#12: Rahul Vohra, Superhuman

Welcome to From Startup to Grownup, the podcast. My name is Alisa Cohn. I'm an executive coach, an angel investor, and the author of From Startup to Grownup. Each week I talk to founders, creators, advisors, investors, and builders of all kinds about their insights and experiences in going from startup to grownup. This is episode number 12, and I'm thrilled to have Rahul Vohra. Rahul is the co-founder and CEO of Superhuman, which promises blazingly fast email. I use Superhuman myself and so do tons of my friends. Prior to that, Rahul was the co-founder and CEO of Rapportive, which they sold to LinkedIn in 2012. We had an incredible conversation. We talked about a lot of the lessons he's learned from being a serial entrepreneur how and why he learned to meditate, and what he's gotten out of working with his various therapists and coaches. We also discuss the specifics of how he builds trust with his team, the best tool I've ever heard of to cheer yourself up when you're stuck in the mud of your startup, and the pros and cons of being a celebrity founder. Rahul is such a rigorous thinker and has so much wisdom to share, so I hope you enjoy this incredible conversation with Rahul Vohra. Rahul, welcome to the show. I'm so excited to talk to you today, and I wanted to start off by just talking about your background as a gamer. And I know that you think of yourself as a gamer, and what I've read somewhere is that you, at this time of year, you tend to play games to sort of see what the best are from this past year. Are you playing a bunch of games right now? And what's your favorite or your biggest takeaway from the games that you're sampling?

Yes, I am. And normally I play very narratively driven games. These are very enjoyable for the narrative themselves, but also because they provide case studies on how to tell captivating and engrossing stories. But right now I'm actually playing a very different kind of game that some of our listeners may know called Borderlands 3. It's an older game. It has a relatively loose narrative, but it is nevertheless still an excellent case study on game design. It's essentially a cooperative shooter, and it's fascinating to see how they scale the experience so that it's fun for players of different skill levels all the way from novice to expert. And not coincidentally, that's something I think a lot about for Superhuman. How do we ensure that it is fun, that you get into flow whether you're a novice or an expert?

Wow. So what have you discovered?

Well, one of the interesting things that they do is they actually scale the difficulty, the challenge racing of the enemies that you're up against depending on how leveled you are as a player. So even though you're in the same game and I play with two other friends and we're up against the same set of enemies, the difficulty in overcoming those enemies depends on how far your own character has progressed. So it's actually fine-tuning the difficulty curve, which results in personalized flow for each individual player.

I love that you're both enjoying the game and getting so much out of it. I'm sure there are a lot of takeaways for you with Superhuman.

Yes. One of the things that we study quite intensely is flow, and game design ultimately boils down to the creation of flow. So there's a lot that we can transfer from game design into building amazing products.

Well, I certainly want to get into everything, um, about building Superhuman and also before that Reportive, but I also want to start with, um, You know, your past experience, even before Reportive, I know that you tried a number of startups that didn't necessarily work out. So can you tell us what some of those were and why they didn't work out? And even more importantly, what you learned from those experiences?

The startup just prior to Reportive was called Mojo, and we had figured out how to do part of what AngelList is doing today, equity crowdfunding, and make it work with EU legislation. In other words, we had found a way for startups to raise money online that actually works with EU public securities law. Now, perhaps the coolest thing about Mojo was the domain, which was mo.jo. In case anybody is wondering, the top-level domain there belongs to the country of Jordan. It looked really cool, but it did have the unfortunate side effect of dropping off the internet every now and then. I suppose one of the lesser lessons was this: when you can, get your .com domain. But the biggest lesson for me is that I'm much better as the CEO than I am in any other role. For Mojo, I was a co-founder, but I was not the CEO. I was the CTO. And when I could sense things going awry, it was very difficult to act on in a decisive manner as our CEO, who was and is brilliant, was going to stick with the direction.

So it sounds like That was like the insight for you was that you really have to be the one who's a decision maker.

Yes, I think that'd be a good way of summarizing it. I've often had coaches reflect it as some people make great soldiers, some people make great generals. It's very rare that the same person is going to be excellent at either.

Mm-hmm. You know, I've heard a lot of founders, in particular founder CEOs, feel like they're kind of unemployable and so they had to start their own company?

Well, I think that happens for a whole variety of reasons, but it is definitely the case that the longer you are a founder CEO, the longer you are unemployable because the skill sets that you're developing is that of being a founder and a CEO, which can be very valuable to some companies, but not in the traditional, you're going to be an employee sense.

So you then went on to build Rapportive, which was a Gmail plugin that allowed people to see information about the senders, including their social media links and recent tweets. And I must say, I have a lot of friends who loved that product. They used to, they like were, when Superhuman came out, they felt like, oh, it's like the return of Rapportive where you can see people's, you know, social media. And you then sold it to LinkedIn within 20 months for $15 million. And what I heard you say on a podcast is that one of the reasons you sold it is because you were exhausted and that maybe you could have taken a month off instead. And I later read that you actually talked about hospitalizing yourself after the experience of Reportive. So I'm just curious, like, what was that like and what was, you know, sort of the lead up to those experiences, those difficult experiences?

I did what many founders do, I think, in their 20s. I used working hard as a substitute for working smart. And with the benefit of hindsight, and this is something I am actively working on to this day, I would just have compassion for my younger self. I'm the kind of person who will beat myself up if I fail in any way. And whilst that can be powerful, it can also be quite detrimental. So if I could, I would go back and I would give myself some advice. Number 1, have a strategy and stick to it. Number 2, always raise one round ahead of traction. This is something that we've done for Superhuman. Number 3, think big with visions that scale to hundreds of billions of dollars of value creation. And then number 4, and finally, take care of yourself. Whilst you work on your startup, don't forget to work on your mind, body, and soul. Those are the things that I wish I'd known during the reportive experience.

