Superhuman (with CEO Rahul Vohra)

We wrap up Season 4 with a very special (and accidental!) episode, a conversation with the CEO of Superhuman, the red hot email productivity app which just announced their $33m Series B led by Andreessen Horowitz. While originally intended as a limited release episode, we felt Superhuman would provide the perfect bookend to our “modern enterprise productivity trilogy” following our Zoom and Slack episodes. We hope you enjoy the conversation with Rahul as much as we did, and we’ll see you later this summer for Season 5! Sponsors: Vanta: https://bit.ly/acquiredvantaServiceNow: https://bit.ly/acquiredservicenow26Legora: https://bit.ly/acquiredlegoraStatsig: https://bit.ly/acquiredstatsig26 More Acquired! Get email updates https://www.acquired.fm/email with hints on next episode and follow-ups from recent episodesJoin the Slack http://acquired.fm/slackSubscribe to ACQ2 https://pod.link/acquiredlpMerch Store https://www.acquired.fm/store! © Copyright 2015-2026 ACQ, LLC LinksNew York Times article announcing the fundraise: https://www.nytimes.com/2019/06/27/technology/superhuman-email.html Rahul’s Medium post on acquisitions: https://medium.com/swlh/rip-mailbox-or-founders-how-to-stop-worrying-and-love-being-acquired-261da4f6d566Rahul on finding product-market fit on First Round Review: https://firstround.com/review/how-superhuman-built-an-engine-to-find-product-market-fit/

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

• 0:00David Rosenthal?

  Great.

• 0:02Ben Gilbert?

  One take feels good.

• 0:16Ben Gilbert?

  Welcome to season four, episode 10, the finale of Acquired, the podcast about technology acquisitions and IPOs. I'm Ben Gilbert.

• 0:25David Rosenthal?

  I'm David Rosenthal.

• 0:26Ben Gilbert?

  And we are your hosts. Today, we are covering Superhuman, the fastest email experience ever made. This show was originally going to be a limited partner bonus show with Superhuman CEO Rahul Vohra on understanding his algorithmic approach to find product market fit. But we realized that Superhuman was a perfect way to round out our trilogy on the modern productivity stack on the heels of our Zoom and Slack IPO episodes. And we learned that the timing would be perfect with some big news that just dropped for Superhuman.

• 0:58David Rosenthal?

  Indeed.

• 0:59Ben Gilbert?

  Well, they just raised their $33 million Series B funding led by Andreessen Horowitz on the heels of some very rapid growth, as you'll hear. If you want to read more about the company after this episode, you can click the link in the show notes for the New York Times article that broke the news. All right, listeners, now is a great time to tell you about a longtime friend of the show, Vanta. AI has scrambled the whole security picture. It used to be that you proved that you were secure once a year on audit or a static PDF, then everyone would nod and you're done. But in an AI-first world, that doesn't hold up anymore.

• 1:33David Rosenthal?

  Yep. Your risk surface changes every week now. A vendor turns on an AI feature or someone writes in a new model without telling IT, and your posture is different than it was last week, let alone at your last audit. Vanta's own research found that around 70% of companies have this quote unquote "shadow AI" running with no security review at all.

• 1:54Ben Gilbert?

  Right. And that's where Vanta comes in. They're the leading agentic trust platform, meaning they've built the thing that closes the gap. And the way that they close that gap is Vanta Agent. Think of it as a GRC engineer, that's Governance, Risk and Compliance, except that it's software and it doesn't sleep. It finds the issues, drafts the fixes, and cuts the time that you'd spend on vendor assessments in half.

• 2:16David Rosenthal?

  In half? Which is exactly why more than 16,000 companies today run on Vanta. Companies like Ramp, Cursor and Snowflake all stay audit ready and catch the risks that crop up between audits across every vendor, every AI tool, the whole environment.

• 2:34Ben Gilbert?

  And that's the real value. Trust has to be continuous now, which is why Vanta automates your security, your compliance and the work to earn and prove trust. We're huge fans of Vanta over here and literally hundreds of acquired listeners have become Vanta customers at their companies over the years. So you can get $1,000 off Vanta at vanta.com/acquired. That's V A N T A dot com slash acquired for $1,000 off and just tell them that Ben and David sent you.

• 3:02David Rosenthal?

  Now, without further ado, here is our conversation with Superhuman CEO Rahul Vora.

• 3:09Ben Gilbert?

  So, welcome Acquired LPs to a very special episode of the LP Show. David and I are sitting here in Superhuman World HQ on California Street in San Francisco and we have with us an awesome guest, Rahul Vora, CEO of Superhuman. Welcome to the show.

• 3:27Speaker 02

  Absolutely. Thank you both for having me.

• 3:29Ben Gilbert?

  Yeah, you bet. To give a little brief bio, so Rahul is the founder and CEO of Superhuman, the wildly popular, blazingly fast email app that is changing the way a lot of us think about our relationship with our inbox. And before Superhuman, Rahul was the CEO and co-founder of Reportive, selling that to LinkedIn in 2012. So if you're noticing a pattern there, I think I definitely am. Rahul is also an active angel investor and advisor to several startups and we are lucky to have him with us today. So I already said welcome to the show, so I don't need to say that again, but welcome to the show.

• 4:01Speaker 02

  Thank you.

• 4:04Ben Gilbert?

  Are we right that this is your second office?

• 4:07Speaker 02

  This technically is our fourth office.

• 4:11Ben Gilbert?

  Fourth office. Wow. And you're about 30 people now here, it looks like?

• 4:14Speaker 02

  We are, yes.

• 4:15Ben Gilbert?

  It's nice and decked out in Superhuman colors. It's like...

• 4:19Speaker 02

  Yeah, we do like our pinks and our purples and our blues. Although we're sort of trying to keep the we just moved in vibe. We don't want to go too crazy here.

• 4:27Ben Gilbert?

  Yeah.

• 4:27Speaker 02

  Because what we've found is we grow so fast that by the time we've made a place nice, it's like, okay, time to move on to the next office. It's awesome.

• 4:35David Rosenthal?

  The problem with early-stage startup offices.

• 4:37Speaker 02

  Good problem to have.

• 4:38David Rosenthal?

  Yeah, good problem to have. Let's talk for a minute before we get to Superhuman, which we're going to spend most of the episode on. Can you tell us quickly on Reportive? How did you start it? And it was a very quick turnaround.

• 4:50Speaker 02

  So Reportive was basically started to satisfy my own need. It was a classic case of scratching my own itch. I was at the University of Cambridge at the time, and I, in fact, had just dropped out of the PhD program. I'd started a PhD there in machine learning and computer vision. This was way before either of those things were cool or even feasible. In any case, I dropped out because I realized that what I wanted to be was an entrepreneur. But I didn't have an idea at the time that I wanted to pursue. So I networked my way into the part of the university that helps staff and students create companies called Cambridge University Entrepreneurs. And essentially, what I would do is I would actually come

• 5:31Speaker 02

  to folks like yourself, VCs, angels, big tech companies, and I would say, hey, can I please have some money? And they'd be like, why? And I'd say, well, I want to give that money to staff and students at the University of Cambridge who are making companies. It's gonna be awesome, trust me. And these folks would sort of rub their hands together and go, cool, how much equity do we get? And I would say, none whatsoever. This is a charity that we're running here. We're trying to help people learn how to build businesses. And by the way, we're going to make some amazing businesses as well.

• 6:05David Rosenthal?

  And as we've covered multiple times on the show, Cambridge is actually a really great entrepreneurial hub. I mean, ARM came out of Cambridge, as did many other companies.

• 6:13Speaker 02

  It's crazy. Cambridge Silicon Radio, let's see, who else? There was that company that Qualcomm acquired. I forgot the name.

• 6:24David Rosenthal?

  And more than companies too. My partner Riley at Wave was a grad student at Cambridge. As was our friend Nell's at Eventbrite. Plenty of Silicon Valley has come from Cambridge in the UK.

• 6:34Speaker 02

  Yeah, those VCs should have given you money.

• 6:38Speaker 02

  They did. They did actually give me money in the end. But the point of the story is, I was thrust into this not-for-profit fundraising at a very young age with no training in this field whatsoever. And having grown up learning how to program and being a very competent programmer at the time, I was just wondering to myself, well, what tools would help me do this fundraising better? And I imagined if in my email, I could see what people look like, where they were based, links to their recent tweets, links to their social profiles, then I would be able to authentically connect with that person and establish rapport so much better. Hence, the idea behind Reportive.

• 7:20Speaker 02

  I couldn't find that product in the market, so in about six weeks, I just sat down and built that first version.

• 7:26Ben Gilbert?

  And that was, that was totally magical. I remember the first time I installed the, the plugin was, was it first for Gmail and then Chrome? Or was it, what was the implementation of that?

• 7:35Speaker 02

  It was, in fact, always a Chrome extension. Although before it was a Chrome extension, technically it was a Firefox extension. This was in 2010 where people, it's kind of hard to remember now, but people were still skeptical that Chrome was a great thing. The tastemakers at the time, we were all sitting in Firefox. So it started as a Firefox add-on, and later on, it was a Chrome extension.

• 7:59Ben Gilbert?

  I do definitively remember that eye-opening experience of you can type someone's email and, and then like a second or two goes by and then boom, there's all this enrichment about them. And it's like, now it's taken for granted because this idea has permeated into sort of other products throughout the years, but there's something really magical to it.

