S8E6: How Rahul Vohra's Superhuman Revolution is Transforming Email for Professionals

We imagined an email experience that is blazingly fast, where searches are instantaneous, where every interaction takes place in 100 milliseconds or less. An email experience where you never actually had to touch the mouse, where you could do everything from the keyboard and fly through your inbox. An email experience that also just worked offline, so you could be productive anywhere. And so with that, we built Superhuman.

Welcome back to season 8. Clauds, how we doing?

So well. Can't believe it's 8 seasons of The Room Podcast.

It feels like just yesterday we were getting started in the middle of COVID and had this vision for sharing the future of founding stories to let other founders be in the room where it happened. And so much has changed for us since August 2020 when we first had this inception. You're now a founder and co-CEO of Priv, which is a startup unlocking and disrupting recurring revenue for e-commerce brands.

And Madison, you're crushing it in venture. You're now a partner overseeing investments at DefyVC, an early-stage venture firm in the Bay Area, and of course an investor in Priv. We're just two women navigating our careers and asking the people who inspire us to shed light on their stories. Unlocking access starts with a conversation, context, and As a reminder, we open the door to moments in technology history that traditionally happen behind closed doors. With our guests, we unpack the experiences that led to their success and look towards the future in their verticals.

And we hit an incredible milestone at the end of last season with Spotify sharing that we were a top 5% global shared podcast in the technology sector. And so we wanna thank you for being a loyal listener and helping us achieve this milestone of amplifying more equitable voices in the room where it happens. As you look towards season 8, get excited. We're excited. We have some incredible founders from the founder of Superhuman, the founder of Incredible Health, Webflow, Ty Haney with her new business TYB, and more. So join us every Tuesday where we sit down with leaders, founders, and funders who are changing the way it's always been done. You could expect themes across, of course, generative AI, navigating your startup in a downturn, the creator economy, and more. So be sure to hit subscribe, like, and follow so you don't miss any Tuesdays in the near future. And one quick note, since season 3 in 2021, we have been delighted to work with our partners Kooli and Silicon Valley Bank. This season is no different, although the events of the past few weeks have brought Silicon Valley Bank into the forefront of our ecosystems conversations. Now known as Silicon Valley Bridge Bank, SVB. Thank you. And now a short message from our sponsors. Following message was recorded prior to 3/10/23. Support for The Room comes from Silicon Valley Bank.

What's next? What if?

Now what? Silicon Valley Bank understands these questions can keep founders up at night like Claudia. For over 35 years, Silicon Valley Bank has helped high-growth companies through scalable financial solutions, plus insights and expertise that many other banks just can't, which could be why 50% of US-based venture-backed tech and life science companies bank with SVB. Learn more at svb.com/next. Silicon Valley Bank, built for what's next. Cooley is a global law firm built around startups and venture capital. The firm has been devoted to entrepreneurs and investors, partnering with both to transform breakthrough ideas into successful companies. Cooley works with thousands of entrepreneurs and newly formed companies to ensure that they are structured for growth and long-term success. Since 2005, Cooley has been ranked the number one most active law firm representing VC-backed companies going public. Learn more about the firm at cooley.com and also at cooleygo.com, Cooley's award-winning free legal resource for startups. In today's episode of The Room Podcast, We sit down with Rahul Vohra, CEO and founder of Superhuman. You may have seen the Superhuman moniker below emails you've received, sent via Superhuman. This viral product today has helped to send over 200 million emails across their customers. You might be wondering, how did Rahul become the king of email? As a young boy, he moved around a good bit across the UK, and ultimately he actually taught himself to code. At the age of 8. A builder from the early years, Rahul always knew he was going to become a founder. Through what may have been his 4th or even 5th company, Reportive, Rahul was an early mover in the productivity tools space, which at the time was undervalued and underinvested in. Reportive was one of the first companies Rahul took venture capital for and ultimately sold it to LinkedIn in 2012. And he shares how this story wasn't always up and to the right. After a few years at LinkedIn, Rahul left to embark on the journey to building Superhuman. Superhuman is, in their own words, the fastest email experience in the world. Rahul shared stories about their early and unique approach to go-to-market. Hint, it involves a viral waitlist that wasn't meant to be a strategy. We discuss how today Superhuman has evolved from a pure consumer product to having 30 to 40% of their customers be enterprise users. and at the time of recording, a sneak preview on, quote, Superhuman AI, a new product which empowers Superhuman users to write emails with next-level autocomplete. In today's episode, we explore insights and themes such as a founder's secret superpowers, patience, a tactical how-to for salvaging a dying M&A process, and Superhuman's vision for AI. Let's open the door.

