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SPEAKER_00
Our guest today is the email God Rahul Vora,

SPEAKER_01
founder of Superhuman. And actually a different startup that both me and Sam really love before this, I believe you started Reportive, 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 Reportive is.

Let's start with Reportive. Explain to people who don't know what Reportive is, what it was, and then me and Sam will talk about it a little bit.

SPEAKER_02
Sure. So Reportive 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 that 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. And 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.

SPEAKER_03
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 report of, 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, report of was the first one to do that, and it was so special, and so I invented this thing, this process called stock and talk. And the idea was I was gonna 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 at airbnb.com, and like I would put Brian and then Chesky, and then at airbnb.com. It would give me like a hundred 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 of 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 in 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 the 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.

SPEAKER_02
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.

SPEAKER_01
So I remember thinking at the time, this is like, 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, this is Julie Magni, she's the representative from Columbia, ask her about her son, Roger. That's what report of 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.

SPEAKER_02
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 was 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 brittlest also it 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 bristled business. We'd only figured out how to make 15 cents of revenue in the entire history of the company.

SPEAKER_01
And so why were you tired?

SPEAKER_02
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 reports 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.

SPEAKER_03
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?

SPEAKER_02
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 there wasn't really a break between Portland 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.

SPEAKER_03
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?

SPEAKER_02
The fastest email experience I've made, if you're the kind of person who spends hours on an 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.

SPEAKER_03
And can you give some ideas to how big it is, or anything like that?

SPEAKER_02
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 and Dresen 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 waitlist for our products, that's something that people are often interested in, we now have over 360,000 people on that waitlist.

SPEAKER_01
Does Mark Andreessen use email differently than plebs like us?

SPEAKER_02
Mark 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 like 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 at URI might meet.

SPEAKER_03
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?

SPEAKER_02
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, 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 this 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 onboardings, to think about pricing, to think about positioning, famously products market fits, and that's the kind of person I wanna work with. Other people who also think in a very detailed frameworks oriented fashion.

SPEAKER_03
How old were you when you started Reportive?

SPEAKER_02
I believe I was 26.

SPEAKER_03
So how old are you now? 36? So she's 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 wanna call it, but Sean, I imagine knows it.

SPEAKER_01
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 a charisma in the way you speak.

It's literally just the way you speak. Like we don't know shit about you.

SPEAKER_03
No, he's using concepts and stuff. I mean, you're doing a really, you have like an it factor. It's very clear.

I always have talked to you for five minutes.

SPEAKER_01
Would you wanna be CEO of a big company, like multi-thousand person company that's publicly listed? 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 will dream about that. And so which bucket are you in?

SPEAKER_02
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 wanna 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 impacts on the world, that's exciting.

SPEAKER_03
Were you like this when you were 26 and starting Reportive or did that year off kind of change you?

SPEAKER_02
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.

SPEAKER_01
When you were at LinkedIn, so this is a selfish question, right, so I just got acquired by a company that's a 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 of me.

I'm like, only I could have pulled this off. And then other days I'm like, wow, I'm so 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 can't do all these things that you need to do 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 what was your experience like there?

SPEAKER_02
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.

But guess what? Big companies don't work like that. Other skills like bringing people along, fighting for allocation and for resources. When Repulsive was an independent company, people would line up around the block to wanna work for me.

Apparently, Sam, you wanted to work for Repulsive. And this is, it's exciting. People wanna work for startups.

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 into run product, 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.

SPEAKER_03
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 it with AOL.

My mom still pays for her AOL account. But like paying for email is very, that's a 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 deserves a paid experience that has more features?

SPEAKER_02
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? 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 it's 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 adverts. 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. 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.

SPEAKER_03
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SPEAKER_02
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 an agile fashion.

SPEAKER_03
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?

SPEAKER_02
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? I'm thinking, this one is going to be the big one.

I probably have one company left at 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 professional. There's 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 three 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.

