#135 with Rahul Vohra (Superhuman Founder) - Why He Started Superhuman and The Ideas He'd Like To See Built

Huh.

Yeah. I feel like I could rule the world I know I could be what I want to I put my all.

In it like no days off on.

A road let's travel never looking back.

Our guest today is the email God, Rahul Vora, founder of Superhuman, and actually a different startup that both me and Sam really love. Before this, I believe you started Rapportive.

That's right, I did, yeah.

I actually kind of want to talk about that. I think that was an awesome startup. I think he probably only knows 10% of what he's getting into with this podcast, but he seems game. And he's a brown guy with a British accent, so, you know, I already feel good. I already feel like I'm in good hands. So here we go. Explain to people who don't know what Rapportive is. Let's start with Rapportive. Explain to people who don't know what rapportive is, what it was, and then me and Sam will talk about it a little bit.

Sure. So Rapportive was the first Gmail extension to scale to millions of users. I started it way back in 2010. This is almost a decade ago now. And there, right inside your inbox, it would show you everything about your contacts, just over on the right hand side. So when somebody emailed you, you could see what they look like, where they work, their job title, and even links to their social media, like their recent tweets. So if you can imagine being the kind of person for whom interacting with other people is important, maybe, of course you're a founder, like you, or maybe you're a recruiter, or perhaps you're a salesperson, or maybe you work in bd, or maybe it's just really important to deal with people. It turns out there's a lot of folks like that as well. This thing sort of became this beloved, crucial tool, first starting in Silicon Valley and then spreading to millions of users across the world, ultimately ended up selling.

It to LinkedIn back in 2012, in 2011. So I know a lot about you. You were kind of like someone I looked up to, and I've known a lot about you since.

I know I fell from grace. You stopped looking up to me.

No, but I know a bunch of cool stuff about you. In 2011, I was a junior in college and I found Rapportive. And I was like, I don't think people understand. If you're listening now and you don't, if you're a little bit younger, younger than I am, at least you don't realize that, like, this idea of seeing people's information on the right side of your Gmail, their picture and their LinkedIn, like, that's common now. That's not special. But back then, Reporter was the first one to do that, and it was so special. And so I invented this thing, this process called Stalk and Talk. And the idea was I was going to use it to help me get a job at a company. I made this spreadsheet where I would put someone's first name, their last name, and then their URL. Like@airbnb.com and like, I would put Brian and then Chesky, and then@airbnb.com and it would give me like, 100 possible combinations of what the name or his email could be. And then I would put it in Gmail and I would highlight each one and Report would tell me which email is his, because it would show the social profiles related to each email. I ended up emailing the founders of Airbnb an interview there using Report Of. And so I was obsessed with Report Of. I followed it like crazy. I think you started it with a guy named Sam and a guy named Martin, right?

That's right. You do know a lot.

Yes. And so I, like, friended you guys on social media because I wanted to work for you guys. And then you sold it to LinkedIn for the rumor was 15 million. I don't know what the truth is, but I was all about it.

It was. It was a fun tool. And I really, really fondly look upon those times. Silicon Valley was very different back then. Of course, we're talking a decade ago.

So I remember thinking at the time, this is like, you know, when presidents are, like, kind of important ambassadors, they go to an event and they kind of have that person behind them or the earpiece that's sort of like the Whisperer, which is like, you know, this is Julie Magni. She's the. You know, she's the representative from Columbia. Ask her about her son. You know, Roger, that's what reportive was to me was like I could make everything sound personal, and I could feel. You would feel like I knew you, even though I was just getting it fed to me by my sort of earpiece on the right side, which was Reportive.

That was fundamentally the idea. And I think had I continued to run that company, one day we would have made those earpieces. We would be bringing that kind of intelligence to everybody everywhere. I think the fundamental reason was we were tired. And this is one of the lessons that I learned back then. I think if I were to be in the same situation again, I probably wouldn't sell. Now, that's not to say that selling was the wrong decision. I think it was absolutely the right decision given what the company was, how quickly it had grown, and yet how brutal it also was. So you have to remember that I sold the company only 20 months into its existence for a sum that even to this day remains undisclosed. And assuming it was a good amount of money, then it was a very efficient outcome for the amount of time we put in for what was actually a very bristle business. We'd only figured out how to make $0.15 of revenue in the entire history of the company.

Why were you tired?

I was working 12, 15 hour days. We all kind of were. It was just a really intense period and Burnout's common. I'm sure you've talked about it with other guests. It turns out the thing you're meant to do in Burnout is to take a break, right? Go have vacation for a month. All of the report of users will still be. There would have been a different solution to the problem. But we also sold. I mean, that was fine. It ended up really good for the product. I don't think that many acquirers would have been as good as LinkedIn, but that product survived for about 10 years. It only got shut down earlier this year.