First off, Roel, thank you so much for being on The Room podcast. We're so excited to chat with you today.

Absolutely. Thank you for having me.

Of course. We like to start at the beginning with our guests. In 2002, you started your academic career studying CS at the University of Cambridge in England. Tell us a little bit more about where you grew up and how you came to focus on computer science at an early age.

I grew up in the UK where I actually lived in lots of different places. Cambridge, Birmingham, Manchester, lots of Scotland, Aberdeen, Dundee, Glasgow, Edinburgh. So I moved around a lot. I also started programming early from around the age of 8. Both my parents were doctors and so would often have to work late. And as a result, I would wait after school to be picked up and I would spend that hour or two in the school library. Once I was done with the fiction, I got onto the nonfiction and that's when I found the books on how to program. Now, this was a long time ago, so we're talking languages like BASIC and Assembly. And fortunately, we had a computer at home. My dad had bought a PC, a 286 if anyone remembers those, to write his PhD thesis. And when he was done, it was just lying around unused. So I spent 3 to 4 hours every evening programming, making all kinds of games and apps. And I was super fortunate that by the time I went to university, I'd already spent over, I think I did the calculation one time, over 10,000 hours programming. And I already had a solid intuitive understanding of things like what makes a user experience feel fast or what makes an interaction feel fun.

That's incredible. And we'll get more into fast user experiences with Superhuman. As a loyal user, I can say that Superhuman is the fastest email experience I've ever had. But in that vein of early identity, you're learning, you're programming, you're becoming an expert at 10,000 hours. But did you always think you were going to become a founder?

Yes. I knew with a clarity that in retrospect seems very surprising to adult me that I was always going to be a founder. In fact, I remember thinking it at around the age of 11 to 12, and I honestly couldn't imagine doing anything else.

It's always so interesting to hear from our guests. It's like 50, no, I never thought I would, but maybe I had a bit of an entrepreneurial spirit. And 50, no, I knew at 12 that I was going to build a big business. Fast forwarding a tiny bit, while you were at university, you also worked as a game designer working on one of the most popular RPG games of all time, RuneScape. I definitely played that. How did working as a game designer shape your approach to building digital products?

Oh gosh, it shaped it hugely. Hugely to the extent that now at Superhuman, we build software like it's a game. Most software companies worry about what users want or need, and that certainly is a reasonable thing to do. But here's the thing about games. Nobody needs a game to exist. There are no requirements, so to speak. So when you make a game, you don't worry about what users want or need. You instead obsess over how they feel, because when your product is a game, people don't just use it, they play it. They find it fun. They tell their friends, they fall in love with it. So it turns out that game design is an altogether different kind of product development with its own often unintuitive principles.

That's a fascinating way to sort of apply this very delightful lens on a task that everyone does all day long, which is generally a pretty boring thing, which is email. We'll dive a little bit deeper into those design philosophies and how you translated that into into product. But first, I'd love to dig a little bit deeper into your first founding story. In 2007, you founded Mojo, and then 2 years later founded Reportive. Tell us about how you caught the startup bug with Mojo and how that led to being a second-time founder with Reportive.

I think that Mojo was my fourth or perhaps even my fifth attempt at starting a company. I had tried many times before things started to work. And these are often the stories that aren't visible from a LinkedIn profile. I should probably add the string of all the failures as well, just for balance. And perhaps the coolest thing about Mojo was the domain name, which was mo.jo. And in case you're wondering, that's the country of Jordan. However, it was a lot less practical than it sounds. The country of Jordan at the time, at least, had the unfortunate habit of dropping off the internet, taking our website with it. Yeah. Although Mojo was my 4th or 5th attempt at being a founder, It was actually the first company where we had raised some money. We ended up raising a small amount of angel funding. This was back in Cambridge in England. But ultimately, we were never able to get it off the ground with the level of growth that we wanted. It ended up being mostly a software consultancy. So we returned the capital to our investors with a little bit extra because we were actually making money. And we all then moved on to our next projects.

Could you tell us a little bit more about the second project?