• 8:15David Rosenthal?

  How did the connection with LinkedIn happen? I mean, we've also talked a bunch about on the show about the importance of email to LinkedIn and to LinkedIn's growth and onboarding. So I imagine you popped up on their radar screen pretty quickly. What was the relationship like?

• 8:29Speaker 02

  We had a great relationship and ultimately it ended up in, I guess, a technical consummation. They acquired us. Initially, like many acquisitions, it started with a business development relationship. And the way that that transpired was we were consumers of an API at the time provided by, I don't know if you guys remember, a company called Rapleaf. Oh, yeah. Oh, yeah. Totally. So Rapleaf is one of those first companies to whom Salesforce acquired them, I think? No, so Rapleaf ended up transmogrifying to some degree. They became LiveRamp. And then they were acquired by Acxiom and have recently spun out as a large public company. I think they're now worth $3 billion or more. So they're doing really well.

• 9:13Speaker 02

  But back in the day, it was a relatively small startup called Rapleaf. Yet despite their small size, they were the only company, and remember, this was back in 2010, to whom you could supply an email address and they would give you the full social context about that email.

• 9:29Ben Gilbert?

  And so today, that's FullContact, Clearbit, those are the sort of providers that would be the comps today.

• 9:35Speaker 02

  Correct. Yeah. And now it's sort of, and there are others as well. Now it's sort of a, almost a commodity marketplace for that data. But back then, it was this sort of edgy, crazy new thing that you were able to do. And so me being an opportunistic entrepreneur, I was like, cool, let's take this API, let's package it up, which actually wasn't a crazy amount of work. And let's, let's jam it into Gmail via the use of a browser extension. So that's where the data came from. Now, you can imagine that LinkedIn were non-too pleased about an upstart selling their data. Well, and LinkedIn famously has always made it really hard to get mass quantities of data out of their API because they have a network effect. Indeed. And we definitely didn't want or need mass quantities.

• 10:17Speaker 02

  And everything, by the way, that we were doing was for the benefit of LinkedIn's hardest core members, which is ultimately why it was such a good relationship with them. But they approached us at one point and were like, hey, listen, we really would prefer it if you were not buying our data off third parties. And I was like, cool, I would really prefer it if I had access to the API. Yeah, and so.

• 10:40Ben Gilbert?

  That appears to be only internal right now.

• 10:43Speaker 02

  We both stated our preferences for a while until I think a few months later, we realized that maybe an actual business development relationship would be the best thing, which was truly remarkable, because I think at that point, in fact, it never grew beyond us. There were only ever about 20 companies that had access to this secret LinkedIn API.

• 11:03David Rosenthal?

  That's awesome. And that was that was probably right around the time of their IPO, right?

• 11:08Speaker 02

  This would have been halfway through 2011. I don't recall exactly when they IPO'd. Yeah, it would have been around that time.

• 11:15David Rosenthal?

  It was either end of 2011 or like beginning of 2012, I believe.

• 11:19Speaker 02

  Yeah. The chap I was dealing with is Adam Nash, who went on to be the CEO of Wealthfronting, who's now on Dropbox. And he was super nice about it. So I went in and he was like, can you demo what you would do with the LinkedIn API? And I showed him the workflows. And he was looking for things like, is the copy helpful? Are we trying to deceive users? Clearly no. Are we stealing data? Absolutely not. Is it for the value of the LinkedIn member? Yes, it is. He was like, okay, great. You should be a partner.

• 11:46Ben Gilbert?

  I personally wanted to dive into that to sort of give context on how we got to where we are today. What I'd love to start to steer the conversation to is the founding of Superhuman. And David and I have previously talked a couple of times on the LP show about things that companies do pre and post product market fit and definitions of it. But Rahul, you at Superhuman have actually built metrics around it and found sort of systematic and scientific ways to find product market fit. I'm teasing sort of our analysis section here later because I want folks to know that we're going to dive into the founding of Superhuman right now. But where we got eventually is to a company that waited over two years to launch and really built something sort of amazing in a very sort of both art and data driven way. And then we're going to sort

• 12:30Ben Gilbert?

  of dive in and tell that whole story. But talk to me about the initial idea for Superhuman, where it came from, and how you convinced yourself that there's a business to be started selling a new email platform.

• 12:42Speaker 02

  Right. It isn't necessarily obvious from the outset. I do agree with that. At LinkedIn, I ran all of our email integrations. It was my responsibility, rather, to get LinkedIn data, LinkedIn profiles into other email clients. And so I became very familiar with how professionals do their email. And the TLDR is badly.

• 13:04Speaker 02

  So I took a year off after I left and during that time I was looking for what I wanted to start next. Due in part to the IPO and to the acquisition, I was very fortunate to be in a position where I didn't really have to work. And so I focused on impact. You know, what was the biggest thing that I could possibly do? And my mind kept going back to a 2012 McKinsey study where they showed that the average professional, and there are 1 billion professionals in the world, the average professional spends three hours a day reading and writing email. It's not hard at all to believe.

• 13:40David Rosenthal?

  Right? Like, it's crazy.

• 13:42Speaker 02

  It's, I mean, it's, it's just mind blowing. And, and so during my year off, every single day I was doing the very simple math. 1 billion professionals times 3 hours a day is 3 billion hours a day. That go into email.

• 13:58David Rosenthal?

  Yeah.

• 13:58Speaker 02

  And I couldn't find, I couldn't think of anything bigger than that to do.

• 14:03David Rosenthal?

  A market that big and nobody had built a real business in it.

• 14:06Speaker 02

  Correct, because people were scared because Microsoft and Google between them had systematically almost prevented startups entering this area. Exactly. And so it was during that time when I looked very closely at how people were feeling about Gmail. And bizarrely, I saw this product get worse every single year. I think because I was building on the Gmail, it's not really a platform because I was building a Gmail browser extension. I could, I had a front row seat to what was happening here. So I saw the products becoming more cluttered, using more memory, consuming more CPU, slowing down your machine, still not working properly offline.

• 14:46Speaker 02

  And then on top of that, people were installing plugins like ours, Reportive, but also Boomerang, you'll remember, Mixmax, Clearbit, you name it. Yes, Mail, all sorts of.

• 14:56David Rosenthal?

  You know, Streak and what have you.

• 14:57Speaker 02

  Right. It's kind of guilt inducing for me because Reportive was the first to get to millions of users. And I'm like, I am sorry, guys. I did not intend it to be this way. I know. It's, it actually makes me sad.

• 15:12David Rosenthal?

  Well, and like one of the, you know, rules, I think we've talked about at various points on the show before, like all rules in startups and ventures meant to be broken, but you can't build a big company on the back of somebody else's platform. Like, there are very, very few examples. And as long as Gmail and Microsoft are the platforms and you're just building plugins. Report of being the most successful among them, you're just going to be a plugin.

• 15:36Speaker 02

  I think that's true, although I would like to see, for example, Grammarly be the exception to that rule. I think at this point, they're probably the highest valued, most successful plugin business. And fingers crossed, they actually break the barrier and break out into their own thing. But you're right, that there's a lot of existential crises around there.

• 15:55David Rosenthal?

  Yep.

• 15:56Ben Gilbert?

  Can I ask, when you were thinking about what to start and you were fully impact driven on that, was your mind able to go to places that weren't email? Because you knew it like, is it, is it that you knew it so well that you felt that you sort of were uniquely positioned and owed it to the world to fix that problem? Or was it more like, I tried to think of other stuff and email is where my head was?

• 16:16Speaker 02

  So I did absolutely go to other ideas. I spent time in the summer of 2014, researching any number of things I could do. And I got quite deep into what you would now call concierge health. So an on-demand doctor who might turn up and sort you out with whatever ailment you might be feeling. Again, I, I saw the potential for a very large amount of impact there. But it's interesting that you, you mentioned this idea of owing it to the world. I very much felt like I did and still do. I do believe that there is the perfect startup for every founder. The one where if you do it, you have an outsized chance of success.

• 17:02Speaker 02

  The story arc is just perfect. And it's, it's kind of the startup where if you do, everybody will cheer you on because they want you to succeed. Because it feels like it's, you know, it should be destiny that this thing works.

• 17:14Ben Gilbert?

  Yep.

• 17:15Speaker 02

  And that startup exists for most founders. And for me, I believed that it was superhuman. It was the natural, logical, progressive evolution from Repulsive. It is the thing that we always wanted to build anyway. And was actually the solution to all the problems that we created whilst we were messing around at Repulsive.

• 17:33David Rosenthal?

  Well, you just said it resonates so much because like, at the stage, at the seed stage that we invest in a way, even that the PSL works out like, I have some version of that conversation like every week, you know? Like, how, so I'm just, I'm just curious, were there people who helped you through that phase? Or was it like a journey you had to go on, on yourself, on your, by yourself to realize like, okay, like the destiny is superhuman?

• 17:58Speaker 02

  There were definitely lots of people who helped me through that phase. We just mentioned Adam Nash earlier. And I remember when I left LinkedIn, he was CEO of Wealthfront at that time. And I went to him and I said, hey, I have this idea for a new email experience. It's called Superhuman. Here's what it's going to do. It's amazing. I want to go and start it. He was like, whoa, whoa, whoa, slow down. Are you going to take any time off? And I said, yeah, I'm planning to take some time off. And he said, well, how much time do you think you need? And I said about three months and he was like, wrong. However, much time you think you need, it's actually more like three times that. You probably need nine months off. And in retrospect, he was completely right.