But then you did something really cool that not a lot of people do. But I followed you on social media. I know this is kind of weird, but you went and bought a Lamborghini. Was it a yellow Lamborghini you bought?

Yeah, well, that was actually a few years later when I left LinkedIn, I was burned out again and I needed to take some more time off. And this time I actually decided because it wasn't really a break between Portum and LinkedIn, I actually decided I'm genuinely going to take some time off and just be me for a good year. I went out, I bought the really fast car, I had fun, and I unwound before I started Superhuman.

So Superhuman. We can talk about that for a minute. For people who don't, who aren't in the know, you guys are kind of like a darling, a media darling. You're talked about a lot. How do you describe that business to someone who doesn't know anything?

The fastest email experience ever made. If you're the kind of person who spends hours on email a day, many hours on email a week, with Superhuman, you can get through your inbox twice as fast as before, reply to important emails sooner, and even sustain inbox Zero.

And can you give some ideas to how big it is or anything like that?

So we don't publicly disclose user numbers because we are venture backed. That's something that we keep to ourselves. Other proxies or other things that people are interested in. We're about 60 people today. We've raised $51 million plus from investors like First Round Capital, Andreessen Horowitz. Mark Andreessen sits on our board. It's really exciting to be able to work with the likes of him. And let's see what else. We have a wait list for our products. That's something that people are often interested in. We now have over 360,000 people on that wait list.

Does Marc Andreessen use email differently than plebs like us?

Marc Andreessen is different in many ways to folks like the three of us. He's one of the most intelligent people I've had the pleasure of being able to work with. One of the things that I think separates Mark from most people is his clock speed, so to speak, is really, really high. And you might think, you know smart people, but there's a whole other level of high which is just immediately apparent when you talk to him. And as a result, he's also very intentional. Quite a lot more intentional than most people that you are I might meet.

What does that mean? This guy, he's like an oracle. He's kind of mystical a little bit. What does that mean? He's intentional.

This also happens to be a superhuman company value. So it's something that I put a great deal of interest and value on. When someone is intentional, they are a very deliberate thinker and actor. They tend not to react and. But they proact, they preempt, they get ahead of things. They have a model for how the world or how their business might work. And when the data stops matching reality, they immediately update the model. As opposed to constantly being on the back front, back foot rather. Let me describe it another way. Many people who know me well know me as a frameworks thinker. I have a framework to think about wait lists. I have a framework to think about onboarding, to think about pricing, to think about positioning. Famously, products market fits. And that's the kind of person I want to work with other people who also think in a very detailed, frameworks oriented fashion.

How old were you when you started report of?

I believe I was 26.

So how old are you now? You're 36.

37.

37. So you have this. I've only talked to you for 10 minutes. Now or however long this has been, you have this thing about you that you are clearly going to be a CEO of a very large company because you have this intangible kind of charisma. I don't know what you want to call it, but Sean, I imagine knows it.

I feel like when you're talking, you're not talking, you're narrating, right? It's as if you have left the scene, you are observing the scene and you're not caught up in the hustle and the bustle of the scene because this already played out or you are the one narrating the story. It's a calmness and charisma in the way you speak. It's literally just the way you speak. Like we don't know shit about you.

No, he's using concepts and stuff. I mean you're doing a really. You have this, you have like an it factor. It's very clear. I always have talked to you for five minutes.

Would you want to be CEO of a big company like multi,000 person company that's publicly listed? Is that a, is that a goal of yours? I know for myself, for example, I love the start and the bigger the company gets, the less fun it becomes for me. And I've learned that over time. And so some people love it, some people dream about that. And so which bucket are you in?

Yeah, good question. I probably find myself somewhere in the middle. I've had at this point now just one or two friends who've had the amazing outcome to take a company public and it doesn't seem that much fun. They don't seem to be having that much fun. They'd be the first to say that. It was obviously a huge ambition point for them, so they pursued it. Nevertheless, I'm very excited about learning and scaling. I think in order to create a business that really, truly has outcomes on the world that we as the founders get to play a large part in, we do have to scale in some part with the companies or as far as we can. Now this idea that you want to have thousands of employees, apparently Larry from Google was known for wanting to have tens of thousands of employees. I don't really resonate with that. That's not a motivating factor for me. Taking the company public, not a motivating factor for me. Having a very large private company that has a tremendous amount of impact on the world, that's exciting.

Were you like this when you were 26 and starting rapportive or did that year off kind of change you?

I think the year off helped me recover from what was a very sort of taxing experience building reports of them being at LinkedIn. But I don't personally think I fundamentally.