I dabbled a little bit for about a year with creating a series of trading card games. If you ever played Magic: The Gathering, and then there's a sliding scale between trading card games and collectible card games, but in the vein of a high fantasy series where you collect or buy cards, trade them, and then play those in battles with other people. This was during the heyday of Facebook gaming and online gaming in general, so it was very good timing. And I also happened to be very plugged into the fantasy scene, being an avid reader of high fantasy books myself. So I actually negotiated a license with a very well-known fantasy author to then turn those into a trading card game, but ultimately did not actually launch that. And very shortly after that started Reportive.

Do you still own the rights to those trading cards?

Good question. I, it's been such a long time since I read the contract. That was back in 2010. So I have literally no idea. I doubt it.

Maybe something to check in on. You mentioned you founded Rapportive and you actually ended up selling to LinkedIn. Would love for you to tell us a little bit more about what Rapportive did and a topic that I think founders are always really fascinated to learn a little bit more around is what it was actually like to make an acquisition happen and sell a business to someone incredibly large, like LinkedIn. So walk us through that Rapportive journey a little bit more.

Rapportive was the first Gmail extension to scale to millions of users. Imagine being in Gmail and on the right-hand side being able to see what people look like, where they work, links to their social profiles, and their recent tweets. If you're the kind of person who deals a lot with people, that's actually a lot of professionals. You could be a founder, you could be an investor, but you could also be a recruiter, a customer-facing person. You could be a product manager, you could be a salesperson, you could be in customer success. So many different job functions. If you're one of those kinds of people, this information turns out to be incredibly valuable at being highly effective in your communication. So it grew really rapidly and we did ultimately end up selling that to LinkedIn just shy of 2 years after we started. Now we were simultaneously fundraising, so we ended up with an interesting choice: raise a Series A, and we did have a decent term sheet, or sell to LinkedIn. And we chose to sell to LinkedIn for 2 reasons. Number 1, at the time LinkedIn had 250 million members and was growing very rapidly. And it was clear to me that the fastest path to having tons of people using Reportive would be via acquisition. There was no way that we were gonna get to 250 million people anytime soon. And number 2, I'd heard from other founders just how important and life-changing it is to make those first few million dollars, but not for the reason that you might expect. Making that money is so important, not because it lets you buy things, but because it grants you an unusual degree of patience. And then that in turn enables you to take on ideas that are really large, really scary, and which take a great deal of time. And I think a good example of that is Superhuman. You really do have to be a crazy person who wants to take on Google and Microsoft in the email client game. And here we are, we're doing it and doing great. And that's due in no small part to patients.

That's a unique and really powerful way to think about a sale early in a life cycle of a business. Claudia, you're the founder, so I want you to weigh in on how that hits you.

Even for myself as an early-stage founder, there might be some ideas that I'm truly deeply passionate about going after, but I know it's like creating a new market. It will take 7, 8 years for that to potentially pan out. Versus the tension of, oh, this is something that works, this builds revenue quickly. We're sort of seeing the business top line grow. And I can imagine that once you've had an acquisition under your belt, you have a little bit of a, a cushion and a safety net there. You're probably more comfortable with saying, I'm in a position where I am financially free to spend 7, 8 years building something net new. Something incredibly scary and risky. It definitely resonates. So thank you for sharing that.

One thing I would add for founders who have already sold or are about to enter a larger organization, this is something that I had to learn firsthand with LinkedIn. And I spoke to a whole bunch of experts on how to do that well, and I ended up writing this up. So if anyone is in that scenario, go ahead and Google Founders: How to Stop Worrying and Love Being acquired, it's chock full of advice on how to navigate that transition from a ton of people that I respect.

We'll be sure to link that absolutely here. It's fun to see the journey from Reportive into the conglomerate of LinkedIn, which I believe would've been prior to their Microsoft acquisition. So before they joined the mothership there, and then back out to Superhuman, which of course we're gonna spend most of our time talking about today, but really quickly. In that era of the early 2010s, was productivity tools a term? And did people think about productivity in the same way we do today, almost 12 years later?

In 2010, the productivity/collaboration space was almost dead from a venture perspective. There have always been individuals and indie developers making their own task managers and calendar apps and email clients, and so forth. And that's because they are intellectually satisfying and everyone has an opinion on how those things should be. But from a venture market perspective, they had been dead for a very long time. It took two major successes of Slack and GitHub, which were very early collaboration successes, for the market to ignite. But once those things had happened, everyone started building productivity and collaboration experiences. And now, of course, we have things like Notion and Airtable and Loom and Figma, and it's a very rich and vibrant space.