I wanna, I wanna talk more about the sort of the working on yourself and working on your mind, body, and soul. And I would also say pacing yourself. I know the founders that I work with, they have a very hard time pacing themselves and things like panic attacks and depression are kind of normal in that environment. If you put yourself back in that experience, what do you think was driving you?

I think what was driving me was— I mean, gosh, any number of things. The joy and satisfaction of delighting our customers, the utter refusal to fail at any costs, the realization that everything I had done up until that time, I was about 26, 27 years old, was resulting in the opportunity that I had there and then, and I didn't know if or when it would come round again. The realization that my team was phenomenal. I'd come out of the University of Cambridge, which I think a lot of people who go to schools like that kind of take it for granted. So if anyone again is listening and has the the great fortune of having gone to a great school, you know, stay in touch with those people because they're going to go on and do incredible things. It becomes incrementally harder to make fast connections like that. And I could see it at the time that the team I had was utterly remarkable compared to most startup teams that, uh, that get created. So it was all of these things and just wanting to take the best advantage of what we had. And Reportive really was sort of, uh, runaway growth story. We got 10,000 users in the first 20 hours, many tens of thousands over the course of the next weeks. We were the first Gmail plugin to scale to millions of users. And in that short period of less than 2 years before we sold to LinkedIn— I didn't know this before we'd sold— but we had essentially captured most of LinkedIn's daily active users on this one platform and this one product, which is a remarkable achievement for just 5 people.

That is very remarkable.

Wow.

So, I mean, you gained all this traction, it went fast, but I, it sounds like also it just came at a cost, like for you, it just took a large toll on you personally.

I was tired. My co-founders Martin and Sam were tired, and I was working so hard, in fact, that I managed to cause irreparable damage to myself. And like you mentioned, I spent a week in hospital and I still have a hiatal hernia. And so when the offer came in, it was something that we took very seriously. The economic outcome was fantastic, especially if you adjust for the 20 months that we were running the company. But even more importantly to us was the idea that we could get Reportive in front of LinkedIn's, at the time, 250 million members. And that plan largely worked. LinkedIn finally shut it down, I think in, gosh, was it 2021 in March. And Reportive was a thing that millions of people relied upon for over a decade, which to me feels like, like a good success. And then, as you mentioned, of course, we've built it again inside of Superhuman.

Yeah. So I just want to sort of continue talking about this notion of like building yourself and, and your body and your mind, and, you know, I think also your emotional stability. And I know that now, or I've read before, that You now work with a number of coaches. You said a therapist and two different executive coaches. Is that still true? And could you tell us about the journey that you've been on since Reportive and then through Superhuman to sort of maintain yourself at your best in terms of your health, your spiritual health, your mental health, your physical health?

Yes, that's absolutely still the case. So today I work with three, I guess, coaches, one therapist. And 2 executive coaches, although they're quite different, which I can get into in a moment. And during the course of the last 4 or 5 years, I've also worked with coaches of many various kinds. I'm a huge believer in coaching as something that is very effective for me personally. For example, I've worked with a nutritionist, I've worked with a physical trainer, both of those to help me get into really great shape. I've worked with animal coaches. I've had some very difficult pets in the past. And I guess it's the founder CEO mentality. I'm not one to give up, so I just lean into the problem and try and make the best of it. But today I'm working with 3, and we can start with my therapist, if that's interesting.

Yeah, please. Very interesting.

So I started working with my therapist in about 2016, and initially we would do work just for me, such as what is my outlook on life, what is my outlook on work, or how was I feeling about my relationships. But today, I actually see that therapist with my partner. We see her weekly, and we're working on improving the quality of our personal relationship. But I think a lot of the things that we work on also translate into the work context. So she's helped my leadership in a lot of ways. And a lot of those lessons actually come from personal relationships. For example, she's helped me realize when in previous relationships, I was tolerating bad behavior. And at the time, I had rationalized it. I'd convinced myself it was okay because I'm always fighting for the underdog and I always want people to succeed. I never give up. And my therapist helped me realize that maybe that's an okay attitude in work. You don't want your founder— as a founder, you don't want to ever give up, but it's not something that you should do in a relationship necessarily, especially when it comes at the cost of your own wellbeing. Bringing that back into the company, she's helped me hold a higher bar for what it means to be at Superhuman because the company, like any of us, deserves the very best. And now I'm more comfortable in holding that bar with other people.

I love everything you just said. I mean, first of all, of course, love that you're a fan of executive coaching. As an executive coach, I'm like, yes, yay, coaching and also therapy. And I love that you've now kind of brought therapy into your own relationship, your own personal relationship. Do you think that there's still— or I guess I'll say this— I experience that people, certainly men, certainly men in Silicon Valley, you know, a certain kind, have a little bit of a stigma around getting help. And maybe a coach is okay, but a therapist makes you uncomfortable. Do you see that? And did you have to overcome anything inside of yourself to, to get that kind of help?

Actually, I don't see that at all. It's interesting, as you were saying that, I was trying to think of anybody I know who seems resistant to the idea of getting help. I think maybe there's a nuance there, which is it often has to get bad enough until it really hurts. Something has to catalyze the— provide the activation energy to get a therapist, to go through the research, to find a good one, to find one you gel with. It's a lot of work to get started. And something bad often has to happen in order to make that something that people want to do. But I don't think there's a stigma today, perhaps in the way that there used to be, at least not in my circles.

Mm-hmm. Not in your circles. Yeah, no, that's great. And can you tell us more about what you get out of your experience with your coaches?