• 18:40Speaker 02

  I ended up taking about nine months off before I felt comfortable settling into what was essentially the same business idea that I'd been working on for about four years. So during that time, I did explore lots of other ideas. I had a few mentors that I would constantly bounce concepts off. But I just felt myself always coming back to this, this one idea because I, it's hard to explain. I just, I couldn't stay away from it. I think that's a good sign when you can't stay away from an idea. It's, it's a strong indication that you should probably go and do it.

• 19:13David Rosenthal?

  Yeah, totally.

• 19:14Speaker 02

  No matter how bad the idea is.

• 19:15David Rosenthal?

  Resonates so much for, you know, certainly for me and Starting Wave. I assume for you and PSL.

• 19:19Ben Gilbert?

  Hundred percent.

• 19:20David Rosenthal?

  For Kimberly and Glow, like everything acquired, like, yeah, totally. So cool to hear.

• 19:25Ben Gilbert?

  Okay. So Superhuman.

• 19:26Speaker 02

  So Superhuman is the fastest email experience of all time. Our users get through their inbox about twice as fast compared to in Gmail. They respond more quickly to the emails that matter. And many of them see inbox zero for the first time in years. So you can imagine that's pretty life changing.

• 19:43David Rosenthal?

  Tell me more.

• 19:45Ben Gilbert?

  You sound like you've never said that before, I'm sure.

• 19:49Speaker 02

  I just wake up saying that every day.

• 19:52Ben Gilbert?

  Not to overly fanboy here, but I can absolutely vouch for all of that. And it's especially in a day like today where I'm, I'm down in San Francisco and traveling. Literally feel like I have superpowers plowing through my email at the end of the day. And you guys have built something amazing. So.

• 20:06Speaker 02

  Thank you.

• 20:07David Rosenthal?

  During those, either during the nine months or, or at the end of it, when you first started working on it and then into the. To your process, we'll get to you before you launched. There are a couple of value props in there, but like one of them is like fast, right? Did you land on that? Like, how quick did you get to that? Or whatever, like you, in your mind is like the most specific value prop you needed to nail?

• 20:27Speaker 02

  Speed was a value prop from very early on. And I think as I introspect this, it came out of some of the frustrations developing Reportive on Gmail. Obviously Gmail at the time was my primary email interface. I was the founder and CEO of a, of that startup and I was doing a lot of email based work. And so I was intimately familiar with how slow Gmail was and how slow it was getting. And I had therefore this, this hunch, this inkling that speed was going to be a very big deal. But like with any hunch or inkling, one does have to validate it.

• 21:07Speaker 02

  So in the first year of Superhuman, as we were primarily building, we threw up a landing page. It was a terrible landing page, just like a basic Squarespace thing that took us all of two hours to put together. And all you could do on this page was throw in your email address. And when you threw in your email address, you got an automatic email from me. And in that email, there were two questions. Number one was, what do you use for email today? And number two was, what were your pet peeves about it? And I had two hypotheses going in. Hypothetically, number one was that for Gmail, people were upset about how slow it had gotten, how it wasn't working properly offline and how they had to use Gmail plugins to

• 21:51Speaker 02

  make it do the things that they want it to do. And then for third party email clients, people were upset about how buggy they were, how unstable they were and how they don't sync properly, all of which is still true today.

• 22:03David Rosenthal?

  So much head bobbing on this side of the table.

• 22:05Ben Gilbert?

  You're talking to an Apple Mail comfort.

• 22:07Speaker 02

  Oh, boy. Yeah, I feel for you. So we had to validate that. In that first year of Superhuman, I think that we had maybe in the region of 5,000 signups on that landing page, 5,000 emails that went out, 1,000 conversations that actually happened, therefore 1,000 interviews that I did with early users, probably way more than most founders would actually do. And resoundingly, those two hypotheses were confirmed. People disliked Gmail for the speed and the lack of offline and the clutter and the plugins. And people disliked third-party email apps because of the stability and the sync and the bugginess.

• 22:47Ben Gilbert?

  How did you drive traffic? Like, how did you get top of funnel to get all of those responses on your landing page?

• 22:52Speaker 02

  In the early days of a startup, I think, and this is what we did. The best way to do it is to pick one or two events per year where you can insert yourself into the cultural zeitgeist. So for us, one such event was when Mailbox was being shut down. And

• 23:12Ben Gilbert?

  R I P.

• 23:13Speaker 02

  Yeah, sadness, right? But it was the perfect narrative to say, hey, I'm over here. Come, come look at our company. And the trick when doing these is to think of interesting evergreen content. So you guys are the perfect people to talk to about this. You know more than anyone else just how hard acquisitions are. I currently have one of the most widely read articles on how to survive an acquisition. And it was written in response to the Mailbox shutdown.

• 23:43Ben Gilbert?

  I think it's your only Medium post, right?

• 23:45Speaker 02

  It's probably my only Medium post, correct, because I usually end up, I mean, the sort of second part to your question. I usually actually end up syndicating posts. You get far more reach that way. And so that post ended up on Medium, also was syndicated to QZ.com. And yes, it was about how do you survive an acquisition? And we were able to insert it into the zeitgeist because relevant to our company, some news event was happening. And I think if we as founders think hard enough, there's probably one or two things a year where that's true. And you only need one or two things a year. Now, it's a pretty intense period. I think to write that article probably took me about three days of not doing anything else. And then another day of shopping it around.

• 24:27Speaker 02

  So four days all in, but those four days bought, I don't know, north of 5,000 signups. And then those are the signups that you need to validate your initial idea.

• 24:36Ben Gilbert?

  Yeah.

• 24:37David Rosenthal?

  When you saw the news, the mailbox was being so like, how quickly did your mind go to opportunity? Like, I'm gonna, I'm now gonna go take four days to do this, like?

• 24:47Speaker 02

  Practically immediately. Immediately, I said to the team, this is something that we need to capitalize on and take advantage of. We have to make ourselves relevant. We didn't actually do anything, and this is just often how startups go, until there was about a week to go. So the last week was an extreme scramble. I was like, remember that idea that we had a few months ago? Well, like, we need to do it right now.

• 25:12David Rosenthal?

  Amazing.

• 25:12Ben Gilbert?

  Yep, startups. All right, listeners. Now is a great time to thank our longtime friend of the show, ServiceNow. If you are running a large enterprise, AI agents are likely spread across every team, and deploying them is no longer the hard part.

• 25:28David Rosenthal?

  Yeah, the hard part is knowing what permissions they have, what employees are using them for, or what decisions AI is making. AI security for an enterprise at scale is not a small concern. Like, the risks are real.

• 25:42Ben Gilbert?

  Exactly. And the challenge with AI is governing it, securing it, measuring it, and making sure that it actually delivers value. That is why ServiceNow built the AI Control Tower.

• 25:52David Rosenthal?

  Yep, AI Control Tower gives enterprises a single place to see, manage, govern, and optimize AI across the entire business. And it works with any AI, not just theirs. Every device on your network, every permission across every system, every AI agent, visible and secure in one place.

• 26:10Ben Gilbert?

  And ServiceNow can do this because they've spent more than 20 years building the operational backbone of the enterprise, the workflows, governance, approvals, security controls, and institutional knowledge that power how work actually gets done across IT, HR, customer service, finance, and security.

• 26:26David Rosenthal?

  ServiceNow already runs more than 100 billion workflows annually, and trillions of transactions for more than 85% of the Fortune 500. So when companies need a place to govern AI at enterprise scale, they're building on a platform at the center of how their business already operates.

• 26:42Ben Gilbert?

  And in a future that isn't going to be one AI, it's going to be thousands of AI agents working across every function of the company. But the question is, who's managing them all?

• 26:52David Rosenthal?

  So if you're trying to turn AI ambition into real business outcomes and make it work safely, securely, at scale, go check out servicenow.com/acquired and tell them that Ben and David sent you.

• 27:03Ben Gilbert?

  Before we get into kind of our discussion, I want to talk about a kind of a provocative question. Have we reached the end of the era of the MVP or ship a crappy version? But before we get there, for the listeners who don't know, Superhuman costs $30 a month for an email client. Like, talk about a narrative violation. This is, I think, the last browser that tried to charge for you to use was like OmniWeb in the early 2000s. And I think it would be absolute heresy today to say, oh, it's not even a mail service. It's backed by Gmail. It's an application through which to interface with Gmail. But, boy, is it great. And, oh, my gosh, I pay $30 for it. How did you

• 27:45Ben Gilbert?

  come to a revenue model of we're just going to ask people to pay? How did you pick a price point? And how'd you validate it?

• 27:52Speaker 02

  I think, overall, with pricing strategy, you have to analyze what you're going up against. And we were going up against free or nearly free. Gmail and Microsoft are practically free if you are a consumer. And if you're in the enterprise, it's being paid for you anyway, so you don't see or feel the cost. The only way to win, and I think it's Reid Hoffman who popularized the following statement, is to be contrarian and right. I don't necessarily know how to be right, but I do know how to be contrarian. And there's nothing more contrarian against a free product than to charge as much as seems reasonable, or maybe even more than seems reasonable. Yeah.