And Superhuman is right up there in terms of empowering people with knowledge in real time to do their day job better and quicker and more efficiently. But the aha moment that brought Superhuman would have been before it seemed obvious. So tell us, what was the aha moment for Superhuman?

It's always felt obvious to me over the 2 years of being independent, the CEO of Reportive, and then the 2 years at LinkedIn, I could personally see Gmail getting worse every single year, becoming more cluttered, using more memory, consuming more CPU, slowing down your machine, still not working properly offline. And on top of this, people were installing plugins like ours, Reportive, but also things like Boomerang, Mixmax, Clearbit, you name it, they have it. And each plugin took those problems of clutter, memory, CPU performance offline, and made all of them dramatically worse. So we decided that it was time for change. We imagined an email experience that is blazingly fast, where searches are instantaneous, where every interaction takes place in 100 milliseconds or less. An email experience where you never actually had to touch the mouse, where you could do everything from the keyboard and fly through your inbox. An email experience that also just worked offline so you could be productive anywhere, and an email experience that had the best Gmail plugins built in natively, and which was still somehow subtle, minimal, and visually gorgeous. And so with that, we built Superhuman, and it actually ended up working way better than I ever thought it would, because today our customers are getting to their inbox about twice as fast as before. They're replying to their important messages way faster, and they save 3 hours or more every single week.

It's not intuitive that we need to be trained how to do email, because in general, email is something that most of us unfortunately have been doing maybe since we were middle schoolers. And now the cool thing about Superhuman is that from early days, it actually required an onboarding call, which again was a little counterintuitive. How did you come up with this idea of an onboarding moment with a product that most of us feel we know how to use?

I get asked a lot by founders, should my company do manual onboarding? And I'll put it this way. I no longer believe in the idea of a traditional launch. Let's say you've built a new email client or a new task manager or a new calendar app. The surface area for these products is absolutely massive, bigger than almost any domain that you could think of. What that unfortunately means is you also get a massive surface area for bugs, as well as massive variability in how users want to use the product. Now, traditionally, most companies would just launch their app, and because the demand for these products is so high, you can fairly easily, quickly get tens of thousands of users. But guess what? These users will find hundreds of thousands of bugs, And as a company, you would quickly get overwhelmed. You would not be able to fix the issues fast enough. And so what generally happens is these users become disappointed, they churn out the product, and then they tell everybody about their experience. That is the very definition of a net detractor. So in my experience, it's significantly better to do what we did, which is to onboard customers at a measured pace each week. That way you have the bandwidth to fix any issues they find, and you can focus on making them exceptionally happy. And once you've done that grind, which can take years depending on the complexity of the product, you can then widen your funnel. And today we have multiple options. You can still do the amazing one-to-one onboarding. You can also attend a group onboarding if that's more your style, or you can also self-service.

I think it is important to take a step back and ask, when I'm building this specific product, how does it meet people where they are in their user experience journey? But also what you just shared, allow us to build this product at scale and do so in a way that meets the needs of the company as well. And so I love that really happened here with, as you're building out the Superhuman onboarding experience and ultimately like you guys did get to an incredible product market fit, but I'm wondering what was the moment that made you feel like you'd hit this elusive product market fit moment and maybe how that differed from the decision you made with Reportive.

It certainly wasn't easy. Ultimately, we had to build a product-market fit engine, and this is not something we had at Reportive. At Reportive, I just intuited it, but Superhuman, the stakes were much bigger. I knew it would take much longer, and the problem itself was much harder. So what the product-market fit engine gives us is a way to define product-market fit, a metric to measure product-market fit, and also a methodology to increase product-market fit. It can actually even write our roadmap for us. And if you dive deep into the methodology, it's a roadmap that pretty easily you can see will take us to increasing amounts of product-market fit over time. But product-market fit is a, it's a very nebulous term. And so at the beginning of this journey, I reached out to lots of people to see what they had to say about it. Like, what is the definition? Folks like Paul Graham would say it's when you made something that people want. Sam Altman has said that it's when users spontaneously tell other people to use your product. It's a very different style of definition. But it's actually Mark Andreessen who I think has the most vivid definition. He's written that you can almost always feel it when product-market fit is not happening. Customers aren't quite getting value there. Not growing that fast, word of mouth is not spreading, the press reviews are kind of blah, and the sales cycle takes too damn long. But you can almost always feel it when product-market fit is happening. Customers are buying as fast as you can add servers, you're hiring sales and support as fast as you can, reporters are calling you about your hot new thing, investors are staking outside your house, and money is piling up in your checking account. And it's funny, it's Indeed, a vivid definition. It's one that I was staring at actually through tears in the summer of 2017, because it seems so subjective, so unactionable. What do you do if by this definition you don't have product-market fit? Indeed, can you measure product-market fit? And that's when I started looking for the solution, spoke with all the experts, and I started to build the product-market fit engine.