Absolutely. So I work with two, the first of all being a meditation coach. And I've been working with my meditation coach since about 2019. Now, I've had several false starts with meditation. I've tried various apps and techniques over the years, but I was never able to stick to a practice. But then several friends recommended that I talk to Laurent Wallesek, and he comes from an organization, the Peak Leadership Institute, and he specializes in teaching Transcendental Meditation, but with the specific goal of maximizing leadership performance and potential. Now, he's been the CEO of 3 technology companies, so he knows exactly the kind of stress that I face. And I thought, well, people work with coaches for things like nutrition, physical training, executive function, why not meditation? So I now have a quite developed TM practice. I do it twice a day, once in the morning for half an hour and once in the afternoon for another half an hour. So it's a full hour of meditation per day, if not more. And I'm very excited to share that it's actually been life-changing. Now, initially, I simply felt happier, more buoyant, some flashes of euphoria even. But then later on, the effects became much more profound. I am now today much more creative, I think, than I was. And I can stay focused for much more longer. And these are really noticeable effects. So I owe all of that to the practice of TM and specifically working with a coach. Like I said, I've tried to teach myself to meditate in the past, but it just didn't really work. Working with a coach and having that kind of external commitment and obligation and tutelage was the thing that made it click.

Um, as a, as a coach myself, and also as someone who has struggled with meditation and being consistent about meditation, you're really kind of making me think that it's, it's always true that having a partner in helping you do hard things, or things that are hard for you, is always much more effective.

I couldn't agree more.

Yeah. And how about your other— was there another coach that you have? I'm so curious. About the team around you.

Yes. I also started working with a CEO coach earlier this year, and I realized that I needed a CEO coach specifically after I spent a weekend with our Series C lead investor just a few months ago. Now, it was an amazing weekend. He invited me out to his place in Utah, and we spent the weekend relaxing. So we were getting to know one another. We were hiking, we were in the hot tub, We were just chilling out, but we were also talking about plans for the future of the business. And I'd gone into the weekend, Alisa, I tell you, with a tremendous amount of stress. It had been a tough month and I had just made some really hard decisions, but I came out of the weekend very happy. I was fully energized. I was extremely optimistic. And it's worth asking what had changed. And the answer was almost nothing. The business was exactly the same. The challenges from Friday were still there on Monday. And what had changed was my mindset. And I realized that mindsets needs constant training and nourishment, much like anything else we're trying to develop. But whereas a CEO coach specifically comes in is that they're very familiar with the trials and tribulations of being a CEO. Whereas a normal therapist might say, "Oh, you seem really unhappy and you've been unhappy for a while. Maybe you should think about a different path for yourself." A founder CEO coach knows that that's not a realistic option and it's not actually what you want. But they're going to engage with the problems that you have, whether it's on the personnel side or on the strategy side or on the financing side, really whatever it is, and deploy all of the things that they've learned from being a CEO, all of the things that they've learned. In this case, my CEO coach has also been an investor and has also coached many hundreds of other very high-profile CEOs. So they're able to deploy all of that pattern matching into helping me figure out what it is that I need to do.

I think that's so powerful. It's interesting that you say a therapist would look at any founder and say, "Why are you doing this?" Right? Like, you're just beating yourself up over and over again because the intense experience of being a founder and the ups and downs of being a founder are not necessarily familiar to someone who's not been in that world at all. So I think it's like so interesting that of course you have to find someone who can, who can relate to that.

Exactly. You do need a balance between someone who's looking out for you and someone who's looking out for the business. And when you hire a therapist, they're 100% looking out for you and you definitely need that person. But if they're always 100% looking out for you, I think for most founders, there's going to be a prolonged period of time where at least they're going to ask, should you be doing this?

This. Right.

And what you really need is someone to come in and say, okay, I'm assuming you want to do this and you want to continue to do this. Let's help you figure this out. Let's fix the problems.

And can you— so it sounds like you've just been recently working with a CEO coach. Would you want to share who that is and, and what, what are one or two things you've gotten out of that experience?

Absolutely. So his name is Darren Gold, uh, I, I believe his website is darrenjgold.com. He's, uh, He's got a book, he's got lots of really incredible assets out there, and a very interesting blog. We spent the first few sessions actually focusing on founder mentality. I wanted to get to grips with that a little bit more. It's not really something I'd engaged with, with previous CEO coaches. I'd mostly gone in with relatively tactical challenges I was facing. And he's also very widely read, which is something I appreciate. After a few sessions of working with me, he had the very accurate observation. And actually, before I share the observation, let me share the questions that he was asking. He would ask things like, "Well, how do you spend your time? What do you do when you wake up? What do you do during the day? When do you finish working? What do you do on the weekend? What do you do on Saturday? What do you do on Sunday?" And for those who know me, they'll know I'm I'm a very busy person. I also run an angel fund, which I put in time on Saturday morning. I'm, as you noted, a very avid gamer. I also run a biweekly D&D campaign. I do all of these things. And then he asked me the killer question, which is, when is the last time you didn't do anything? And I was like, well, I practice TM twice a day. I spend an hour a day, not I'm not really doing anything. And he's like, "Uh-uh, that doesn't really count because you're still doing something. You're practicing meditation and there's a specific goal there. When was the last time you did nothing?" And it dawned upon me the implication of what he was saying. And I said, "Well, Darren, I actually quite honestly can't remember the last time where I did literally nothing, where I was just with myself." without an agenda, without something I was trying to do. And he was like, "Okay, I think we're starting to unravel this." And a conversation or two later, he'd recommended that I read a book, The Death Fallacy. And he thought that I am an archetypal representation of the kind of founder who is at the deepest level, operating out of a fear of death. And this isn't just with respect to the work that I do, but it's how I live my life. It's how every single minute almost has something that I'm trying to do in that period of time, whether it's work or not, whether it's a weekday or the weekend, whether it's trying to build a company or whether it's trying to advance a hobby. And it's become increasingly acute over time. As I've gotten older, I found myself feeling that I have less and less time, not just because I've gotten busier at work, but also because I genuinely feel like I'm running out of time in life. And so he was able to pinpoint that very accurately. And the awareness, of course, is just the first step with any kind of change. But now that I'm aware of that, we're starting to to deal with the implications of that? And how do I become okay with the idea that life is finite and I'm not going to be able to do all the things I'd ideally like to be able to do? And how do I get to peace with that and to really live life in the most joyous way nevertheless? So that was the first theme of work that we started with. And now that it's the middle of December and it's Q4, I think we're doing what most founders and executive coaches are doing, which is working on 2022 planning. So it's been a little bit of both of those.

