over every detail, and positioning around a single attribute: speed | Rahul Vohra (CEO)

25:49But over time, I found that my ability to focus was increasing. I could hold attention on something for much longer. But I also was able to become much more creative and much more expressive. These are well -known side effects, as it were, or intended effects for some people of TM. And interestingly about TM, if you compare it to other forms of meditation, they don't have quite the same impact across quite as many executive functions. So there's something particularly interesting that's going on with transcendental meditation as opposed to other forms that folks are still trying to unravel and figure out.

26:25Folks want a third inspired. And they want to check out this form of meditation and advice on where they could go learn. Absolutely, a lot. But in summary, have a coach teach you. I had many false starts myself with meditation, trying the various apps, learning from books. None of it really worked for me. What worked was having one on one teaching from someone themselves who had been taught one on one, the yogic or the Raj tradition of teaching. And this person in particular, had also been a venture -backed founder multiple times over. And so they're very well aware of the kinds of stresses that I tend to be under and all of his clients are mostly in technology as well.

27:10If you're in the Bay Area, this person's name is Laurent Valisek and they run an institution called the Peak Leadership Institute. And this is all about how we can live a more integrated and whole life -integrating wellness practices like meditation, but for the purpose of unlocking peak performance in life and in business. Thank you for sharing that. That is very actionable. We're gonna link to that in the show notes. Okay, and we're gonna try to bring us back on course. The other thing you mentioned that I think is really interesting is hiring a president. A lot of founders and leaders might be hearing this and be like, going from eight reports and doing all these things they don't want to spend most of my time on the product and design and marketing amazing.

27:51What did this president take off your plate and what is their responsibility and that allowed you to do the stuff you wanted to do? The biggest thing was taking off the operations and the management of the executive team and the rest of the company. So think of the president role in superhuman as an operationally, extremely challenging and a very growthful role. Like it is perfect for someone who wants to go on to be a CEO in their next role. And instead of hiring and firing that team, instead of managing and setting their goals, instead of the accountability, conversations, someone else is now doing that.

28:35In addition, because that's not the only job, in addition, there also a very strong thought partner when it comes to corporate strategy, when it comes to where do we take Act One? Our email product. How far do we go down the multiplayer path? How aggressively should we lean into AI? What's a reasonable gross margin in a world with AI? Are we from a financial perspective okay, dipping now and then coming back later? When should we start building our second product? How do we think about our R &D strategy? Should we keep on hiring in the Bay Area or as we've done for many of our recent hires, should we continue hiring in Latin America?

29:17Should we consider other time zones as well? And so on and so on and so on. I mean, I'm just randomly coming up with questions, but the list is truly endless. It is another way to think about it is, it's like a, it's almost like a grown up co -founder. The two people I co -founded the company with Conrad and Vivek, they've long since gone from superhuman, we're now a 10 year old organization and I'm one of those rare founders that is persisting and thriving actually 10 years in. That said, the journey never gets easier, it gets different and you still need that co -founding energy around you. And I have a handful of people in the organization who are in their roles, providing that kind of energy, that kind of inputs and who thrive off doing so and then the president role is definitely one of them.

30:07Incredibly interesting. There was so much there. One, just a couple of things I'll share and then I want to move on to a different topic. One is just, it's cool this solution to help you move faster and do the work you want to do is org design. That feels like a really doable thing. If you're finding you're not spending time and things you want to spend on time on and things aren't moving as fast as you want, it's essentially, you can find people to take on things that you don't want and shift the way that the org is structured and that could solve a lot of problems that's what it did for you.

30:39And then I think it's also really interesting. There's this lesson here as a founder if you're just feeling like, I don't know, depleted or just like not, don't have the partner you want. You could bring someone on. That could be that person. Absolutely. Okay, there's so much there. That was much more of a rich area than I even expected. I want to zoom out a little bit and there's a couple of themes that came up again and again when I talk to folks that you've worked with, investors and superhuman and the two themes are contrarian thinking in terms of building the company and strong attention to detail.

31:13Let's spend a little time on attention to detail. And like I said, this is one of the things that came up again and again when I was asking people about you. So I have this quote from Ed Sins. Maybe your first investor, were they your first investor? Yeah, there's a bunch of people on Twitter who are going to fight for that but to record straight, Ed Sins did actually write the first three checks into superhuman. First three checks, I like subsequent rounds. Well, yeah, I mean quick sidebar on that. He runs both start benches alongside his partner, Elliott Durban. And they have a particular interest in backing second time founders but they'll also back first time founders and they love application and infrastructure areas like superhuman.

31:58So we were like the perfect investment. He also wrote a check from his previous fund into a reportive and I think I'd made him like 5X that money. Nothing to write home about but definitely, I'm going to back this guy again, right? And so I went to him and I said, hey listen, I think this is going to sound crazy. I want to take on Gmail. He said, do you have a deck? I was like, yeah, here it is. One slide, here it is. And it was a screenshot of Gmail with most of it scribbled out. I want to build that. And it was going to be amazing. So he said, cool, we're in, kind of why are you the money? And I said, no, I don't even have a bank account yet.

32:31I come back two days later with a bank account. And he's like, cool, I want to wire you 750K. And I said, I don't even know what I'm going to do with that money. I'm not paying myself. I won't for a while. We don't have any employees. I can't think of anything I want to spend it on. Tell you what, I'll just take 250K. It's like, cool, what? No, yeah, I'll just take 250K. We start having the conversation around venture economics. I'm like, yeah, you know, it's fine. We'll figure it out. And then a few months back, I took another 250K. And a few months back, I took another 250K. As I began inventing ways and finding channels to deploy capital properly.