Is this a publicly available resource or is this a Superhuman super tool?

It's a little bit of both. It is also publicly available. If you were to Google how Superhuman built a product market fit engine, there is an article on First Round Review where I go into it in great detail.

We got two links coming in on this podcast, which I'm looking forward to following up and reading. And it's no doubt that today you have found product market fit. I mean, we have users on this call even, and you've raised over a $108 million in funding from the likes of icons such as Andreessen, First Round, Tiger, IVP, and some pretty cool angels from the Chainsmokers to the Dropbox founder Drew Houston. First of all, congratulations. So incredible and never stops being incredible even though you've been on this journey now for some years. We're curious who, going back when you're first launching, was the first person to say yes to investing in Superhuman?

The first investors to say yes, who were also the first investors I approached, were Ed Sim and Elliot Durbin from Boldstart Ventures. Now, in case folks don't know, Boldstart specializes in first-check investing, and they are hands down the best first-check SaaS investor around. They backed my last company, Reportive, and so they were the first folks I went to when I started Superhuman. Once we had Boldstart and a few other rapporto investors in as what these days you would call a pre-seed, our seed round was preempted roughly a year later. And in case the idea is new to folks, there are broadly two types of fundraise. There's preempted and then there's the marketed fundraise. And ideally you want to be preempted. You do not want to be in market for too long, not at all actually, if you can help it. And the best way to be preempted is to be perpetually in a state of not raising, but simultaneously, number one, be making great progress with the company and being, two, being open to preemption by a good enough firm.

Claudia and I talk about this and the art, not science, to never fundraising while fundraising and what that process entails. And frankly, part of it is shifting under our feet right now with the macro market, what it is. And we know alongside your incredible work as CEO, CEO and founder, you also do angel investing. And so you have this dual lens right now of being a scaled CEO as well as an angel investor too. What advice would you have to a founder right now who maybe is at that seed stage, that Series A stage? How can they be thinking about their fundraising journey given the context of what's going on around us?

The market for Series A and later stages is pretty brutal. There's no other way to say it. My advice there is to make the money you have last as long as possible and cut down on expensive growth. For example, it is almost certainly better to grow at 2x and not burn that much capital, perhaps not burning any, versus growing at 3x and being in a position where you have to raise in this market. In other words, if you can avoid raising in this market, you should. The market for seed companies is actually pretty healthy and valuations are still high. For example, currently the median Y Combinator valuation is roughly $20 to $30 million. And part of that's driven around the opportunity for AI. Part of it is later stage funds shifting earlier stage. Uh, whatever the reasons, it's actually a really great time to be a seed stage company. So great for seed stage founders. But my advice there would be to leverage the higher valuations to raise more than you think you need. It's actually unclear when the Series A market will recover. So you need time to get to whenever that is. In other words, act as if the seed money is the last money you'll ever raise.

Thank you for that perspective. It's definitely true. Like I've been hearing word on the ground, other friends that are raising Series A's where the metrics maybe 6 to 9 months ago was, you know, you have half a million to a million in revenue. Like there's a very large possibility that you'll be able to close a round and now more like 1.5 to 3 as an entry point. It's super helpful to, to give that context. Fundraising is one area in which Things sometimes go really well, sometimes they don't go quite as planned. We know that being a founder is not always up and to the right, despite what we see on a LinkedIn. Could you share with us a moment in your founding journey when things didn't go quite as planned?

There are so many. Let's see. When we were selling Reportive to LinkedIn, we went through a fairly conventional process that starts with a verbal offer, then onto a draft term sheet, then a signed term sheet, then a definitive agreement. Quite similar to a venture deal. However, the unplanned moment was when LinkedIn decided a few days before Christmas and less than a few months before we were going to run out of money to walk away from a signed term sheet. And this was for a company that was making zero revenue. Now, in venture, this is almost unthinkable. There are perhaps a few investors who are sought after enough that they could get away with it. But venture, generally speaking, is a multi-turn game of reputation. You never know what company is going to be the next Facebook or the next Uber or so on. It turns out that M&A is not, and so the behaviors are wildly different.