Right. So from the death fallacy to 2022 planning, it's like from the sublime to the mundane, right?

Well, this is why you need specifically a CEO coach, an executive coach, someone who can flip from founder therapy, which every founder needs, to, okay, you've got ambitious goals for next year. Let's figure out how to help you get there.

Right. Right. Like, let's go do that. Right. Well, I'm glad I asked that. That's very rich. The death fallacy sounds like something I myself would benefit from. And I'm sure that people who are listening to this all feel the same way. You know, the people that I work with and that, you know, my listeners are very like, let's get everything done. And I appreciate what you said is that something's driving us. And there's, oh, I have found with myself, with everybody I work with, there's always something underneath that's driving you. And it's very helpful to your point about awareness to pinpoint that or to get a handle on that because then you can begin to unwind it in some way. Exactly. Beautiful. Wow. Well, I would love to know, I'm going to switch gears a little bit because I'm super interested in how people grow as leaders. And, you know, I'm also very, I'm a big fan of feedback. I do 360 feedback for everybody. And the founders that I work with love feedback because it's really, it's helpful to get the truth from the folks around, from folks around them. I know that you have talked a lot about I mean, you've talked a lot about the sort of the systems and frameworks that you use to take in feedback about your product, about Superhuman, and, and from the users. Do you have similar frameworks or, or a way to think about how you take in feedback as a leader, either from your employees or from other people? How do you think about taking feedback in?

I do, and I get feedback in, I would say, 3 different ways. So number 1, we run pulse surveys across the organization, and this gives folks the chance to provide feedback anonymously. It also measures happiness and well-being along a number of key dimensions. It actually gives you numerical scores around things that folk, CEOs should care about. Any leader should care about how long people see themselves staying at the company, how satisfied and stretched and challenged they are, along with a number of other things. So that's the first way. The second way is I simply ask for it. Sometimes feedback comes up in one-on-ones. And sometimes, and actually this is maybe where it's more helpful, it comes up in group settings such as staff offsites. And we're actually about to head into a staff offsite tomorrow. By staff, I mean my leadership team, the set of people who report to me. We have a very tight-knit group. So the folks on my team are very candid with me and with one another, especially in a safe place like a facilitated offsite. The facilitation is very important to make sure that the candidness levels remain high and people stay fully open and accepting and ready to receive feedback. And then third, I run unusually frequent board meetings roughly once every 6 weeks. And this was actually a mistake that I made at Reportive. We didn't really have a board. I never ran a board meeting. And so there was never really that level of accountability at a higher level. I was only at Reportive ever really accountable to myself. And honestly, that's a mistake. I think every founder, every CEO should have a high-functioning and diverse board of successful people, everything from investors to operators, to people who've had the job before, people who've been founder CEOs, who can help hold the founder accountable to the high-growth targets that we should all have.

And you get feedback from your board is what you, you were saying. You have the, the regular board meetings, and do you feel you also get feedback from your board?

I do, every 6 weeks, and then a lot of backchannel feedback as well. I have very strong relationships with every single person on the board. They're all on speed dial. I can text them any time of the day, and that's a really another valuable channel for feedback.

Mhm. And so I think that's You have a lot of processes, right? You have sort of a lot of rich ways to get feedback. What is some of the feedback that you've gotten recently that maybe you had either a hard time accepting or a hard time actioning or, you know, surprised you in any way? Anything come to mind?

This isn't a recent example, but something that it took feedback to unwind was actually when I was raising our Series B, which happened back in 2019. So I had met with an investor, David Urovich, from Andreessen Horowitz. And he had asked me, what is your sales strategy? And I was immediately turned off. I thought, we're not doing sales, we're doing one-to-one concierge onboarding. We might do it down the line, but today we're a B2C company. This is very different. I told David in that meeting, I don't see us doing B2B sales anytime soon. And I left that meeting thinking, he's not our guy. I guess we're not going to do the Andreessen deal. But I was wrong. And I'm very fortunate to have some of our earliest investors be able to help in detail with fundraising. And our first investor, Ed Sim from Bold Start Ventures, he's very close with David. And this is an example of the board helping. He spoke backchannel with David. And Ed was like, something doesn't add up here. He realized that David wasn't asking what our sales strategy was, even if those were his words. He was really asking what our go-to-market strategy was. And so Ed called me up and he explained that David and I were actually way closer than it seemed. We were actually on the same page and that I was just getting hung up on semantics and wording. And he encouraged me to take another conversation. So I did. And a few weeks later, David ended up leading our Series B from Andreessen Horowitz.

Well, that's very nice. And I think it speaks to the power, I should say, of backchanneling when sometimes you need it. I think it's really helpful to have trusted people, whether it's your board or your employees, to be able to go back and say, hey, what just happened around here? What you're talking about here is also misunderstanding, to clarify misunderstandings.

Absolutely. And when I've got feedback that maybe I do like or I don't like or I'm not sure about, I'll often get those second and third opinions from these outside experts, these people I trust really deeply. The caveat, and this is the trick, is to make sure that they present a truly unbiased picture and that you really are talking with people who will tell you how it is. You want to avoid talking to those folks who'll just tell you what you want to hear.