Changed when you were at LinkedIn, so this is a selfish question, right? So I just got acquired by a company that's 2000 person company. LinkedIn I bet was even bigger at that point in time. I found it good and bad interesting to be an entrepreneur inside of a company like this. And some days I feel like I kick a ton of ass and I'm like, oh my God, only I in this company could do this. That's the ego in me. I'm like, only I could have pulled this off. And then other days I'm like, wow, I'm so used useless at this company. I don't have any of these skills that these other people have and I don't want those skills either. And I, you know, I can't do all these things that you need to do to function, to be a high functioning person in these companies. And so I'm curious, when you got acquired, were you a good employee? Were you just in sort of chill mode like some people go into when they get acquired or, you know, what was your experience like there?

I certainly gave it my all, but to be honest, I ended up struggling a fair amount. And the reason is I think I'm a pretty good founder. I'm at best a mediocre product manager of a large company. And LinkedIn was about 1700 people at the time. Our product management organization was 70 people. I came in right in the middle. I was a senior product manager, one of the very few who could simultaneously code, design, market and conceive of new products, which is the thing that makes me a good founder. But I also didn't have the skills that a product manager should have. Things like being able to establish consensus. I don't have to establish consensus. I just say this is the direction we're going and you're either with me or without me. Well, guess what, big companies don't work like that. Other skills like bringing people along, fighting for allocation and for resources. When Rapportive was an independent company, people would line up around the block to want to work for me. Apparently, Sam, you wanted to work for Rapportiv and you know, this is, it's exciting. People want to work for startups and that's not the case at LinkedIn or at any other large company. At any other large company you generally have to fight and play the politics game in order to get your projects funded. And to get people to work on your things. And that was a switch that was really hard for me. The other thing is just what's important to the company. Unless you come in to run products, you've gone from your thing being existential to your thing is now probably an experiment or a strategic bet. As a founder, your job is to find a needle in a haystack. As an acquired founder, your job is to move the needle. The haystack has long since gone.

I'm a customer. How much do I pay? 20 or $30 a month.

$30 a month?

When you were starting Superhuman? I mean it's becoming a little bit normal now, or more normal. But paying for email, I mean, I guess we did with aol. My mom still pays for her AOL account. But you know, like paying for email is very, that's very original thinking. That's something not a lot of people would pay for. You're proving wrong. What else is out there that is a free service that you think people would have an appetite to pay for if they applied some of the framework or however, whatever insights you had to really like? Well man, people would pay for faster email. Is there anything else there that you, in your head, you're like, man, that, that deserves a paid experience that has more features.

Not one that I've put a tremendous amount of thought to, but we can try and come up with a framework on the fly. So what is it that makes Superhuman work as a premium prosumer product? Well, first of all, a premium prosumer product in the space does not exist. So there's a gigantic amount of white space for a high end version of that product. Then you have to start asking questions like, well, why doesn't it exist? Or why has not Google or Microsoft created a premium email experience? Why have they not made Superhuman?

What was the answer to that?

Well, let's take them each in turn because I think they're quite different. For Google, I believe the fundamental business model doesn't support creating a premium email experience. And the company is so large now that it doesn't matter. The fundamental Google business model is of course ads and adwords. It's to know everything they can possibly know about you secondarily to keep you in the browser. Hence Gmail. Both of those things feed into Gmail so they can better monetize you in the Google world, you are the product. Now of course people pay Google for the enterprise solutions for G Suite, but that is a vestigial business by comparison to their overall business. And that explains why when inboxed by Google grew to 500 million users, it was still considered a failure. That would have been a runaway success story for any independent company. So that's Google. It's just simply business model. It doesn't fit for Microsoft. I think it's a little bit different for Microsoft. They sell through bundling. Almost all of their money comes from companies buying the all you can eat Microsoft platform and they just expect every single box to be checked. One of those boxes is of course email. Outlook was built many, many, many years ago. It does all kinds of different things. It has to be a one size fits all solution. And so that's what it is. Now both Outlook and Gmail are great products for what they are designed to do, but it does leave underserved a premium segment of users that we were able to go and sell to. Now then beyond that you have to start looking at the products themselves and asking well what is the product white space to do better? And we identified two things, number one, speed and number two, design. Two things that both Google and Microsoft for various reasons are unable to compete on in a nimble or in an agile fashion.

But why did you start with email? Just because that's like the biggest thing there is or because you liked email? Because of reportive?

All kinds of different reasons. I think one of the biggest is impact. I remember when I was coming towards the end of my time at LinkedIn thinking about well what is Rahul going to do next? And thinking this one is going to be the big one. I probably have one company left of me, so it better be really big at best accounts. And I recall reading at the same time the now famous McKinsey study that showed that of the 1 billion professionals that there are in the world, on average we're still doing three hours a day of email. That's the average, average professional does three hours a day of email. And as we just discussed, they're doing it with one size fits all tools. Things like Gmail, things like outlook. So 3 billion hours per day, every single day go into email. There's in fact only one thing we do more than email and that's sleeping. And when I looked at my ability to be a founder working on sleep versus my ability to be a founder working on email, where I'd already sold a company, knew all the people and could raise arbitrary amounts of capital, I was like, well clearly that's the one for me.