• 28:33Speaker 02

  But then to back it up with the goods that actually make it worthwhile. So, before we tried to address pricing, we actually first addressed our positioning. And we ran through a series of questions. I'm a car guy, so a lot of my analogies to do with cars. And so, for example, we asked ourselves, are we the Ford of email? No, not really. Are we the Mercedes of email? Not quite, but maybe we're getting there. Are we the Tesla of email? Okay, this is beginning to feel about right. And there's a classic positioning game that you can do. It's a little bit of a Mad Libs exercise,

• 29:10Speaker 02

  where you say, for a target customer, who has a need or an opportunity, my product is in this category, and this key benefit, unlike some other competitive products, will create this primary differentiation. From crossing the chasm.

• 29:32David Rosenthal?

  Yeah, yeah. I believe Jeffrey Moore in Crossing the Chasm came up with that frame. And then like, it's been used many times, but.

• 29:38Speaker 02

  Gotcha. So I'm clearly not as widely read as you are.

• 29:42Ben Gilbert?

  That's a frameworks guy.

• 29:42David Rosenthal?

  Well, when you go to business school, you learn a lot of like useless trivia.

• 29:49Speaker 02

  So I actually found this piece of wisdom, as I find much of my wisdom, off the first round review. Journal, which is incredible. And it was written by Ariel Jackson, who listeners may not know, but she was the product marketing manager at Google who launched Gmail. And I was like, wow.

• 30:07David Rosenthal?

  Like, okay, here we go.

• 30:08Speaker 02

  I have to meet her. Unfortunately, we were a first round or are a first round investment. And so that was very easy. And so I got to spend a lot of time with her working on our positioning. And I have it right here. So we came up with, for founders, CEOs and managers of high growth technology companies who feel like their work is mostly email. Superhuman is the fastest email experience ever made. It's what Gmail could be if it were made today instead of 12 years ago. Unlike Gmail, Superhuman is meticulously crafted so that everything happens in 100 milliseconds or less. And we've since expanded beyond that very, very.

• 30:47Ben Gilbert?

  Narrow. That's very narrow.

• 30:49David Rosenthal?

  So great.

• 30:49Speaker 02

  That's what you have to do. You have to start with something that narrow.

• 30:52David Rosenthal?

  Yeah.

• 30:52Ben Gilbert?

  Is there a risk in starting with something that narrow that you're not going to be able to expand outside of it? Or do you feel like if you can nail it for that core group, then you're always going to be able to find more room around the edges?

• 31:05Speaker 02

  Very much the latter. So I think we should come back to that point because I have a.

• 31:10Ben Gilbert?

  Yeah, let's do it.

• 31:11Speaker 02

  I have a thing that I should probably share with the listeners, but just to tie the positioning back into the pricing, because this is a very methodical exercise that we ran through. So, so step one is understand the lay of the competitive environment. In our case, we were going up against two incumbents whose products are free or practically free. Step two is come up with the positioning like I just described. And when you read our positioning, it's clear that Superhuman is a premium tool for a premium market. And step three is develop your pricing. Now, there are many, many ways to develop pricing, but one of the easiest ways, this will appeal to the business school guy in you, is the Van Westendorf pricing sensitivity meter. I see head nods going on over here.

• 31:55Ben Gilbert?

  That sounds like a fancy name.

• 31:56Speaker 02

  Yeah, it's just some dude's name, I think.

• 32:01Speaker 02

  He was probably very smart, very clever, did a lot of pricing. Anyway, so he said, "Ask your target users four questions. Number one, at what price would you consider Superhuman to be so expensive that you would not consider buying it? Number two, at what price would you consider Superhuman to be priced so low that you would feel the quality couldn't be very good? Number three, at what price would you consider Superhuman to be starting to get expensive so that it isn't out of the question, but you would have to give some thought to buying it? And number four, at what price would you consider Superhuman to be a bargain, a great buy for the money? Now, most startups actually orient around the fourth question, the bargain

• 32:43Speaker 02

  for the money, because there's some kind of network effect, or a greenfield effect, or they're trying to take advantage of a first mover effect, or so on. So there's a land grab. They want to go get all the users, so we may as well price as low as we can to get them all. Exactly. Which is why most founders I know have the experience of a board meeting where your board members are like, "Hey, you know what? Maybe you should half the price. Maybe we should just like make this free and like give this away for me." Oh god, you're giving me the heebie-jeebies here. Wait, have you done this to founders? I've done this, yeah, yeah. Well, guilty. Committed the cardinal sin here. Guilty as charged. My point is- I think I did this last week. It's actually entirely the correct thing to do if you're building in a new market, or there is a land grab or a first mover advantage that you're trying to chase. However-

• 33:28Speaker 02

  Definitely not the case with email. Not the case with email, where there's a big incumbent and the competitive products are great. Startups like Superhuman should orient around the third question. When does it feel expensive, but you'd still buy it anyway? And that makes sense if you're building a premium product. Now, for us, the median answer to that third question was $30 per month. And that's how we picked the price. So we very methodically went through competitive landscape, positioning, and then pricing, using this very simple pricing methodology. Mm-hmm. And were you using people who had engaged with the survey that you were driving traffic to? This was actually well before-

• 34:10Speaker 02

  We started doing the service. So this is when we were onboarding our first 100 customers. I did all of these manually in the onboarding and these onboarding used to be much longer. They were one hours or one and a half hours. I'd give them a demo of the product and then I'd look them in the eye and I'd be like, hey, this is the thing that you have to pay for now.

• 34:33David Rosenthal?

  They didn't know going in with the demo.

• 34:34Speaker 02

  I mean, they kind of knew, but like I was reminding them.

• 34:38Ben Gilbert?

  You can't see Rahul right now, but like it's almost like this like a terse dad look that he's giving you. It's like, now, son, I have some news for you.

• 34:48Speaker 02

  And I would actually very sternly look them in the eye and say, hey, this is the thing you have to pay for. Can I ask you a few questions about how you feel on pricing? And they'd be like, yes. And then I just, I'd go into it and I'd write down the numbers. And after we'd done a hundred of these, the answers were pretty clear.

• 35:06Ben Gilbert?

  That's awesome.

• 35:06David Rosenthal?

  That's amazing. And you haven't changed the pricing since?

• 35:09Speaker 02

  Well, actually, the initial pricing was $29 per user per month. We didn't think too hard about that. That was just like, well, you know, it seems to be the right price, roughly the right order of magnitude. And then I had a few conversations with some pricing experts who pointed out that if we are truly owning the premium experience in our category, then ending your price with a nine probably isn't the best thing to do. So we pretty quickly rounded it up to $30 a month.

• 35:40David Rosenthal?

  Interesting.

• 35:40Ben Gilbert?

  That's fascinating. I never thought about that before, especially because like Apple does, you know, $12.99 for your iPhone or, you know, I think it's $12.99. I know Walmart undercuts at like $12.95.

• 35:52David Rosenthal?

  Interesting.

• 35:53Ben Gilbert?

  That's super interesting psychology.

• 35:54David Rosenthal?

  Wow. Super cool. You said you wanted to circle back on the positioning.

• 35:58Ben Gilbert?

  Oh yeah. So let's dive in now to this, this analysis section. So for listeners, I want to set the stage on sort of a timeline for this whole thing because I do think it's, it's kind of crazy how long it waited before seeing the light of day. When did you break ground on designing Superhuman? When was the first line of code? And when did you start rolling out to these first hundred users?

• 36:17Speaker 02

  I first started sketching out the concept and the business model for Superhuman in February of 2014. That's five years ago now.

• 36:26David Rosenthal?

  Wow.

• 36:27Speaker 02

  Or more, rather. And then it wasn't until nearly a year later, in January of 2015, when I started designing the product. That's when I first put pen to paper. I wrote the landing page before I did anything else. All of the copy that you see on superhuman.com is actually copy that was written in January of 2015. And I created hundreds of detailed wireframes. And the first line of code was not written until May the 4th in 2015.

• 36:57Ben Gilbert?

  And just to get nerdy, like, how are you doing the wireframes? Is this in sketch? Are you literally sketching it out? Is it, what's your preferred methodology here?

• 37:05Speaker 02

  It depends on how clearly I can see it in my head. It will often start with an extremely sketchy sketch on paper. And then, once I can begin to see it, my tool of choice is still Bostomach. I'm kind of old school about this. I can use it extremely fast, way faster than I am in sketch. So that's what I did it in.

• 37:26Ben Gilbert?

  It's your superhuman of prototyping technologies?

• 37:29Speaker 02

  Pretty much.

• 37:31Ben Gilbert?

  Okay, so started sketching for a year, then did a year of design after that?

• 37:36Speaker 02

  In the week after I left LinkedIn, in my gusto to get something done, I actually went out and pitched a bunch of VCs that same week. This was the February of 2014.

• 37:49David Rosenthal?

  Before Adam Nash's advice to...

• 37:50Speaker 02

  Yeah, he was like, yo, chill out, bro.

• 37:56Speaker 02

  Which was great advice. And so I had term sheets at that point. I could have raised money, but he suggested, as did many others who knew me, they were like, listen, you're really burned out. Maybe you don't see it yet. And I did go through this roller coaster of emotions in the following months as I was processing the burnout from the last four years. So let's say that there was like a few weeks in early 2014. And then most of 2014 was time off.

• 38:20Ben Gilbert?

  Break time, yeah.