SPEAKER_01
How did the actual idea come about? So you're sitting around. Are you brainstorming on a whiteboard? Is this like, what was the actual idea? When did the lightning strike? And you understood, OK, what if I built a pro-sumer email to it? 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?

SPEAKER_02
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 Reportive 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 moments, 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 or the capsule to make it happen.

SPEAKER_01
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.

For example, Superhuman for calendaring, which I'm sure you guys either already do or about to do, or you have a really good reason why you're like, that doesn't work. And then there's people who have done it in the, let's say, bug tracking space, right? So I think why use JIRA when you could use this, you know, this 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?

SPEAKER_03
Or doing it for browsers, which is the very obvious one.

SPEAKER_02
Sure. And, you know, there are great companies going after all of this, MyC for browsers, Linnea 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 funds 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 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 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? One 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're then 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 notes? It might be in 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? Command E type in their name, we'll take you straight to the Birch House record. Once it updates the lead or the opportunity in Salesforce, Command E, 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.

SPEAKER_03
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?

SPEAKER_02
Well, we have two funds. We have an early stage angel fund, which is about $7.5 million.

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.

SPEAKER_03
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? Like, what's your deal? How are you able to get this done?

SPEAKER_02
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.

SPEAKER_03
Yeah, no shit. That's like the two minutes with you, and I can tell that. You just, you scream that, man.

You whisper that.

SPEAKER_02
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 inveterate student. I'm not the best learner, but I respond well to coaching, and that for me was the thing that made it work.

SPEAKER_01
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 that the, like what were the two or three of the things that the key points at the coach sort of highlighted to you?

SPEAKER_02
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 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 we know is what he's talking about.

He's not just sort of spouting mystical bullshit. Like this is actually grounded both in his experience as well as in science.

SPEAKER_01
What's his name? You wanna give him a shout out or is it intentionally stealthy?

SPEAKER_02
Happy to refer folks for 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 cause 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 Switchlog. 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 fuzzing out fires, what actually happened? And so I invented this thing called the Switchlog. 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 was. 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 Switchlog does and it's very easy and you don't even have to worry then about maintaining a calendar.

SPEAKER_03
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?

SPEAKER_02
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. I used it. 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.

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 it's 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. So some of my personal investments that I've 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 interested, because once they get ingrained in a company, the next one possible to work out.

SPEAKER_03
Would you say that one example of that is Zapier? Yeah, exactly.

SPEAKER_02
Zapier would be the archetypal infrastructure company.

SPEAKER_03
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.

SPEAKER_01
So people love to just hear 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?

SPEAKER_02
Actually, no. I'm more of a let's make it great machine. Give me an idea where 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.

SPEAKER_01
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.

SPEAKER_02
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. So Superhuman works in the browser. It also works in the native Mac app.

We will one day build a native Windows app. When you type, I would love to be able to auto correct the errors in your typing in the same way that macOS 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 that iPhone and the Android and having it just fix itself. That's what I'm talking about.

Things like missing capitalization, missing punctuation, transposition errors, conjoined words, all of these things should just self-ammonently 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.

SPEAKER_01
That's shocking to me that doesn't exist.

SPEAKER_03
And this is something that devs would buy this when they're building their stuff.

SPEAKER_02
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.

SPEAKER_03
That's interesting. That's a cool one.

SPEAKER_01
Yeah, love that. Thumbs up on that one for sure.

SPEAKER_02
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 documents 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 think 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 five megabytes. Or you can download what I believe is a Java library, I think from box. Box acquired, it was Crocodoc 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.

SPEAKER_03
And you're gonna use this in superhuman?

SPEAKER_02
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 this stuff.

SPEAKER_03
Like 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?

SPEAKER_02
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 gonna 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

SPEAKER_03
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, and I think, what's that guy's name? Tom. Tungs. What is it?

SPEAKER_01
Tom is Tunga or whatever it's name is.

SPEAKER_03
Yeah, yeah, yeah. VC. Red point. Yeah, yeah, he's got this 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 Belford 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 Reportive. What was it called? 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 in one year.