Yeah, that's definitely true. But how do you create that kind of environment inside of your company? Because the truth is that you're the founder, you're the CEO. Also, you have a certain kind of figure. Like, I have found you, you know, having met you in Lisbon, I found you very polite and very approachable and very accessible. But I'm not sure if you come across that way immediately. So I'm wondering, is there ever a time where you have to really proactively help people know that they could tell you the real truth?

Yeah, and it actually, it's less of a problem early on because with any new hire, you're going to develop a certain rapport, a cadence of meeting. We do a lot of social engagements as a leadership team. We're going to have a dinner tonight and an all-day offsite tomorrow, and these things build up the social fabric, which becomes the foundation of trust between me and the people who work for me. Where it's more challenging as we scale are the folks who don't report directly to me. And we've scaled tremendously over the course of the last year. We've gone from around 50 people this time last year to north of 100, including some new product managers and some new designers. And I realized I'd made a bit of a bumpy start with these folks. Halfway through the course of this year, there were some projects that were a little bit contentious because I was giving all of this feedback to the team, but without having built up the immense levels of trust that I had previously built up with all the product managers and the designers that had come before them. Because for the PMs and the designers that had come before them, I had basically hired them and I had trained them and I had ramped them. And so we had a very high degree of trust. Also, it was before COVID so we'd spent a lot of time physically in person together, whereas this new cohort didn't have the advantage of any of those things. And so there I was saying, "Here are the 25 things I think we need to improve about this design," which anyone who's worked with me and has built up trust knows that that's normal. And it's not meant as like, criticism. It's just I'm really pushing for remarkable quality. And by the way, you're totally allowed to say, "I disagree with all of these 25 things and here is why." But I realized I hadn't made it explicit that that was an okay thing to say. And that really what I was hoping for was a robust and academic debate about the thing that we were trying to build, not trying to exert any kind of authority. And so it's a classic error in scaling. Unfortunately, we course-corrected really quickly. And I went back to those folks and I apologized and I was like, "Hey, listen, I realize we didn't build a foundation of trust. Let's have regular weekly one-on-ones. Let's have those one-on-ones not just be about the artifacts that we're building, but about personal care. Let's have that go both ways. I want to really demonstrate care for you, and I'd love it if you demonstrate care for me as well. Let's have a real relationship here." That's going to be the foundation of trust for the work that we're also trying to get done.

How did you realize that? How, like, when you were giving them all these, you know, things and you got off on the wrong foot, what made you realize that you had gotten off on the wrong foot with those folks?

It was feedback. Not necessarily directly, but from folks who mutually work with them who said, you know, the way that you handled yourself in that meeting is fine for someone who knows you and with whom you've built trust, but for someone who's just meeting you can be a little bit overwhelming. And so they're actually quite upset. I recommend you have a conversation with them.

Did you at all fight back against that? Like, oh no, I, you know, it's obvious what I meant. Or did you just say, oh, okay, thanks?

I honestly can't remember the specifics of the conversation. I'm going to guess I had some level of defensiveness. I probably tried to explain myself for a minute or two, but at the end of the day, look, if someone is unhappy, they're unhappy, and it kind of doesn't matter whether I think I did the right thing or not. It's my responsibility. I created some discomfort there. And so pretty quickly I just owned it. And the next week I was having those one-on-ones and reflecting and trying to diagnose what happened so that we could build a better working relationship going forwards.

I kind of want to say it's so complicated, like dealing with people, right? People bring their own baggage and you think you're just being you and they think they're just being them. But I think at the end of the day, you've put it very well. And in some ways it's simple in the sense that it comes down to rapport and trust and knowing each other. So then they give you a break when you make a few missteps, and that you also give them a break if they don't kind of catch it all at the same way the first time.

I agree. I would also add two more things. I think genuine symmetric care is crucial for any relationship of this kind, and also, uh, social time, just actually spending time together. One of the best things we did as a product and design team is we did a week in San Francisco This was just a month ago or so. And then for 2 days of that, we actually went up to Sonoma. We went to some really great restaurants. We hung out. We stayed up until the wee hours in the morning. We played beer pong, whatever it is. We just had a good time. And the feedback that I got after that was, "Oh my God, this was incredible." Because the new PMs and the designers on the team, You know, they see I'm just another person, right? And I'll have a drink with you or I'll have a meal with you and we're like, we'll shoot the shit and it's fine. And that just creates a much more friendly, collegiate atmosphere whenever we're actually discussing a work artifact like a design or a product specification.

Right. I love that. It's so, I think that time away from work is so important. It's hard because actually everyone's busy and founders aren't always oriented that way. So, I appreciate that you've sort of seen the value in just going and hanging out together for a sustained period of time.

Absolutely. And it's always fun. I'm always down to hang out. It's never a bad time.

Right, right. And what we've been talking about here, and you mentioned this a little bit, the idea of culture. So, I guess I'm interested, especially because you had some startups that didn't go well, then you had Reportive, which went well, and now Superhuman, which is going really well. How have you grown or changed, if at all, in the way you think about culture and how important culture is when building a company, including maybe it's not something that's on your mind? I'm just curious how you've thought about culture as you've changed as a leader yourself.

Well, at Reportive, I didn't really think about it. And when you're 5 people, it might be a little premature. Culture is the 5 people that you are. But today, it's hugely important to us. So for example, during hiring, we look for really strong alignment with our company values. Our company values is the way that we codify and spread the culture. And I think that most companies take a few iterations to get their values right. They often write down vague concepts that are table stakes and which don't really differentiate them from any other company. So to avoid this, we went through a fantastic process from the book The Advantage by Patrick Lencioni. And in the book, Patrick introduces the idea of core values. And even better, he gives you an efficient process for identifying them. Now, core values are those which you can credibly claim to uphold more intensely than 99% of all other companies. That's his definition. And they are so important that you would continue to uphold them even if they would be detrimental to your company. So let's just let that sink in for a while. These are things that are so important to you that even if you know they're doing harm, you're still going to uphold them. That's why they're so special. And for Superhuman, our core values are create delight, be intentional, and remarkable quality. And so these are things that we now screen for in every single interview that we have.