• 38:22Speaker 02

  And then I really got going again around Q4 of 2014. And my advice to any listener who's going through the same thing, or who shortly will be, is don't try and just jump straight into it. You can't go from being a professional party animal like I was into, okay, I'm now going to do 12-hour days again. It just doesn't work. I went from not working to four hours a day, to five hours a day, to six hours a day. And I slowly built that muscle memory back up. And the first few things were things like, let's buy superhuman.com. Let's investigate trademarks. Let's raise some seed capital. Were you pulling together a team at this point, too? I was trying to, but that is a longer term thing.

• 39:05Speaker 02

  And there are things you can do even when you don't have a team. What I did in Q4 was I bought superhuman.com and I raised about $750,000 of seed capital. And then in January, I did the wireframes. Then in February, I engaged with a design agency to make those wireframes into really beautiful mockups, high fidelity mockups.

• 39:28Ben Gilbert?

  I think that's a little bit of a contrarian thing to bring in a design agency sort of that early in a startup, rather than hiring a designer or doing it in-house.

• 39:37Speaker 02

  It is, and it's turned out to be super expensive compared to hiring a designer. I think I spent $45,000 on turning these wireframes into high fidelity mockups. I do, speaking of frameworks, I do have a framework on this, which explains why I think it was the rational thing to do in my case, if you want to hear.

• 39:57Ben Gilbert?

  Oh, absolutely, yeah.

• 39:58Speaker 02

  Okay, cool. So I think the fundamental job of a founder is to create momentum. And in my mind, I like to imagine this gigantic flywheel, and it's made up of the most dense material in the universe. And the job is to get this thing moving. Now, most founders, the first time, are probably technical. And the way that you get this flywheel moving is you make a thing, you launch a thing, and hopefully people like your thing, and it starts moving by sheer force of user numbers. This was certainly how Reportive worked. It took me about six weeks to build the first version, tens of thousands of users in 24 hours, and it just kept on growing dramatically thereafter.

• 40:42Ben Gilbert?

  Yeah.

• 40:42Speaker 02

  Which is cool. So the flywheel just started moving by itself. And at that point, it's like, okay, can I now hold on to this thing? Yeah.

• 40:50Speaker 02

  When you are a second time founder and you're coming back at it again, you get to do things in weird, strange orders, but it's still moving the flywheel. So for example, the money, that initial $750,000 that was raised in 2014 for Superhuman, was raised on the basis of primarily one slide where I took a screenshot of Gmail and I just red lined out everything I didn't like. And I said, I'm going to make this pretty and fast. Amazing. And you'll believe me because of what I did previously. Because you built a report. Right. So there is no execution risk here. I know how to build a thing. I know how to hire the team. I know how to market the thing. This is what I'm going to do. Yep.

• 41:33Speaker 02

  And that $750,000 starts this flywheel moving. So now I'm like, cool, a single founder, I've got this money in the bank. I'm not paying myself, obviously. I don't need to do that. What else can I do to get this flywheel moving? Well, that domain name looks pretty juicy. Let's see if I can make that happen. And the guy who sold it to me wasn't the most pleasant of individuals. They like never are. No. Never fun. He took a perverse sense of enjoyment out of sending me abusive and insulting emails. But fortunately, I didn't have to deal with this myself. I hired an expert broker to go after the domain. Oh man. And we ended up getting a very good deal. But that's another example of how you can get this flywheel moving.

• 42:15Speaker 02

  Now, you might think, as many people said at the time, whoa, so you just raised 750K and you're going to spend what was like, I don't know, 20% of it or something on buying a domain name? Yeah, right. That's crazy. I don't know how you would feel about that as a seed investor. Yeah, I would be like, we need to have a conversation. How about the dot co? So I think I did buy the dot co and then I let it lapse. Someone else probably has it now. In any case, I thought about it long and hard and I realized that in the grand scheme of things, this is going to turn out to be no money whatsoever. Most importantly, this is a sign to the world that this flywheel is moving.

• 42:58Ben Gilbert?

  We're serious about this.

• 42:59Speaker 02

  I'm super serious about this. And the people I'm really signaling to at this point are potential co-founders, number one, and potential investors, number two.

• 43:08David Rosenthal?

  Yeah. And Well, also it comes back to the market too. Like if you were trying to create a new market, it would be wholly irrelevant, right? But you're trying to compete with established entrenched competitors and back to your positioning, like you are the, you know, the Tesla, not the, what was Tesla before it was Tesla? What was the name of the company?

• 43:27Ben Gilbert?

  The E1 or something like that?

• 43:29David Rosenthal?

  Yeah, the EV1. Yep. Not the EV1.

• 43:32Ben Gilbert?

  Which of course Rahul is staring at us like we're crazy. Of course you wouldn't know because it wasn't the Tesla.

• 43:37David Rosenthal?

  Right, right, right. Before the roadster, before Elon Musk joined Tesla, it was the EV1.

• 43:42Speaker 02

  Yeah, that is a pretty terrible name.

• 43:44Ben Gilbert?

  Yeah, actually it was the T zero.

• 43:45David Rosenthal?

  The T zero.

• 43:46Ben Gilbert?

  That's because it was mathematician. So it was like at time zero.

• 43:49Speaker 02

  That's kind of cool, although it just reminds me of a Terminator, which has its own sort of murderous connotation that you probably don't want in a self-driving car. Yeah. So in any case, the flywheel, the domain was another piece. Then the landing page, like a really well crafted landing page where every single sentence had been iterated hundreds of times over. I'm not even exaggerating, by the way. I spent four to six weeks writing the copy for the landing page and then another six weeks doing the wireframes and then $50,000 to the design agency to create these beautiful designs. These are all examples of how a single founder who once upon a time was technical, I wouldn't

• 44:32Speaker 02

  claim to be particularly technical nowadays, can create

• 44:35Ben Gilbert?

  You did drop out.

• 44:36Speaker 02

  I did drop out and then I instantly forgot everything. Exactly. It's an example of how a single human being can start the flywheel spinning and that helps both with recruiting co-founders as well as with raising investment.

• 44:52David Rosenthal?

  Yeah.

• 44:53Ben Gilbert?

  All right, listeners. Now is a great time to talk about a new partner of ours here on Acquired, Logora, the agentic operating system that is redefining how the world's best legal teams work.

• 45:06David Rosenthal?

  Yep. It's sort of obvious that AI is going to completely change the legal industry. I bet most of you listening have dropped a contract into some sort of AI chatbot out there. Logora took that insight and asked the question, what if you really built something with that power from the ground up for the legal industry?

• 45:23Ben Gilbert?

  So the founders did exactly what great founders do, operate with obsessive customer focus. They embedded inside a massive law firm for months. They sat with the lawyers just watching how the work really gets done.

• 45:38David Rosenthal?

  And that's how you get features that customers love, like tabular review, where you drop in a folder of hundreds of contracts and it pulls every key term into a grid a lawyer can actually work with. Logora's bet here is interesting. Since it lets each lawyer handle more complexity, any given person can increase the quality of their work and do higher value work. And this means that the pie can grow even as each individual task takes less time.

• 46:01Ben Gilbert?

  And they recently launched Logora Agent, offering greater intelligence and performance. The agent lets lawyers set an objective. Then it can handle the planning and the execution and delivery of the final product. Legal teams get to maintain full control and transparency since they're still involved where judgment is required.

• 46:20David Rosenthal?

  And Logora works where you already work. You can use it within Microsoft Word while redlining or drafting. The early Logora numbers essentially speak for themselves. When they have a head-to-head pilot with their top competitor, they win 70% of the time. Logora now has over 100,000 lawyers on the platform from 1,200 legal teams in 50 countries. And crazily, they went from 1 million to 100 million in ARR in about 18 months.

• 46:51Ben Gilbert?

  Truly insane numbers. And that is the real test. Plenty of things demo well, but the question is whether a busy associate actually reaches for it during crunch time, or whether a partner trusts it before going into a conversation with a major client. If your legal team wants to check it out, whether you're a law firm or you're in-house at a company, you can learn more at logora.com/acquired and just tell them that Ben and David sent you.

• 47:16Ben Gilbert?

  I'm going to catch us up on the timeline. So it's summer 2017. So we started in February 2015. So we're two and a half years in. It's a 14 person team, still haven't shipped. This is fricking heresy for startups that are supposed to be embarrassed of your first version. So Reid Hoffman, there's this famous sort of Reid Hoffman mindset. If you're not embarrassed by the first version of your product, you've launched too late. So could Superhuman have done this and sort of put your, maybe your worst foot forward to get some signal and then sort of iterated, iterated, iterated? Or did it have to be done in this way where you and a team went away for two and a half years and sort of created the magic internally?

• 47:53Speaker 02

  I think it had to be done this way. I noticed with almost every single other email app, every single other productivity app, they went through the following motion. They would raise some seed money. They would make a thing. It wouldn't be a very good thing, not because the teams weren't talented or well intentioned. Most people here are.

• 48:12David Rosenthal?

  But you're competing with Microsoft and Google.

• 48:14Speaker 02

  That, and the domain is so inherently complex. It is a very, very difficult thing to build an email client that people actually want to use. And it does take more than two years. I challenge anybody to do that faster. I don't think it's possible. And the same is true, by the way, of a web browser or of a database or of a compiler. Any sufficiently hard productivity tool will take many, many years to build. But back to the Reid Hoffman quote, you know, I'm still embarrassed today by many aspects of Superhuman and I probably always will be. So I think Reid is actually still correct. The nuance here though, and I think this is the question that you might be asking, is how applicable is the advice to Superhuman?

