Superhuman (with CEO Rahul Vohra)

Great.

One take feels good. Welcome to Season 4, Episode 10, the finale of Acquired, the podcast about technology acquisitions and IPOs. I'm Ben Gilbert.

I'm David Rosenthal.

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.

Indeed.

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.

Okay, listeners, now is a great time to tell you about a new friend of the show we are very excited about, WorkOS.

Yes, WorkOS is the enterprise-ready platform used by OpenAI, Cursor, Perplexity, Vercel, Plaid, and literally hundreds of other winning companies.

So what are all these companies using WorkOS for? Imagine you're a fast-growing startup. You've got product-market fit and you're getting inbound interest from big enterprise customers. Very exciting. But then they send you their security questionnaire.

Yep.

And it's like 47 pages long with requirements that kind of sound like alphabet soup. Do you support SAML 2.0? Can you integrate with our Okta? Do you have SCIM provisioning? SCIM. What about RBAC?

RBAC.

And you're thinking, I have no idea what these acronyms even mean, let alone how to implement them.

So here's the thing. These are not nice to haves. These are deal blockers. Without SSO, without SCIM, without RBAC, without audit logs, you simply cannot close enterprise deals, period.

But none of these features make your core product better. They don't make your beer taste better, to use our favorite analogy here on Acquired. So if you're building like a design tool, spending 6 months building SAML authentication doesn't make your design tool more powerful.

So this is where WorkOS comes in. They've built Stripe for enterprise features. WorkOS turns enterprise authentication requirements into drop-in APIs, abstracting away as much unnecessary complexity as possible.

So instead of your team spending months reading SAML specs, you can implement enterprise SSO in minutes. WorkOS handles user provisioning, permissions, audit logs, all the checkbox items that enterprise IT requires.

So whether you are a seed stage company trying to land your first enterprise customer or already big and expanding globally, WorkOS is the fastest path to becoming enterprise ready.

Just visit workos.com or just message their Slack support. They have real engineers in there who answer questions fast. And when you get in touch, just tell them Ben and David sent you.

Now, without further ado, here is our conversation with Superhuman CEO Rahul Vohra. 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 Vohra, CEO of Superhuman. Welcome to the show.

Absolutely.

Thank you both for having me.

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 Rapportive, 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.

Thank you again.

Are we right that this is your second office?

This technically is our fourth office.

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

We are, yes.

It's nice and decked out in superhuman colors.

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.

Yeah.

Because what we 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.

The problem with early-stage startup offices.

Good problem to have.

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.

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 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 going to be awesome, trust me. And these folks sort of rub their hands together and go, cool, how much equity do we get? And I would say, none whatsoever. This is, 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.

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.

It's, I mean, it's crazy. Um, Cambridge Silicon Radio. Let's see who else. There was that company that Qualcomm acquired. Um, I forgot the name.

And more than companies too. Um, my partner Riley at Wave was a grad student at Cambridge, uh, as was our friend Nels at Eventbrite. You know, plenty of Silicon Valley. —come from Cambridge in the UK.

Yeah, that's a little bit of a monster.

They should have given you money.

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 Rapportive. I couldn't find that product in the market, so in about 6 weeks I just sat down and built that first version.

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

It was, uh, 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.

I do definitively remember that eye-opening experience of you can type someone's email in 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.

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

We had a great relationship. 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 Axiom 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. 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.

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

Yeah. Now it's sort of— and there are others as well. And 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 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 none too pleased about an upstart selling their data.

Totally. 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. 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 we used to be only internal right now.

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.

That's awesome.

And that was, that was probably right around the time of their IPO, right?

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

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

Yeah.

The chap I was dealing with is Adam Nash, who went on to be the CEO of Wealthfront and who's now at 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. 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, you at Superhuman have actually built metrics around it and, 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, the founding of Superhuman right now, but where we got eventually is to a company that waited over 2 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 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 you convinced yourself that there's a business to be started selling a new email platform?

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 TL;DR is badly. 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 3 hours a day reading and writing email.

It's not hard at all to believe, right?