Is there a way that you can imagine that it would actually— that these core values would be detrimental to the company?

Sure, absolutely. I think the most obvious one— actually, they all share the same potential flaw, and it's probably helpful if I just explain what the values are, and then I think it'll become obvious how they could be detrimental. So create delight, that I would say is our most important core value, our super value, if you will. Superhuman exists to create delight. And this value stems from my background in game design. Now, in game design, which I actually used to do professionally before I was a founder, we define a very specific definition of delight, which is pleasant surprise. So imagine a delightful moment that you experienced. It would both have to have been pleasant to experience and also surprising. And it's that combination that makes it delightful. The next value is be intentional. Whilst create delight talks about what to do, be intentional talks about how to do it. And those who know me and the others at Superhuman will know that we are incredibly intentional. We don't act arbitrarily. Instead, we act with reason, thought, and deliberation. And we've found that this trait is quite rare and we really care about it, so we made it a core value. And the last value is remarkable quality. It's not enough to just create delights and to do so very deliberately. We also strive for exceptional quality in everything that we do. And so we love to work with people who are excited to produce work that is striking, worthy of attention, and a contribution to the state of the art. So I think the unintended consequences of these then become clear. Do your customers care that your work is a contribution to the state of the art? Did my customers care that I obsessed so hard about product-market fit that we actually rewrote the whole way that Silicon Valley does that? No, they probably don't. It's completely arbitrary. But I care so much about advancing the state of the arts, even if it's in the processes of how we do products, that I'm going to push myself to that level. Now, the downside is that that can take time. It can be distracting. Do your customers care that you're being super intentional and thoughtful about decision-making? Maybe down the line, if you get all of these things right, but it's definitely going to slow you down in the short term. Now, we've made the choice that that's the kind of company we're going to be, and we're always looking for ways to do these things, but to do them quickly. But you definitely do sacrifice some things which you might have if you chose the opposite set of values. For example, if you had Facebook-style values, move fast and break things, that's the literal opposite to everything I just said. Move fast implies maybe taking decisions less intentfully and caring less about delight and sacrificing quality. But that would be an anathema to all of the people who work at Superhuman. Mm-hmm.

And also maybe to you and your makeup, like you're just not made that way.

Oh, absolutely. And these three values are a direct reflection of also my personal values, which I think is very important for any founder CEO. If your personal values and your company values are even slightly at odds, you are going to be unhappy. So they should be very one-to-one.

You know, on that topic, since you mentioned move fast and break things, which is another, you know, sort of in some ways has been a Silicon Valley rallying cry. I think things are changing now. But there's another rallying cry that I've heard, which is the idea of building in public. And if you're not embarrassed by your first version that you ship too late. But I know that, that again is not really not what you just said. And also I know you waited quite a while between founding the company and building the product, then finally launching Superhuman. So I guess I'm wondering, is, are those kind of platitudes wrong or they're just not you? And, and what was there a downside about waiting so long to launch?

I don't think so. And I've seen a lot of companies, especially in our space, which I would broadly define as productivity and collaboration, basically get this wrong. Now, I personally no longer believe in the traditional launch. Let's say you've built a new email client or a new task manager or a new calendar app. The surface area for these products is absolutely massive, bigger than almost any domain you could think of. And what that means is you also get a massive surface area for bugs, as well as massive variability in how users want to use the product. Now, traditionally, most companies would launch their app, and because the demand for these products is so high, they would quickly get tens of thousands of users. Today, that's not that impressive. But guess what? These users will find thousands of bugs and the company would quickly get overwhelmed. The company would not be able to fix the issues fast enough. And so those users will become disappointed, they'll churn out of the product, and then they'll tell everybody about their experience. This is the very definition of a net detractor. And so in my experience, it's significantly better to do what we do, onboard customers at a measured but increasing pace every week. And that way you then have the bandwidth to fix any issues they find, and you can focus on making them exceptionally happy.

Also, I'm just reflecting on my own onboarding, which was a couple of years ago, and there was a delight actually in talking to a human being when someone onboarded me onto Superhuman. I was like, oh, this is like so, it felt so, I don't know, white glove, I guess I would call it.

That was the idea. In fact, we even have used that phrase internally for a very long time.

So, going, just going back to the idea of, you know, sort of taking this much time to launch, what I've heard you say is that, you know, you had an internal stress about it, that on the one hand, you had these incredible engineers working on this thing and you were sort of, it was almost like I picture you holding back these thoroughbred horses, um, from launching. And maybe it was hard for you to talk to them about, you know, why we're waiting, you know, sort of, can you talk about what that was like pre-launch and how, I think, bigger picture, how you navigate the times when you need to be transparent and want to be transparent, but also maybe can't be transparent?