• 48:59Speaker 02

  And I think his advice applies most to startups that are creating new markets and especially to startups that have network effects. So for startups that are creating new markets, the alternative is usually a terrible experience. You guys will talk about this on Friday, but remember trying to hail a cab in San Francisco before Uber existed.

• 49:22David Rosenthal?

  Well, you could have used Capulis or Taxi Magic, but yes, yes.

• 49:27Speaker 02

  I remember, I remember standing in the rain, which of course made everything worse, on the Embarcadero for like 30 to 40 minutes, waiting for a taxi to arrive and they keep on whizzing by you. It was the worst.

• 49:39David Rosenthal?

  But exactly to your point, there was a moment in time after, after iOS was open to third-party developers where the time had come and there were, there were probably seven companies, legit companies, that all got started. And like then it was like, you need to move, you need to ship yesterday, you need to move as soon, as fast as possible, lock up all the supply and all the demand.

• 49:58Speaker 02

  Exactly. Because at that moment in time, anything you release, even if, as Reid says, it's embarrassing to you, is going to be worth it for a critical mass of users.

• 50:09David Rosenthal?

  Yeah.

• 50:10Speaker 02

  And that gives you a small advantage. And when you have a network effect, as all of these companies did, that small advantage is going to start compounding on itself. Great for that kind of company.

• 50:21David Rosenthal?

  Yeah.

• 50:22Speaker 02

  But for a startup like Superhuman. In an existing market. Exactly. Where the alternative product is Gmail. And without an explicit network effect built into it right now, the bar is very different.

• 50:33David Rosenthal?

  I want to double click a little bit on the network effect piece. Obviously, Reportive had a network effect, or at least you were building on other people's network effects. Maybe would be a more accurate way to put it. Were you intentional about at least this first, you know, act of Superhuman not being a network effect business?

• 50:49Speaker 02

  I don't actually think that Reportive had a network effect. We may be using the term in, in a different way.

• 50:55David Rosenthal?

  Yeah.

• 50:56Speaker 02

  So by a network effect, I mean where the value of the product becomes more valuable, the more people are using it.

• 51:01David Rosenthal?

  Right, right.

• 51:02Speaker 02

  Different, for example.

• 51:03David Rosenthal?

  As I caught myself, they're like, you didn't really, you were building on the fact that like LinkedIn had that. And then you were using their data.

• 51:10Speaker 02

  Yes. I think it's always great if you can build in a network effect. We believe that with Superhuman, there are underlying network effects that will become apparent over time. And that in the meantime, we don't need one. And the reason why we don't need one is that we can solve the marketing and the retention challenges in a different way.

• 51:33Speaker 02

  Which would be enabled to by making the product very desirable, very viral, and very sticky. Once you actually start using it.

• 51:40Ben Gilbert?

  Yep. So you mentioned competing in an existing market where the bar is already very high versus a land grab opportunity as a framework for can you sort of take your time and be very intentional and methodical and frankly, spend a good amount of money developing your first version of your product. Are there other sort of vectors on which to sort of decide whether you need to launch yesterday or you can take your time other than other than that market timing?

• 52:07Speaker 02

  Yes. So I have another framework for you.

• 52:10Ben Gilbert?

  Excellent. David would be very excited.

• 52:11Speaker 02

  Yeah, I can see.

• 52:14Speaker 02

  I'm not going to claim credit for this one because it's not mine, but it is. Oh, boy, it's right. So this one came to me from Shishir Mahotra. He is founder and CEO of Coda, another great productivity tool. And we were talking about our respective attitudes to launch. And, you know, sort of as you've been alluding to, Superhuman has at this point famously held back from a public launch. So too has Coda. And he was able to put into words what I'd been feeling for a very long time. And he said, "A startup should only launch for one of three reasons. Number one, either you need more users or customers

• 52:56Speaker 02

  to sell to. Number two, you need more capital to spend. Or number three, you need more candidates to hire. If you're benchmarking well across all three, if you're attracting all the users you need to, if you have all the capital you could spend, and if you have no trouble hiring, then why would you launch? It's a relatively expensive, distracting, one-time event that's going to bring an influx of people into your product. They'll find a myriad of bugs because of course, we're all startups. We don't have perfect products. And you won't be able to fix them on a responsible timeframe. So you'll just

• 53:37Speaker 02

  end up with thousands, if not tens of thousands of disappointed people." And I was like, yes, that's exactly the problem.

• 53:44Ben Gilbert?

  What he said.

• 53:45Speaker 02

  True. This is the problem that happens in productivity. And so we just decided that that we wouldn't. And, you know, who knows, maybe we never will launch.

• 53:55Ben Gilbert?

  Yeah, you're pre-launched today, right?

• 53:58Speaker 02

  I mean, at this point, it's like we have a lot of users, we have a lot of revenue, we're growing very quickly. Are we pre-launch? Who knows? I think we're just doing it in a very different fashion.

• 54:10Ben Gilbert?

  Yeah.

• 54:10Speaker 02

  And the way that we actually model the company is from my favorite Paul Graham essay, Startup Equals Growth.

• 54:17Ben Gilbert?

  Yeah, you know the one. Oh, yeah.

• 54:19Speaker 02

  This is such a good essay, probably his best. For listeners who don't know, he basically says, "The most important thing a startup needs to do is to grow." And especially if you're a technology startup, you probably like to optimize things, and you like to optimize things on a short-term basis. So let's optimize short-term growth rate. Pick a weekly growth rate that you like. It might be 2%, it might be 3%, it might be 4% per week, and just do it. Do it every single week, and you will be shocked at how fast you grow every month and every year. And we've been running Superhuman that way for the last two years. Every single week, we just pick a number of users that we will

• 55:02Speaker 02

  onboard the following week, and that's how we grow.

• 55:05David Rosenthal?

  You have the finest control knobs on that of any company I've ever heard of.

• 55:11Ben Gilbert?

  Well, I mean, you have a waitlist of 180,000 people who are dying to use the product and can't. So you just choose every week how many of those people we're going to let in. Is that about capture it?

• 55:24Speaker 02

  That's more or less correct, although I would say that the waitlist is a relatively small funnel into the product. The fastest way in, and one of the reasons why Superhuman is so exciting, is that each week, 70% of our new users are virally referred within products from the previous week.

• 55:46Ben Gilbert?

  Huh. Fascinating. So do you put a governor on how many referrals can start the next week? Or if you're referred, is it, "We will grant you access no matter what"?

• 55:58Speaker 02

  There's still a qualification process. Yeah. We were pretty clear on who Superhuman is good for and who it's not going to be good for. I got qualified out six months ago because I'm a primary iPad user. There you go. This was before we had iPad shortcuts and now we do. I'm very excited to be now qualified back in. It's gonna be good.

• 56:17Ben Gilbert?

  So I'm going to blatantly steal from your essay on first round review, which if you're listening to this and you're finding this interesting, you are just going to be beside yourself reading this awesome piece that Rahul wrote on the first round review. But you basically at Superhuman developed a way to measure product market fit and a four step process to get there. Can you sort of talk about what that process is?

• 56:40Speaker 02

  Sure. The context for this or the motivation was we had to spend a number of years to get the product to the point where people would actually pay for it. That's not something that most teams want to go through. Most teams want to build a thing, launch the thing, make money, go, go, go. But it was very obvious to me as a member of our target market that we didn't have product market fit. I didn't need to do the big splashy launch in order to convince myself to my own level of satisfaction that our product wasn't good enough. It was just obvious and it was obvious because I couldn't personally switch away from Gmail to Superhuman. And if I couldn't, then why would anybody else? Do you feel like you were uniquely equipped to be able to hold yourself to that bar because you were a second time founder?

• 57:25Speaker 02

  Yes, but only because founders were a core target market for who we were going after. Because I had experienced the pain that we were trying to solve when I was running my last company. I very clearly could see, oh, we haven't solved that pain, not yet. And I could feel ourselves getting closer every single day. But I had to find a way to explain this to the team. You know, these are hyper ambitious, super intelligent engineers and designers and people of all disciplines who'd poured their hearts and souls into the product.

• 58:00Ben Gilbert?

  Right.

• 58:01Speaker 02

  They needed a way to understand not only that we weren't ready, but how not ready we were or how close we were. And the precise steps that we could do in order to get there. So I went out and about, I read everything I could find and I started searching for definitions of product market fit. And there's quite a few out there. So for example, Paul Graham would say it's when you made something people want. And I think that's a pretty good definition. But I wanted something more actionable. And I think Sam Altman had a slightly different take, which is it's when users love your product so much that they spontaneously tell other people to start using it without you even asking them to do that.

• 58:44Speaker 02

  And that's a different take on it. So PG's take is around desire. Sam's take is around distribution or sort of net promotion. But perhaps the best definition I found, or the most interesting at least, was Marc Andreessen's. And he had the most vivid definition. So he would say, and I have it right here because it's quite lengthy and detailed. Number one, you can always feel it when product market fit is not happening. Customers aren't quite getting value, users are not growing quite that fast. Word of mouth is not spreading, press reviews are kind of blah, and the sales cycle takes too damn long. But you can always feel it when product market fit is happening.

• 59:28Speaker 02

  Customers are buying as fast as you can add servers, you're hiring sales and support as fast as you can. Reporters are constantly calling you about your hot new thing. Money is piling up in your checking accounts, investors are staking out your house and you start winning company of the year awards from Harvard Business School.

• 59:45Ben Gilbert?