How did the actual idea come about? So you're sitting around, are you brainstorming on a whiteboard? Is this like, you know, what was the actual idea? When did the lightning strike? And you understood, okay, what if I built a prosumer email too? What if I built an email experience that you would pay for because it was slick, it was fast, it was well designed, et cetera, et cetera.

It's hard to pinpoint the exact moment. I think it was perhaps six months before I left LinkedIn. I was having lunch with my team. The report of team in the LinkedIn Mountain View offices. We just all started naturally talking about what might come next. And I was like, hey, folks, I think we kind of ruined Gmail. And they said, well, what do you mean? And I said, well, we were the first browser extension on Gmail to really go mainstream and to get millions of users. And now everybody's copied us. You have things like Boomerang, Mixmax, yesware, Clearbit, you name it, it exists. All of these products, including our own, are just almost like a virus, just sort of sitting on top of Gmail. There's no API, they don't belong there. They slow down the experience, they clutter it visually. They take all of the problems of Gmail, the problems that it's going slower, that it doesn't work properly offline, that it's visually cluttered, that it consumes ever increasing amounts of CPU memory and so forth, and it makes all of those things dramatically worse. What if we just built it from scratch? What if we built an email experience the same way that Apple built a laptop? For me, that was like the aha moment, that no one has done that because it's really scary and nobody knows how and it's very expensive. But I might be one of the few people in the world that could actually pull it off in the sense of pulling together the team and the capital to make it happen.

You said you hadn't given a lot of thought to the. Where else could you do Superhuman? I don't believe that. I think you probably think about it all the time and you also hear all the Superhuman for X that gets built, right? Like, I've been pitched probably 10 different versions of Superhuman for X, you know, for example, Superhuman for calendaring, which I'm sure you guys either already do are about to do, or you have a really good reason why you're like, that doesn't work. And then there's, you know, people who have done it in the, let's say, bug tracking, you know, space, right? So I think, why use JIRA when you could use this, you know, this new, new and special one? I Forgot the name of it, but it's a good one.

Are you serious?

You really haven't thought about the other spaces that you could Superhuman up or.

Doing it for browsers, which is a very obvious one.

Sure. And there are great companies going after all of this. Mighty for browsers, linear for the issue tracking. There's a number of Superhuman for calendar ideas and I'm very fortunate to see most of these through the context of either friendly founder who can help or through the possibility of being an angel investor with the angel fund that I run with Todd. When I said I haven't given it significant thoughts, what I meant is I haven't given it rigorous thoughts in the same way that I gave email back in the day. In the same way that when I committed to giving the next 10, 15 years of my life to this project, I hadn't done that for these other ideas. But with a surface level analysis or with sort of an angel investors level of analysis, they all seem very plausible. I do think that Superhuman for X is, is a. It's a very real thing. There's going to be multiple billion dollar products and billion dollar companies to be made. In the last YC demo day, Superhuman for X was the most common. X for Y. It's pretty interesting to see the trend take off.

Have you invested in any yet or.

What would you invest in?

1 superhuman for X that we've invested in is Command E. So Command E is A. It's kind of actually modeled off Command K which we popularized in Superhuman. But you press the keyboard shortcuts and you able to search across everything. Not only all of the data that you have locally, but all of the data that you might have on the cloud. So where did you last leave that note? It might be an Apple Notes, it might be in Evernotes or it might be in Google Drive. This thing will find it. Who is the candidate that is on your calendar that you're going to speak to in half an hour? Commandee. Type in their name. It will take you straight to the greenhouse record. Want to update the lead or the opportunity in Salesforce? Commandee, you can do that as well. And so this is taking a lot of the same product sensibilities that we had and applying it to a different workflow which is search and updating records.

You seem incredibly calm and you mentioned that you and Todd. What's his name? Todd G. Yeah, Todd Goldberg. Goldberg. You guys have. How big is your fund? Like a 10 or 15 rolling fund, right?

Well, we have two funds. We have an early stage angel Fund, which is about seven and a half million dollars. And we also have a rolling fund, which is more of an opportunity fund. And that's to invest in the breakout companies from the first fund, just as well as other amazing companies that we see coming from our network.

So you have two funds, you have a company that has 60 employees, you have a lot of users, you have a lot of investors you have to deal with. How are you managing your time right now? Have you delegated everything at Superhuman? What's your deal? How are you able to get this done?

I actually haven't. I'm working on building up the team so I can delegate more and more as time goes on. I'll answer your questions separately because I think the answer to them is different. How can someone be calm and how can someone in my position manage their time? How am I calm? I'm a huge believer and I would say a journeyman practitioner of transcendental meditation.

Yeah, no shit. That's like the two minutes with you. And I could tell that you just. You scream that, man. You whisper that.