One of the key things that I was looking for before we do a big launch was this notion of product-market fit. I think most of us know what that is, but in short, it's the number one reason why startups succeed, and the lack of it is the number one reason why startups fail. Various folks have pithy definitions. Paul Graham would say it's when you made something people want, and Sam Altman would say it's when users spontaneously tell other people to use your product. But the definition that is the most vivid and which has always stuck with me, is Marc Andreessen's. And he would say, you can always feel it when product-market fit is not happening. Customers aren't quite getting value, users are not growing that fast, word of mouth is not spreading, the press reviews are kind of blah, and the sales cycle takes too damn long. But you can always feel it when product-market fit is happening. Customers are buying as fast as you can add servers, you're hiring sales and support as fast as you can. Reporters are calling you about your hot new thing. Investors are staking out your house, and money is piling up in your checking account. Now, the thing is, I couldn't just say to my team, "We don't have product-market fit." Because if we were using Andreessen's definition, the rational response is, "Cool, let's try it and see. Let's see if reporters are constantly calling us and money piles up in our checking account." But as we just discussed, that's how many companies fail, and I was personally extremely confident that "try it and see" would not go well. And so I took it upon myself to search for what felt like the holy grail for a way to define product-market fit, for a metric to measure product-market fit, and for a methodology to systematically increase product-market fit. Now, for those who followed my journey, I did actually find all of these things, and I came up with what we now call the product-market fit engine. And this has kind of become the new standard for what almost every venture-backed company does to measure whether or not they have product-market fit and to help themselves get there. And back to Superhuman, with this engine, not only did I have a way of measuring how we benchmarked, I had a way of showing that to the team and I also had a way of systematically generating a roadmap that I could show would lead us to success. So this is the big difference between saying to your team, hey folks, I think we have a problem, and saying, hey folks, I think we have a problem, but here is an algorithmic solution. Here is a plan which, if we simply follow, will lead us to success. And ultimately, that's what I think folks are looking for out of their leaders.

Mm, I absolutely agree with that. And didn't it take you kind of a long time? I mean, you know what you've just said, and I certainly did follow your journey in the first round review article. And, you know, I really admire that you— it's almost like you created a new category in a sense of product-market fit. But that took you some time, no? And, you know, I was wondering how you communicated with the, with the team as you were sort of searching this out yourself.

It was a thing that had been at the back of my mind for a very long time. And actually, even in the first week of Superhuman, I sketched it out poorly and incoherently on a whiteboard for the 4 or 5 of us who were in the room then. I only really turned it into a polished presentation, I believe, in early 2017, I think it was. Early 2017 was the first time, and so for context, this was maybe after 2 years of full-time work with the team, was the first time that I had taken this set of ideas. I mean, it's kind of a radical idea, the notion that you can measure product-market fit and then algorithmically make that number go up. It was the first time I had taken that, really polished it up, and presented it to the entire company. I think there were maybe 12 of us at the time at a whole company offsite. And I was really putting myself out there and I was saying, "Hey folks, this is the path to success. If we just follow this, everything will work out." And it really worked. I think it was a compelling and watertight story, fully resourced with links for people to read up on these things and articles that I had drawn from. And people left that offsite energized and excited for us to use this methodology to get to success.

Yeah, I just love your rigor. And you talk about that. So you talk about that time and there were 12 people in the company, and I guess now you have 100 people in, in your company and, you know, probably more by the end of next year. And, and as the CEO of a fast-growing startup, what I observe, and I'm sure you can relate to this, is that your job changes like every 6 months, certainly every year. What are some changes that have been the most challenging for you? Or, or maybe what are the most, um, I guess I would say the, the inflection points that stand out to you as you've grown as a CEO, as your company has grown, and what have been the most challenging for you to navigate?

I think the most challenging change occurred just after raising our Series B. Up until raising our Series B, we had been exceptionally scrappy. Instead of hiring people who knew how to do things, we always took the approach of figuring out how to do those things ourselves. But when you raise a Series B, this— and this may sound obvious in retrospect— but this becomes the wrong trade-off. At that stage, founders need to start hiring experts, and not just experts, executives, people who have built their teams multiple times before and who can preempt everything that will happen over the next 2 years. People who have done this stage of the journey several times before. And I think that's a real mindset shift for most founders. And it took me well over a year to realize what I should have done is immediately after raising the Series B, I should have intensely focused on hiring world-class executives.

And you must have corrected that. I mean, I think you must have decided, sort of seen that and then decided to make a change. Is that right?

Oh, absolutely. And my board was telling me, "Hey, you need to hire people who've done this next stage of the journey. Trust us, you're going to regret it if you don't." And I was like, "Yeah, yeah, yeah. I'm still just trying to figure out how to hire engineers." And I always had an excuse. Of course, the ironic thing is us trying to figure out how to hire engineers or salespeople or whatever it was, is the very thing that executives will come in and just know how to do. And so there's this shift in— you don't have to figure everything out for yourself anymore at a certain point. And I think many founders make that shift way too late because by definition, we're good at figuring things out. Like our whole raison d'être is to go into a market that we may not have full information on that maybe doesn't even exist yet. We're going to make our stamp, we're going to make our dent in the universe. But you don't want to be doing that for literally every aspect of your company. That's just too much innovation and too much figuring out to take on. Where possible, you should be hiring people and bringing folks in who already know how to do those things.

Right. At the right stage, not doing it too early because then that brings its own challenges.

Of course, not doing it too early. And it's fairly obvious that you can't do it too early. You don't have the money. And they wouldn't want to work for you anyway because you're not at that level of traction. Most people leave this way too late.

I think that's very insightful. Was there anything inside of you, if you think about your own personal growth during that period or even later, that you feel like you had to grow something inside of yourself to be the kind of person to sort of expand your capacity in your internal state to overcome challenges?

I don't think so. I think that the biggest personal change has really come out of a combination of working with the 3 coaches, the therapist, the meditation coach, and the CEO coach. And the net output of that is I'm probably, I don't know, 2 to 5x more emotionally resilient today than I was 3 to 4 years ago.

Mm-hmm.

And this is important because the companies become no less chaotic over time. Indeed, the swings up and down just get on an absolute scale, larger and larger. And one of the things that a founder needs to do is to increase their own emotional reservoir to accommodate that.

Yes. That's very well said. I think for you, this is not true for all founders. In fact, very few founders. You know, Rahul, I sort of see you as like a celebrity CEO. You're very well known. You have a lot of things out in the world. People reference you. I guess, with your high profile, you're kind of famous. What prepares you to be so well known, or what have you observed about that status for yourself and kind of what are the upsides and what are the downsides of that?

