Superhuman's secret to success | Rahul Vohra (CEO and founder)

Rahul Vohra is the founder and CEO of Superhuman. Prior to Superhuman, Rahul founded Rapportive, the first Gmail plug-in to scale to millions of users, which he sold to LinkedIn in 2012. He is also a prominent angel investor, and his fund has invested $50 million in over 120 companies, including Placer, Supabase, Mercury, Zip, ClassDojo, and Writer. What you’ll learn: 1. The unexpected insight about virality Rahul gained from LinkedIn’s head of growth. 2. Why Rahul restructured his entire executive team to spend 60% to 70% of his time on product, design, and marketing instead of the typical CEO responsibilities. 3. The counterintuitive approach to finding product-market fit using a methodical system inspired by Sean Ellis, and how this algorithmically determines your roadmap. 4. How manually onboarding every user (Superhuman had 20 full-time people doing this at peak) created superfans and allowed engineers to focus on product rather than onboarding flows. 5. The “Single Decisive Reason” framework for making better decisions by avoiding collections of weak justifications. 6. How Superhuman’s AI features have evolved to create a truly intelligent email experience that works while you sleep. — Brought to you by: • Eppo—Run reliable, impactful experiments: https://www.geteppo.com/ • Fundrise Flagship Fund—Invest in $1.1 billion of real estate: https://www.fundrise.com/lenny • OneSchema—Import CSV data 10x faster: https://oneschema.co/lenny Find the transcript at: https://www.lennysnewsletter.com/p/superhumans-secret-to-success-rahul-vohra Where to find Rahul Vohra: • X: https://x.com/rahulvohra • LinkedIn: https://www.linkedin.com/in/rahulvohra/ • Email: [email protected] Where to find Lenny: • Newsletter: https://www.lennysnewsletter.com • X: https://twitter.com/lennysan • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ In this episode, we cover: (00:00) Introduction to Rahul and Superhuman (05:00) The most pivotal moment in Rahul's career (07:01) The secret to virality (11:02) Superhuman’s product evolution and core values (13:32) Overcoming slowdowns at scale (18:06) Time management and meditation (27:35) The role of a president (30:56) Attention to detail (43:00) Finding your unique position (47:32) The power of manual onboarding (52:37) Mastering product-market fit (59:33) Game design in business software (01:05:35) Contrarian pricing strategies (01:09:29) Leveraging AI (01:15:40) Transitioning to enterprise solutions (01:19:08) The Single Decisive Reason framework (01:22:32) Conclusion and final thoughts Referenced: • Superhuman: https://superhuman.com/products/mail • Rapportive: https://techcrunch.com/2012/02/22/rapportive-linkedin-acquisition/ • Elliot Shmukler on LinkedIn: https://www.linkedin.com/in/eshmu/ • What Are ‘Whales’ in Video Games: https://gamerant.com/video-games-whales-concept-term-explained/ • Figma: https://www.figma.com/ • Notion: https://www.notion.com/ • Loom: https://www.loom.com/ • How to use Team Comments to reimagine email collaboration: https://blog.superhuman.com/how-to-use-team-comments-to-reimagine-email-collaboration/ • Rajiv Ayyangar’s post on X about Superhuman: https://x.com/rajivayyangar/status/1816176308130570385 • Transcendental Meditation: https://www.tm.org/ • Laurent Valosek on LinkedIn: https://www.linkedin.com/in/laurent-valosek-18708b5a/ • Peak Leadership Institute: https://www.peakleadershipinstitute.com/ • Ed Sim’s website: https://edsim.net/ • Adelle Sans: https://fonts.adobe.com/fonts/adelle-sans • Comic Sans: https://en.wikipedia.org/wiki/Comic_Sans • Greenfield project: https://en.wikipedia.org/wiki/Greenfield_project • Why Mailbox died: https://www.theverge.com/2015/12/8/9873268/why-dropbox-mailbox-shutdown • Bill Trenchard on X: https://x.com/btrenchard • How Superhuman Built an Engine to Find Product-Market Fit: https://review.firstround.com/how-superhuman-built-an-engine-to-find-product-market-fit/ • Using the Sean Ellis Test for Measuring Your Product-Market Fit: https://medium.productcoalition.com/using-sean-ellis-test-for-measuring-your-product-market-fit-c8ac98053c2c • Sean Ellis on LinkedIn: https://www.linkedin.com/in/seanellis/ • The original growth hacker reveals his secrets | Sean Ellis (author of “Hacking Growth”): https://www.lennysnewsletter.com/p/the-original-growth-hacker-sean-ellis ... References continued at: https://www.lennysnewsletter.com/p/superhumans-secret-to-success-rahul-vohra Recommended books: • Positioning: The Battle for Your Mind: https://www.amazon.com/Positioning-Battle-Your-Al-Ries/dp/0071373586 • Monetizing Innovation: How Smart Companies Design the Product Around the Price: https://www.amazon.com/Monetizing-Innovation-Companies-Design-Product/dp/1119240867 Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected]. Lenny may be an investor in the companies discussed.

Speaker names marked ? are inferred from speaking time and the show’s known hosts — they are not voice-verified.

• 0:00Lenny Rachitsky?

  Let's talk about product market fit.

• 0:01Speaker 01

  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. That's what we're here to do is to make something that people want. But it can't be all people. 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? The trick here is.

• 0:26Lenny Rachitsky?

  You're not doing what a lot of CEOs think they need to be doing with their time. A lot of CEOs think they need to spend time on hiring or org building. And you intentionally, I will spend time on product and marketing design.

• 0:36Speaker 01

  So this is a technique that I call the switch log. And it's born out of the observation that your calendar says what you thought you were going to do. But it's really only your trail of work that describes what you actually did. How can we capture that? I came up with the following idea. What if I just did whatever the heck I wanted?

• 0:55Lenny Rachitsky?

  What's the most pivotal moment in your career, in your life?

• 0:58Speaker 01

  I learned the real secret behind virality. There is no such thing as a truly viral product. What then is the true secret? It is.