Well, I'm glad to see the aura conveys over camera, but I do meditate twice a day. So I meditate usually the first thing in the morning for about half an hour and again in the afternoon at around 4:30 for another half an hour. I'm early in my practice. I've only been doing this for about six or seven months. For me, it clicked when I hired a coach to teach me how to do it. I'm also an even bigger believer in coaching. I've had coaches for nearly every aspect of my life. I've worked with maybe five or six different coaches. Not just meditation, but also things like nutrition for physical training, obviously being a CEO and being an executive. And for me, meditation did not work until I hired a coach to actually drag me through the learning process. I think I'm an investor at students. I'm not the best learner, but I respond well to coaching. And that for me was the thing that made it work.

Can you give us like the two or three things you either were getting wrong on your own or you were looking at the wrong way. What were two or three of the things that the key points at the coach which sort of highlighted to you.

Mental fallacies like, well, I spent the 20 minutes of my meditation just thinking about stuff, not repeating my mantra. Surely, therefore, I'm not meditating. That's actually a fallacy. That is in fact what you're meant to experience six months into your journey in meditation. It Means that it's working. It means that your body is beginning to unwind and you're just effervescing all of these thoughts and you're meant to actually experience them. And every time you notice you're thinking, of course, bring yourself back into the meditation. But the fact that your body is taking you there is a good thing. I previously thought that was failure when I tried to self teach through one of the many meditation apps. Another one would be the fallacy of I simply don't have the time. Right. An hour a day is a lot. That's five hours a week depending on how much you work. It's, you know, double digit percentage of the amount of time that you have. The answer, of course, is that through the time that we spend in meditation, we make everything else way more efficient and effective. And that's hard to believe until you experience it for yourself. I respond well to authority. One way that you can start to believe some of those things is have a world expert in meditation simply tell you that and back it up with science. And so the coach that I work with, the reason I believe him is he's a scientist and he's also been a tech founder, venture backed several times. So he knows what he's talking about. He's not just sort of spouting mystical bullshit. This is actually grounded both in his experience as well as in science.

What's his name? You want to give him a shout out or is it intentionally stealthy?

Happy to refer folks who are interested. His name is Laurent Valasek. He runs the Peak Performance Institute. He focuses on leaders and executives with the purpose of performance. So he's not after specifically spiritual awakening. Although if you find that that's wonderful, it really is around how can leaders unlock performance? Okay, so that's calmness. I think the other question was how do I manage my time? Right. I track it assiduously. And subscribers of Superhuman will know both of these things because I've just sent out a number of sort of productivity tips. One on meditation, another on time tracking. I do this perhaps somewhat weird thing called the switch log. I, like many of the founders, used to have the experience where I get towards the end of the week and I feel sad. Well, where did that week go? I don't feel like I achieved anything. I felt constantly interrupted, forever putting out fires, what actually happened. And so I invented this thing called the switch log. It's very simple. Every time I start a task, end a task or switch a task, I simply go over to slack, go to a channel I have specifically for this purpose, type in TS colon and then the name of the task that I am switching to. And this turns out to be remarkably effective because then I can go back afterwards and analyze exactly where my time went. Your calendar in theory does this for you, but your calendar at best says what you wanted to do. And for most founders it doesn't record what actually happened. The switch log does and it's very easy. And you don't even have to worry then about maintaining a calendar.

As an angel investor, are you seeking out anything right now? Are you seeking a category or an idea that you're wanting to invest money in if there was the right team or someone trying to make it happen?

Incredible founders in fast growing markets. I think as pretty much every angel investor seeks out. Todd and I are fairly generalist investors. So our themes of interest are viral SaaS, of which productivity and collaboration are good examples and we've made some bets there. For example, folks might know Tandem is building the water cooler for the remote age. We're really interested in health, fitness and wellness. So we've invested in a company called Future that is taking training into the application era. The remote area. Fantastic. We've also invested more recently in an amazing company called Levels, which builds a continual glucose monitor so you can see the real time metabolic response of your body to anything you eat or do.

I'm an investor in that one as well.

Fantastic. Yep, we're really super excited about levels. So you have viral SaaS, you have health, fitness and wellness. We also are a big believer in infrastructure business infrastructure companies. And not really at the nuts and bolts level of hardware, we don't really understand that, but we're a big believer in API companies. Some of my personal investments that have done the best have been companies like Clearbit, which is a rather well known API for data enrichment. Everything from an IP address to an email address to easypost, which is an API for really super simple and rapid shipping. API companies are particularly interesting because once they get ingrained in a company, they're next to impossible to rip out.

Would you say that like one example of that is Zapier?

Yeah, exactly. Zapier would be the archetypal infrastructure company.

I have a bold prediction. I think Zapier is going to be as big as Atlassian. I think Zapier is going to be a $50 billion software company.

Yep. I think if they play their cards right, they could be.

I think it's going to be huge.

