🎧🍌 Inside the New Superhuman: $700M ARR, 40M Daily Users with Rahul Vohra
Closing an acquisition with two weeks of runway, almost dying, and why you should design your product like a video game
You might know Rahul Vohra as the Founder and CEO of Superhuman Mail, which he started back in 2014. It’s the premium email client used by busy professionals, including me, to get work done faster.
Rahul recently sold the company to Grammarly, which had just acquired Coda, and then rebranded the combined companies to Superhuman.
I personally loved this conversation, because Grammarly is quietly one of the most underrated companies that no one talks about, having grown to 40 million Daily Active Users and over $700M in ARR. Its the original generative AI product, first started in 2009 to help you write better. It’s fascinating, because they’ve spent years building a backdoor into over a million other products, that they’re now building more AI products on top of.
We talk through key moments in Rahul’s journey building Superhuman Mail, go behind the scenes and unpack the lessons he’s learned from selling two companies, why you should design your product like a video game, and we re-visit his famous quantitative guide to finding PMF.
One of the wildest stories - Rahul almost died when closing his first acquisition, which led to a pulled term sheet. He was saved by a homeless person outside a McDonald’s, and rushed to the hospital. He was finally able to close the deal with less than two weeks of runway left.
Thanks to Todd Goldberg, Ed Sim, Shomik Ghosh, Ryan Hoover, and Gaurav Vohra their help brainstorming topics for this one.
Brought to you by Hanover Park
Hanover Park is the modern, AI-native fund admin for investment firms.
Hanover Park vertically integrates fund administration, portfolio management, and LP experience for finance and investment teams.
Upgrade to the 21st century at hanoverpark.com/Turner
To inquire about sponsoring future episodes, click here.
Timestamps to jump in:
2:42 Inside the Superhuman acquisition
11:09 Grammarly: $700M ARR, 40M DAUs
18:53 How to sequence your product roadmap
24:43 Vision for the new Superhuman
32:43 Build your product like a video game
38:24 Designing Karamja island in Runescape
41:10 Build products like toys and games
44:53 Starting a Machine Learning PhD in 2006
48:49 Dropping out to start his first company
50:47 Rapportive’s crazy accidental launch
57:56 Meeting Superhuman co-founders
1:02:17 Being 1 of 20 to access LinkedIn’s API
1:06:38 Almost getting acquired by LinkedIn
1:10:32 Nearly dying, getting acquired with 2 weeks of runway
1:20:08 Diligence from VCs vs Acquirers
1:26:37 Rahul’s quantitative framework for PMF
1:30:45 How to build an enduring brand
1:31:51 Rahul’s AI-powered productivity stack
1:35:01 Todd and Rahul’s angel fund
1:36:45 We need more solo founders
Referenced:
High Resolution Fundraising by Paul Graham
Superhuman Quantitative Framework for Finding PMF
Find Rahul on X / Twitter and LinkedIn.
Related Episodes
👉 Stream on YouTube, Spotify, and Apple
Transcript
Find transcripts of all prior episodes here.
Turner Novak:
Welcome to The Peel. I’m your host, Turner Novak, founder of Banana Capital. Today’s guest is Rahul Vohra. You might know Rahul is the founder and CEO of Superhuman. It’s the premium email client used by busy professionals, including me, to get work done faster. Rahul recently sold his company to Grammarly which had just acquired Coda and then rebranded the combined companies to Superhuman of which he’s now the CEO of Superhuman Mail. But I personally love this conversation because Grammarly is one of the original Generative AI products first started in 2009 to help you write better. It’s quietly one of the most underrated companies that no one talks about. Having grown to over 40 million daily active users and over $700 million in ARR, it’s fascinating because they spent years building a back door into over a million other products that they’re now building more AI products on top of.
We talk about Rahul’s journey building Superhuman, go inside the acquisition, talk about the grand vision of the new company and all the lessons he’s learned from this acquisition plus selling his first company Rapportive to LinkedIn in 2014. We also revisit his famous quantitative guide to finding PMF, designing your product like a video game and why we need more solo founders.
A quick thank you to Todd Goldberg, Ed Sim, Show McGosh, Ryan Hoover and Rahul’s brother Gaurav for helping brainstorm topics for the conversation. A reminder, I publish two episodes of The Peel every week exploring the world’s greatest start-up stories just like this one. Check with the back catalog of over a hundred episodes and tune in next week for our conversation with Eight Sleep founder Matteo Franceschetti on all things sleep and health optimization. Let’s talk to Rahul after a quick word from Hanover Park.
Hanover Park vertically integrates fund admin, portfolio management and the LP experience for finance and investment teams. Most of you have probably interfaced with a fund admin provider in some way, they’re a necessary evil for every type of asset manager across, not just venture, but also private equity and private credit. They provide bookkeeping and accounting so investment firms can report to their investors on a quarterly basis. What’s crazy is they charge hundreds of thousands or millions of dollars per year to basically not screw up your accounting, they sit together third party software like QuickBooks, build.com, Salesforce and Excel and then throw a bunch of bodies at you. And that’s where Hanover Park comes in, they built their own accounting system from scratch which ingests all your firm’s data and documents and their AI native solution automates all the manual work that drives private market investors crazy. Head to hanoverpark.com/Turner and try the AI native ERP for private market funds. That’s H-A-N-O-V-E-R-P-A-R k.com/Turner and 10X your fund admin.
Rahul, welcome to the show.
Rahul Vohra:
Hey, thank you for having me.
Turner Novak:
Yeah, this should be fun. You are fresh off some pretty big news. I guess maybe we’re a month in now. I actually don’t know. I don’t know how far in we are from this happening. But tell us what happened recently and then we can go behind the scenes of how it all went down.
Rahul Vohra:
Of course, yeah. Well, I feel like I’m fresh off two pieces of pretty big news. I’m guessing you’re referring to the fact that my company Superhuman was acquired by Grammarly and you were asking me just before the show when that happened and I was racking my brains because I forgot. I didn’t remember the exact date so this is a good reminder to put it into my permanent memory. It was July 1st this year that we announced the acquisition although, of course, we’d been working on it for quite some time before then.
And the other piece of news that we’re fresh off of is, just last week, our parent company Grammarly announced, we announced that we will now be known as Superhuman going forwards which was quite interesting. We were trending on Twitter, my phone’s blowing up as you can imagine, it’s obviously absolutely the right thing for us to do and the products that I started way back 11 years ago is now known as Superhuman Mail going forwards as we build out the AI productivity suite of choice.
Turner Novak:
Amazing. So, there’s a lot of different things I want to talk about based on everything you just said. So, I guess the acquisition, you said it was a long time coming. How did it come about?
Rahul Vohra:
Yeah. Well, I met the CEO of Superhuman which is Shishir.
Turner Novak:
That’s so crazy to say. The CEO of Superhuman who you were previously the CEO of Superhuman.
Rahul Vohra:
I know, it’s ... And, usually, those kinds of things happen in less than ideal circumstances. You would’ve seen this as a VC many times, it’s often a founder who’s run out of steam or maybe they’re not achieving the results they need to. That’s usually the scenario where you have another CEO of the company you founded. This is a weird and unusual situation where we were required and then the acquired company takes the name. Anyway, I met Shishir many, many years ago back in 2017 and back then he was the co-founder and CEO of Coda. And we were at a conference and it was one of those special moments where no one else was around so, he and I, we could get into some really deep conversation. And this was the Lobby Conference out in Hawaii. At the time, David Hornik who organizes it, he was at August Capital, of course, now. He is at, I think it’s Lobby Capital, the conference and the VC fund are now the same and the team do an absolutely phenomenal job, just the most incredible set of people that they bring together.