  My favorite is the part about staking out the house.

• 59:49Speaker 02

  Does actually happen, can confirm.

• 59:51Ben Gilbert?

  Wild.

• 59:53Speaker 02

  So I can tell just by your reaction, whilst this is a vivid and accurate definition, there is a challenge to using this in running the business, which is that it is a post hoc definition. By the time investors are staking out your house or blowing up your phone, you probably already have.

• 1:00:15David Rosenthal?

  Your last concern is achieving product market fit at that point.

• 1:00:18Ben Gilbert?

  You're no longer interested in quantifying it.

• 1:00:22Speaker 02

  So I remember staring at this definition through tears in the summer of 2017, thinking, oh, boy, we don't have this and we are so, so far away from having this, but how do I explain that?

• 1:00:37David Rosenthal?

  Did you have a board at this point?

• 1:00:38Speaker 02

  Did we have a board at this point?

• 1:00:40Ben Gilbert?

  David, why is that relevant?

• 1:00:43David Rosenthal?

  Well, I

• 1:00:46David Rosenthal?

  You know, when you're a hammer, everything looks like a nail. But you obviously had investors. Was there a group of people to whom you felt beholden to explain this current state of the business to?

• 1:00:58Speaker 02

  That's a good question. So as I cast my mind back, the answer is yes, of course, we did have a board. We never did any board meetings, which is why I had to think about it. So our board formerly at the time was Bill Trenchard from First Round, who's been incredible to us. And informally, I would speak basically every two or three days with Ed Sim from Bold Start. They're a New York-based fund that does really great enterprise investments.

• 1:01:29Ben Gilbert?

  They led your seed round, right?

• 1:01:31Speaker 02

  They, yes, they actually wrote the first check in. Yeah, that first 750 was from them.

• 1:01:35Ben Gilbert?

  Got it.

• 1:01:35Speaker 02

  And they wanted to write a million dollar check. I was like, no, I'll take 250 at this cap. And then I went away and made some progress and I came back like, I'll have another 250 now. But it's had a more expensive price. And then the next 250 was at an even more expensive.

• 1:01:51Ben Gilbert?

  Hashtag second time founder.

• 1:01:52Speaker 02

  Yeah. Yeah, just play the game, play it nicely and everyone will enjoy themselves. So yes, we did have a board, but it wasn't really a thing that I was turning to them for help on.

• 1:02:06David Rosenthal?

  So the tears through your eyes were like yourself, like not, not just like less so like yourself and like, oh shoot, now I gotta go. Explain to everybody where we are.

• 1:02:16Speaker 02

  Oh, sure. Yeah. Like explaining it to the board was the very least of my concerns.

• 1:02:20David Rosenthal?

  Yeah.

• 1:02:21Speaker 02

  Because you know, these are, Ed, I made money for in the past at Reportive. Bill is a long-term investor. He just fundamentally believes in what we're doing. All of our other investors fundamentally believe in what we're doing. If I went to them and I said, hey, this is the direction I think we should go. They would always be like, good, we believe in you. This, this is why we invested in you. It was the team who are working On this day in, day out, I wanted to give them a path and an engine that could work. And so I found a piece of work by Sean Ellis, who's famous for coining the term. Exactly. He came up with that.

• 1:03:05Speaker 02

  And he ran early growth at Dropbox, LogMeIn, Eventbrite. And during his days of doing growth consultancy to startups, he found a benchmarked predictive way to measure product market fit. You simply ask your users, how would you feel if you could no longer use the product? And you let them answer either, I would be very disappointed, I would be somewhat disappointed, or I would be not disappointed. And you measure the percentage that say very disappointed. And what he found is that the companies that struggled to grow

• 1:03:49Speaker 02

  almost always had less than forty percent very disappointed. And the companies that grew the most easily almost always had more than forty percent very disappointed. In other words, if more than forty percent of your users would be very disappointed without your product, guess what? You have initial product market fit. Threaten to take it away and see what they say. Exactly. It's a stroke of genius. I'm not going to claim to invent it. He did. It's more predictive of success than net promoter score. It's benchmarked across hundreds of venture backed companies. It's a really phenomenal metric. And you know, the most exciting thing about this metric,

• 1:04:34Speaker 02

  and the thing that we did at Superhuman, is that you can use it to build your very own product market fit engine. You can use it to come up with a systematic methodology to numerically optimize product market fit, which sounds crazy, but it's true. You can actually build this thing.

• 1:04:54Ben Gilbert?

  Fascinating. So that is the measuring stick by which you can determine if the changes that you're making in the product are bringing you closer to product market fit. What then is the other side of that equation to actually govern how you should change the product to hopefully get you closer when you measure that? Like, how do you figure out what the inputs need to be in your product changes?

• 1:05:16Speaker 02

  So we have a whole very lengthy article about this. I'll give you the

• 1:05:22Ben Gilbert?

  We'll put it in the show notes.

• 1:05:23Speaker 02

  Yeah, I'll give you the quick summary, but I would very much recommend reading the article because there's a ton of subtlety around how to do this correctly. So it begins fundamentally with surveying your users. For every user who comes into your product and who then experiences the core benefit of your product, that usually means they've done the thing, whatever it might be, two or three times. They've probably been there for about two weeks. You send them a survey. And in that survey, you ask a number of questions. You ask four questions. Number one, how would you feel if you could no longer use, I'll

• 1:06:05Speaker 02

  take Superhuman as an example, how would you feel if you can no longer use Superhuman? With the answers that I outlined. Number two, what type of people do you think would most benefit from Superhuman? Number three, what is the main benefit that you get from Superhuman? And number four, how can we improve Superhuman for you? Free text or dropdowns? So the first one is a tri-state, like I described, and the other three, yes, free state. Free text. Yeah. And type form is what we use. It's probably the easiest way to get this done.

• 1:06:40Ben Gilbert?

  Nice keyboard shortcuts.

• 1:06:41Speaker 02

  Great keyboard. That's actually why we chose it.

• 1:06:44Ben Gilbert?

  That's like, that's our primary at Pioneer Square Labs. That's like all we use for validation now.

• 1:06:49Speaker 02

  I wish everything had keyboard shortcuts that would just make everybody's lives so much better and faster.

• 1:06:55Ben Gilbert?

  How do you then use those four questions to guide you toward what features should we build or change?

• 1:07:00Speaker 02

  So we then have a four step engine to systematically generate your roadmap and increase product market fit. And the four steps that you go through are number one, segment, number two, analyze, number three, build, and number four, repeat. And it just occurs to me that this creates a nice acronym, which is SABER. Segment, analyze, build, and repeat. So you've got to saber your users. That sounds quite violent, actually.

• 1:07:31Ben Gilbert?

  This is getting, so it's interesting because like you're an artisan, like you are someone who, I mean, you spent three, four weeks writing copy on a landing page. Like you're an artisan. And yet, what you're describing here, it's an algorithm to start a product market fit startup. It sort of begs the question, like, if you have the right sort of team who are capable of doing all of these functions, writing that survey, analyzing the results, you know, doing saber, will every startup idea end up at an end state of product market fit if you apply the correct algorithm to it?

• 1:08:05Speaker 02

  I think that this greatly increases your chances, but the sad and realistic answer to your question, I think, is obviously no.

• 1:08:14Speaker 02

  Why? Well, let me give you three big reasons.

• 1:08:19Speaker 02

  Number one, many startups will run out of money before they finish this process. Number two, many co-founding teams will have disagreements and fall apart. And number three, many teams will just get tired.

• 1:08:30Ben Gilbert?

  Yeah.

• 1:08:30Speaker 02

  And go, you know what? I can't do this anymore. And those are the three fundamental reasons that people will fail, even given the saber products market fit engine.

• 1:08:42Ben Gilbert?

  Yeah, and it could be too, if you start with a kernel of an idea that is sufficiently bad for a sufficiently incorrect market, it could just take too long to ever iterate your way toward whatever the ultimate correct end state is.

• 1:08:54Speaker 02

  Yes, I do have some rules of thumb around that. So the first step of this engine is to segment. And if you like, we can get into the details of how you might do that. But if after that first segmentation step, your very disappointed score, your product market fit score is in the region of five to 15%, my considered advice to you would be to suggest not doing that product. And I mean, like in all, you know, Totally, yeah. Realistically. We all have only so many years on this earth. Yeah. Take the capital you've raised, take the team that you have and do a brainstorm and try something else. And I'm sure your board will be supportive if you have the data to show that it's not really working. Yep.

• 1:09:38Speaker 02

  But if you're in the 15 to 25% mark, Yep. Uh, which is where we were after that original segmentation, then I do believe you can actually iterate your way to success. And it's, the challenge then becomes raise enough money and keep morale high enough for long enough so that you actually have the time to make it work. Yeah. Hence the job of the CEO, the momentum creator.

• 1:10:01David Rosenthal?

  Well, it also strikes me that, um, I'm curious if you'd say this has to be the case, uh, but in your case, certainly is the case. You have this engine, and this is a mixing metaphors. The engine is the like transmission of the startup, but the true engine of the startup is like your passion, like this is your destiny. Right? Like you were through that nine month process, like there was no other company that you would start. And I would imagine that is, you know, in many ways, given you the perseverance, the drive to look at your 15 to 20%, 25%, you know, score on that, on that rubric and say, okay, we're going to make that better, you know, versus like, ugh.