33:11I love the story. I love all the stories you're sharing. I've never heard before. And by the way, it is awesome. We're talking about him coming on the podcast, maybe breaking our VC rule. So specifically the story he shared with me that is maybe an example of you in your tension in the detail is he said that you created your own font because existing fonts weren't good enough. Is that true? Kind of. OK. The font that we used today is a modified version of Adele Sans. And the story there is I looked at all of the major font families. And honestly, none of them was what I would call truly excellent.

33:48And that may sound like an odd thing to say. So let's, if you will, pin that me to talk about typography and email from. So the first thing we did was we took our UI and we laid it out in about 15 different styles using examples of the major font families. We actually printed these out and we left them on a desk in the middle of our office. Sometimes with design, you want to tune in to your immediate most visceral response. But sometimes you want to truly let a design marinate. And this was the latter. So we let these designs marinate. We let these font choices percolate. And like I said, none of them was truly excellent.

34:31Number one, I was looking for a font that was in and of itself gorgeous. Number two, I was looking for a font that could also convey a message of any kind without overpowering the sentiment of that message. For example, does the font work when this is inviting you to a party? Many fonts, including almost all serif fonts, are actually too somber or too sober for that. Or to pick another extreme, does the font work if it is informing you of somebody's passing? Many fonts are just too jointy for that. You wouldn't want that kind of message in comic sands, for example. And number three, I was optimizing for a font that made reading speed and comprehension really fast.

35:14And number four, I was looking for a font that made email addresses themselves look great. So I discarded all the 15 because they weren't good enough. And after searching high and low, I came across a font called Adele Sands, which is designed by a foundry called Type Together with Type -Hitem Together .com. They have a whole bunch of lovely fonts. Go check them out. And if you go through my list, number one, Adele Sands is gorgeous. I think each character is a work of art. It's beautifully formed. Number two, Adele Sands is, I would say, a beat, it's optimistic. Yet it's serious enough to convey any kind of message.

35:50It has just the right amount of personality, yet not too much personality. Number three, Adele Sands is also an usually narrow, and that actually fits email particularly well. One of my pet peeves, which email, which by default uses Ariel, is that the lines are as wide as your window. So if you're in a wide screen, then the lines get really arbitrarily long. And the problem with a really wide, really long lines is that they decrease reading speed. Because by the time you've reached the end of online, your eyes have lost track of the start of the next line. And Ariel itself has fairly wide characters, which further exacerbates that.

36:29So it's superhuman. If you've used the product, you know this. We fix the line length, or the typographical measure, to the optimal length for reading speed, which, depending on the font, is around 90 to 120 characters. And Adele Sands is quite narrow, so it actually lets us do this on quite small windows with a fairly dense line. So we get a lot of information on fairly small windows without getting a very long typographical measure, optimizing for reading speed and for comprehension. And then number four, finally Adele Sands has very unusual treatment of the app symbol in an email address. It actually puts the base of the A in the app on the same baseline as the rest of the text.

37:15So for example, if your name hasn't A, my name does Rahul at Voraz, three A's and two A's and then at. They're all actually on the same baseline. It's a small thing, but it makes the email addresses look incredibly natural. If you look at that and then you actually look at email addresses laid out in other fonts, those other fonts look really clunky and awkward because the A is kind of shifted around in it. It just looks a bit silly in my opinion. Now Adele Sands is it perfect. So we then worked with a type designer on some of the specific details that there are some of the glyphs which get a little pinsery as it were.

37:51And what we use today is very close to retail Adele Sands. And this was pre -launch or this was after you'd already launched. We'd probably had about 10, 15 users appetite. So I think that's pretty contrairin. Unique to be this focused on the font and the typeface before you even launch. This was like, is this even going to be a thing? Will anyone even care? And I think this has a lot about the way you think about product. Oh yeah, that, I mean, that thought never crossed my mind. I think we'll probably come to it later, but the idea that is this never going to be a thing. I think that's a dangerous thought.

38:30We can't start thinking that way because at what point do you stop second -guessing yourself? Interesting. So you're like, you were confident this was going to work. So because I am so confident it will work, I will make, I need to make it this right. There's also just, you know, this trap founders fall into you of just spending too much time perfecting a thing that never works. And there's always advice launched early, launched off. And well, thoughts there, just like, how do you find that balance with your advice there? How much to spend time ahead of launch really does depend on the markets and the structure, the nature of your business model.

39:06For example, let's say you're building a marketplace in a green field opportunity. So imagine the lift or Uber in their heyday. And there's a strong network effect because the more cars you have on your platform, the shorter waiting times are there for people who are going to preferentially use your app versus the other person's app. That's when there's no time to spare. That's when, you know, you probably shouldn't even be sleeping. You're going to hire the most aggressive, maniacal people possible. You're going to work 120 hour weeks because every marginal minute actually does matter. Every marginal minute in the market growing compounding is going to make your next year even better.

39:50That's actually not true of all startups. And it certainly isn't true of something like superhuman. Yes, working harder is always better and we work tremendously hard at superhuman. But not to the point where it made sense to release something that didn't work. I'm reminded of a story of a founder that was in Y -combinator told me about their demo day experience and they used mailbox, which some folks may remember, was also a startup and Dropbox famously acquired them for about $100 million. And the reason that they were well known apart from the acquisition is they were the first to popularize swipe to archive or swipe to mark them, which of course is now standard and in superhuman than every other app.