Like, that's crazy. It's—

I mean, it's, it's just mind-blowing. 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. Yeah, and I couldn't find— I couldn't think of anything bigger than that to do.

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

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

They had all sorts of with, you know, Streak and what have you.

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 to be this way. I know, it's— it actually makes me sad.

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 venture is 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 as long as Gmail and Microsoft are the platforms and you're just building plugins, reported being the most successful among them, you're just going to be a plugin.

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, there's a lot of existential crises around there.

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 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?

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 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. 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. Yeah. And that startup exists for most founders. And for me, I believed that it was superhuman. It was the natural, logical, progressive evolution from Rapportive. 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 Rapportive.

What you just said, it resonates so much because like at the stage, at the seed stage that we invest in at Waven that PSL works at, 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 by yourself to realize, like, okay, like the destiny is Superhuman?

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 3 months. And he was like, wrong. However much time you think you need, it's actually more like 3 times that. You probably need 9 months off. And in retrospect, he was completely right. I ended up taking about 9 months off before I felt comfortable settling into what was essentially the same business idea that I'd been working on for about 4 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. Yeah, totally. No matter how bad the idea is.

Resonates so much for, you know, certainly for me in starting Wave, I assume for you in PSL, for Kimberly and Glow, like everything acquired, like, yeah, totally. So cool to hear.

Okay, so Superhuman.

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.

Tell me more. It's really useful.

You've never said that before, I'm sure. Nope.

I just wake up saying that every day.

Not to overly fanboy here, but I can absolutely vouch for all of that. And it's— especially on a day like today where 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— Thank you. During those—

either during the 9 months or at the end of it when you first started working on it and then into the— to your process will 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.

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 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 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. 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 2 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 2 questions. Number 1 was, what do you use for email today? And number 2 was, what were your pet peeves about it? And I had 2 hypotheses going in. Hypothesis number 1 was that for Gmail, people were upset about how slow it had got and how it wasn't working properly offline and how they had to use Gmail plugins to 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.

So much head bobbing on this side.

You're talking to an Apple Mail convert.

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. How did you drive traffic?

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

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— RIP. Yeah, sadness, right? But it was the perfect narrative to say, hey, I'm over here, 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. I think it's your only Medium post, right? It's probably my only Medium post, correct? Because I usually end up— I mean, the sort of second part to your question. Yeah, 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 3 days of not doing anything else. And then another day of shopping it around. So 4 days all in. But those 4 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. Yeah.

When you saw the news that Mailbox was being sold, like, how quickly did your mind go to opportunity? Like, I'm going to— I'm now going to go take 4 days to do this.

Like, 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. Amazing. Yep, startups.

All right, listeners, now is a great time to thank new friend of the show, Intapp. You are probably most familiar with their product DealCloud.

Yeah, DealCloud is the premier deal management and intelligence platform for private capital and investment banking. So if you're at a PE firm, there's a pretty good chance your pipeline and CRM is running on it right now.

Yep. But Intapp is actually much broader. It's essentially the operating system for professional firms— financial, legal, accounting, and consulting. Intapp powers the workflows that run these firms— origination, business intake, compliance, and time capture.

And they just announced a product last month that's super interesting. Celeste, their agentic AI platform. We spent some time getting a tour of the product and we instantly got it. It's not just an individual productivity tool. It's firm-wide AI for institutional knowledge with workflows, collaboration, and your firm's history just built right into it.

Which, uh, that's probably, David, why they call it firm AI over there at, uh, Intapp. Yes. Yes, indeed.

It isn't just general purpose AI that just ingests everything and can be a huge liability for professional firms. You need AI that knows your deal history and your confidentiality requirements and things like MNPI controls or conflicts of interest and respects all of it natively.

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For these professional firms, the competitive advantage is proprietary knowledge, relationships, and deal history, all of that, that is their moat. And Celeste makes that scalable. It connects to Snowflake and Microsoft Copilot and other ecosystem partners. And they just announced partnerships in February with both Anthropic and Harvey.

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

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

It's from Crossing the Chasm. Yeah, yeah. I believe Geoffrey Moore in Crossing the Chasm came up with that frame and then like it's been used many times, but—

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

That's a frameworks guy.