That must have been quite a not so nice Christmas surprise. How did you navigate the acquisition from that standpoint? How did you bring them back to the deal?

You're right. It wasn't a particularly pleasant Christmas break, but I learned a lot about myself during that process. And in particular, I learned that I'm a much better wartime CEO than I am a peacetime CEO. We only had a team of 5 people. We were very small. I took about 4 or 5 days off just to play video games and clear my mind. But once I'd done that, I then went to the team and I said, okay, here's our plan. Me and this one other person, we're gonna focus on the deal. And the way that we're gonna focus on the deal is by showing them they'd be crazy not to acquire us. And what that means is we're gonna drip feed over the course of the few months that we have left, every week or two, a new thing that we've built that it would be insane for them not to own. And we created that roadmap, and these were conceptual demos. They worked, they were code, but they weren't things that were ready enough to launch. And it turns out that when the bar is there, you can actually make a lot of these relatively quickly. The other 3 or 4 of the team were going to work on monetization. So they quickly started building features inside of Reportive that we were then going to threaten to turn on. Idea was we would never actually turn these on, but we knew we could, uh, if we needed to. That would then generate a revenue for the company. I then went back to LinkedIn and there's a very interesting dynamic here where acquirers will get you to sign a no-shop in the term sheet. And typically they'll ask for 30 days. The fastest you'll see it is 15 days. I've seen it go up to 45 or 60 days where as the company being acquired, you are not allowed to go and talk to other companies. Most founders see that as a tremendously scary thing. How do we know we're going to get a good deal? If there's a no-shop, and also if you're telling us you're going to walk away from this deal. I think what most founders also forget is it cuts both ways because as the end of the no-shop approaches, that's when the acquirer, or at least some people at the acquirer, will start to get really worried that you're going to go and shop the deal and talk to other people. And at least at the time, LinkedIn and Salesforce were at a what appeared to be a clear collision course. Or the trifecta of Microsoft, LinkedIn, and Salesforce was certainly really interesting. And so putting all of this together, I actually deliberately and strategically waited until the no-shop was about to end so that the leverage is now back in my court. We'd been drip-feeding all of this amazing stuff we'd been building, and I also said, we're about to turn on monetization, and this was just a bluff, I was like, our existing investors are going to re-up into the company. And that combination of all of those things was enough to get the deal done at a massive premium for a company that made no money with just a few weeks left of runway.

Thank you for sharing that. Most founders don't get such insight into what actually goes down at that inflection point of whether a deal is going to happen or not from an acquisition standpoint. So it's fascinating to hear how you set up all these levers to make it still happen even when they were willing to walk away.

I also just would add, in this market right now, I think as we look at what would bring liquidity for many companies in the upcoming year, the IPO markets continue to be closed, and especially as investors are likely going to have to go out to market themselves to raise for their funds, they're going to be hungry for DPI or distributions paid into their investors. And so having stories like these of how you can play the game of getting acquired for what sounded like a decent premium on what was the existing product and monetization. Like, there can be another turn of the cards. It might not be with this company, but it can happen. And getting there over the finish line is really powerful.

Absolutely. And depending on how early you invest, even these small deals can be quite lucrative. Our earliest investors ended up making 25x their investment.

We chatted a little bit around the founding journey of Superhuman, but I'd love to shift gears a little bit and look to the future, as well as how you scaled Superhuman to where it is today. Superhuman's waitlist was such an iconic lever in your go-to-market strategy. Tell us a little bit about how you first went to market as a consumer product and really how that strategy has changed as you've scaled.