And as you know, back then, we did only one-on-one VIP concierge onboardings and we were either early or late, I don’t really remember which, but it was just me and Shishir around the pool, this hotel in Hawaii, margaritas in hand and I asked him, “Who are you? What do you do?” because it’s the first time I met him. And he told me that he ... He told me his career path and that his first job was actually at Microsoft working on Outlook and I was like, “Oh, boy, do I have a product for you.” I onboarded him right there and then right by the pool. And as those who’ve done onboardings with us know, one of the very last steps that we do is we ask you to close Gmail. And when I asked him to close Gmail, his mouse was moving up to his pinned tabs and another tab caught my eye which was an app called Krypton.
And I asked him, “Hey, what is this Krypton thing?” and Shishir then proceeded to give me the best product demo I’d seen in years. It was a document, it was also a spreadsheet, it was also a database, it was this collaboration tool, it was a mini app builder. And after that conference, we stayed in touch. Shishir invested in Superhuman, I invested in Krypton, Krypton renamed to Coda and then, of course, late last year, Grammarly acquired Coda. And in their acquisition announcement which I think came out middle to late December, I don’t remember the exact dates, maybe it was December.
Turner Novak:
I’m seeing headlines, yeah, December 17th of 2024.
Rahul Vohra:
That sounds about right, yeah. So, December 17, December 18, 2024, that was announced. And in that blog post, the one that Shishir wrote at Coda, he said something like, “I’m watching how AI changes just about how every tool and service operates and I drafted my 2025 planning memo and I titled it the AI Native Productivity Suite.” And my jaw hit the floor because, if I were to show you our fundraising decks, and we should do that at some point, I think there’s this ... Especially now that we’re acquired, there’s this fun thing that we can do or we can go through our fundraising decks over time and you’ll see that, for a long time, we’ve been pitching that, at Superhuman, we’re going to build the AI native productivity and collaboration suite of choice.
And so, just from that, it was obvious that we had this overlap and email is a critical part of this suite. It’s also a much bigger problem than most people realize. There are roughly 1 billion professionals in the world, on average, we spend three hours a day in email, that’s 3 billion hours every single day, it’s north of a trillion hours every single year.
Turner Novak:
That’s insane.
Rahul Vohra:
It’s crazy. We actually spend more time in email than any other work app. So, as soon as I saw this acquisition announcement, I texted him and we jumped on a Zoom, I think it was December 26 that we jumped on a Zoom because we were trying to schedule and that was literally just before he was about to take his family on vacation. I think they were heading to Brazil or something and I caught him before he went to the airport and he pitched me basically what he pitched Grammarly. And, apparently, there was this all hands and he shared his vision with Grammarly, he then shared that deck with me and then I pitched my deck to him and it became pretty obvious pretty quickly that we shared the same vision which is to build AI native productivity suite of choice. We immediately agreed we should at least have the conversation.
It was funny because he was like, “Okay, yes, we’ve announced this acquisition but here’s the problem. I’m technically not CEO until January 10th and, even then, I will just have become CEO, I’m obviously not going to start buying companies immediately.”
Turner Novak:
Yeah. The first day, we’re doing a massive acquisition.
Rahul Vohra:
Exactly. So, I was like, “Okay, cool. It’s December 26, you need a break, I need a break, our respective teams are probably burnt out and need breaks, let’s all take a chill pill and come back in January and you need to do your listening tour and let me think about how I want to even proceed with any acquisition scenario. And of course, I’m a good founder, I’m going to find my options, I’m going to run a fulsome process and let’s just everyone take the time to do this properly.” And we came back in January and then we really got into it.
Turner Novak:
And so, Coda was acquired by Grammarly and then he was, as part of that acquisition, they’re like, “You’re going to lead the combined entity,” that was the plan?
Rahul Vohra:
That was the plan, yeah. I think the Grammarly team really knew that they wanted a change of god and a change of leadership and Shishir is one of the all-time greats and we’re very, very lucky to have him as CEO. But it does mean that this ... I was remarking yesterday to a friend who was asking how it’s going and I said this is one of the most exciting places I can possibly imagine being. Just a year ago, not only were we not called Superhuman, not only had we not acquired Superhuman, not only was Shishir not the CEO, not only had we not acquired Coda, we were just a completely different company doing something completely different and all of that has changed in the space of a year. There was just so much change and so much momentum and so much excitement that we have going on.
Turner Novak:
So, I think it might be interesting. I think Grammarly is quietly one of the biggest products that most people don’t know of. What is it? Actually, the core, initial product of Grammarly and then how big has the whole umbrella that you guys have gotten to at this point?
Rahul Vohra:
Yeah, great question. Grammarly, I also had no idea how big it was. I kind of knew how big it was. It’s in venture circles, it’s talked about but also very misunderstood, bootstrapped primarily for the most of its life.
Turner Novak:
That’s the issue. There was no VC content marketing machine, they were reminding everybody about how great it is because no one was incentivized because no VCs owned it.
Rahul Vohra:
Yeah. Which is a good reminder that, when a company, quote-unquote, goes hot, how much is it actually a phenomenal business versus the investors are very, very good at helping that story be told in the press and the founders as well. Obviously, some founders, the kinds that you and I like to invest in are phenomenal press machines.
Turner Novak:
Which is good. Yeah, you should make a good product, the company should be good and you should maximize people talking about it. All those things are beautiful when they work together.
Rahul Vohra:
I love doing that. I think it’s one of the things I can operate at a world-class level in is ... Gosh, darn it, we went into email which is a product dominated by incumbents which are free and, despite everyone before us failing, actually managed to succeed and build a product that people love and pay for but that requires building momentum, that requires building a brand, i requires telling the story. But yeah, people just weren’t really talking about Grammarly and I think it’s because they didn’t really raise funding. I don’t remember the exact numbers but I think the first funding raised was hundreds of millions of dollars, it was a fair amount of secondary, some primary, it was definitely growth stage by the time that it happened and, as a result, it’s just not part of the normal Silicon Valley.
Turner Novak:
The lore kind of or the narrative, yeah.
Rahul Vohra:
Yeah, exactly. Which is one of the things that we wanted to change with, of course, this name. We are here and we’ve arrived and we’re on the map and watch out because we’re doing some incredible things. So, you were talking about how big is-
Turner Novak:
Yeah, I’m just curious because I think I remember seeing something 70 million active Grammarly users a couple of years ago. I don’t know how correct directionally that number is but ...
Rahul Vohra:
Yeah, directionally correct. So, I could share that we are north of 40 million daily users of Grammarly, now known as Superhuman, and we make north of $700 million of revenue every single year. And when I heard that, I was like, Wait, what? 700 million? 40 million users? That’s insane.” And as we were starting to dig into the acquisition rationale, there were really three things that got me. I think first there was this strong and obvious strategic overlap. Not only is it at scale, it turns out that email sits at the very heart of where Grammarly is used today. For professionals, email is actually the number one use case for Grammarly. Three of the top 10 apps that Grammarly is used in are email apps and Grammarly helps write more than 50 million emails every single week. That was the first thing.