40:42So this founder was using mailbox and was having an amazing demo day. They're working the room, they're missing investors, they're pitching the photography app in this case. And he went home that night and went to his laptop, fired up mailbox and sent off a bunch of follow -up emails. He waited a day, didn't hear back. He waited two days, didn't hear back. On the third morning, he figured something was up, so he fired up Gmail, went to his sent mail and you guessed it, there were no sent mails there. So something had broken with mailbox. So he's cursing to himself, trying to remind himself everything's going to be okay, sent all the same emails from Gmail manually.

41:33And they all came through. But then one of the investors said, hey, by the way, you might want to check your email client because I've been getting some of your emails twice. And then he goes back into this Gmail, he sees that, yes, actually the original emails that were cute up in mailbox have now indeed been sent. And some of the investors, unfortunately, most of the investors, he actually pitched twice. Now, is this the end of the world? No, an investor can either look at probably a good thing that you're trying new apps. But was it horrifying? And was it, like was it really scary? Absolutely.

42:08And imagine this wasn't investors, imagine this was a customer, someone who you were trying to convince that, to buy your thing and that you knew what you were doing and you had attention to detail and you had everything just buttoned up and under control. Well, now you've lost face, now you look foolish. And that's why when you have a mission critical products, like email, where you are interfacing with customers, with candidates, with investors, it turns out to really matter. Email is mission critical. So it's not something where you can simply launch with a half -baked product. This is such an important nuance taken.

42:42There's always this debate. How much to focus on craft and use your experience, how much to focus on time to launch and get it out and speed. And what I'm hearing here, which I completely agree with, is it depends on the market you're in and the criticality essentially of your product. So if it's email, it just needs to work and you get that right. You need to spend all the time. You need to get that right. This reminds me of something else that when your early investors shared with the Bill Trenchard from First -Rome Capital, he talked about how speed was the thing that you just dialed up as a lever to 11.

43:14That's where you just, we will make this the focus. Speed, speed, speed. And I think that maybe the lesson there is just, you pick the thing that you think will most differentiate you, make you significantly better than what's out there. So I guess just thoughts and just how to decide. How you decide it? Speed was the thing you were going to obsess with. And just, I don't know, advice for folks that are trying to decide where to dial up things to 11. Bill is right and I agree with him. You have to pick something. Knowing what to pick is the trick. And in the early days of superhuman, I've read a book on positioning that really influenced my thinking.

43:50And it is, I believe, called positioning the battle for your mind. And it struck me how the most well -known brands have stood for one clear thing, like they have a clear position. And so in order for superhuman to be memorable, I believed that we needed to occupy a clear position that was unique and which was available and which reinforced our product strategy. In the first year of superhuman, therefore, I interviewed hundreds of potential customers about their experience with Gmail and with Outlook. And predictably, almost everybody said that email takes way too much time. But interestingly, many people also said that Gmail and Outlook were way too slow.

44:33And that was how I first thought that speed could be an interesting position for us. And then asked myself, is the position of speed unique and is it available? And the answer was overwhelmingly yes, because almost no software was being sold or has ever been sold on the value proposition of speed. The last time I could remember anyone trying to do this was when Google launched Chrome, and obviously that went incredibly well for them. And you may remember, they had slow motion videos where they were comparing Chrome render web pages and showing that was faster than an actual strike of lightning.

45:13No one had done it since then. And I then asked, well, the speed reinforced our product strategy. And again, the answer was overwhelmingly yes. I knew that our competition was not going to be startups. It was incumbents. And I also knew that incumbents generally struggle with speed because by definition, they have massive scale and usually entrenched architecture. And then finally, I did what I call the cocktail party test, which is to look at the cocktail parties and to watch how people pitch your product to other people. And in our case, the pitches were simple. People would say, dude, you have to use it.

45:53It's really fucking fast. And that's it. That was the pitch. And that's how I knew that speed would be a really great position for us to start with. I'm excited to chat with Christina Gilbert, the founder of OneSkima, whenever a long time podcast sponsors. Hi, Christina. Yes, thank you for having me on, Lenny. What is the latest with OneSkima? I know you now work with some of my favorite companies, like Ram, Vanta, Scale, and Watershed. I heard that you just launched a new product to help product teams import CSVs from especially tricky systems like ERPs. Yes, so we just launched OneSkima file feeds, which allows you to build an integration with any system in 15 minutes, as long as you can export a CSV to an SFTP folder.

46:34We see our customers all the time getting stuck with hacks and workarounds. And the product teams that we work with don't have to turn down prospects because their systems are too hard to integrate with. We allow our customers to offer thousands of integrations without involving their engineering team at all. I can tell you that if my team had to build integrations like this, how nice would it be to be able to take the software roadmap and instead use something like OneSkima and not just to build it, but also to maintain it forever. Absolutely, Lenny. We've heard so many four stories of multi -day outages from even just a handful of ad records.

47:05We have laser -focused on integration reliability to help teams end all of those distractions that come up with integrations. We have a built -in validation layer that stops any bad data from entering your system. And OneSkima will notify your team immediately of any data that looks incorrect. I know that importing incorrect data can cause all kinds of pain for your customers and quickly lose their trust. Christina, thank you for joining us and if you wanna learn more, head on over to OneSkima .co. That's OneSkima .co. The next area I wanna spend time on and I imagine we'll have much insight is some of the contrarian ways you approach building superhuman that a lot of companies never thought about doing that you did that worked out for you.