• 1:11Lenny Rachitsky?

  Today, my guest is Rahul Vohra. Rahul is the founder and CEO of Superhuman and one of the most thoughtful and insightful and articulate founders that I've met. As you'll see in our conversation, it's hard not to be captivated by Rahul's storytelling skills and also his really insightful takes on how to build great products and teams. This episode is for anyone who's looking to build their product taste, help their teams move faster, learn how to think better from first principles, and also learn about Superhuman's very unique approach to building their company, including why they manually onboarded every single new user for years and why they decided to stop, why they ignored most of their customer feedback on their way to finding product market fit, and also how you can use his approach to finding product market fit for your own company.

• 1:56Lenny Rachitsky?

  Also, the power of game design in building great products, a very contrarian take on pricing strategy, what Rahul has learned about building scaled products on top of AI and LLMs, and so much more. A huge thank you to Ed Simms, Conrad At Erwin Beltranchard and Gara Vora for suggesting questions and topics for this conversation. If you enjoy this podcast, don't forget to subscribe and follow it in your favorite podcasting app or YouTube. Also, if you become a yearly subscriber of my newsletter, you get a year free of Superhuman that you can start using immediately. You also get a year free of Notion, Perplexity Pro, Granola, and Linear. Check it out at lennysnewsletter.com. With that, I bring you Rahul Vora. This episode is brought to you by EPO.

• 2:41Lenny Rachitsky?

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• 3:22Lenny Rachitsky?

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• 4:07Lenny Rachitsky?

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• 4:51Lenny Rachitsky?

  before investing. Find this information and more in the fund's prospectus at fundrise.com/flagship. This is a paid ad.

• 5:03Lenny Rachitsky?

  Rahul, thank you so much for being here. Welcome to the podcast.

• 5:07Speaker 01

  Hello, hello, and thank you for having me, Lenny.

• 5:10Lenny Rachitsky?

  I have so many questions for you. We're going to have so much to talk about. I actually want to start with your time before Superhuman. When I was preparing for this chat, I actually asked you, what's the most pivotal moment in your career, in your life? And you told me that other than starting Superhuman, it was selling your previous company, Reportive, to LinkedIn. So let me just start there. What was that experience like? What do people not know about this phase in your life? And just why was it so pivotal?

• 5:37Speaker 01

  So for folks that don't know, Reportive was my last company. It was the first Gmail extension to scale to millions of users. Basically, on the right-hand side of Gmail, we would show you what people look like, where they work, links to their recent tweets, their LinkedIn profile, and everything else that they were doing online. So if you were hiring, marketing, selling in BD, super useful. It turns out we somehow attracted most of LinkedIn's daily active users onto this one free app. And I then ultimately ended up selling that to LinkedIn. And that by far, as you said, was the most pivotal thing I'd done in my career prior to starting Superhuman.

• 6:22Speaker 01

  Now, had I known that we'd amassed most of LinkedIn's active users onto one app, I would have sold it for far more. But the actual pivotal moment was really who I got to work with. Because I reported to LinkedIn's Head of Growth, Elliot Schmuckler, and he was responsible for scaling LinkedIn from 25 million members to, when I joined, north of 250 million members. And during my first one-on-one, I learned the real secret behind virality. And big hint, it's not about viral mechanics. And overall, that acquisition experience gave me the time to figure out what was next and the resources to truly swing for the fences.

• 7:02Lenny Rachitsky?

  Okay, well, I have to follow this thread that you put out there of what the secret is to virality. What did you learn there?

• 7:08Speaker 01

  Well, in my first one-on-one, I sat down with Elliot and I said, "Hey, I'm here to learn. Please teach me everything that you know about virality." And he said, "Okay, well, hate to burst your bubble, but there is no such thing as a truly viral product." I said, "What do you mean? How do you explain Facebook for that matter? How do you explain LinkedIn?" And he said, "What I mean is, no app has sustained a viral factor of greater than one for any real period of time. Even Facebook in its heyday had a viral factor of about 0.7. And he told me that lasted for perhaps a year.

• 7:51Speaker 01

  So one person was creating about 0.7 new users.

• 7:56Speaker 01

  And I double clicked again. I said, well, Elliot, what about the address book imports? This is one of the things that LinkedIn got famous or infamous for. You could import your address book and then it would spam slash invite everyone who happens to be members of LinkedIn in your address book. And then eventually it would just invite everyone to LinkedIn. And he said, that's an amazing feature, but you have to remember, not everyone is going to use it all the time. So even that feature had a lifetime viral factor of about 0.4. And that's considered good. So 0.4 is good for a viral feature. 0.6 is great. Something like 0.7 is absolutely incredible. You're in the stratosphere up with Facebook at that time.

• 8:41Speaker 01

  So I said, well, okay, all of these things by definition are going to peter out. There's going to be an asymptote. None of these viral mechanics keep on compounding, which actually makes sense. It would be a little absurd if things just kept on growing. What then is the true secret behind virality? And he said, it is word of mouth. It is the virality you can't measure that isn't a mechanic that isn't in a feature. It is when one user spontaneously tells another user about your product. And that really colored how I think about growth and virality. Since then, it has shaped so much of what we do at Superhuman and so much of how I think about growing brands.

• 9:23Lenny Rachitsky?

  Wow, you're such a great storyteller. I'm just like listening here, just captivated. What is he gonna say next? That was fascinating. I actually have a post that I'm going to link to that very much aligns with what you're talking about, which is titled "Virality is a Myth Mostly." And it's based, I forget, on this book where they do all this research on like actual viruses. And it turns out they're not actually spreading in this like exponential way. There's like one person that spreads it to a lot of people and it keeps happening. And that's actually apparently what the data shows. And I'm curious if you've found this same thing, which is when people think of an app as going viral, it's like one person with a massive platform sharing it and their audience adopts it. And it's like, that's just one to many. And then it just happens a couple of times and it looks like it's going viral, but it's

• 10:08Lenny Rachitsky?

  like a person to many people, not many people to many people. Thoughts on that?