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

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, like, okay, here we go. I have to meet her. And fortunately, 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 tight. It's so great. That's what you have to do. You have to start with something that narrow.

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? Very much the latter.

So I think we should come back to that point because I have a, Yeah, let's do it. 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 1 is understand the lay of the competitive environment. In our case, we were going up against 2 incumbents whose products are free or practically free. Step 2 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 3 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 Westendorp pricing sensitivity meter. I see head nods going on over here.

That sounds like a fancy name.

Yeah, it's just some dude's name. I think he was probably very smart, very clever, did a lot of pricing anyway. So he said Ask your target users 4 questions. Number 1: At what price would you consider Superhuman to be so expensive that you would not consider buying it? Number 2: At what price would you consider Superhuman to be priced so low that you would feel the quality couldn't be very good? Number 3: 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 thoughts to buying it? And number 4: 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 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. We may as well price as low as we can to, 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 halve the price. Maybe we should just like make this free and like give this away for free.

Oh God, you're giving me the heebie-jeebies here. Wait, have you done this to fans? I've done this. Yeah. Yeah. Well, no, no, no, no.

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, Definitely not the case with email.

Not the case with email, where there's a big incumbent and the competitive products are great. Uh, 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.

And were you using people who had engaged with the survey that you were driving traffic to?

This was actually well before 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 onboardings used to be much longer. They were 1 hour or 1.5 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.

They didn't know going into the demo.

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

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

And I would actually very sternly look them in the eye and say, hey, this is 'cause this is a 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'd just, I'd go into it and I'd write down the numbers. And after we'd done 100 of these, the answers were pretty clear. That's awesome.

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

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, seems to be the right price at 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 9 probably isn't the best thing to do. So we pretty quickly rounded it up to $30 a month. Interesting. 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 it like $12.95. Hmm. Interesting. That's super interesting psychology. Wow.

You said you wanted to circle back on the positioning. 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 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 100 users?

I first started sketching out the concept and the business model for Superhuman in February of 2014. That's 5 years ago now. Wow. 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 4th, 2015.

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?

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 Balsamiq. 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. It's your superhuman of prototyping technologies. Pretty much. Okay. So, started sketching for a year, then did a year of design after that.

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.

Before Adam Nash's advice to—

Yeah, he was like, yo, yo, chill out, bro. Cool your jets. Yeah, slow down. 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, as I was processing the burnout from, from the last 4 years. So let's say that there was like a few weeks in early 2014 and then most of 2014 was time off, break time. Yeah. 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 4 hours a day to 5 hours a day to 6 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, uh, you know, that, that is a longer term thing. And there are things you can do even when you, you don't have a team. What I did in Q4 was I bought superhuman.com and I raised about, uh, $750,000 of seed capital. And then in, in January I did the wireframes. Then in February, uh, I engaged with a design agency to make those wireframes into really beautiful mockups, high-fidelity mockups.

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.

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 Absolutely. Yeah. 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 6 weeks to build the first version, tens of thousands of users in 24 hours, and it just kept on growing dramatically thereafter. Yeah, 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. 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 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 Redlined out everything I didn't like. 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 Reportive. 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. 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 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. 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.co?

So I think I did buy the.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 gonna turn out to be no money whatsoever. Most importantly, this is a sign to the world that this flywheel is moving. We're serious about this. I'm super serious about this. The people I'm really signaling to at this point are potential co-founders, number one, and potential investors, number two. Yeah. And 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?

Oh, the E-One or something like that?

Yeah, the EV-One.

EV-One.

Yep. Not the EV-One.

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

Right, right, right. Before the Roadster, before Elon Musk joined Tesla, it was the EV one.

Yeah, that is a pretty terrible name.

Actually, it was the T Zero.

The T Zero. That's a good name.

It was mathematician, so it was like at time zero.

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, uh, the, the domain was another piece, uh, 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 4 to 6 weeks writing the copy for the landing page, and then another 6 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 claim to be particularly technical nowadays— can create— you did drop out. 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. Yeah.

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Thank you, Sentry. I'm going to catch us up on the timeline. So it's summer 2017. So we started in February 2015. So we're 2 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, you know, be embarrassed of your, 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 2.5 years and sort of created the magic internally?