47:46So the first is manually onboarding every single new user. Sure, startups have done this like founders bring on some folks and then like cool, show it to them and then they stop doing that and then it's like self -service or sales teams. How far did you scale this manual onboarding phase of your company? Like how many people did you have onboarding? People have any people that you man, manual onboard? Yeah, so for folks that don't know, in those early days, we insisted on one -to -one, concierge onboarding and it was absolutely the right thing to do. You couldn't use superhuman unless you went through the onboarding experience and now it's almost the reverse.

48:26Almost every new superhuman customer goes through self -service. The onboarding experience is still there, but again, it is absolutely the right thing to do. To answer your question peak, we had about 20 people doing manual onboarding. Okay, so it's not that many people, that's really interesting because I always imagine it was like a massive team but 20 people can handle a lot is the takeaway there. What was the scale, I guess, where you stopped manual onboarding just for folks that are thinking about doing this and went to stop? So I think the reason to stop is that there will always be certain personality types who do not want to go through a one -on -one onboarding and at a certain point, those people will become very important and you will need to be ready with a world -class self -service option.

49:11When we started building self -service, it seemed nearly impossible. In fact, it was terrifying because it's difficult to overstate how much the entire DNA of the company was built around this idea that we would onboard users manually. And after all, we did so much in our one -on -on -on boardings and there's only so much that software can do. Now, we did after a lot of grind and persistence eventually figure it out and we have a world -class self -service experience today, but we did not at the time. So the flip side is, why would you even do this to begin with? What we found is two things. Number one, the user metrics are excellent for things like engagement, retention, product market, fit score, NPS, virality.

50:02For all of those metrics, I think you will significantly beat your industry benchmarks if you go to the effort of one -on -one onboarding your early customers and it becomes so powerful to have that early cohort of super fans when it comes to things like building a brand. And if folks remember that conversation from way up at the top of what is it that creates true virality, it's not viral mechanics, it's word of mouth, it is brand. This is how you can kickstart a brand. And number two, in a world where you can easily and quickly raise funding like for example, the zero interest rate for nominal error, you can actually use dollars to avoid building a first -time user experience and all of the normal gross loops that you would then have to build.

50:47You would then instead focus all of your engineers on finding products market fit or in solution deepening or in market widening. But not for example, on a first -time user experience. Not for example, on activation because you have humans doing activation for you. And by contrast, I saw other companies often competing spend almost half their engineering dollars on those things, on self -service flows, for products that ultimately did not find products market fit. So make sense to do if you really want to create that brand which I think all consumerist companies need to do. And if there is money falling off trees for whatever reason which we did have for a period of time, arguably AI companies have that again today.

51:33So if you can weave this into your strategy, I think you should, but you should also know when to stop. Super interesting. So I guess some factors to think about, because I wanted to ask you, when should people consider doing this, if they're hearing this and are like, this is awesome, so many problems solved. If I just have somebody onboarding every user, everyone's activated, amazing. So some of the variables you're sharing is, do you have cheap cash to invest and say, like it doesn't have to be 20 people, could be a few people to start. And then if there's like an LTV kind of ACV element of just like, are you gonna make enough from a new customer?

52:09Imagine that's a variable. Is there anything else you think founders should think about? Absolutely, you don't wanna lose money doing this. And we always made money doing onboarding to be clear. It's just that at a certain point, that the mass market, whether it for us as enterprise or all of the prosumers in the world, you hit a top of funnel with, it needs to be wide enough, where manually onboarding no longer makes sense. Awesome, okay. Let's think about product market fit. I know that everyone, when they think of, we're who will they think, product market fit. You wrote this epic first round post that described the way you guys approach product market fit.

52:48We're not gonna spend a lot of time on describing it because people can look it up. So let me just ask you this, just what are, I don't know, a couple of things that you think people still don't understand about finding product market fit, getting to product market fit. Considering it's the most important thing you gotta figure out as a founder, right? If you don't find something people want, nothing else matters. Anything there you wanna share? The core ideas are still weird enough that I'll start there, which is number one, you can measure product market fit. Number two, you can optimize product market fit.

53:23Number three, you can systematically, even numerically increase product market fit and number four, you can even have an algorithm write your roadmap for you and that is a roadmap that is guaranteed to increase product market fit. Now if that sounds crazy, I would be the first to admit, it doesn't seem like that should be true, but go check out that post. I think it is still the most widely shared post on first round review, it's called, I think how superhuman built an engine to find product market fit, or just Google the superhuman product market fit engine and you'll see the algorithm laid out there fully explained and why it works.

54:08And I'd say the second thing is to get to product market fit, you have to deliberately not act on the feedback of many of your early users. And this is at the same time as listening to people intensely and building what people want, right? That's what we're here to do is to make something that people want, but it can't be all people, it can't be everybody and the question becomes, how do you listen to them? And then even of what they say, what do you pay attention to and what don't you, all of that's covered in the product market fit engine. Okay, I got to follow this thought on algorithmically building your roadmap to increase product market fit, talking about just what that, how and when would do that?