• 1:10:38Speaker 02

  I think so. I suspect I may just be on the far end of persistence compared to most people. We had a very interesting debate as a, um, as an executive team over the last year about redefining our company values. And this idea of persistence kept coming up over and over again. And I was like, you know what, maybe we should have persistence as a value now. Ultimately, it didn't end up becoming a company value, but, um, I do believe that even if it's not a company value, every single founder needs to exhibit unnatural levels of persistence.

• 1:11:18Speaker 02

  I think again, to quote Paul Graham, he talks about grimly determined founders and how during the days when he was operating Y C, he would see these people come out of And they're like, they're super nice and bubbly. And then like a year or two later, they're just these sort of grimly persistent people who will stop at nothing. And they've got the battle scars from running through brick walls over and over and over again. And I do genuinely believe that if you're a co-founder, if you're a founder, especially if you're a CEO, this is your job. You have to run through the brick walls over and over and over and over again. And when it's time that other people might be thinking of giving up or backing out,

• 1:12:03Speaker 02

  you have to be the person to say, nope, we're going to keep on going. Mm hmm. Absolutely. Yeah. Also resonates so much.

• 1:12:09Ben Gilbert?

  So we're going to loop back to a previous question that we sort of talked about to end this this segment here. I'm going to read it from my my Google Doc here, which is written much more eloquently than I phrased it earlier. So when you're building for a narrow segment of users who love you at the start, how do you think about building for them without overfitting the product to them such that you can't serve the broader market later?

• 1:12:33Speaker 02

  So I'm going to read the answer from my equivalently formatted Google Doc. It's not even my answer, but this is this is just something I believe so strongly because it seems so self evidently true to me. And again, it's going to be a Paul Graham quote.

• 1:12:47Ben Gilbert?

  Oh, is it about local maxima?

• 1:12:49Speaker 02

  It is, yes.

• 1:12:50Ben Gilbert?

  Yes.

• 1:12:50Speaker 02

  I'm going to quote two different of his essays. Ooh.

• 1:12:54Ben Gilbert?

  D D D J Rahul.

• 1:12:58Speaker 02

  So number one is going to be from Startup Ideas, where he talks about how you find startup ideas and some good startup ideas. Incidentally and tangentially to this answer, one of them is just build Gmail but fast. And that was public on the web for about 10 years before we started Superhuman. So the idea was out there. That was one of PG's startup ideas? I'm pretty sure it's in the essay Startup Ideas. Wow. He says, and I'm going to try and quote this from memory, he's like, just build Gmail but fast. It's become so slow. There are sufficiently many people like me that, and he had some insane price, that would spend $1,000 a month on Gmail because it's literally all we do. Yeah. I mean, he should have started Superhuman.

• 1:13:40Ben Gilbert?

  He wasn't grimly determined.

• 1:13:41Speaker 02

  He was not grimly determined. Okay, so Startup Ideas, he says.

• 1:13:47Speaker 02

  When a startup launches, there have to be at least some users who really need what they're making, not just people who could see themselves using it one day, but who want it urgently. Usually, this initial group of users is small for the simple reason that if there were something that large numbers of people urgently needed and that could be built, with the amount of efforts that a startup usually puts into version one, it would probably already exist. Which means, you have to compromise on one dimension. You can either build something that a large number of people want a small amount, or something that a small number of people want a large amount. Choose the latter.

• 1:14:28Speaker 02

  Not all ideas of that type are good startup ideas, but nearly all good startup ideas are of that type. In other words, what he's saying is, don't worry too much about building for a narrow segment of users and therefore overfitting. It's precisely what he's advising that you do. And then you might say, well, doesn't that give you the problem of being boxed into a particular niche or a particular segment of the market? And then to quote from a different essay, one that we've already referenced, Startup Equals Growth, he says, "In theory, this sort of hill climbing could get a startup into trouble.

• 1:15:11Speaker 02

  They could end up on a local maximum, but in practice, that never happens. The maxima in the space of startup ideas are not spiky and isolated. Most fairly good ideas are adjacent to even better ones." And to this, I'll give two very classic examples. One, of course, is Airbnb, where the idea of couch surfing is extremely adjacent to the idea of houses being hotels. And the other, very timely, is Uber, where the idea of a luxury car that comes to your house with a chauffeur is adjacent to peer-to-peer driving.

• 1:15:52David Rosenthal?

  It's amazing. I mean, literally, every single one of the, quote-unquote, "A-plus" companies that we're going to cover on this season of the IPOs. Airbnb, Pinterest, Lyft, Uber, Slack, Stripe fits this definition.

• 1:16:05Ben Gilbert?

  Even Stripe. I mean, I'm thinking about Stripe now, too. Like, the original market was startups that need to get their merchant accounts faster and implement them quickly. And it turns out, everybody that needs better merchant accounts. So it's

• 1:16:18David Rosenthal?

  Yeah. Well, I guess, well, to put words in your mouth for email, like, yeah, who, the business people and executives who spend three hours a day on email, they need like, they like really desperately care about faster email. But everybody cares about really faster email, right? Like,

• 1:16:34Speaker 02

  Absolutely. And the good thing for us, it turns out that even that particular market will lead to a multi-billion dollar company. And so there is this potential to create a enduring franchise, a company that could last for over 100 years. And that's certainly our goal here.

• 1:16:54Ben Gilbert?

  All right. Well, we very much look forward to covering the Superhuman IPO on the the main show next.

• 1:17:00David Rosenthal?

  What's the next acronym gonna be?

• 1:17:03Ben Gilbert?

  I don't know. Who else is in your cohort that's gonna be all IPO-ing around the same time?

• 1:17:08Speaker 02

  I'd love to see all the great productivity companies right now. Notion, Airtable.

• 1:17:13Ben Gilbert?

  We're in a total renaissance.

• 1:17:14Speaker 02

  We are. We really are.

• 1:17:16Ben Gilbert?

  It's so cool. Well, before we break, Rahul, where can our LPs find you on the internet? And two, what is the best way for them to get access to Superhuman?

• 1:17:27Speaker 02

  Okay, so I am on Twitter at Rahul Vohra. That's my name, R A H U L V O H R A. And of course, at email at Rahul at superhuman.com. And to get access, by far, the best way is to get a referral from an existing user. I would just recommend going to search twitter.com and typing in Superhuman. And there is a high volume of tweets. There's a lot of very helpful Superhuman users out there. You can see which ones the most helpful users are just by who's jumping in on which threads, giving out invites. If you don't feel inclined to do that level of work, then you can sign up on the website, but that will be a fair bit slower.

• 1:18:09David Rosenthal?

  All right. What about, um, what are you hiring for? I'm sure there are lots of listeners who would love to come work here.

• 1:18:16Speaker 02

  Well, you mentioned that just before we started, your primary audience is actually product managers right now. And it turns out that I'm hiring for our very first product manager.

• 1:18:26David Rosenthal?

  Whoa.

• 1:18:27Speaker 02

  So this is a super exciting role. You get to work with me for better for worse, all day, every day, on building the fastest email experience of all time. And I'm really thrilled to be hiring for this role. I've carried product in the company for a number of years, and it's a really fantastic opportunity for the right person.

• 1:18:45David Rosenthal?

  Terrible boss, but like, great.

• 1:18:48Speaker 02

  I don't know. I think I rate okay. I think I rate okay. But yes, really great product.

• 1:18:53David Rosenthal?

  Really great product.

• 1:18:54Speaker 02

  And in addition to that, engineers of all types, lead backend engineer, frontend engineer. If you're a phenomenal developer, we'd really love to speak with you.

• 1:19:04Ben Gilbert?

  Awesome. Well, we rarely do LP shows, I think, with early-stage companies that are still early-stage in quotes here. But I think we very intentionally and selectively reached out. And I think we think incredibly highly of Superhuman. So LPs, if you do feel so inclined that that may be interesting for you, please don't hesitate to reach out.

• 1:19:22Speaker 02

  Thank you.

• 1:19:22Ben Gilbert?

  Awesome.

• 1:19:24David Rosenthal?

  All right, listeners. Now is a great time to talk about one of our favorite companies, Statsig.

• 1:19:30Ben Gilbert?

  Yes, there is a reason why the best product teams rely on Statsig, whether they are iterating on their core product features or shipping AI-powered experiences at scale.

• 1:19:41David Rosenthal?

  Yep. In the crazy speed of today's AI world, shipping fast is just table stakes now. It's basically trivial to build and deploy your app constantly. The real advantage is how quickly you learn what changes actually created value for customers and how fast you can use that signal to guide what you ship next.

• 1:20:01Ben Gilbert?

  This is where Statsig comes in. It brings experimentation, feature flags, and product analytics into one unified system so teams can ship safely, test rigorously, and directly link what they changed to how users actually behaved.

• 1:20:14David Rosenthal?

  So if you want to make learning your competitive advantage, whether you're building new AI experiences or just evolving your existing core product, go to statsig.com/acquired to get started.

• 1:20:25Ben Gilbert?

  All right, well, listeners, if you aren't subscribed and you like what you hear, you totally should. And also, if you were way too excited about this episode earlier to pause and fill out the season four survey, now is literally the perfect time. You should totally click the link in the show notes, or you should go to acquired.fm/survey. You should take the survey, and you could win a pair of second-generation AirPods, or one of 10 Acquired LP subscriptions. Thank you so much for doing that. We really appreciate it. Thank you, everyone. And we will see you next time. Thank you, everyone. Later, David.