So people love to just hear sort of like your half baked startup Ideas. I don't know if you have any. I don't know if you're an idea machine that just can't turn the switch off, but most of the founders I meet tend to be that way. I'm going to take a shot in the dark and say you are. Am I right on that or is that not the case for you?

Actually, no, I'm more of a let's make it great machine. Give me an idea. I can describe how to do it fantastically, but I'm less of an ideas machine. That said, I do have a few ideas. If you want to go into them.

Give us a couple of ideas. And then I actually want to ask you about the other thing you said too. So let's start with a couple ideas.

So these are ideas that I have stumbled upon or opportunities that I've stumbled upon through my role of running Superhuman. And they're all things that I wish existed in the markets but I cannot buy. And so we're probably just going to have to bite the bullet and build them. One is a plug and play library for autocorrect. Superhuman works in the browser. It also works the native Mac app. We will one day build a native Windows app. When you type, I would love to be able to autocorrect the errors in your typing in the same way that Mac OS does natively. By the way, Windows doesn't do this natively. So if you live on a Windows machine, you probably don't really know what I'm talking about. But everyone's familiar typing into their iPhone and the Android and having it just fix itself. That's what I'm talking about. Things like missing captions, capitalization, missing punctuation, transposition, errors, conjoined words. All of these things should just self eminently fix. I have put so much time into looking for a library or a piece of technology that does this and it does not exist.

That's shocking to me. That doesn't exist.

And this is something that devs would. So a dev would buy this when they're building their stuff.

I think the reason it doesn't exist is not too many apps are creating new editing services. But if you are building an app and you have an editor and you want to actually innovate on the writing experience itself, you would just put this thing in there and you would take your web writing experience to be as good as any native writing experience like Mac OS or the iPhone.

That's interesting. That's a cool one.

Yeah, love that. Thumbs up on that one for sure.

Okay, you'll invest. Excellent. Next one would be. And again, this is something that I just wish existed, but it doesn't, which is document preview. Now there was once upon a time a number of companies like Crocodoc where you could give them any documents and they would give you a web renderable preview really quickly. Obviously this is important for Superhuman. We want folks to be able to preview their attachments super fast. As far as I know, there are only two ways, three ways that I can think of of doing this right now. You can upload it to someone's G drive and then download it as a PDF. Obviously user space takes time. You can use Microsoft's free libraries to do this maximum file size limitation of 5 megabytes. Or you can download what I believe is a Java library I think from box box acquired it was Crocodile back in the day and I think that was the ultimate evolution of that product. All of these three approaches obviously have major cons as well as the benefits they bring. As far as I can tell, there isn't a really great document preview library that you can just throw any file and it will produce a zoomable, interactable, renderable preview.

And you're going to use this in Superhuman?

That would be how I use it. But I imagine any enterprise tool, any tool at all that has to deal with files would make good use for this. I would happily invest in the startup. If you're building it, please let me know.

If you were running this business or you had started it, how much would you. I'll ask you about pricing a little bit, but for this one, like what would you sell something like that for? Like what would you price it at?

And I'm not an expert on API pricing at all. But what I've seen is that you start with a pay as you go model. It's going to be this much for this many documents or maybe you're actually selling it based on the file size of the documents. I suspect that will be a good proxy to the compute power that you spend on passing the documents and rendering it. And then at the high end, what you're really charging for integrations, SLA service to the organization that you're integrating with.

The reason I'm asking is like superhuman at $360 a year. A lot of software people say that like the. There's a dead zone of around. You're in like the dead zone of like basically it's really hard to price stuff around that price. And a lot of the more successful SaaS companies am. I Thinking, what's that guy's name? Tom Tongues. What is, what is it?

Thomas Tungas or whatever his name is.

Yeah, yeah, yeah, like VC Red Point. Yeah, yeah, he's got, it's great post and he's like, analyzes all the SaaS, IPOs and he's like there's some stuff that it's like free or next to very cheap. And then most all the successes are like it's at least $5,000 a year. And it's very, very hard to scale because like HubSpot, they have this cool study or this cool. What's his name? Brian Belfort has this thing called Reforge. You know Brian, I bet. And he basically says like when he was at HubSpot he helped launch this thing called. It was your competitor at Report of. What was it called?

Sidekick.

Sidekick, yeah, he like built this thing called Sidekick, which is basically kind of like reportive but a little bit different. And he charged $30 or $20 a month and he grew it and it like got to $300,000 a month one year. And eventually they're like, no, we got to shut this down. There's no way that this could become a big business because it costs too much money to acquire customers. When you're thinking of Superhuman and this new in all the products that you've named seem like they actually would cost in the thousands of dollars a year. When you're thinking of Superhuman, are you like we're going to have to figure out a way to sell something else to make a lot of money or do you figure are you think you're going to be able to get a million users for a very low cac?