• 10:14Speaker 01

  Yeah, we've definitely found that there are whales, to use the gaming terminology, that one person is going to be responsible for inviting 25, 50, 100 people. And they may have various motivations for doing that. In Superhuman, as an individual subscriber, if you refer somebody else and they sign up, you both get a free month, which is a great incentive if you're paying out of pocket. So we have people who send many, many hundreds of invites. And there are some people who essentially have free Superhuman for life now due to how many people they've invited. But of course, that incentive doesn't necessarily work inside of a company or inside of a team where ultimately it's the company paying for the product.

• 10:59Speaker 01

  So you have to then come up with new motivations for those people. And that's where there really isn't any substitute to having a genuinely multiplayer or a genuinely collaborative product. And that's one of the huge evolutions we've taken Superhuman through over the last, probably about two years. Early last year, we launched what we call Superhuman 2.0. And the basic idea is we saw almost every single other app of note become collaborative by default. Figma, Notion, Loom, these are all multiplayer or collaborative by default. Yet email, the one tool that we all use more than anything else, even more than things like Slack, was still firmly stuck in its single-player origins.

• 11:43Lenny Rachitsky?

  I want to come back to something that you mentioned that I didn't come back to. And I think is really core to what you just shared, which is word of mouth being so important. Like, people talk about all these viral features and sharing contact books and all these things. And your point is that takes you to a place. But really, what helps a consumer-ish product spread is word of mouth, people sharing with each other. Which then the question is, how do you do that? We're going to talk about a lot of things that you did to make Superhuman something people want to share. But in the end, it's just like making something people want to share. That's like the definition almost. So then it's like, what makes people want to share stuff? It's amazing. It's helping them. Something that is remarkable.

• 12:21Speaker 01

  Well, it turns out you mentioned remarkableness. That is one of our core company values. And if you think about what a company has to do, it has to grow. How do things grow? Well, let's take Elliot's advice at Face值, and I believe it's true. It's creating something that people share.

• 12:40Speaker 01

  You mentioned one way of doing it, which is something that people want to share. There's actually another way, which is simply creating something remarkable. You use that word, and that is one of the core values of Superhuman. So we have create delight, create something that is so joyful, that really truly brings people delight. We have deliver remarkable quality, something that is so striking, so compelling and worthy of attention that people can't but help tell others about it. And then we have build the extraordinary, which is a measure of the efficacy or the innovativeness of what we want to build. So that's another trick, which is literally baking these raw ingredients for growth into your company values.

• 13:22Lenny Rachitsky?

  I didn't know that was one of your values. That makes so much sense. Okay, we're going to come back to that because I think that is, there's so much to learn about how you think about product and how you think about building the company that builds the product. But I want to actually start here with how this conversation came to be. So the CEO of Product Hunt, Rajiv, tweeted months ago, he tweeted this. And we're going to show this if you're on YouTube. "Superhuman's product velocity feels like it's kicked into another gear as of late." Does anyone else notice this? And I saw that, I'm like, I completely have noticed this. It feels like there's just feature shipping left and right, AI this, AI that. It feels like it's just like a new company. And I tagged you on the tweet, I'm like, hey, we're whole, it's changed.

• 14:05Lenny Rachitsky?

  And you answered with a few things and it just made it clear there's a lot to learn about what you did, because a lot of companies are in this phase, I think, of just like, things are moving as fast as we want. We used to be so much faster, we used to ship all these features, and now we don't. And so I think this is a really cool, real case study illustrative example that we can analyze. So let me ask you this, what did you notice that told you something needed to change at Superhuman? And then what did you change that actually had the most impact on your ability to ship and move faster?

• 14:37Speaker 01

  I think what we noticed was this sentiment and we felt it first ourselves, but we also started hearing it from the market, from our users, from our customers, that we'd slowed down. And as a founder, as a CEO, that's the absolute last thing you want to hear. It's our job, after all, to speed things up. And when I asked people, what do they mean by slowing down? They didn't mean the product, of course. The product wasn't working any slower, but that the pace of delivery seemed to have slowed down. So I think to break this down, it's important to start by defining what we mean by a slowdown. There's the kind of slowdown that is unavoidable in certain spaces. And then there is the kind of slowdown that is quite avoidable.

• 15:22Speaker 01

  We actually had both. So starting with unavoidable slowdown. You can classify anything that you build in a company into one of two categories, solution deepening and market widening. Now, solution deepening means making your product better for its existing users, but not making it available to more users. Whereas market widening means making your product available to more users, but not making the product itself any better. And there are some spaces, there are some markets, there are some platforms where market widening is really fast and really easy. And there are some spaces, email is one of them, where market widening is really hard and really slow. When we started, we had a great deal of focus.

• 16:07Speaker 01

  We only supported Gmail. We were only on the web. And in those early years, we could pour every ounce of R and D energy, every engineering dollar into solution deepening, making the product better for existing users. And of course, users loved it. It's how we got to product market fit. It's how most startups do. But at a certain point, almost every company then has to start investing in widening the market. For example, The market of people who will use a new Gmail front end, but without a mobile app does exist, but it is relatively small. And then this is something that every new email startup is going to learn sooner or later. In order to keep on growing, you are going to have to need to add an iOS app, and then a macOS app, and then a Windows app, and then an Android app.

• 16:52Speaker 01

  And then you'll soon want to support Office 365, but that's not one thing. That's actually three things, because you have to support Office 365 on desktop, and then on iOS, and then on Android. And that's all much easier said than done. I think we at Superhuman now know things about these APIs that literally no other company knows, and I would not wish it upon my worst enemy. So fast forward to today, and Superhuman now works wherever you do, on every combination of Gmail, Outlook, Mac, Windows Web, iOS, Android. And this actually turns out to be a really great technology moat. Almost no other email app can claim this. It's taken many years of intense investment. And I think we'll touch on this later, but it's one of the main reasons why we can sell into the enterprise, because we now know everyone can use it. But this is the hard part.