A lot of people thought that the waitlist was a way to generate demand. That is actually not the reason why we did it. The reason why we did it was to get thousands of people, initially just dozens of people using the app, but people using the app Understanding what their bugs are, and then fixing those things so that the next cohort of users didn't run into those issues. We're all product people on this call, so I think we'll all be familiar with the idea of bug fatigue. The idea of bug fatigue is that any given user, I think, will report maybe 2, 3, 5 bugs if you're lucky. Yes, there are always those amazing users who years in, continue to send their issues, but most people will give you 2 or 3, which is why you don't want thousands of people really early, because they'll give you the same relatively small collection of bugs, and then you don't find the next ones. And also it causes the net detraction problem that we outlined earlier. So the waitlist, the primary reason for it was not to generate demand. That was a happy side effect. Zooming a little bit out, the overall strategy for Superhuman's go-to-market in those early days always had 3 pillars. Number 1 was virality. As an email product, as a communications product, it's actually relatively easy for us to be viral. We are literally communicating on behalf of our users in their name. There is the sent by Superhuman signature. Which is shockingly effective. I think our users have sent north of 200 million emails to date, around 30 to 40% of which have had the Sent by a Superhuman signature turned on. So it is by far the largest driver of site traffic. In a typical month, 50 to 60% of our site traffic comes from that signature. So that's pillar number one. Pillar number 2 is content marketing, but not content marketing in the way that most companies approach it. Most companies have approached content marketing with the strategy of writing perhaps 100 articles per year, but not necessarily adding anything new to the discourse. My take was always very different. What if I wrote just one article every year or two, But that one article would drive way more relevant traffic and be a genuine addition to the state of the art and therefore be evergreen and last for many years. So the first such article I wrote is the product-market fit engine, the one that we already discussed on First Round Review. It is the most widely shared entrepreneurial article on their site and now in general. And you may have come across this before? How would you feel if you would no longer use the product? And the idea is, if more than 40% of your users say they'd be very disappointed without the product, that whole thing has now become a standard that venture-backed companies use to measure product market fit, up there along Net Promoter Score. So that was the first such article. I then made a second article, uh, which is Game Design, Not Gamification. And we continued the cadence. In the early days of Superhuman, That was our content marketing strategy and it was super effective. And then the third piece has always been press. Now this doesn't work for every company, but if you are a mediagenic company, if the problem that you are solving is in a space that the press cares about, and email is such a problem because journalists get a ton of email, it's as simple as that, then you can do a lot of press around what you are building as well. So for us, it was virality, content marketing, or perhaps more accurately thought leadership and press.

Thank you for that 3-pillar breakdown. And I think especially early founders, whether it's B2B or consumer, don't realize how many different ways you can cut going to market. It's not just about launching a product and waiting. And related to kind of your initial go-to-market strategy and those 3 pillars, you were marketing and selling directly into consumers. But Superhuman has recently started to expand from an individual product to one built for teams. Can you tell us a little bit about this evolution and what you've learned away in terms of selling to teams rather than individuals?

About 2 years ago, almost none of our revenue was coming from teams. And today, about a third of our revenue is coming from teams, and it's the fastest growing part of our business. And the main lesson for us was simply that we should have done it sooner. I personally was always hesitant. I thought we needed a lot of team features or team value propositions in order to make the sale, but I was just plain wrong. If you have a strong enough individual value proposition, then that, plus the convenience of centralized billing and some discounts, can be good enough to get started. And in our case, the value proposition of saving 3 hours per person per week is absolutely strong enough. All of that said, I do think it is important to build value propositions for the team use case. You just don't need them to get started. Two that we've built recently are team reply indicators and team read statuses. With team reply indicators, you can see when your team is replying, so you can avoid that embarrassing collision when you reply at the same time. At best, it looks like you're just not organized, but at worst, that's when you say different things. And with team read statuses, you can share read statuses across your team. So even if you did not send the email, say to an investor or a candidate or a customer, you can still see when they open that email. And in doing so, you can hand off work and collaborate more effectively. So for example, if one of you emailed me and CC'd the other, The other can also see if and when I opened the email.

Certainly interesting to see how it was actually a very natural extension to sell into companies and certainly food for thought for many B2C businesses, especially in this market. We mentioned AI super briefly when we were talking about YC, but AI has obviously been a key theme on this season's podcast. And with ChatGPT-4 blowing our minds just months after the release of ChatGPT-3, How is Superhuman thinking about AI?

This is not gonna be a hot take. This is, I think, the obvious take for anyone who's in the space, but we think that AI will completely change how we work. And so it is an area of very heavy investment for us. In fact, we are set to release our first AI feature in just a few weeks, which isn't going to be what people expect. We are not integrating GPT as The first thing, although of course we are working on that, the very first AI feature we're releasing in a few weeks is going to be autocorrect, which is going to fix all of the errors and mistakes that you make as you type. Now, you may be familiar with this from Gmail or Outlook if you use those products today, but we've taken that feature to the next level. And our version of autocorrect is beating Gmail and Outlook across all different kinds of benchmarks. And what we found in our experiments with folks is that you can type 30 to 50% faster with Superhuman Autocorrect. So I'm incredibly excited to get that out very shortly.