54:54Well, I mean, that's really the meat of the engine. So let's see if I can condense it here in a very easy to grok fashion. So let's assume for the sake of argument that you can put a number on product market fit. And it turns out you can. Very simply, you're going to ask people, how would you feel if you can no longer use this product, you give them three responses, one of them is very disappointed, the other is somewhat disappointed and the other is not disappointed, very disappointed means I'd be like devastated. I love this product or I need this product. And what Sean Ellis found, Sean Ellis, if you don't know him, is the guy who coined the term growth hacker and he instrumented benchmarked this initial question, what he found is that the companies that struggled to grow, almost always had less than 40 % very disappointed, whereas the companies grew the fastest, almost always had more than 40 % very disappointed.

55:54And this question, this metric, is way more predictive of success than something, for example, like net promoter score. Okay, so far so easy. How do we make this number go up? Well, you want more people to be very disappointed without your product. And the trick here is not to act too much on the feedback that the very disappointed people are giving you because they already love your product. Also not to act at all really on the feedback that the not disappointed people are giving you because they're so far from loving your product that they are essentially a lost cause, but to focus on the segment of the somewhat disappointed people, they kind of love your product, but something, and I would wager something small is holding them back.

56:42So you then divide them into two camps, the camp for whom the main benefit of your product resonates in the camp for whom it does, and what do I mean by that? Well, you go back to the people who really love your product and you basically ask them, why? What is it about my products that you really love? In the early days of superhuman, it would have been speed and keyboard shortcuts and the overall design aesthetic as well as the time that we were saving you. You then go back to the somewhat disappointed users and in the superhuman example, I would simply ask, wait, do you like superhuman because of its speed or for something else?

57:15And if it's something else, well, and this is hard to do, but politely disregard those people and their feedback, because even if you built everything that they asked for, they're still pulling you in a different direction and the thing that they like the most from your product isn't actually what the people who on mass love it the most for is. So you have then articulated the sub segment of the sub -sigma that it makes sense to pay attention to, and there's another question in the engine to figure out what they don't like about the product. Now you have a list of things people love, you have a list of things people don't love, and you can work down that list to make the product market fit score go up.

57:58And basically at the start of every planning cycle, I advise spending half your time doubling down on what people really love and half your time systematically overcoming the objections of the somewhat disappointed users, but specifically those for whom the main benefit resonates. That was an excellent summary. I know I said we wouldn't spend a ton of time here, but I'm really glad we did. That was really helpful. Let me ask you this. I know you used this initially in the early days. Are you still operating this way in some form? We don't run the engine as is for superhuman as a whole. There are enough sub components of superhuman now that are almost individual products.

58:35For example, superhuman for sales, our multiplayer and collaboration features, how we think about the enterprise, AI, is its whole thing, but we do sometimes run it on those individual pieces. For example, we'll ask a sales person, the product market fit engine, as it relates to superhuman for sales. And as we think about starting new products, we would absolutely deploy the product market fit engine. Awesome. And the way you ask this question is an in -product interstitial sort of survey pop -up thing? You can do it however you want. The way Sean initially benchmarks the number was via email surveys.

59:10I think email surveys were just fine. The key thing is, and this applies to any survey methodology, if you're going to change the method of surveying, all of your old numbers are immealdated. So it's just a new baseline going forwards. Got it. And we had Sean on the podcast, and he describes this method in detail. So folks want to explore this Sean Ellis test. Listen to that podcast, we'll link to it. Okay. Next topic that I'm excited to get your take on is game design versus gamification. This is one of the more unique ways you think about designing product. And when people hear you talk about this, they think it's like, oh, gamification, making things like games, Zingha Farmville, I don't wanna do that.

59:49We actually have a really different perspective on how to make why you need to think about game design as you design products. Talk about your insights there. Yeah, well, I strongly believe that we should make business software like we make games because when we make products like we make games, people find them fun. They tell their friends, they fall in love with them. It's another way actually you're back into where we opened this conversation, which is you're making a brand, you're giving a reasonable word of mouth. It's actually an altogether different kind of products development. So how do we do this?

1:00:26Well, as you said, it's not gamification, that doesn't work. Game design works. The game design is not gamification. It's not, for example, simply taking your product and adding points, levels, trophies or badges. And to understand why gamification does not work, we actually have to start with human motivation. And there's a very interesting study from Stanford, I think, that demonstrates the difference perfectly. In the 1970s, these Stanford researchers recruited children who were age three to four years old. And all of these kids were generally pre -interested in drawing. Some kids were told they would get a reward, a certificate with a gold seal and a ribbon.

1:01:07And some kids were not told about any reward and they did not even expect one or didn't know of one. Now, each child was then invited into a separate room to draw for six minutes. And 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. So the children with no reward, they spent 17 % of their time drawing. But the children who expected a reward, sadly, they only spent 8 % of their time drawing. The very presence of a reward halved their motivation. So what's happening here is researchers differentiate intrinsic motivation and extrinsic motivation.

1:01:53With intrinsic motivation, we do things because they are inherently interesting and satisfying. And with extrinsic motivation, we do things to earn rewards and to achieve external goals. And that's the problem with rewards is they just massively undermine intrinsic motivation. And that's why gamification doesn't work. And when gamification does work, it's because the underlying experience was already designed like a game. What makes something, I guess, like a game? I know superhuman is really good at this. I've just like your inbox zero, quests that you're on. I guess just to make that a little more real, what is game design?

1:02:29What does that mean to you? What makes it feel like a game? Well, many people don't know this. But before I was a founder, you can probably tell, I was actually a professional game designer. And as it turns out, there is no unifying theory of game design. To create games, what we need to do is draw upon the art and the science of psychology, mathematics, storytelling, interaction design. And at superhuman, we've identified five key areas that we really care about, goals, emotions, toys, controls, and flow. And across these, we've identified many principles of game design. And one example principle would be make fun toys and then combine those into games.