• 17:37Speaker 01

  When you're doing that market widening, you're not solution deepening. And so your perceived product velocity may decrease. You can avoid some of these things with some smart technology decisions, but mostly you just have to grind through it, and it is worth it to get to the other side. Then, there's the kind of slowdown that is avoidable. And if I remember my answer to Rajiv's tweet, that was the kind I was talking about. And in that case, it was our management structure, or who does what. When we hired our initial executive teams, I followed very conventional wisdom. I ended up with a set of VPs and eight, I think, direct reports, maybe even nine. And I thought, that's what you were meant to do. That's how startups are meant to scale.

• 18:23Speaker 01

  But as anyone who's been there knows, eight direct reports is a lot. It's a lot of hiring, it's a lot of goal setting, it's a lot of OKRs, it's a lot of accountability conversations. And fortunately also, it's a lot of firing. No CEO ever gets their executive team right on the first try. So that time I had for the things that I think I can genuinely be world-class at, things like product and design and technology and marketing, that all began to rapidly disappear. And as a result, the organization began to slow down. Fortunately, I was also tracking my time very closely. I had this crazy way of tracking it. And at one point, I noticed I was spending 6% to 7% of my week on these areas, these areas where I can truly be world-class at.

• 19:09Speaker 01

  So I had two realizations. Number one, as CEO, once you get to a certain scale, and we were definitely at that scale, you can actually define what you want the role of a CEO to be at your company. And number two, the superhuman opportunity deserves everyone who works at the company to spend as much time as possible in their zone of genius. And so that includes me as well as everybody else. So what I did is I hired a really great president. I went from eight direct reports to two. And the amount of time that I spend on product, design, technology and marketing went up from 6% to 7% to about 60% to 70% of my week.

• 19:49Lenny Rachitsky?

  Just to mirror back a few things. One is, people may feel like you are not shipping as much as you used to because you're actually building things they don't care about, which is support for office and all these things that they don't need. But the business needs to expand. Integrations with Microsoft and Android and all these things. I think that's such a good point, that like it looks like nothing's happening when there's a lot of good stuff happening for other users that aren't you. And then there's this point about people delegate and then they're like a leader delegates, hires all these execs and then like, this is not what I wanted. Why have I done this? And things and you think it's gonna speed up, but it slows down. A couple of threads here that are really interesting. One is this time tracking thing. I need to know what,

• 20:32Lenny Rachitsky?

  how do you do this? This is the fact that you knew like seven to eight percent or whatever the number you said, like to that granularity of your time you're spending on things you wanted was that low? How, how do you do time tracking? Let's not go super far, but just what's your, what's your approach?

• 20:47Speaker 01

  So this is a technique that I call the switch log. And it's born out of the observation that your calendar says what you thought you were going to do. But it's really only your trail of work that describes what you actually did. So how can we capture that? And actually, how can create a system of work? That isn't tethered to a calendar where you aren't at the behest of what some timetable says you do, or you don't have to do.

• 21:19Speaker 01

  So I came up with the following idea. What if I just did whatever the heck I wanted? What if every single time I change task, I just Slack DM'd my EA? But this also works in Slackbot, like you can just, it just has to go somewhere. I Slack DM my EA and I said TS colon, and then a few words for the task I was doing. Well, that would create certain changes. Instead of having to constantly look at the calendar and think, oh, should I stop this task, start that task? I can just do what I want. Like if, if what I feel right now is, oh, boy, I really need to prepare for Lenny's podcast. I'll go ahead and do that.

• 22:01Speaker 01

  And if I get bored or distracted eight minutes in, which sometimes happens, because something else just bubbles up to the top of my mind. Well, there's a reason that my body is bubbling it up to the top of my mind. I also practice transcendental meditation, so I'm very keen on the idea of being aware and listening to what's bubbling up. And so it's okay for me to then go and attend to that thought, as opposed to start to expend my focus points or my discipline or willpower on the thing that I thought I was meant to be doing. All I'd have to do is I'd go back to Slack TS colon dealing with this other thing. And by the way, you should obviously turn up for your meetings. I'm not saying just like a blow through your meetings and not turn up for your one on ones. Definitely do those things.

• 22:45Speaker 01

  What I'm saying is do what feels right for as long as it feels right to do. Then at the end of the week, you can see where your time is going. And I realized at one point that I was spending only in those days, like 5% of my time on recruiting. Whereas perhaps I should be spending 20 or 30% or more of my time on recruiting. But the biggest thing was I saw I was only spending six to 7% of my time on product, on design, on technology and marketing. And these are things where I know I'm really good at them. I should either be teaching people how to do them or doing them or some combination of both. That's probably the best thing for me. It keeps me really happy, very joyful, keeps me sharp, but it's also scaling the organization. And so that's how we had that kind of an insight.

• 23:30Speaker 01

  Once you have this Slack log, you can then graph it and chart it and see where your time is actually going.

• 23:37Lenny Rachitsky?

  How cool. Clearly, this is an app opportunity or like an agent opportunity where you're just telling this thing every time. It's essentially tracking context switches, which we're always hearing. Try to not to avoid context switches.

• 23:49Speaker 01

  Yeah, I think context switches are fine. I mean, there's definitely this idea that for every interruption you have, the brain does take roughly 21 minutes on average to recover, to get back to the efficacy before that you were disturbed. And it's a big deal. Of course, I'm building productivity software. We design Superhuman to minimize the amount of distraction and disruption that's possible within the app. But if you're working on something and at the back of your mind, something bubbles up, you have to attend to it in one way or the other. Sometimes I just write it down and I have a, actually, I don't have my notebook with me, but it's really big. I have like a gigantic, whatever twice the size of A4 is, I guess,

• 24:29Speaker 01

  A3 sketchbook. And I always have a 4H pencil. So whenever one of those thoughts comes up, I just scribble it down or I actually stop what I'm doing and I attend to that task. Because there's a reason it's bubbling up right now.