I desperately need this product, so I'm also very excited for this to hit the Superhuman inbox. And one more question around how Superhuman is thinking about the landscape, because you guys are a preeminent application layer product that people are using across the board. 200 million emails sent. It's just a bananas number. And we've spoken to other guests this season who are thinking about the application layer as the core focus, which you've been doing. And there's others who are thinking about it from a vertically integrated all the way down to the model level. What is your perspective, both for Superhuman and for perhaps new builders in the space who are thinking about how to be across this stack?

I think if you are working in the application space, it doesn't necessarily make sense to start by owning the model, although that may inevitably be your destination. I think it makes sense, and Sarah Groh has said this better than I have. I would check out her recent tweetstorm on AI strategy, but I think it makes sense to start by integrating GPT or an alternative into your application layer. It's not gonna be super tuned. You may be able to do better. By training your own model or by using a different model. But simply getting going, getting it in the hands of users and getting feedback is probably the correct starting point. And then you can get on to phase 2, which is, okay, now we have GPT or large language models more generally integrated into the surface area of our products. How can we make all of those things better? Does it make sense to roll our own? Does it make sense to switch provider? Does it make sense to maybe use a different style of machine learning for some of these features and for some of these workflows? What new workflows can we create and come up with? And so I think we as an application company are gonna go through that series of steps, and it's what I see most application companies doing as well.

I love that. A try before you buy on, do you need to build and buy your own full model when you can use some of these now publicly available ones and then go from there? 'Cause you need to learn about how your user base is gonna appreciate and value this product and experience. I'm excited for the road ahead for Superhuman, and you gave us a little bit of a sneak preview around what's around the corner with autocorrect, but we'd love to ask what's next for Rahul.

It's not that different. As the CEO of the company, it's leading Superhuman to the next level of growth. I think the thing that's most exciting for me is that we have a product that people really love, which was one of the key goals I had when starting the company. We touched on this a little bit earlier when we were talking about the value of patience and how there are different kinds of founders. But you're right, there are some founders for whom that's not important. And actually having a thing that grows really fast and makes a lot of money and is a super powerful business is the most important thing. And that is really important. Don't get me wrong, but just as important for me is having a product that people really love. And for me, it's super exciting to be able to work with that. So, as a product leader, I think that this is going to be our best year yet. On the platform side, we have things like our Windows and our Android apps coming out very soon. On the Teams side, we have a variety of new features that will make it faster and easier for teams to work together. And on the AI side, we have autocorrect. And as far as after that, I would say stay tuned.

We certainly will, and our listeners will, too. And we have our final closing question that we ask all our guests for you today. Who is a woman in your life that has had a profound impact on you and your career?

In a professional capacity, it would absolutely, I think, have to be Kristen Haywood, who is our head of people here at Superhuman. And before she joined Superhuman, Kristen was actually a customer, which I think is always the best way to get to know a company. And when she started, she was initially consulting with us. On hiring a head of talent. And after helping me interview many potential heads of talent, it became very clear to me that the best possible head of talent was right there in the room with me. So I asked her if she would want to join, and af— after a little bit of convincing, she became our head of people. And since then, she's helped build the executive team, and she's helped me run the company whilst doing so. So for example, in, in addition to running the people function, She has also been managing finance, sales, and customer teams and lifting a great weight off my shoulders in doing so. That, I think, is the hallmark of a great executive, when you can keep on giving them more.

She sounds like an incredible woman, someone we hope to meet someday and perhaps have on the podcast at some point. But, uh, well, thank you for jumping on with us today to tell your story from building games in your childhood bedroom to ultimately becoming the founder of Superhuman. And empowering everyone to be superhuman. Really appreciate your time today.

Thank you so much for having me.

Thank you so much for joining us at The Room Podcast. If you want more from The Room every week, subscribe to our newsletter at theroompodcast.com/newsletter. We'll be back next week with a new episode, Tuesday, 10 AM Eastern, 7 AM Pacific. See you in the room.

All opinions expressed by Claudia Madison of Madison and podcast guests are solely their own opinions and do not reflect the opinion of The Five AC. This podcast is for informational purposes only and should not be relied upon as a basis for investment decisions.