So the good news, and this was the tail end of every VC pitch that we ever made last year, was we clearly don't need a million users in order to be a billion dollar plus company. It turns out that when you sell a product at $30 a month, which by the way, I agree is a hard price point, but I'll come back to that in a second. It turns out that when you sell at $30 a month, all you need is 300,000 subscribers to be at 100 million. Exactly. It's 108 million. In today's markets, you'd be valued at four or five billion dollars, probably assuming you were growing non trivially at the point of 300,000 subscribers. And so the question that we asked is we don't need to get to millions of users. Can we see a path to hundreds of thousands of subscribers? And me and every other VC who is interested in this said, yes, obviously there's 1 billion people who do email professionally, so there must be some subset of that that we can get to 300,000 subscribers. Now, that doesn't mean to say that we won't, down the line, explore ways to increase average revenue per user, but I do believe that we can create a good CAC LTV ratio just with this core product alone.

The thinking is like, let's just get to 200,000 users. Let's be laser focused on that and then we'll figure out the rest as we go.

Exactly. And this is one of the things, by the way, where Mark, talking about him again, his presence, his wisdom is actually very useful. So I recall a previous board meeting where I was going off on a little bit of a tangent about, well, maybe we should go and acquire this company, or perhaps we should think building the thing that they make, stuff like that. And he said, well, it's going to be relatively expensive now. You'll end up giving up a fair amount of equity or using a lot of your cash. The alternative is we walk the fairly well understood path to hundreds of thousands of users, and then when we're making that revenue, just spend the revenue on buying the next piece of the puzzle. And it kind of makes sense that when you hear it laid out like that. Now I just want to go back to this idea of a dead zone because I find it fascinating. And I think there's a lesson in here which is future success will not always look like previous success. And I think if we're a founder and we're trying to come up with something really big, something really cool, we have to deliberately. This goes back to that idea of intentionality. Pick something that is on purpose, not like all the things that came before. And the thing that I observed is that I thought the time was right to start to go after the prosumer, the $30 a month price point, precisely because everything prior had been very cheap or very expensive. And I thought there was a new path to growing a company in the middle.

I hear you a little bit, but to play devil's advocate, I'd be like, well, why would you make this needlessly tough on yourself?

Superhuman doesn't have competition. No one else is selling a $30 a month email experience, and they would have to catch up with everything that we built in order to try and do so. So you bring with it other benefits.

I think the key is you don't say, okay, what is the perfect price? Instead you say, all right. For us to realize our ambitions, we want to be a billion dollar company. You need $100 million in revenue to get to $100 million in revenue. You need 300,000 users at this price point. Do I believe that I can do that? Yes, I believe I can do it. Then it's the right price for us because there's a competitive advantage, like the lower your price gets, generally the more customers you're going to be able to acquire because there's less friction along the way. So I think that's their hook. And I would guess the retention is pretty strong. Although I did churn out a Superhuman, I would assume. I think most people who are power email users, it's very hard for them to churn once they get a better experience and they go back to a slow thing.

Exactly. All of this relies on the idea that you have a high retention product that people do genuinely love. The thing that you've built, you are creating the light and that you can build a revenue stream that lasts for a long time.

And you haven't even really gotten into companies yet. Because I know when I used it, I couldn't use it for my work email because it wasn't like it didn't pass the security, whatever. Not that there was anything wrong with it, but the security team at the company was like, we haven't vetted this, so it doesn't work with our work email yet. There's probably ample room to grow just in that one regard.

Exactly. We think there's a ton of headroom there. We're now starting to see really big company accounts organically form that classic bottoms up motion. And we're beginning to develop some competency. This is new for us, so obviously there's something new every time. But competency at going through the vendor approval process, it used to take us, gosh, three days. It took us three days to get through Uber's questionnaire, and now we can get through a security questionnaire in two hours. So there's been a lot of learning since condensing that down.

Before you were starting Superhuman, I bet you were thinking of one or other two things that you were passionate about, even if they were related but a little bit different. What were they?

The one other thing that came up against Superhuman, obviously Superhuman was by far and away the one that I chose, was this notion of small scale private equity applied to SaaS businesses. The idea that the first two, three years of a company, not very much happens. You're not making that much revenue, you're spending a Lot of time pulling together capital people and building a product. And a lot of people make that journey and then flame out, either because life happens or they lose interest, or they literally don't know how to do the next stage. And so I think there is a very good business model to be had. And I do know some people pulling this off. Where you find companies that have done that phase, maybe they're making $100,000 a year, sorry, a month, or maybe they're making $10,000 a month. And you spend anywhere in the region of half a million to 5 million to 10 million to buy these companies outright. You own all of them. And maybe you raised some money to help you do this, but ultimately you own these companies, scale them 10x. That is a relatively well understood problem. There's only a few ways you can scale companies like that. Maybe even support the companies with some kind of centralized resource pool, whether it's development or sales or support, and then sell them on to the next buyer once they reach. Let's say you can go from a million dollars of ARR to $10 million of ARR. You can then sell it for more than 10 times than when you acquired it.