• 24:44Lenny Rachitsky?

  I love that you know exactly the type of paper and pencil for each pencil, A3 paper.

• 24:50Speaker 01

  Very specific.

• 24:50Lenny Rachitsky?

  Very, okay, this is gonna be a theme. You mentioned meditation, you said you do TM. So you do 20 minutes in the morning, 20 minutes, do you do it that style or you do a longer session?

• 25:01Speaker 01

  I do about half an hour in the morning, including rest time. The physical rest component of it is very important to me. It's 20 minutes of the actual meditation, then 10 minutes of rest. And I do that in the morning as well as in the afternoon at around 3pm.

• 25:13Lenny Rachitsky?

  And you just carve that out in your calendar, you know, everyone knows Rahul at 3 o'clock, he's gonna be out.

• 25:17Speaker 01

  Absolutely. And my EA knows, they are the one who's organizing the calendar and making sure things happen when they need to happen. They also know that nothing can override this TM block. Without it, I genuinely start to fall apart. But with it, I'm able to access some very deep competencies that I didn't have before. I've been doing this now for about four or five years. And initially, I simply felt happier, occasionally even more euphoric, coming out of a really great meditation session. But 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.

• 26:02Speaker 01

  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.

• 26:25Lenny Rachitsky?

  Folks wanna, if they're inspired and they wanna check out this form of meditation, any advice on where they could go learn?

• 26:32Speaker 01

  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. If you're in the Bay Area, this person's name is Laurent Valosek.

• 27:14Speaker 01

  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.

• 27:30Lenny Rachitsky?

  Thank you for sharing that. That is very actionable. We're going to link to that in the show notes. Okay, I'm going to 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 I don't want to, spending most of my time on the product and design and marketing, amazing. What did this president take off your plate? And what is their responsibility and that allowed you to do the stuff you wanted to do?

• 27:58Speaker 01

  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 very growthful role. Like it is, it's 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. In addition, because that's not the only job, in addition, they're also a very strong

• 28:41Speaker 01

  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 and D strategy? Should we keep on hiring in the Bay Area? Or, as we've done for many of our recent hires, shall we continue hiring in Latin America? Should 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.

• 29:25Speaker 01

  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, Comrade 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.

• 30:07Lenny Rachitsky?

  Incredibly interesting. There's so many, 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, the solution to helping 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 on 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. And then I think it's also really interesting, there's this lesson here of 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.

• 30:50Speaker 01

  Absolutely.

• 30:52Lenny Rachitsky?

  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 talked 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. Let's spend a little time on attention to detail. And like I said, this was one of the things that came up again and again when I was asking people about you. So I have this quote from Ed Simms, and maybe your first investor? Were they your first investor?

• 31:26Speaker 01

  Yeah, there's a bunch of people on Twitter who are gonna fight for that. But to put it straight, Ed Sim did actually write the first three checks into Superhuman.

• 31:35Lenny Rachitsky?

  First three checks? I like subsequent rounds.

• 31:38Speaker 01

  Well, yeah, I mean, quick sidebar on that. He runs both start ventures alongside his partner Elliot Durbin. 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. So we were like the perfect investment. He also wrote a check from his previous fund into Reporative. And I think I'd made him like 5X that money. Nothing to write home about, but definitely I'm gonna back this guy again, right? And so I went to him and I said, hey, listen, I think this is gonna sound crazy. I want to take on Gmail. He said, you have a deck. I was like, yeah, here it is. One slide. Here it is.

• 32:19Speaker 01

  And there was a screenshot of Gmail with most of it scribbled out. I want to build that. It's gonna be amazing. So he said, cool, we're in. Can I wire you the money? And I said, no, I don't even have a bank account yet. I 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 gonna 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 was like, 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

• 33:02Speaker 01

  a few months back, I took another 250K as I began inventing ways and finding channels to deploy capital properly.

• 33:11Lenny Rachitsky?

  I love this story. I love all these 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 attention, the details, he said that you created your own font because existing fonts weren't good enough. Is that true?

• 33:31Speaker 01

  Kinda.

• 33:31Lenny Rachitsky?

  Okay.

• 33:32Speaker 01

  The font that we use today is a modified version of Adel 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. And that may sound like an odd thing to say. So let's, if you will, permit me to talk about typography and email. 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

• 34:14Speaker 01

  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. Number 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

• 34:54Speaker 01

  that. Or to pick another extreme, does the font work if it is informing you of somebody's passing? Many fonts are just too jaunty for that. You wouldn't want that kind of message in Comic Sans, for example. And number three, I was optimizing for a font that made reading speed and comprehension really fast. And number four, I was looking for a font that made email addresses themselves look great.

• 35:20Speaker 01

  So I discarded all the 15 because they weren't good enough. And after searching high and low, I came across a font called Adel Sans, which is designed by a foundry called Type Together, it's type-together.com. They have a whole bunch of lovely fonts. Go check them out. And if you go through my list, number one, Adel Sans is gorgeous. I think each character is a work of art. It's beautifully formed. Number two, Adel Sans is, I would say upbeat. It's optimistic, yet it's serious enough to convey any kind of message. It has just the right amount of personality, yet not too much personality. Number three, Adel Sans is also unusually narrow. And that actually fits email particularly well. One of my pet peeves with Gmail, which by default uses Arial,

• 36:05Speaker 01

  is that the lines are as wide as your window. So if you're in a widescreen, then the lines get really arbitrarily long. And the problem with really wide and really long lines is that they decrease reading speed. Because by the time you've reached the end of one line, your eyes have lost track of the start of the next line. And Arial itself has fairly wide characters, which further exacerbates that. So at 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 Adel Sans is quite narrow.

• 36:45Speaker 01

  So it actually lets us do this on quite small windows with 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, Adel Sans has very unusual treatment of the at symbol in an email address. It actually puts the base of the A in the at on the same baseline as the rest of the text. So for example, if your name has an A, my name does Rahul@Voras, three As or two As and an at. They're all actually on the same baseline. It's a small thing, but it makes the email addresses look incredibly natural.