The second thing was the people. Shishir, he’s very special, he’s actually ... I was remarking upon this to my co-founders who I think you know, Vivek and Conrad, and he’s one of the few people that I would actually work with and for and that is because he’s one of the best systems thinkers I know. And I think, when you’re building a company and you want to hit 50 billion of market cap, 100 billion plus in market cap, you need a full stable of the best people in the world, people who are the best at what they do. And in those January meetings, we started discussing the vision and I said, “Shishir, you are hands down one of the best architects that I know and I bet that I’m one of the best artists that you know. And in order to pull this thing off, we are going to need a bunch of the best architects and a bunch of the best artists,” and that really resonates with him. And so far I’ve found that everyone at the company has just really been so impressive.
You’ve seen the rebrand, I don’t know if you’ve been to the website or seen the new identity, the quality of this thing is incredible. It is one of the best pieces of identity work that I’ve ever seen. And then, of course, to your point, it was about the upside that we have north of 40 million daily users, we make more than 700 million of revenue a year and this is a set of people. Think about the people who use Grammarly, they’ve already demonstrated that they are into productivity, that they want tools to make themselves better at what they do and so there’s so much potential value in bringing these users new products, cross-selling, creating this bundle, products that make their lives even better.
Turner Novak:
So, there’s $700 million of revenue, is it as simple as 40 million people that pay X amount per month or year to get the core Grammarly? I think it was spell checking and then autocomplete and layering in completion Generative AI into the keyboard. I think it was a Chrome extension or something if I’m remembering right. I don’t know if I explained this right because you’re probably way more familiar with it than I am.
Rahul Vohra:
Yeah. So, the original Grammarly product can be used as a Chrome extension, it can also be used as a native app that I think we confusingly internally refer to as [inaudible 00:17:04]. And it was, what, Facebook Club? No, not Facebook Club, okay. It’s a native app that also annotates your screen. And yes, to your point, the core products that Grammarly grew up with is spelling and grammar correction. What’s really interesting is, if you go back 10, 15 years ago, that was AI. That was actually one of the best examples of AI at massive scale was advanced grammar correction. And it’s interesting how these goalposts change and now, of course, what AI is, it’s still partially that, of course, especially for ... If you are maybe English as a second language or it’s really, really high stakes communication and we can, compared to those early days, we can now deliver really interesting and complex insights on what you’re writing based on data about who you are and where you work and the kind of people that you’re writing to.
So, I think it is still considered AI but it’s just so interesting how the goalposts shift. So, yeah, that is the core and the bulk of that revenue. It is primarily a free experience, it is a freemium model or that core business line and so there’s a smaller set of people than the 40 million that pay for Grammarly. And of the overall set of revenue, there’s now a fairly substantial part of that that is Superhuman Mail and then also another big chunk that is, of course, Coda.
Turner Novak:
Interesting, okay. And you mentioned that you learned a bunch of lessons on systems thinking from Shishir or he is one of the best systems thinkers. Can you just explain maybe what you’ve learned that might be surprising to people or helpful for people?
Rahul Vohra:
As founders, we have these grand visions, we have these master plans. We talk about things in terms of act one, act two and act three and, at Superhuman, independently of course, we had an act one, an act two, an act three. We wouldn’t have reached scale or been able to raise money unless we did and it was extremely and incredibly compelling. And that was the stuff that I was sharing with Shishir and he was sharing his version of that with me when we were doing our founder dating, so to speak. And I think one of the most palpable things for me and one of the most exciting and compelling things for me about the acquisition is, as an independent company, you have to do these things in succession.
You have to do, okay, act one, we’re going to build the most productive e-mail app ever made, we think we can easily get this to $100 million dollars or plus ARR, by itself it’s going to be worth billions of dollars. Why? Well, there’s a billion people in the world who spend, on average, three hours a day on e-mail, just 300,000 people paying you $30 a month is $100 million of ARR plus. So, that’s really not a question of if it’s a question of when and how can we accelerate that and that then leads us to act two is X, Y, Z which leads us to act three which is this whole ecosystem of applications and agents, it’s that the AI native productivity suite of choice. And as an independent company, you have to do these things in sequence. You do act one and then you do act two and then you do act three and, if you’re lucky, you get to do some things along the way but, at the same time, there’s so much competition and the AI space changes literally every week.
The amazing thing at ... I have this hyphenated name, Grammarly-now-Superhuman, GNS. The amazing thing at GNS is that we can legitimately and are actually pursuing these acts in parallel. We are pursuing act one at the same time as act two at the same time as the various components of act three at the same time as the agent platform that underlies this whole thing. And when I say systems thinking, I mean the courage and the conviction and the wherewithal and, actually, the brilliance to zoom out and say, all right, this is the big picture, this is all what we’re doing and marshalling then on top of that the capital and the resources and the energy, really, to go after it in a fulsome fashion. It’s rare, it’s not common. I think part of the reason it’s not common is it’s a set of instincts that are actually unhelpful for most founding situations. You don’t necessarily want your ...
Yeah, look, as a seed founder, Series A founder, to be thinking ... If your instinct is build all the things at the same time and we’re going to have this we’ll figure out the strategic pathway to do that, you can very easily trip up in products market fit. I think one of the most interesting things about Shishir as a founder is one of his most formative experiences, and I know this because it’s the basis of almost every example, he would not mind me saying that, is it is his time as, I think, simultaneously as the chief product officer and the chief technical officer of YouTube and he saw YouTube and led YouTube’s growth through, really, its most exciting period which requires a tremendous ability to handle complexity and to marshal those resources and to operate inside a larger mothership which is its own skill altogether and it’s very, very impressive, it is a very, very rare skill and that’s what I call an architect.
And at the same time, you need artists. I’m not the best person to do that piece that I just articulated but I think I am really, really good and I can play at a world-class level when it comes to taking one, two, three, four, it doesn’t really matter how many of those products and then building them and making sure that those products win in markets even when it’s as insane as pay email.
Turner Novak:
Yeah, yeah. And if I were to go full galaxy brain on what is Superhuman’s strategy a year ago or two years ago, it was probably, oh, you probably want to get into calendar which I think you guys did start to add some calendar features, you probably want documents, you probably want other productivity apps, you’re probably going to make some agents that save me time and, to your point, it’s, okay, well, it’s all here already. I get to do those alongside and it’s all together. Is there anything challenging about just combining these multiple ... When I think of Grammarly, Coda, Superhuman, maybe more in there but those are three businesses. You had teams, procedures, motions. Was there anything you’ve learned about just how do you get them all working together or maybe you’re still figuring it out?
Rahul Vohra:
Definitely still figuring it out. I think that it is an ongoing process and maybe, fortunately for Superhuman, the Coda acquisition happened first and there were a number of things that went really well but I think there are also a number of things that we learned from and have ... One of the things I really like about this team, by the way, is the ability to go, “Okay, that was a mistake,” boom, we’re going to fix it and do it better next time which we then did in the Superhuman acquisition and I’m sure we’ll take all the lessons from this one and apply it to the next one whatever and whenever that may be. So, yeah, there’s a strong learning machine here that gets continually applied to everything we do.
Turner Novak:
You’ve mentioned a little bit about the big vision for the company. What is it? You’ve hinted on it but what’s the big vision for Superhuman 10 years, 20 years in the future? What does it look like?