1:03:12So a question I like to ask is, are toys the same as games? They do seem different. For example, we play with toys, but we play games. A ball is a toy. The football is a game. And as it turns out, the best games are constructed out of toys. Why? Because then they are fun on both levels. The toy and the game itself. So for example, in superhuman, one of our favorite toys is the time or to complete it. If you use superhuman, this is the thing that appears when you hit H, when you snooze or set reminders on emails. You can type whatever you want. It can be gibberish, and it does its best to understand you.

1:03:53For example, if you type in 2D, that becomes two days, three Hs, three hours, one M, O is one month. And the time or to complete it is fun because it indulges your playful exploration. In onboarding, it wasn't long before I saw people asking, what can it do? Where does it break? How does it work? What happens if I keep on typing in a series of tens? Well, it turns out that's October 10th at 1010 PM. Well, how about the series of twos? Well, that's February 2, 2022 at 2PM. And then you start trying more complex inputs like in a fortnight and a day, and that works, which is a pleasant surprise. And it's not long before you find more pleasant surprises, like time zone math happens without you thinking about it.

1:04:38You can just type in 8am in Tokyo and it turns out that's 8pm Eastern time, and you no longer have to do the time zone math. And then most people were really delighted to find out that if you really want, you can snooze emails until never. I, you can literally type in never and the email will never come back. And I had like a little shrug emoji at the same time. So, is it, is this toy going to win awards? Nope. But is it fun actually surprisingly, yes? So what I would encourage people to do is think about the features of their product. Do those features indulge playful exploration? Are they fun, even without a goal, and do they elicit moments of pleasant surprise?

1:05:20If so, you have a toy, and you can combine that with other toys and actually start to build a game. If people were to listen to the segment of the podcast, they would never guess we're talking about B2B software and email, which I love. Let's talk about pricing strategy and your approach to pricing. Another very contrarian approach that you guys took where you charged $30 a month for email. That was free, that people don't need to pay for anywhere. And it's worked, and now a lot of companies are thinking of it this way. You've even raised your prices recently. What have you learned about pricing strategy that you think may be helpful to folks?

1:05:58I always say the same thing when it comes to pricing, which is before you figure out pricing, you must first figure out positioning. And superhuman is the best email tool on the market. We fortunately have the metrics to show this. One of the cool things about selling an email tool is you can compare the 30 days prior to using superhuman to the 30 days after, or the year before to the year after. And we do that, obviously. We're able to show that people get through their email twice as fast with superhuman, that they respond one to two days faster, and that they save four hours or more every single week.

1:06:35Because of that, we're very confident in saying that superhuman is the best email tool on the market, and that we're building it for high performing teams and high performing individuals. In other words, we serve the high end of the market. Once you understand your positioning, you can then move on to pricing. And one of the best books on this is a book called A Monetizing Innovation by Madhavand Ramajam, and Madhavand covers a lot of ways to develop pricing. We used one of the easiest methods, which is the Van Westendorp Price Sensitivity Visa. And in the early years, we asked, I think it was around a hundred of our earliest users, the following four questions.

1:07:15Number one, at what price would you consider superhuman to be so expensive that you would not consider buying it? Number two, at what price would you consider superhuman to be priced so low that you'd be worried about its quality and you wouldn't buy it? At number three, what price would you consider superhuman to be starting to get expensive so that it's not out of the question, but you'd have to give some thought to buying it. And number four, at what price would you consider superhuman to be a bargain, a great buy for the money? Now, most startups orient around price point number four. This is especially true for Greenfield opportunities, marketplaces, you've got to set the transaction value around price point four, basically when you want as many people to sign up as being humanly possible at the top of the funnel.

1:08:05But the price point that supports our best in class, best in category position is actually the third one. It starts to feel expensive, but then you sit down and you think about the time that you spend an email, the ROI, and you still buy it anyway. And it turns out that the median answer for the third question was $30 per month, and that's how we picked our price. And once we picked our price, we then do a quick gut check on market size. For example, we're a venture scale company, but at the time the good question that we have to ask is could we grow into a billion dollar valuation? Well, let's assume that at that point, our valuation is 10 times our ARR, so our ARR would have to be $100 million.

1:08:47Well, that would be 300 ,000 subscribers at $30 per month, and that is conservatively assuming no other ways to increase ARP, you mentioned price increase, you can also go at market, you can sell new products and so on. But we asked ourselves without those tricks, do we think we can get to hundreds of thousands of subscribers, and we answered emphatically yes, and so we went ahead with that price. Okay, there's a couple more things I want to chat about in the time that we have, and then I know you have to run. One is around AI, and the work you guys are doing there, I know that's been a big on lock, and then two, the stuff you're doing in enterprise, and then if we have time, there's a question I want to ask that I think it's a really interesting way you guys operate.

1:09:29So let's talk about AI first. It feels like there's this like being in the right place at the right time. It feels like you guys, we've been building this for a while, and then AI just unlocked another stage in what you're able to do with email. I guess just talk about what you've done, and how you think about AI integrating, and what you're doing, how it's enabled you to kind of take off. Again. It's true that sometimes startups boil down to being in the right place at the right time, and we actually had a massive AI launch recently about two weeks ago, but even before then, we had multiple flagship AI features.