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.

But you're competing with Microsoft and Google.

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 2 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? 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, right? Well, you could have used Cabulus or Taxi Magic, but yes, yes, 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. 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 7 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, as fast as possible, lock up all the supply and all the demand.

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

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 it 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?

I don't actually think that Reportive had a network effect. We may be using the term in a different way. Yeah. So by a network effect, I mean where the value of the products becomes more valuable the more people are using it.

Right, right. Different, for example— As I caught myself there, like, you didn't really— you were building on the fact that, like, LinkedIn had that, uh, and then you were using their data.

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. Which we've been able to by making the product very desirable, very viral, and very sticky once you actually start using it.

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 other sort of vectors on which to sort of decide whether you need to launch yesterday or you can take your time other than that market timing? Yes. So I have another framework for you. Excellent. Dave would be very excited.

Yeah.

I can see him grinning from gratitude as we speak.

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 the 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 to sell to. Number two, you need more capital to spend. Or number three, you need more candidates to hire. Mm-hmm. 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 end up with thousands, if not tens of thousands of disappointed people. And I was like, yes, that's exactly the problem. What he said. True. This is the problem that happens in productivity. And so we just decided that we wouldn't. And who knows, maybe we never will launch.

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

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. And the way that we actually model the company is from my favorite Paul Graham essay, Startup Equals Growth. Yeah, you know the one. Oh yeah. 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 2 years. Every single week, we just pick a number of users that we will onboard the following week, and that's how we grow.

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

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?

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

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?

There's still a qualification process. We were pretty clear on who Superhuman is good for and who it's not going to be good for.

I got qualified out 6 months ago because I'm a primary iPad user.

Well, there you go. This was before we had iPad shortcuts, and now we do.

Yeah, I'm very excited to be now qualified back in. It's going to be good.

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 4-step process to get there. Can you sort of talk about what that process is?

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?

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, right? 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. 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. 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 1, 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. 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.

My favorite is the part about staking out the house.

Oh, does actually happen. Can confirm. Wild. 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 Your last one is achieving product-market fit at that point.

You're no longer interested in quantifying it. Yeah, right.

So I remember staring at this definition through tears in the summer of 2017 thinking, oh no, oh boy, we don't have this and we are so, so far away from having this. But how do I explain that? Did you have a board at this point? Did we have a board at this point?

David, why is that relevant? Well, I, I, I don't know.

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?

That's a good question. So, uh, as I cast my mind back, the answer is yes, of course we did have a board. Uh, we never did any board meetings, which is why I had to think about it. So our board, uh, formally at the time was, uh, Bill Trenchard from First Round. who's been incredible to us. Uh, and informally I would speak basically every 2 or 3 days, uh, with Ed Sim from Boldstart. Uh, they're a New York-based fund that does really great enterprise investments.

Uh, and they led your seed round, right? They—

yes, they actually wrote the first check in. Yeah, that first $750,000 was from them. Got it. 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 price.

Hashtag second time founder.

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.

So the tears to you guys were like yourself, like not, not just like less so like yourself and like, oh shoot, now I got to go explain to everybody where we are.

Oh, sure. Yeah. Like explaining it to the board was the very least of my concerns. Yeah. Yeah. Because, you know, these are folks— 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 growth hacking. Exactly. he came up with that. And he, 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 almost always had less than 40% very disappointed. And the companies that grew the most easily almost always had more than 40% very disappointed. In other words, if more than 40% 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 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.

It's 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, how do you figure out what the inputs need to be in your product changes?

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

We'll put it in the show notes.

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, 2 or 3 times. They've probably been there for about 2 weeks. You send them a survey, and in that survey you ask a number of questions. You ask 4 questions. Number 1, how would you feel if you could no longer use— I'll take Superhuman as an example. How would you feel if you can no longer use Superhuman with the answers that I outlined? Number 2, what type of people do you think would most benefit from Superhuman? Number 3, what is the main benefit that you get from Superhuman? And number 4, how can we improve Superhuman for you?

Free text or, or dropdowns?