Rahul Vohra:
Yeah. My gosh, it gets me so excited. Okay. So, our vision is to give you superpowers everywhere you work and we’re starting by building the AI native productivity suite of choice. And that suite starts with, of course, Superhuman Mail, which, you know, it’s the most productive email app ever made. It also starts with Coda, which is the all-in-one AI workspace for teams. It’s actually an incredible product. It’d been a while since I used it and come back and it’s phenomenal. And Grammarly, which is your trusted, always available, writing partner that works wherever you work. And, again, we already talked about it. It’s not really a known entity inside of Silicon Valley, for most of the knowledge workers here, but this is... Oh boy, is this a business at scale that many, many millions of people live and swear by every day?. And then, of course, a new product that we announced as part of the rebrand last week, which is Superhuman Go. That’s a proactive AI companion that works in every app you use.
Turner Novak:
Oh, I didn’t even see that one.
Rahul Vohra:
Right. We have big plans for this suite, and our goal with it is to unlock the superhuman potential in everybody.
Turner Novak:
Interesting. I’m looking at Superhuman Go right now because I missed that one. That’s really interesting. So is it similar to Grammarly where it kind of embeds or it looks like you sync it with different things you can integrate with, like Calendar, it looks like. [inaudible 00:26:23] syncs with your email. How exactly does that work?
Rahul Vohra:
Both of those things are true. And this is a good example of systems thinking or strategic thinking. Grammarly, as they were figuring out what the next steps for the company would be, of course you analyze what are you good at, what are you not good at, where are the advantages? And one of the most strategic assets at Grammarly is that over the last 15 years, the team has done this incredible grind. I mean, it really cannot be overstated that Grammarly works with over 1 million applications and websites and it literally plugs into the DOM. Or if using the native app via the accessibility tree, it feels native. You download the Grammarly app and you’re in Microsoft Word or whatever, Slack, Granola, all these things that we use every day works in Figma as well. These are my daily apps and it’s annotating and it’s writing and it feels native, like it’s a part of those applications.
That is not easy. That is really, really hard. There is a large contingent of the company that exists to make that work and to keep it incredible. So that’s an asset. What can we do with this? Well, this asset is like we’ve built an AI superhighway that we have built these rails or this road network across every application and website that people use, but there is only one car that is allowed to drive on this highway, and that is your grammar car or your language car, which, that’s kind of nuts. So what the team correctly identified is this is a massive opportunity, this grammar thing you can think of as an agent. It’s a [inaudible 00:28:07] agent it’s one of your first agents if you will, relatively limited in terms of skill, but turns out that one agent is an amazing business. What else could we put here?
Well, we could actually just build all the superpowers wherever you work, and we could have it be connected to all the tools and applications you already use. So imagine you or I are working together and let’s say we use Slack and we’re talking about a design. Maybe where you Slack me a Figma link and I’m like, this is really cool, but there are some things I want to talk about live. And one of both of us is running Superhuman Go. Let’s say I’m running it. When I say we should talk about this live, imagine that getting an underline, an annotation inside of Slack and I hover over it and Superhuman Go says, hey, it looks like you want to schedule a meeting. As soon as I hover over it, actually, in line in that canvas, I see your calendar and my calendar side-to-side, [inaudible 00:29:07] this where we can leverage what we’ve been building at Superhuman Mail.
To your point, we’re really, really deep on calendar, very close to an experience that we could pull out as a separate calendar app. Whether or not we do that, we’re still debating, but we could do it. And you can then click and, without leaving, without me leaving Slack, without me breaking flow, without me losing concentration, without me losing focus, I can create a calendar event for you and me. And because Superhuman Go is connected and it can read the screen and it knows what’s going on in our apps, it’s not just an empty calendar invite. It can pre-populate it with the Figma link that we were discussing and maybe even a summary of the conversation that you and I were having. That’s a very, very simple example, but you can imagine these types of assistance that Grammarly, sorry, that Superhuman Go gives you, becoming increasingly more powerful. And the core strategic advantage here is it’s ubiquitous. It works everywhere you work. It’s proactive. It works without you having to remember to use it or without you having to know how to prompt AI, which is two big friction points.
Turner Novak:
That’s a barrier. Yeah.
Rahul Vohra:
Huge barriers. Both of them actually. There’s this really interesting study by MIT, I think, that looked at the efficacy of people using mainstream LLMs like ChatGPT and Claude and so on. And they found that if you look at the efficacy of the results, more than half the efficacy is as a result of how well you are able to prompt the AI, not the differences between ChatGPT and Claude. In other words, half the battle is knowing how to prompt it. This may sound obvious, and then the other half of the battle is just remembering to go there. And so if we can fix those problems, that’s a really big deal.
And then the third advantage is it’s connected. One of the really cool things about the Coda acquisition is when we say it’s the all-in-one AI workspace, it’s actually the most connected AI team workspace that exists today. I think it’s integrated with [inaudible 00:31:18] of 800 different applications and websites.
The volume of... transactions is the wrong word. Automations. The volume of automations that happen through Coda is actually comparable even to Zapier, it’s really, really high. So a lot of these rails already exist. And so this is a smart application of strategic advantage. Okay. We’ve built this AI superhighway that we can put any agent in. We’ve built in this one product. We’ve built this ecosystem of connections in this other product. What we can now build is proactive AI that works wherever you work, that knows what you know. Knows what your team knows, and it’s really just the kind of UI that people haven’t experienced yet.
Turner Novak:
Yeah, it sounds like the Grammarly has got this almost backdoor into every keyboard, and you can create some automation experiences using AI. Any place someone would type to interact with a computer, is that just a super fair way to really succinctly summarize it?
Rahul Vohra:
Definitely fewer words than what I’ve used.
Turner Novak:
Yeah, yours was way more elegant. Mine was the most simple. That’s the sound bite, I guess.
Rahul Vohra:
Yes, I think we would say it’s AI that works wherever you work, that you don’t have to remember to use and which knows what you know.
Turner Novak:
So then, because I feel like with Superhuman people have always loved the product. That’s just something I would never identify somebody who says, oh, I love my email provider, but I have probably paid Superhuman four figures.
Rahul Vohra:
Thank you.
Turner Novak:
Yeah, you’re welcome. Actually, probably not four figures, I guess if it’s 30 a month. I had an employee though, who use it, so I may have paid you over four figures. And people love the product. I mean, I think we can maybe talk a little bit about this right afterwards. People just talked about it all the time. Because they loved using it. How do you think about making an AI product now that people love? Are there certain things that you’re kind of thinking about, is just like I’ve got this good hit rate in Superhuman. How do I keep it going in this new almost interface that people are using?
Rahul Vohra:
Yeah. In many ways it has not changed from making a product that people love prior to AI. Of course, the skills changed and the pace of innovation has changed for sure. What made a good beautiful UI had not really evolved for a very long time. And we have some credits, I think, to take for changing the way the industry has done certain things. We popularized Command K. We were the first venture-backed app at scale to sort of really bring it to knowledge workers, and then it made its way into Slack. And almost every [inaudible 00:34:14] tool Figma has it.
Turner Novak:
Command K was just like you tap command K and search and you can get anything you want, right?
Rahul Vohra:
Yeah. Yeah. Not search in the sense of searching the content of the app, but the idea is, look, we all want our tools to be visual and minimal, but somehow at the same time, easy to use. We want to avoid enshittification, if you know what I mean by that, the crap that tends to develop over time. But at the same time, we as a company and as product leaders, we need to expand our markets. If we started by selling to founders and CEOs, possibly one of the most niche markets you could have come up with.