• 37:30Speaker 01

  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 and it just looks a bit silly, in my opinion. Now, Adel Sans isn't 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 pincer-y, as it were, and what we use today is very close to retail Adel Sans.

• 37:55Lenny Rachitsky?

  And this was pre-launch or this was after you'd already launched?

• 37:58Speaker 01

  We'd probably had about 10, 15 users at the time.

• 38:03Lenny Rachitsky?

  So I think that's pretty contrarian, unique to be this focused on the font and the typeface before you even launched. This was like, is this even going to be a thing? Will anyone even care? And I think this says a lot about the way you think about product.

• 38:17Speaker 01

  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. We can't start thinking that way because at what point do you stop second guessing yourself?

• 38:35Lenny Rachitsky?

  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 get this right. There's also just, you know, this trap founders fall into of just spending too much time perfecting a thing that never works. And there's always advice, launch early, launch often. Thoughts there? Just like, how do you find that balance? What's your advice there?

• 38:57Speaker 01

  How much to spend time ahead of launch really does depend on the markets and the structure, the nature of your business model. For example, let's say you're building a marketplace in a greenfield opportunity. So imagine Lyft or Uber in their heyday.

• 39:17Speaker 01

  And there's a strong network effect because the more cars you have on your platform, the shorter waiting times are therefore people 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. That's actually not true of all startups and it certainly isn't true of something like Superhuman.

• 39:57Speaker 01

  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 done, which of course is now standard

• 40:39Speaker 01

  in Superhuman and every other app. So this founder was using Mailbox and was having an amazing demo day. They're working the room, they're meeting investors, they're pitching their 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.

• 41:24Speaker 01

  So he's cursing to himself, trying to remind himself everything's going to be okay, sent all the same emails from Gmail manually and they all came through.

• 41:36Speaker 01

  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 and says Gmail, he sees that yes, actually, the original emails that were queued up in mailboxes 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 overlook that. Probably a good thing that you're trying new apps. But was it horrifying? And was it like, was it really scary? Absolutely. And 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

• 42:21Speaker 01

  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.

• 42:40Lenny Rachitsky?

  This is such an important nuanced take on. There's always this debate, how much, how much to focus on craft and user 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 the criticality essentially of how of your product. So if it's email, it just needs to work and you need to get that right. You need to spend all the time. You need to get that right. This reminds me of something else that one of your early investors shared with me, Bill Trent, from First Round Capital. He talked about how speed was the thing that you just dialed up as a lever to like 11. That'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

• 43:21Lenny Rachitsky?

  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 decided 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.

• 43:37Speaker 01

  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 read a book on positioning that really influenced my thinking. And 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.

• 44:20Speaker 01

  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. And that was how I first thought that speed could be an interesting position for us. I 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

• 45:05Speaker 01

  where they were comparing Chrome render webpages and showing that was faster than an actual strike of lightning. No one had done it since then. And I then asked, will the speed reinforce 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 cocktail parties and to watch how people pitch your product to other people. And in our case, the pitches were simple.

• 45:49Speaker 01

  People would say, dude, you have to use it. It'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.

• 46:01Lenny Rachitsky?

  I'm excited to chat with Christina Gilbert, the founder of OneSchema, one of our longtime podcast sponsors. Hi Christina.

• 46:08Speaker 02

  Yes, thank you for having me on, Lenny.

• 46:10Lenny Rachitsky?

  What is the latest with OneSchema? I know you now work with some of my favorite companies like Ramp, 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.

• 46:25Speaker 02

  Yes, so we just launched OneSchema 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 holder. We 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.

• 46:47Lenny Rachitsky?

  I can tell you that if my team had to build integrations like this, how nice would it be to be able to take this off my roadmap and instead use something like OneSchema? And not just to build it, but also to maintain it forever.

• 46:59Speaker 02

  Absolutely, Lenny. We've heard so many horror stories of multi-day outages from even just a handful of bad records. We are 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 OneSchema will notify your team immediately of any data that looks incorrect.

• 47:18Lenny Rachitsky?

  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 want to learn more, head on over to oneschema.co. That's oneschema.co. The next area I want to spend time on, and I imagine will 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. So 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.

• 48:01Lenny Rachitsky?

  How far did you scale this manual onboarding phase of your company? Like, how many people did you have onboarding people? How many people did you manually onboard?

• 48:12Speaker 01

  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. Almost 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, at peak, we had about 20 people doing manual onboarding.

• 48:40Lenny Rachitsky?

  Okay, so it's not that many people. That's really interesting because I always imagined it was like a massive team, but 20 people can do, can handle a lot is the takeaway there. What was the scale, I guess, where you stopped manual onboarding? Just for folks that are like thinking about doing this and then when to stop?

• 48:55Speaker 01

  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. When 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-to-one onboarding and there's only so much that software can do.

• 49:40Speaker 01

  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? Well, we found two things. Number one, the user metrics are excellent for things like engagement, retention, product market fit score, MPS, virality. For 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, what is it that creates true virality?

• 50:26Speaker 01

  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 phenomenon era, you can actually use dollars to avoid building a first time user experience and all of the normal growth loops that you would then have to build. You would then instead focus all of your engineers on finding product 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,

• 51:11Speaker 01

  on self-service flows for products that ultimately did not find product market fit. So makes sense to do if you really want to create that brand, which I think all consumer companies need to do. And if there is, you know, 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. So if you can weave this into your strategy, I think you should, but you should also know when to stop.

• 51:39Lenny Rachitsky?

  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 like, this is awesome. So many problems solved if I just have somebody onboarding every new user. Everyone's activated. Amazing. So some of the variables you're sharing is, do you have like cheap cash to invest in? Say, like it doesn't have to be 20 people, it could be a few people to start. And then if there's like an LTV kind of ACV element of just like, are you going to make enough from new customer? I imagine that's a variable. Is there anything else you think founders should think about?