1:10:08Our first AI feature was right with AI, drop down a few words, and we'll turn them into a fully written email. We actually match the voice and tone in the emails you've already sent, so unlike co -pilot, unlike Gemini, unlike basically every other email app that email sounds like you. And this AI feature is way more popular than I expected it to be. On average today, users are using it 37 times per week. Number two, our next AI feature was AutoSemurize, which shows a one -line summary above every conversation, and as new emails arrive, it updates instantly. Again, unlike co -pilot and Gemini, it's pre -computed.

1:10:46One of the things we do is we go above and beyond to make these features really premium and feel amazing. The next AI feature after that was Instant Reply. Imagine waking up to an inbox where every email already has a draft reply. You would simply edit and then send. And sometimes you wouldn't even need to edit. And I can share, because we just finished this analysis that over 2024, the percentage of emails that our AI written and sent with superhuman has grown four times just in one year. Then if I remember correctly, the feature after that was Ask AI. Email, of course, is this treasure trove of critical information, things like project statuses, customer communication, meeting updates, deal execution, and so much more.

1:11:35And for over 40 years, we've had to rely on what we hilariously call search. You have to remember senders, guess keywords, scan subject lines, and now you can just ask. Where is the keyword on the site? Or what are my flight details? Or what is the top five most positive customer responses to the Ask AI launch? A task, by the way, which previously used to take me 20 or 30 minutes to read through all the emails and then create that report now happening in less than five seconds. And recently, we, like I said, announced our biggest evolution yet and superhuman AI is constantly helping you. It's organizing your inbox.

1:12:17It's also making sure you never drop the ball. So we have things that we call auto labels. You can now write a short prompt like job applications or requests to review work. And you can then immediately see when emails match that prompt, when people apply for a job, or they ask you to review work with auto reminders if your email needs a response. Superhuman will now automatically set a reminder. You don't have to remember to do that. And you'll never drop the ball again. All you need to do is hit send. With auto drafts, superhuman will now automatically draft your follow up emails for you and will soon be draft your replies to basically every email that needs a response.

1:12:59And finally, with what we call workflows, you can now turn email into repeatable automated workflows. For example, I often get emails from people who are interested in working at superhuman. And I would normally reply to that candidate, I know I would let them know that the team will take a look. I'll then forward the original message, including any resume or any letter to our head of people and operations and ask her to reach out if interested. With workflows, I can now automate this entire process. And you can imagine sort of creating a little flow chart of what has to happen. And not only does that save a huge amount of time, with workflows, you don't even have to be in your inbox.

1:13:45In fact, you don't even have to be working. You could be on vacation while superhuman AI is working for you. This sounds like product market fit to me. This all sounds wonderful. Like it just makes sense. This is the stuff we've been promised. Underwater cities and flankers and then just email they just works magically and replies for us and all these things. So I love all these things you're doing. For folks that are building with AI, I'm curious to just, what's been maybe been the biggest surprise, either good or bad, building so deeply on top of AI models that you think might be helpful for folks to just like watch out for this or hey, check this out.

1:14:25I think for me the biggest surprise has been how unpredictable the user love has been in terms of what they love and what they don't love. For example, right with AI. This sounds like a commodity feature and on our surface level it is every email app, every writing surface has a right with AI feature in. I would wage hours is the best at emails and surprisingly that's what we do. But the surprising thing was just how much people love it and how often it gets used. 37 times per user per week is still mind blowing to me. I had not expected that. So that's the most surprising thing. And on the flip side, there were certain AI features where I did expect a ton of usage but we didn't quite get the usage that we were perhaps hoping for and hopefully I'm not AI -cramer but basically everything I thought would work out well, people used it less than I thought they did and everything was like, let's build the thing, people love that.

1:15:32So maybe I should just create an anti -meet to do AI road mapping. That's in a simple agent right there. Whatever a host says do the opposite. Yeah. Okay, another maybe a last topic. I know that you guys are starting to move into the enterprise when people think of superhuman they think of just, you know, it's like consumery, it's like for people and you guys are doing a lot of work to make it a B2B enterprise product. For founders maybe better starting to think about this, transitioning from PLG to sales led and be enterprisey. What have you learned about just what it takes to get to that point and just what does that sales motion look like for you guys?

1:16:10In some ways it's very like selling to prosumers except these users are not coming from Gmail where prosumers would normally come from, they're coming from Outlook and Outlook users have very different expectations to Gmail users. For example Outlook users expect that email app to also be a fully featured calendar app whereas Gmail users are happy with those two things being entirely different. So as a result we've invested in calendar very heavily and we continue to do so. And there's only so much I can say that but it's pretty exciting. Mm, Outlook users. Yeah, Outlook users are also used to certain safeguards like if you've used Outlook and the enterprise warnings when a recipient is external to your domain or what Outlook users might know as sensitivity labels and as a result we've built support for external recipient indicators and sensitivity labels.

1:17:09But in some ways it's very different to selling to prosumers because there are other stakeholders involved. For example, we've built support for enterprise mobile management by implementing Microsoft Intune. We recently sold one of the big three strategy consulting firms which is super exciting. I can't say which one but they love superhuman and they have thousands of people internally using superhuman. But we, and this is after a year, they've been piloting for a year and then accelerating over the last few months. We only just got them the mobile app, believe it or not, because at an enterprise like that there are significant controls on what a allowed compliant mobile app can and cannot do.