Turner Novak:
Yeah, venture-backed founders and investors. Yeah.
Rahul Vohra:
Yeah. There’s maybe a few thousand people, a market of a few thousand for this company. Which, by the way, I think is a great strategy. I love it when founders are like, yeah, my initial market is a few thousand people, because it lets you solve very, very tightly for their needs and expand from there. Anyway. Of course, we have to keep on expanding, and as you expand, you need to add features, you need to push the product in lots of different directions. How do you keep it visually minimal? And part of our answer to that was Command K. What if whenever you needed to do anything, you just hit Command K, type in a few characters of the thing you’re trying to do, and it’s a fuzzy logic match. You can even get the characters in the wrong order. And we had a lot of fun building that.
And it gives you the commands and not only does it give you the commands, it shows you the shortcut for next time. So you don’t even have to hit Command K. And people just fell in love with it. And of course now it is considered table stakes in productivity, software of choice. And I say of choice because not everyone has implemented it. But if you’re a discerning user then it’s the kind of thing that you’re going to look for. So the point I was making was UI, what good UI was really hasn’t changed that much. We pushed the envelope in terms of keyboard shortcuts, in terms of Command K and then I think later on in terms of what does a great onboarding look like. But in terms of making software that people love, I think it’s because we make software like it is a game.
Most software companies worry about what users want or what users need, but nobody needs a game to exist. There are no requirements for a game. And when you make a game, you don’t worry about what users want or need. You instead obsess over how they feel. And when your product’s just a game, people don’t just use it, they play it, they find it fun, they tell their friends, they fall in love with it. And game design turns out to be an altogether different kind of product development. And I think that’s the real secret too, to what we do at Superhuman.
Turner Novak:
Do you think to make a good AI product, it almost has to kind of feel like a game?
Rahul Vohra:
Look, I mean, there are many ways to skin a cat, and there are many roads to success at Superhuman Mail, that was definitely the lens that we had, which is make this as fun as a game. Apply the principle of game design.
Turner Novak:
Yeah, because I remember, I think one of the things really got me interested in it and reason to use it was the shortcuts. If you’ve used Excel, if you do any kind of finance job, they’re like, don’t touch the mouse. Only use the keyboard. And then if you go back to video games, I was literally playing Age of Empires one a couple nights ago. I don’t know if you’ve ever played Age of Empires, but with those games, you need to use the keyboard. So what I’ve been doing is I’ll play Age of Empires one on hardest difficulty. I don’t know if you’ve ever. Basically, they just get unlimited resources.
Rahul Vohra:
Yeah, there are a lot of cheats [inaudible 00:38:01].
Turner Novak:
Yeah, they basically get to cheat. So you have to figure out, my advantage is, I literally just know the hot keys to quickly create and move things around as fast as possible. So I mean, that’s a gaming design 101 for these more advanced games is the shortcuts, the hot keys.
Rahul Vohra:
Exactly. Yeah, totally. So I mean, it turns out there’s a lot that goes into great game design, and I’ve actually been obsessed with game design my entire life.
Turner Novak:
Yeah, I was going to say. Yeah. So you were a game designer for a while, right? So did you get into it? What was the first game you played? Do you remember?
Rahul Vohra:
That’s a great question, but one of my first experiences as a game designer, I was six or seven years old, and my parents were doctors when they were working. And I remember waiting for my dad to come home and I would have sketched out a little mini maze or a dungeon on paper. It was a pen and paper game, and I would kind of wait behind the couch, apparently with this pen and paper thing.
Turner Novak:
Like hiding?
Rahul Vohra:
Yeah, I would jump out to surprise him when he would come home. And it’s obviously not a surprise because if that happens every day, it’s not surprising.
Turner Novak:
To you, as a six-year-old. You’re like, oh, I bet he forgets. He doesn’t know [inaudible 00:39:26]
Rahul Vohra:
I bet he forgets because boy, I forget everything day to day. So anyway, I did that. And then once I had his attention, I’d be like, cool, okay, we’re going to play a game. And I just drew this maze and I just drew this dungeon and he would humor me. But that was my earliest memory of creating a game that someone else would then play. And so really early on, I fell in love with this idea of creating fun gaming experiences for other people. Before I was a founder, I actually worked as a game designer. I worked at Jagex, which fun fact, most people, I bet no one listening to this will know this, but stands for Java Graphical Extensions, because back then online games used to be built in Java. And at the time, we built the world’s largest online-free, massively multiplayer role-playing game and focus [inaudible 00:40:17] that because it was called Runescape.
And I had the really fun job of developing a fair amount of content for that game, including a lot of the southern tropical island. It was the island of Karamja. And I can’t tell you how many people, I mean, I can, it’s not that many, but it’s surprising. I can tell you precisely how many people, like two or three people a year who ping me, who are like, hey, Superhuman. Yeah, whatever. But that thing that you made when you were 18, 19, 20 years old, that was a formative memory for me as a child. I was like, click, click, click, click, click all the way through that. And it was so cool. And the quest I made that people really to this day, remember and pink me about all the time, is Monkey Madness, which was a very, very ambitious quest for the game engine that we made.
Anyway, so yes, I did work professionally as a game designer for a while. And during that time, and as a founder, I took the opportunity to go really deep into the principles of game design. And it turns out there is no unifying theory of game design. To create games, we need to draw upon the art and science of psychology, of mathematics, of storytelling and interaction design. And at Superhuman, we distilled these down to five factors to consider, which are goals, emotions, toys, controls, and flow. And across those things, we then identified about 13 principles of game design. And one example principle would be, make fun toys and then combine them into games. And so a fun question to consider is, are toys the same as games? It’s a philosophical question. What do you think? Are toys the same as games?
Turner Novak:
I would say probably not, because I think a game is a system of fun things or designs kind of stitched together. And a toy is just one single experience, if that’s how I maybe define it. Yeah.
Rahul Vohra:
Yeah. I mean, there’s no right or wrong answer here, but I think that’s right, that there’s a level of complexity to games and then often comprised of toys. There’s also a linguistic difference. We play with toys, but we play games. That’s an interesting difference. A ball is a toy, but football is a game. And to your point, it turns out that the best games are built with toys. Why? Because then they are fun on both levels, the level of the toy and the game itself. Now in Superhuman Mail, a favorite toy is the time autocompletor, which you use to snooze emails. This is when you hit H and you then pushing the email out and you can type whatever you want. It can be complete gibberish, and it still does its best to understand you. And I realized this was fun when in onboardings, I would see people just start playing with it.
Quite literally. You can type in 2D and it becomes two days, 3H becomes three hours, 1MO, is one month. And then people start to indulge in what I call playful exploration. They’re thinking, what can it do? Where does it break? How does it work? And it’s not long before people start doing this. I wonder what happens if I keep typing 10? Well, it turns out that’s October the 10th at 10:10 P.M. Well, how about the sequence of twos? Well, that’s February the second, 2022 at 2:00 P.M. And then I saw people trying to do more complex inputs. Like, will it get in a fortnight and a day? And then lo and behold, it works. And it’s not long before people start finding pleasant surprises. And by the way, pleasant surprise is the fundamental underpinning of joy. The emotion. For example, time zone math happens without you thinking about it.