So Constellation Software, I think, does this, right?

Constellation Software is one. There's also Xenon Software run by my good friend Jonathan Siegel.

Yeah, I know those guys.

And there's another German outfit as well. So there's maybe five or six small scale private equity funds that essentially do this kind of operation.

What would you do a little bit differently as them? Or, or is there just enough out there that you don't really have to be that different as long as you execute? Okay, it would work.

To me, this feels like the very earliest days of venture capital. I don't think you necessarily have to do anything specifically different. People are still buying companies by what they're interested in running. So for example, my friend Jonathan Siegel, he recently bought Earth ClassMail, which is a mail forwarding service. There's a location down here in San Francisco. I don't think I'd want to run Earth Class mail. I'm sure it's a really good way to make money. But I don't have any particular interest in running a mail scanning and forwarding service. So I think folks are simply buying things that are interesting to them that also happen to make money that they see an opportunity to work with. It's mostly greenfield. I think there's a ton of room for folks to come in and try something like this now. In any case, I ended up comparing that to the thrill and the excitement of building a big household brand like Superhuman and working on something that I know incredibly well, productivity in email and having a vehicle to make the best email experience that exists and do some of the best work in my life. And for all of those reasons and more, I ended up choosing Superhuman.

Yeah, I think one definitely is more fun than the other. And you're probably going to create a significant amount of wealth with Superhuman. It does seem that the second idea is easier actually to get rich, but.

Maybe not as fine. It's probably more reliable because by definition all of my eggs are in one basket. Whereas by definition you're creating a portfolio when you're buying multiple SaaS companies.

We're at the hour mark and I know you said you go to Yahoo. Finance, so make sure you're not late for them. So tell us if we got a wrap up. But I liked the ideas that you had shared because they fit this thing that we talk about on the podcast called my import export framework, which is I learned that one of the best ways to generate ideas is to go work at a company and then think about what businesses, what solutions would we import in? Like, we would pay for this if this existed and solve these problems. That's a great way to generate ideas. And the other is the export. It's like, like we hacked together this crappy solution for ourselves. There's probably a thousand other businesses that have the same problem, a third of which are hacking together their own crappy solution. And if someone just made the good solution, if we just took this thing we made and productized it, that's going to be a standalone business of its own. And so it sounds like you had a couple ideas in that realm.

For me personally, that's always how I've come across business ideas.

Well, cool, man. This is wonderful. I'm happy I was able to talk to you finally. I like I said, I think we're Facebook friends or something like that where you've like, I've been an admirer from a little bit of a distance. Again, that sounds really creepy, but I've been an admirer for a while, so I'm happy we were able to talk.

I like how you were like, sean, do the intro. When actually this is like your hero that you've been stalking for a decade and you should have done it.

No, you got look, Rapportive was special because how many people worked there?

5, including myself.

It just seemed like kind of a ragtag group. You guys seemed pretty hardcore nerds and hackers. Which I like.

It was also really non obvious to do an email extension that wasn't even a business space. I didn't feel like before. I never used a single product in that space before. Rapportive. And so was that just like a hobby project that turned into a real thing or you intentionally were like, no, this is how we should build this company?

It was the thing I built for myself. It was a hobby project. And then I realized that a browser extension could be a real company. And today we have outcomes like honey, multibillion dollar company, Grammarly, another multibillion dollar extension company. People are building real businesses on these platforms.

Let me ask you one more question before you leave. It looks like you're in, if I had to guess, maybe Soma or the financial district in San Francisco. That's right, because everyone's talking about it. Are you going to stay? Are you going to go? What's your plan?

My plan currently is to stay. I think that perhaps in the long term I end up not being in the Bay Area. Maybe I raise a family somewhere else. But in the meantime, my focus is on being here. I actually think that the founders teams, the investors, really everybody who stays over the next 12 to 18 months in San Francisco will have the edge when the city inevitably, as it has done multiple times in the past 15 years, rebuilds.

Why?

Because that connective tissue will already exist. There will be an enthusiasm to get things done and for all of the reasons why location was important to begin with, they will be important again. The fact that you can get a deal done just by walking down the road and walking into somebody else's office, it's pretty special.

I agree. I lived there for. I just moved a few months ago, like a lot of people. But it was a hard decision. But I agree.

They should come back.

We should wrap it up. Rahul, thanks for coming, man. And congrats on building something that's legit. I think a lot imitation is the greatest form of flattery, as they say. And there's a lot of people out there who are trying to build Superhuman for X. And I think that's probably the highest compliment one entrepreneur can give another is like, oh, the thing you did to your space, I want to do to whatever the next space I can do it to.

Well, thank you so much for saying so and thank you to both for having me. It's been really fun.