And eventually they're like, no, we gotta 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, and all the products that you've named seem like they would actually cost in the thousands of dollars a year.

When you're thinking of superhuman, are you like, we're gonna 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 gonna be able to get a million users for a very low-cac?

SPEAKER_02
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 $4 or $5 billion probably, assuming you were growing non-trivialy 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 was interested in this said, yes, obviously, there's one 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 rates to increase average revenue per user, but I do believe that we can create a good cat LTV ratio just with this core product alone.

SPEAKER_03
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.

SPEAKER_02
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 of 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 accuracy, you're 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 the side 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, and this goes back to that I drove 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.

SPEAKER_03
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?

SPEAKER_02
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.

SPEAKER_01
I think the key is you don't say, OK, what is the perfect price? Instead, you say, all right, to the rest of realizer 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 turn 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.

SPEAKER_02
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 lights and that you can build a revenue stream that lasts for a long time.

SPEAKER_01
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, ah, 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.

SPEAKER_02
Exactly. We think there's a ton of headroom there. We're now starting to see really big company accounts organically form that classic bottom 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 question there.

And now we can get through a security questionnaire in two hours. And so there's been a lot of learnings in condensing that down.

SPEAKER_03
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?

SPEAKER_02
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 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 raise 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 onto the next buyer once they reach, let's say you can go from $1 million of ARR to $10 million of ARR. You can then sell it for more than 10 times than when you acquired it.

SPEAKER_03
So cancellation software, I think, does this, right?

SPEAKER_02
Constellation software is one. There's also Xenon software run by my good friend Jonathan Segal. Yeah, I know those guys.

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

SPEAKER_03
What would you do a little bit differently as them? Or is there just enough out there that you don't really have to be that different? As long as you execute OK, it would work.

SPEAKER_02
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 Segal, he recently bought Earthclass Mail, which is a mail forwarding service. There's a location down here in San Francisco. I don't think I'd want to run Earthclass 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 green fields.

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. I'm working on something that I know incredibly well, productivity and 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, I more ended up choosing Superhuman.

SPEAKER_03
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 fun.

SPEAKER_02
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.

SPEAKER_01
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 solutions would we import in? We would pay for this if this existed and solved these problems. That's a great way to generate ideas. And the other is the export.

We hack together this crappy solution for ourselves. There's probably 1,000 other businesses that have this 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 could be a standalone business of its own.

And so it sounds like you had a couple ideas in that realm.

SPEAKER_02
But me, personally, that's always how I've come across business ideas.

SPEAKER_03
Well, cool, man. This is wonderful. I'm happy I was able to talk to you finally.

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.

SPEAKER_01
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.

SPEAKER_03
No, you guys, look, reported was special, because how many people worked there? Five, including myself. It just seemed like kind of a rag-tag group. You guys seemed like pretty hardcore, like, nerds and hackers, which I like.

SPEAKER_01
It was also really non-obvious to do an email extension, right? That wasn't even a business space I didn't feel like before. I never used a single product in that space before a report. 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?

SPEAKER_02
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, multi-billion dollar company, Grammarly, another multi-billion dollar extension company. People are building real businesses on these platforms.

SPEAKER_03
Let me ask you one more question before you leave. It looks like you're in, if I had to guess, maybe SOMA, or it was Financial District in San Francisco? That's right. Because everyone's talking about it.

Are you going to stay or are you going to go? What's your plan?

SPEAKER_02
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, there will be importance again, the fact that you can get a deal done just by walking down the road and walking into somebody else's office.

SPEAKER_03
It's pretty special. Yeah, I agree. I just lived there for, I just moved a few months ago, like a lot of people.

But it was a hard decision. But I agree.

SPEAKER_02
They should come back.

SPEAKER_01
We should wrap it up. Rahul, thanks for coming, man. And congrats on building something that's legit.

I think a lot, Imitations to 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's in the next space, I can do it too.

SPEAKER_02
Well, thank you so much for saying so. And thank you to both for having me. It's been really fun.

SPEAKER_00
See you next week.