You can say, hey, send this message 8 P.M. Tokyo time. And it turns out that’s 8:00 PM Eastern time, who’s going to stay awake until 8:00 PM Eastern time? And most people are really delighted to find out that if you really want, you can snooze emails until forever. They never come back. You can literally type in H never, and then the email will never come back. And there’s a fun little ASCII shrug emoji, the one that [inaudible 00:44:28] has. That’s the representation of it. So yeah, I would say to people interested in game design, think about the features of your product. Do they indulge playful exploration? Are they fun? Are these features fun even without a goal? And do they create moments of pleasant surprise? Because if so, congratulations. You have a toy and you can use that to build a great game.
Turner Novak:
Interesting. So your company that you made that you built before Superhuman, it was called Reportive. It was kind of email based, right? Am I remembering right? It was like a LinkedIn email overlay or something.
Rahul Vohra:
Yeah. It turns out I have an email problem.
Turner Novak:
Yeah, you just can’t get away.
Rahul Vohra:
I can tell you exactly why. I went to the University of Cambridge and I started a PhD because I had the absurd delusion that a PhD would be a great way to start a company. And it turns out to be one of the worst possible ways to start a company. And the best way is in fact just to start a company. And so I learned that about a year in, I had a great time. I really.
Turner Novak:
What were you studying?
Rahul Vohra:
Machine learning way before anything worked. So this was 2005 to 2006. I did a year, a year and a half.
Turner Novak:
So this was literally if then statements kind of a thing, like earliest version of it.
Rahul Vohra:
Really interesting points during the state of the art, we’d gone beyond if then statements, neural networks were decidedly unfucking cool. Which today is kind of like what? But it was a dead technology at the time. It was all Bayesian inference and regression, and it was a different time and very little actually worked.
Turner Novak:
Yeah. What was the coolest thing you could do?
Rahul Vohra:
Automatic scanning of deposited checks and knowing what those numbers were from handwriting. Yeah. Look, it was 2005, 2006.
Turner Novak:
That’s impressive.
Rahul Vohra:
Maybe actually no, more impressively than that with large scale translation. And very few companies could do this, right? Google could do Google Translate, but it was not that impressive. And so I also realized I’m not an AI researcher. Maybe I could have been, but I’m much more an entrepreneur. I’m really a designer at heart, and I made a name for myself at the computer laboratory at Cambridge in the UK by being the hype man. A lot of these researchers were not good at explaining their ideas and they were not great at writing papers. And I’m like, I’m a pretty good communicator. I can take your idea and you tell me where you want to get it published. I will get the paper published. I’ll craft the perfect abstract. I’ll think of really, really good examples to market. Basically product market. I would product market.
Turner Novak:
The AI research.
Rahul Vohra:
Yeah, yeah, yeah. Which weirdly, now that I think about it, why isn’t that how academia works? Every department should just hire product marketers to help their researchers. It’s kind of not structured that way, but it should be.
Turner Novak:
Someone will write a paper of like CRISPR, we can edit DNA, we can literally create anything. We can cure and solve all problems in the world. It’s just like no one knows it exists because no one has marketed the paper correctly. I feel like that’s probably one of the biggest, the highest ROI unlocks anyone could do. Maybe after post Superhuman, you go back and you’d be like an academic research hype man again.
Rahul Vohra:
Maybe. Maybe. One of my co-founders did precisely that, and he’s made quite the name from [inaudible 00:48:24] from Superhuman. He’s made quite the name for himself. Martin [inaudible 00:48:27]. Well, what do I know? That was two decades ago. For all I know, this is exactly what they do. Point is, I was not a great academic and I have completely lost the track. Why am I telling you the story? What was the original question?
Turner Novak:
Wolfo reported. So you somehow dropped out of your PhD and started the company, right?
Rahul Vohra:
Yeah. Okay. Here is why. I knew I wanted to be an entrepreneur and I was like, okay, I’m not going to be an academic. How do I be an entrepreneur? I networked my way into the part of the University of Cambridge that helps staff and students create companies. This thing is called Cambridge University Entrepreneurs. We would literally give money to teams to go and then we would, like, first money in, right? Pre-precede. Incorporate money and not huge checks, like, in the region, 25,000 pounds, so call it 30, 40, $50,000 at the time. So it was a kind of dead organization.
It’s student run, it’s volunteer. It’s entirely grant-based, we would come to people like you and beg and be like, hey, Mr. VC, can you please give us some cash so we can give it to the founders and to the staff. And like most student run organizations, it was in a complete shambles. The previous guy did a terrible job running this. Most people are doing it for resume points. They end up going to work for Goldman Sachs and McKinsey. No one really cares. And I did not want to work for a consultancy or a bank. And for me, I really, really cared. I was like, “No, this is my life. I’m going to be an entrepreneur. I’m going to be a founder.” And so I whipped this organization into shape, and I started fundraising. No one had ever taught me to fundraise before. I was 21 probably. And this is the hardest kind of fundraising. Founders sometimes complain about fundraising, but let me tell you, founders, we get it easy, because you’re selling equity. I was selling good vibes. I was like, “This is grant money.” You give me money. And I say Turner, “Give me money.”
Turner Novak:
You don’t get anything back.
Rahul Vohra:
What do I get? I’ll be like, I’ll maybe buy you coffee, although I’ll kind of expect you to buy me the coffee. That’s it. So, it was a good trial by fire. It really taught me how to fundraise in the most hardest circumstances, and it also taught me some of the finer points of BD, and how do you build relationships? How do you maintain a massive network? And I realized the problem that led me to my last company, Reportive. Now, with Reportive, you could see everything about your contacts right inside your inbox. You could see what people look like, where they’re based, where they work, what they do.
You could find ways to break the ice topics, bond over, reasons to get back in touch, and you could learn how to be astute, personal, effective, and ultimately brilliant with people. And by the way, this feature is built into Superhuman Mail. It’s awesome. It’s pretty unique. It’s one of the reasons people love the product. But back then, this was the product. It was the entire thing. And knowing that a product like this just had to exist, I came to that realization through running this organization, Cambridge University Entrepreneurs.
Turner Novak:
And it got pretty big, if I’m remembering right, I forget. I actually have never seen an actual number. I just know that it got pretty big. But what was the scale of this, and then what happened? Ultimate outcome of the business.
Rahul Vohra:
Yeah. Yeah. We scaled initially super rapidly at time. I mean, these numbers will seem quaint in retrospect, but-
Turner Novak:
This was in 2009, right? 2010-ish.
Rahul Vohra:
Yeah. I started writing the first line of code. This was a single founded company to begin with. Actually, so was Superhuman, by the way, I think that’s the best way for companies to start. We can talk more about that in a bit, but I wrote the first line of code January 10th, 2010. And then six weeks later I was done. It was such a simple product, and I’d applied to Y Combinator. Now, if you’ve applied to Y Combinator, you would know this, that one of the fields is please give us the link to your demo if you have one so we can play with it. Actually, I don’t know if they still have that, but they did at the time, and I didn’t want to create any unnecessary friction, so just password unprotected. I applied to Y Combinator, and I put in the link, and it was a Friday, I think 2:00 PM, 3:00 PM. Turner, what do we do in the UK at Friday at 2:00 PM?
Turner Novak:
Go get a beer.
Rahul Vohra:
We went, and got a beer, so-
Turner Novak:
Yeah, wait, was I right?