1:17:59For example, IT needs to be able to control which apps can save attachments or which apps you can copy and paste text into from email. And for many enterprises those controls are super important. Wow, okay. So it sounds like essentially just building all these features that large companies need is kind of the rodeo on right now. Exactly, and there's two stakeholders. There's the users which are actually quite different because they're Outlook users and Calendar is one of the main ways that manifests. And there's a whole bunch of other stakeholders. IT is one of them but there are others as well.

1:18:33For example, companies this large have work place management groups who want to see analytics of how people are working, how they can make their teams more efficient. And so it truly is a multi threaded sale with multiple stakeholders. We had a linear on the product, the head of product from linear on the podcast, non and you actually, I don't know if you heard that episode but he talks about how they decide what to prioritize. The thing they never build is middle managers needing to track how their reports are doing and things like that. So that's an interesting opportunity for you guys maybe to cut stuff.

1:19:06I don't know. Anyway, I want to end on one more nugget. Okay, I'm glad we have time for this. So you sure that you have this system in terms of superhuman for making decisions. You call it single decisive reason. SDR, what is that? SDR is a thinking tool that I picked up from Reed Hoffman during my time at LinkedIn. And the idea here is that for important decisions, you should be able to identify one reason that on its own supports the decision. And it's based on the observation that all too often we rely on a collection of weak reasons to justify decisions. And it's very, very easy to do this.

1:19:50Imagine your contemplating a decision. You write a list of the pros and the cons. There are three pros, but let's say there are 10 or 15 cons. The sheer number of cons, the efforts of thinking them through the time it took to write them down is going to affect you consciously or worse, subconsciously. And this is especially true I've seen in group settings, which just in general are a little bit more risk -averse and a little bit more consensus -driven. So whenever anyone is making a decision and they bring that decision to me and they say, well, we want to do this because of XYZ and there are multiple reasons I'd ask them, what's the SDR?

1:20:29What's the single decisive reason? If they can't yet isolate it, that tells me they haven't yet figured out why they want to make the decision. It doesn't mean the decision is wrong. It just means that they haven't figured out the singular reason why we should do the thing. They can then go through their list of reasons and ask, is this alone enough to support this decision, meaning if this was true and all the other things were not true, would I still do it? And sometimes we still do, but actually sometimes we don't. And we realize that a collection of weak reasons alone means that, for example, the outcome is less likely than we thought it was, or it was hiding a really strong reason on the other side of the decision.

1:21:11That is very cool. So this is just when you're, when someone comes to you with a decision, the way you use this idea, as you ask them, what's the single decisive reason? Pretty much, yeah. And what they can't do, I mean, obviously this happens, people are human and natural. They'll usually start mentioning three or four things and that's fine. And then I will say, okay, but if only one of those was true and you're still advocating for this decision, what is it? And I think that's just a bar for a good decision. Why is that important because you found that just like a bunch of low quality reasons, just going at up to a good reason to do something?

1:21:50Multiple reasons, which is ironic, but that's my SDR for YSDR's work, which is yes. Multiple low quality reasons rarely add up to a high quality reason to do something. But there are also other things as well, which is any decision you take has an opportunity cost, any feature you build is another feature that you didn't build. And if we're going to build this for a collection of weak reasons, whereas we could build that for one strong reason, I'd much rather build that for one strong reason. This is all other things being equal and these things often end up being quite complicated, but you can apply SDR all the way down.

1:22:27I mean, you just did that to me. What's my SDR for SDR? There we go. Cool. Does there anything that we haven't covered that you wanted to cover? Is there any last piece of wisdom you want to leave listeners with before we let you go? I feel good. So I think we covered a lot. Thank you for asking amazing questions. This is really fun. This was incredible. Okay, so let me just ask you this then, where can folks find you online work and they check out superhuman? What should they know before they try it out? And then just how can listeners be useful to you? If you want to find me online, I'm generally on x, that is x .com slash Rahul Vura, R -A -H -U -L, the O -H -R -A, and my DMs are open.

1:23:11So for you'll feed to ping me. If you're going to do that, I would suggest also emailing me that's Rahul at superhuman .com. And hopefully I'll see you a message soon. If you haven't tried superhuman, then gosh, what are you doing? This is my call to you to do so, because your time is worth more than whatever you think it might be. So go download superhuman and give it a shot and invite your team. The metrics are real. I know they sound like the kind of metrics that start its makeup, but getting through your email twice as fast, responding once, two days sooner, saving four hours or more every single week.

1:23:50They're all real. Actually, speaking of which, the consulting firm I mentioned earlier, because they're so into data and into analysis, they wanted to corroborate those numbers for themselves. And so they did. They ran their own internal case study on superhuman and they were like, yeah, you're saving our partners 3 .3 hours per person per week. And there's only one other tool that we've bought that does that, which is ChatGPT. So thank you, we love superhuman, we're rolling it up. If that sounds interesting to you or your company, please do give it a shot. Matt is super cool. Reflecting back on what I imagined this conversation looked like, a lot of contrarian thinking and tension to detail, I think that's exactly what it was.

1:24:35Really awesome. Thank you so much for being here. I mean, thank you. Bye everyone. Bye everyone. Thank you so much for listening. If you found this valuable, you can subscribe to the show on Apple podcasts, Spotify or your favorite podcast app. Also, please consider giving us a rating or a leaving review as that really helps other listeners find the podcast. You can find all past episodes or learn more about the show at Lenny'spodcast .com. See you in the next episode.