Well, as being well known goes, I wouldn't say I'm that well known, but to the extent that I am known, it does come with some, I would say, upsides, some downsides, and some random side effects. The main upside is credibility. And as a first-time founder, I remember pitching investors and candidates, and in either case being met with major skepticism.

Them.

And as an unknown entity, they were all wondering whether I could execute, whether I could build a product that people love. And as a serial founder, and having done precisely that a few times, I can fortunately skip that part. Investors and candidates alike today can see that track record, and they can confidently believe that we can and will execute, and that we do build products that people love. We know how to do that. Another aspect of the upside is it makes certain channels easier. So for example, I do a lot of TV media. I was on Fox Business News this Monday talking about my angel investing and what the latest is at Superhuman and how next year we're going to bring it to the hundreds of millions of people who use Android and Outlook. I was on Yahoo Finance just the week before talking about our latest mental health and wellness reports. I'm also regularly on CNBC and I'm covering other things. I've covered Apple earning reports, the Roblox IPO, the DoorDash IPO. But because of my profile as a founder and as an investor, it gives just a— and I think because I've had decades of personal speaking training and public speaking training, I'm able to get some of these PR opportunities, which— and it's a very long game. It doesn't always reflect back on Superhuman, but often it does. And that's very valuable when it does. Now, the main downside, unfortunately, are impersonations and attacks. Attackers are constantly trying to impersonate me, pretend to our employees that they are me. And one particularly intrepid scammer has tried to launch a fake cryptocurrency in my name. Spamming all of my Facebook contacts in the process. So I think that kind of comes with the territory. It's super annoying, but you just have to deal with it. And I would say a random side effect is just being approached when out and about. Fortunately for me, this only happens in San Francisco. I can't imagine what this would be like if you're an actual celebrity and this happens in every city. That would be very frustrating. It only happens in San Francisco where folks will say they'll always say hello at a cafe or a restaurant and at a bar. But I will say, as an introvert, that's actually really nice because especially as a British introvert, I normally would never go out of my way to talk to people that I didn't already know. I like to respect people's personal space and that's just how I was raised. But people approach me all the time and actually it's pretty fun because it means I'm now having conversations I otherwise wouldn't have.

Oh, well, that's a wonderful way to spin it. When you said it only happens in San Francisco, I was thinking some people are TikTok famous, but you're San Francisco famous.

I prefer the geographical restriction because to get away from it, all I have to do is leave the city and then literally nobody knows who I am.

That's great. Your public speaking training shows for sure, and you always come across as so polished and so well-spoken. Have you ever experienced self-doubt or imposter syndrome? And if so, how have you handled it?

I often experience some variants of this, and I think it's inevitable that at some stage every leader is going to feel some self-doubt or imposter syndrome. And I actually I actually might go so far as to say that if you're not experiencing any form of self-doubt, you may actually be overconfident in whatever you're doing. So I think there are two ways that I've handled this. Number one, I just simply take the time to remember what I am world-class at. And for all the things I'm not great at, and there are many, there are some things I can do really, really well, whether it's storytelling or interaction design or product positioning. And I think we can sometimes, as founders, lose sight of this, especially if we're bashing our heads all day long at whatever our current pet challenge is. So that's the first thing. And the second thing is I speak with my investors. I speak with my board, often in a very one-to-one setting. Now, I live in the day-to-day. And so I have to deal with the minute-to-minute chaos of running a company. But my investors, and I deliberately chose them for this quality, have a very long time horizon. And so they can help me refocus on long-term success, all the things that are going well, the market opportunity and how we get there. I think as founders, it's very easy because we only spend, you know, maybe a month or two every 18 to 24 months really living in the fundraising pitch when we're fundraising, it's very easy to lose sight of the ginormous opportunity because you're just dealing with the day-to-day. Actually, one trick that I would highly recommend to all founders is every few weeks or so, just go back to your last fundraising deck and literally pitch yourself. Read through it and you'll be like, "Oh yeah, yeah, this rocks. This is going to be a huge ginormous company. Yes, some things are going wrong. That's normal." Things go wrong in every company, but this is an incredible vision that we're working towards and we're going to succeed.

I love that. I, I tell the founders that I work with to put together a highlight reel, which reminds them of their accomplishments. And really, that's what you're talking about, reminding yourself of what you're world-class at. And then I love this idea of pitching yourself, going back to your deck and reminding yourself what we're doing. We're not, what we're not doing is like this annoying issue that we're trying to solve. What we're doing is changing the world in this fundamental way. It's helpful to remind yourself of that.

Exactly. And that helps put all of the challenges into context. The challenges then actually seem small by comparison to what you're trying to do. And so it's just so much easier to take them with gusto.

Right, right. I love that. I love that so much. Um, you know, my last question, there's so much more to talk about, but just, um, my last question for the moment is what advice do you have for other founders as they embark on their own journeys to grow as leaders?

What a great question. So I would say 5 things. Number 1, work with coaches. Number 2, find a great therapist. Number 3, find a world-class CEO coach specifically. And number 4, find somebody to teach you a powerful meditation practice. And then of course, number 5, pitch yourself your fundraising deck every month or so. I found that each of these has been life-changing in their own That is wonderful.

I just want to remind everybody that what he said was go find coaches for various things that will help you. But in all seriousness, I just want to say thank you. Your insights are so valuable. And to your point about credibility coming from you, I just know how valuable this conversation is and will be for everybody who listened to it. So thank you so much for joining me me today, Rahul.

Absolutely, anytime. Thank you, Alisa.

Thanks for listening to From Startup to Grownup. If you like what you heard, give it a review on Apple Podcasts so other people can find it. And if you know of a founder or someone else who is meant to be on this podcast, drop me a line through my website, alisacohn.com.