Rahul Vohra:
Yeah, of course. Absolutely. 100%. So, cycled from the office where I was squatting to the local pub, which was called the Golden Hind, and I had a pint of beer. We were just hanging out with a bunch of other founders, and we were chit-chatting. My phone-
Turner Novak:
[inaudible 00:53:43] 2009, oh, you did have a phone. I was going to say. You did have your phone. Okay, so this is barely iPhone. It was just kind of out. Yeah.
Rahul Vohra:
Yeah. I was like, I had an iPhone 3GS, I think. Yeah, I think so. And I had a phone, and great industrial design, by the way. It starts buzzing, and I’m like, oh, notifications are coming in for this app Mizumi. Mizumi was an app for Heroku. And I was like, “What the heck is going on here?” And it’s like, sign up, sign up, sign up, sign up, sign up, sign up. And I open the app on the phone, the terminal, and I type in User.count, and I hit enter. By the way, I had 10 users when I left the office, and it was like 500, I do up, and enter, and it’s like a thousand up enter. It was like 2000. I’m like, “Oh, oh shit.” I literally said, “Here, hold my beer.”
And I cycled back to the office, and it turns out that this good friend of mine, Peter, had shared the link, leaked the link with the next web, and the editor at the time, Zima Kane, The Next Web used to be like this really, really big, still is. Used to be this really big deal blog online, had written about it, written an article, and it was like a glowing recommendation, a glowing review. And over the first 24 hours, we had 10,000 downloads. Over the next two, or three days, we got to 32,000 users. And again, now whatever these numbers...
Turner Novak:
That’s child’s play.
Rahul Vohra:
But at the time it was like, I mean, Sequoia reached out, and Jason Calacanis reached out, and all these people randomly reached out to this dude in Cambridge UK, because at the time, that was very, very unlikely, and very rare. And so first of all, I’m eternally grateful to Pete for leaking that link. That’s what a good friend does, is he tips off the press, and doesn’t tell you the next thing you know, it goes super viral. Secondly, it’s exactly what you want when you’re applying to Y Combinator. I think my application kind of sucked, but as soon as that happened, they were like, “Yeah, okay, you’re in.” This is exactly, you clearly hacked the system. You want to do fine, and good job, good job, you’re in.”
It was a little bit weird because we ended up having to have the YC interview 30 days before the actual YC interviews, which they do only very rarely. I don’t know if they do this anymore, but they do. They did very rarely if there were extreme circumstances. So, I remember being on a Skype call that era on a Skype call with PG, and he was kind of pacing around, so we could only really see his T-shirt, and his shorts. He was pacing around. They’re like, “Are you there?”
Turner Novak:
What you couldn’t see his [inaudible 00:56:34] face? It was like... His head was above the screen?
Rahul Vohra:
We saw Jessica’s face. His head was above the screen, it was actually really funny. He just went into view, and we get in, and he said afterwards, that was risky because the acceptance rate for those interviews was apparently way lower than the normal course of interview. But we get in, and yeah, that’s the story of how Reportive took off. The reason the acquisition came about is we scaled to millions of users, and we managed to acquire all of LinkedIn’s daily active users at the time, 2012 into one app, like two million-ish users, which is weirdly high, and weirdly low, but the specific users that we had were a very valuable set of users.
Turner Novak:
You just think of who were at LinkedIn power users in 2012. It was probably just sales people, and recruiters, and someone who would want that bar in their e-mail to just say like, “Hey, Rahul just did this. You should slide in, and suggest this”, or...
Rahul Vohra:
It was a lot of Silicon Valley, a lot of CEOs, a lot of founders, a lot of executives. I would say that’s half of it. And then, yeah, sales, and recruiters. At LinkedIn, we used to say, hire market, sell. So, recruiters, marketers, salespeople.
Turner Novak:
Okay. And then so they got to the point where LinkedIn was like, “Hey, there’s something here. We want it. Come join the company.”
Rahul Vohra:
If only acquisitions were that easy. The Superhuman one was six months of intense efforts. The LinkedIn Reportive one was a bit different. And again, I think there are multiple ways to sell a company, but the Reportive LinkedIn one was a bit more traditional. It was the direct result of a business development relationship, an API integration relationship. To begin with, we didn’t work with LinkedIn directly at all, because as you can imagine, LinkedIn did not want people taking LinkedIn profiles, and sticking it inside of Gmail. You might think, well, that’s good for LinkedIn. This is the classic platform API protectionism debate. Yeah, it is good for LinkedIn, I guess, but in a way, if they control it would be better. And if one of their businesses is monetizing search on both sides for people looking for jobs, and people looking to hire for jobs, then does this get in the way?
There were some big philosophical questions there. So, historically, LinkedIn has never had a public look up people by email address API. So, what we did is we bought the data, and historically there have always been companies that scrape LinkedIn, and sell the data. We bought the data of one of the first companies to do that, which was a company called RapLeaf. RapLeaf, founded by Oren Hoffman, and a bunch of other people, including Vivek Sodera, who became one of my co-founders for Superhuman. A fun story about Vivek is he was the very first person I ever met in San Francisco early in the course of Reportive, I was like, “I need access to some data. I need”, it was basically a small data play. Give me a profile, I’m going to render it in Gmail. Who sells the data? There was really only one company that was doing this well, and they were called RapLeaf.
And I learned through my mentors, from my mentors in Cambridge, what, we’re blessed we have a lot of successful entrepreneurs around the University of Cambridge. A very clear lesson was there is no substitute for simply turning up. And so I just got on the plane, and I landed in San Francisco, and I emailed Oren Hoffman, the CEO of RapLeaf was like, “Yo, this is me. This is what I’m building. You have may seen, we went viral yesterday, or two days ago. We’re interviewing with YC, and just got in. Can I please come, and hang out at your office? And also, by the way, can I have your data? By the way, I don’t have any money. Can I have it for free?” And to my great surprise, but again, if you don’t ask, you’re not going to get it right? You got to shoot your shot.
To my great surprise, he said, “Sure, come swing by the office. We’ll take good care of you.” As I think you might do, this young child is like, “Hey, could I have your attention?” He’s like, “Yeah, yeah, cool. Here’s some attention.” And he pawned me off to Vivek, and was like, “Vivek, you are our startup guy. This appears to be a startup, maybe. Please take care of whatever this is.” And so I get to the RapLeaf office, and I meet with Oren. He gives me 15 minutes. I give him the pitch. He’s like, “Cool, if you’re raising money, I’ll invest 10K.” And he then handed me off to Vivek, and Vivek was like, so I guess he was the second person I ever met in San Francisco. And he then brokered the deal with me, and he was like, “Yeah, we’ll give you four million lookups a month.”
Which at the time I was like, you can cash these lookups, and the data doesn’t change very frequently. I was like, “Wow, that’s way more than we’ll need for a very long time.” And then after that, it was going to be a few cents per lookup. We negotiated the cost, and I went on my merry way. And that was that. We didn’t really talk that much thereafter except for YC demo day. And I do the YC demo day pitch, and it was a very weird pitch because we’d already raised our seed round by then. So, my pitch for YC demo day was like, “Ha-ha, I’ve already raised money, but let me tell you what we’re doing anyway. And if you’d like to stay in touch with Series A, then let’s talk.” The person who came up to me during, after that YC demo day is a person we both know Emily Choi, and has this massive role at Coinbase now.