And, uh, so the first one is a tri-state. Yeah, like I described. And the other 3, yes, free text. Yeah, and Typeform is, is what we use. It's Probably the easiest way to get this done.

Nice keyboard shortcuts. Great keyboard shortcuts.

That's actually why we chose it. Me too.

That's like, that's our primary at Pioneer Square Labs. That's like all we use for validation now. I wish everything had keyboard shortcuts.

It would just make everybody's lives so much better and faster.

How do you then use those 4 questions to guide you toward what features should we build or change?

So we then have a 4-step engine. To systematically generate your roadmap and increase product-market fit. And the 4 steps that you go through are number 1, segment, number 2, analyze, number 3, build, and number 4, 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 a SABER your users. That sounds quite violent, actually.

This is getting— so it's interesting because like you're an artisan. Like you are someone who, I mean, you spent 3, 4 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, doing SABER, will every startup idea end up at an end state of product-market fit if you apply the correct algorithm to it?

I think that this greatly increases your chances, but the sad and realistic answer to your question, I think, is obviously no. Why? Well, let me give you 3 big reasons why not. Number 1, many startups will run out of money before they finish this process. Yeah. Uh, number 2, many co-founding teams will have disagreements and fall apart. And number 3, many teams will just get tired. Yeah. And go, you know what, I can't do this anymore. And those are the 3 fundamental reasons that people will fail even given the SAEBER product market fit engine. 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 that that the ultimate correct end state is.

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 5 to 15%, My considered advice to you would be to suggest not doing that product. And I mean, like, in all, you know, totally realistically, we all have only so many years on this earth. 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. Yeah, but if you're in the 15 to 25% mark, 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.

Hence the job of the CEO, the momentum creator.

Well, it also strikes me that I'm curious if you'd say this has to be the case, but in your case certainly is the case. You have this engine. This is mixing metaphors. The engine is the 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 9-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.

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 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. Ultimately, it didn't end up becoming a company value, but I do believe that even if it's not a company value, every single founder needs to exhibit unnatural levels of persistence. I think, again, to quote Paul Graham, he talks about grimly determined founders and how during the days when he was operating YC, he would see these people come out of college 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, you have to be the person to say nope, We're going to keep on going.

Absolutely. Yeah. Also resonates so much.

Okay. So, we're going to loop back to a previous question that we sort of talked about to end this segment here. I'm going to read it from 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?

So I'm going to read the answer from my equivalently formatted Google Doc. It's not even my answer, but 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.

Oh, is it about local maxima? It is, yes. Yes.

I'm going to quote two different of his essays. Oh, DJ Rahul. 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. He wasn't grimly determined. He was not grimly determined.

Okay, so startup ideas. He says 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 effort that a startup usually puts into version 1, 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. 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. 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.

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

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—

Yeah, well, I guess to put words in your mouth for email, like, yeah, who— the business people and executives who spend 3 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 Absolutely.

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

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

Oh, what's the next acronym going to be?

I don't know. Well, who else is in your cohort that's going to be all IPOing around the same time?

I'd love to see all the great productivity companies right now. Notion. It's amazing.

We're in a total renaissance. We are.

We really are. 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?

Okay, so I am on Twitter @RahulVohra. That's my name, R-A-H-U-L V-O-H-R-A. And of course at email at rahul@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.

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.

Well, you mentioned that, uh, 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. Whoa. So this is a super exciting role. You get to work with me for better or 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.

Terrible boss, but like great. I don't know.

I think I rate okay. I think I rate okay. But yes, really great product. Really great product. 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.

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, that may be interesting for you, please don't hesitate to reach out.

Thank you. Awesome.

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I actually just leased some space for the new acquired studio here in Seattle. And when the landlord sent over a pretty simple lease, I thought, oh, this is totally something I can review myself. I looked at it, but then I also thought, okay, I could use a sanity check. So I uploaded it to Claude and asked if there was anything that I should be mindful of or inconsistencies or anything I should push back on. And Claude actually found 3 things that I totally missed on my own review.

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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 4 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, for doing that. We really appreciate it. And we will see you next time. Thank you, everyone. Later, David.