• 52:14Speaker 01

  Absolutely. You don't want to 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 is enterprise or all of the prosumers in the world, you hit a top of funnel width. It needs to be wide enough where manually onboarding no longer makes sense.

• 52:37Lenny Rachitsky?

  Awesome. Okay. Let's talk about product market fit. I know that everyone, when they think of Rahul, they think product market fit. You wrote this epic first round post that described the way you guys approached product market fit. We're not going to 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 got to figure out as a founder, right? If you don't find something people want, nothing else matters. Anything there you want to share?

• 53:11Speaker 01

  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. Number 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's, 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.

• 53:52Speaker 01

  It's called, I think, How Superhuman Built An Engine To Find Product Market Fits, or just Google the Superhuman Product Market Fit Engine. And you'll see the algorithm laid out there, fully explained and why it works.

• 54:07Speaker 01

  And I'd say the second thing is to get to products 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 products market fit engine.

• 54:45Lenny Rachitsky?

  Okay, I gotta follow this thought on algorithmically building your roadmap to increase product market fit. Talk about just what that, how one would do that.

• 54:55Speaker 01

  Well, I mean, that's, that's really the, the meat of the engine. So let's see if I can condense it here in a very easy to grok fashion.

• 55:04Speaker 01

  So let's assume for the sake of argument that you can put a number on products market fit. And it turns out you can. Very simply, you're going to ask people, how would you feel if you could 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 that grew the fastest

• 55:50Speaker 01

  almost always had more than 40% very disappointed. And 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

• 56:18Speaker 01

  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. So you then divide them into two camps. The camp for whom the main benefit of your product resonates and the camp for whom it doesn't. 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 product that you really love? In the early days of Superhuman, it would have been speed and keyboard shortcuts and

• 57:01Speaker 01

  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? And 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 en masse love it the most for is. So you have then articulated the subsegment of the subsegment that it makes sense to pay attention to.

• 57:43Speaker 01

  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. And 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.

• 58:13Lenny Rachitsky?

  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 in this way in some form?

• 58:24Speaker 01

  We don't run the engine as is for Superhuman as a whole. There are enough subcomponents of Superhuman now that are almost individual products. For 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 salesperson 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.

• 58:59Lenny Rachitsky?

  Awesome. And the way you ask this question is an in-product interstitial sort of survey pop-up thing?

• 59:04Speaker 01

  You can do it however you want. The way Sean initially benchmarked the number was via email surveys. I think email surveys work 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 invalidated. So it's just a new baseline going forwards.

• 59:25Lenny Rachitsky?

  Got it. And we had Sean on the podcast and he describes this method in detail. So folks who 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 some 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, oh, Zynga, Farmville, I don't want to do that. We 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.

• 59:57Speaker 01

  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 of backing into where we opened this conversation, which is you're making a brand, you're giving reason for word of mouth. It's actually an altogether different kind of product development. So how do we do this? Well, as you said, it's not gamification, that doesn't work. Game design works, but game design is not gamification. It's not, for example, simply taking your product and adding points, levels, trophies or badges.

• 1:00:40Speaker 01

  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 aged 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. And 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

• 1:01:25Speaker 01

  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? What's happening here is researchers differentiate intrinsic motivation and extrinsic motivation. With 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.

• 1:02:09Speaker 01

  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.

• 1:02:18Lenny Rachitsky?

  What makes something, I guess, like a game? I know Superhuman is really good at this, of just like your In Box Zero quest that you're on. I guess, just to make that a little more real, what is game design? What does that mean to you? Like, what makes it feel like a game?

• 1:02:31Speaker 01

  Well, many of you folks don't know this, but before I was a founder, you can probably tell, I was actually a professionally 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 arts 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. So a question I like to ask is, are toys the same as games?

• 1:03:17Speaker 01

  They do seem different. For example, 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 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 autocomplete. 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. For example, if you type in two D, that becomes two days, three H is three hours, one M O is one month.

• 1:03:59Speaker 01

  And the time autocomplete 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 the 10th at 10:10pm. Or how about the series of twos? Well, that's February the 2nd, 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. You 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.

• 1:04:45Speaker 01

  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 it had like a little shrug emoji at the same time. So, you know, 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? If so, you have a toy and you can combine that with other toys and actually start to build a game.

• 1:05:28Lenny Rachitsky?

  If people were to listen to this 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 might be helpful to folks?

• 1:05:58Speaker 01

  I 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. Because of that, we're very confident in saying that Superhuman is the best email tool on the market

• 1:06:40Speaker 01

  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. But once you understand your positioning, you can then move on to pricing. And one of the best books on this is a book called "Monetizing Innovation" by Madhavan Ramanujan. And Madhavan covers a lot of ways to develop pricing. We used one of the easiest methods, which is the Van Westendorf Price Sensitivity Meter. And in the early years, we asked, I think it was around 100 of our earliest users, the following four questions. Number 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

• 1:07:24Speaker 01

  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 is humanly possible at the top of the funnel.

• 1:08:05Speaker 01

  But the price point that supports our best-in-class, best-in-cattery 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 in 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. You know, for example, we're a venture-scale company, but at the time, the question that we had to ask is, could we grow into a billion-dollar valuation? Well, let's assume that at that point, our valuation is 10x our ARR. So our ARR would have to be $100 million. Well, that would be 300,000 subscribers at $30 per month.

• 1:08:51Speaker 01

  And that is conservatively assuming no other ways to increase ARPU. You mentioned price increase, you can also go at market, you can sell new products and so on. 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.

• 1:09:13Lenny Rachitsky?

  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 unlock. 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 is a really interesting way you guys operate. So let's talk about AI first. It feels like, like, there's this, like, being in the right place at the right time. It feels like you guys, like, 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 what, how you think about AI integrating into what you're doing, how it's enabled you to kind of take off again.

• 1:09:52Speaker 01

  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. Our first AI feature was Write with AI, jot 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 Copilot, unlike Gemini, unlike basically every other email app, the 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.

• 1:10:33Speaker 01

  Number two, our next AI feature was Auto summarize, which shows a one-line summary above every conversation. And as new emails arrive, it updates instantly. Again, unlike Copilot and Gemini, it's pre-computed. One 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 are AI-written and sent with Superhuman has grown four times, just in one year.

• 1:11:20Speaker 01

  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. And 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 Q1 offsite? 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

• 1:12:02Speaker 01

  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. It'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.

• 1:12:46Speaker 01

  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 drafting replies to basically every email that needs a response. And 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 and 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.

• 1:13:28Speaker 01

  With workflows, I can now automate this entire process. And it's, you can imagine sort of creating a little flowchart of what has to happen. Not only does that save a huge amount of time, with workflows, you don't even have to be in your inbox. In fact, you don't even have to be working. You could be on vacation while Superhuman AI is working for you.

• 1:13:53Lenny Rachitsky?

  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. Our underwater cities and flying cars and then just email that 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 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?

• 1:14:25Speaker 01

  I 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.

• 1:14:40Speaker 01

  This sounds like a commodity feature and on a surface level, it is. Every email app, every writing surface has a Right with AI feature in. I would wager ours 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. Thirty-seven times per user per week is still mind blowing to me.

• 1:15:07Speaker 01

  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 Kramer, but basically, everything I thought would work out well. People use it less than I thought they did and everything where I was like, I don't know, but let's build the thing. People love that, so.

• 1:15:32Lenny Rachitsky?

  Interesting.

• 1:15:33Speaker 01

  Yeah, maybe I should just create an anti-me to do AI roadmapping.

• 1:15:37Lenny Rachitsky?

  That's a simple agent right there. Whatever a hole says, do the opposite.

• 1:15:41Speaker 01

  Yeah.

• 1:15:42Lenny Rachitsky?

  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 consumer-y, it's like for people. And you guys are doing a lot of work to make it a B2B enterprise product. For founders, maybe that are starting to think about this, transitioning from PLG to sales-led and B2B enterprise-y. 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?

• 1:16:10Speaker 01

  In 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 their 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. Outlook users. Yeah, Outlook users are also used to certain safeguards,

• 1:16:53Speaker 01

  like if you've used Outlook in an 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. But in some ways, it's very different to selling to pro consumers because there are other stakeholders involved. For example, we've built support for enterprise mobile management by implementing Microsoft Engine. 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,

• 1:17:38Speaker 01

  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. For 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.

• 1:18:14Lenny Rachitsky?

  Wow, okay. So it sounds like essentially just building all these features that large companies need is kind of the road you're on right now.

• 1:18:21Speaker 01

  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. For example, companies this large have workplace 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.

• 1:18:47Lenny Rachitsky?

  We had a linear on the, they had a product from linear on the podcast, Non, and he actually, I don't know if you heard that episode, but he talks about how the, 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. I don't know. Anyway, I want to end on one more nugget. Okay, I'm glad we have time for this. So you shared that you have this system internally at Superhuman for making decisions. You call it single decisive reason.

• 1:19:19Lenny Rachitsky?

  SDR, what is that?

• 1:19:22Speaker 01

  SDR is a thinking tool that I picked up from Reid Hoffman during my time at LinkedIn. And the idea here is that for important decisions, you should be able to identify one, 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. Imagine you're 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 effort of thinking them through, the time it took to write them

• 1:20:03Speaker 01

  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 X, Y, Z, and there are multiple reasons, I'd ask them, what's the SDR? What'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.

• 1:20:44Speaker 01

  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.

• 1:21:11Lenny Rachitsky?

  That is very cool. So this is just when you're, when someone comes to you with a decision, the way you use this idea is you ask them, what's the single decisive reason?

• 1:21:20Speaker 01

  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 that's just a bar for a good decision.

• 1:21:40Lenny Rachitsky?

  Why is that so important? Because you've found that just like a bunch of low quality reasons just don't add up to a good reason to do something.

• 1:21:50Speaker 01

  Multiple reasons, which is ironic, but that's that's my SDR for why SDRs work, which is yes. Multiple low quality reasons rarely add up to a 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. Now, 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. I mean, you just did that to me. What's my SDR for SDR?

• 1:22:30Lenny Rachitsky?

  There we go. Rahul, is 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?

• 1:22:43Speaker 01

  I feel good. So I think we covered a lot. Thank you for asking amazing questions. This is really fun.

• 1:22:50Lenny Rachitsky?

  This was incredible. Okay, so let me just ask you this then. Where can folks find you online? Where can they check out Superhuman? What should they know? Before they try it out? And then just how can listeners be useful to you?

• 1:23:02Speaker 01

  If you want to find me online, I'm generally on X. That is x.com/RahulVohra, R A H U L V O H R A. And my DMs are open, so for your fee to ping me. If you're going to do that, I would suggest also emailing me. That's [email protected]. And hopefully I'll see your 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, give it a shot, invite your team. The metrics are real. I know they sound like the kind of metrics that startups make up, but getting through your email twice as fast, responding one to two days sooner,

• 1:23:46Speaker 01

  saving four hours or more every single week, they're all real. Actually, speaking of which, the consulting firm I mentioned earlier.

• 1:23:56Speaker 01

  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 out. If that sounds interesting to you or your company, please do give it a shot.

• 1:24:25Lenny Rachitsky?

  That is super cool. Reflecting back on what I imagine this conversation would look like, a lot of contrarian thinking and attention to detail. I think that's exactly what it was. Raul, you're awesome. Thank you so much for being here.

• 1:24:38Speaker 01

  Thank you. Bye, everyone.

• 1:24:40Lenny Rachitsky?

  Bye, everyone.

• 1:24:43Lenny Rachitsky?

  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 leaving a review as that really helps other listeners find the podcast. You can find all past episodes or learn more about the show at lennyspodcast.com. See you in the next episode.