And at the time she was running Corp Dev for LinkedIn, and she said, “Hey, this is really cool. This is really interesting. Would you be down to come hang out at LinkedIn, and speak to”, I think our head of products at the time, who was Adam Nash, who runs Daffy right now, great products executive, great angel investor, rich, really great guy all around. She was like, “Yeah, yeah, can you come hang out with Adam?” So, I was like, “Hey, I don’t have anything to lose. Sure, I’ll come hang out at LinkedIn. Why not?” So, I hang out with Adam, and he’s super lovely. He’s like, “Hey, listen so RapLeaf is stealing our data.”
Turner Novak:
Oh, no.
Rahul Vohra:
“Your product is really, really great, and we just really don’t...” He was trying to find the words without saying, “You got to stop doing what you are doing, buddy. We’re going to...” And he basically said without saying, “We’re going to sue the hell out of RapLeaf. They’re going to die. They’re gone.” He didn’t say that literally, but that was the intimation. What was that? This behavior is not okay, but we like your use case. And I was negotiating on the fly here, a light bulb went off. I was like, “Oh, this is it. This is my one shot.” This meeting honestly probably makes, or breaks the company. And I figured out the right set of things to say. I don’t remember exactly what it was, because it was in an adrenaline blur where I pitched him what we were building. I pitched him where we were trying to go.
I was trying to be as friendly, and as polite, and as collaborative as possible, and he was like, “You seem like a good guy, and you seem like you have really”, this, I remember verbatim, “You have really great product instincts. Let’s work together. I’ll give you the API, but don’t fuck it up.” And I was like, “Okay, all right. I promise I won’t.” We leave. And then he connects me to the API team, and we get access to this API, which by the way, I think at Peak 21 companies ever had. And then the other companies were real companies like Dialpad as the telephony solution, and a bunch of other CRM type things, and then randomly Reportive, because of this one meeting. And with this API, we could give LinkedIn email address, and they would give us a profile, and we’d put that profile in the right-hand side of Gmail.
Turner Novak:
It was all in the name of giving more information to people, and making it more useful, right?
Rahul Vohra:
Yes, yes, yes, yes. We ended up that advantage became such a huge advantage. Reportive, like Superhuman, like any company to get traction that gets traction, attracted a silly number of imitators. I think there were five, or six companies that tried to build Reportive, and were like, “Yeah, we can build this better than you can.” The thing is they just never ever had the data because we were the chosen company by LinkedIn that they were only going to give it to one startup because I guess they wanted to limit their exposure. They trusted me as a founder. We treated their data with super high integrity, and we always protected it. By the way people would try, and scrape it via us, and we promised them that like, “Okay, you put your alarm bells on, and we’re going to put our alarm bells on. If either of us notice scraping, then let the other know, and we’ll fix it.”
But every month people would figure out how to scrape the data from Reportive, and we would fix it. So, this is a classic BD situation. We now have a very privileged integration partnership with LinkedIn, and of course as part of that, we would meet with the corporate development team every three to six months. And of course what’s happening is two things. A, they want to make sure you’re not abusing the, or three things. You’re not abusing the API. B, you’re not headed in a direction that’s going to be competitive, and that you’re still within the parameters of what the API is designed for. And C, of course, they’re talking about this, I didn’t quite realize it at the time, but this is clearly important enough to them that they want to see it exist, but not quite important enough that they want to resource internally. But has it become important enough that they want to now own it? And when it became clear that we had all their daily active users, which had I known at the time, I think I would’ve sold it for a lot more money.
Turner Novak:
Really? Okay.
Rahul Vohra:
Yeah. They were like, “Hey, how do you feel about doing this at LinkedIn?” In reality, it was a lot more complicated. I can tell the story if you’re interested, but the very short version is we were pitching Greylock for our series, and we were pitching Reed, and David C, and Reed came back, and he was like, “There are two ways we can do this. We can write you a term sheet from Greylock, or here’s another idea. Bear with me. What do you think about doing this at LinkedIn?” And we talked a little bit about what that might look like, and I’m like, “You know what? These are both interesting. Let’s parallel track these, and see where these conversations go.”
Turner Novak:
Interesting. Okay. So, you feel like, I guess, summarize the story. It sounds like you had unique product, you had access to some kind of unique thing that no one else had. You were positioned in a way where it was not important to LinkedIn originally. They just were kind of like, “Yeah, we don’t want to build this. We’ll work with this 21 year old kid, and whatever.” But it became so well-performing that they’re like, “Maybe we do kind of want this.” And then you kind of hit a point where you did have almost multiple bidders in a way to the point where you maybe had a little bit of leverage, even though you didn’t even know maybe the true leverage you might’ve actually had with how many people are actually using it?
Rahul Vohra:
Yeah, sort of. So, initial momentum, we built a product that people love based on RapLeaf data, and it took six weeks to build, started going viral, boom. Every investor in the valley is contacting me. I then leveraged that to get into YC. I then leveraged YC to close the funding round actually ahead of demo day, which was unusual at the time. We were the first party round that YC ever saw. Yeah, PG wrote his essay, well, specifically high resolution funding, I think is the name of the essay. He wrote that after we did what we did, it’s kind of in response to the pattern that we had. We then leveraged YC demo day to get a meeting with LinkedIn. We then leveraged the meeting with LinkedIn, and their desire to put that aspect of RapLeaf out of business to get the direct API. We then just kept building good product, and kept growing.
We then leveraged, and then to your point, it performed well. We sort of attracted most of our daily active users into one platform. And I think just as they were growing that they were just post-IPO, they were starting to figure out what application services do they want to own? Email is this perennially strategic thing. It became strategic for a lot of companies at the end of last year as well. That’s how I knew as one of the right times to sell Superhuman. And so it became perennially strategic in 2012, when we sold Reportive, we ended up getting offers from LinkedIn, from Twitter, from Salesforce, I believe, and each with different theses. With LinkedIn, we’re going to put LinkedIn profiles in Gmail, and Outlook. And with Twitter’s going to, we used to show tweets before Elon killed the API.
Turner Novak:
Oh, yeah, you did. Yeah, I remember that.
Rahul Vohra:
Yeah. And with Salesforce, it’s the obvious use case of what if you could see, and update your CRM right from your email.
Turner Novak:
That’d be awesome. Yeah.
Rahul Vohra:
Yeah, it exists. We’ve done it for Salesforce, HubSpot, and PipeDroid. So, very obvious reason, we spoke with Google as well, very obvious reasons for all these companies to own Reportive. And again, we ran a process which was insane, and crazy. I ended up going to hospital, LinkedIn signed the term sheet. They ended up walking away from assigned term sheet, all kinds of drama.
Turner Novak:
Wait, so hospital, how’d you end up in the hospital?
Rahul Vohra:
I was working so hard, and living so badly as a, I think I was 20, 25 at the time, maybe. I’m just not taking care of myself that I burned out mentally, and physically. And that happened in, I was Series C fundraise, and in around the acquisition process. But I’ll tell you this. Let’s see, I’m trying to summarize this. So, I was hospitalized for about a week. Long story short, I ended up... We had an office for Reportive of 588 brand, I think it is, across from Tres Agave, the Mexican place. And I was walking to the McDonald’s that used to be near Fulton King. And I remember walking every single step being more, and more painful, like this sharp shooting pain at my leg. And it was getting worse, and worse, and worse until by the time I get to the McDonald’s, I just can’t walk anymore. And I end up collapsing on the roadside, and because it’s San Francisco, so I was next to this homeless guy.
He looks at me, he is like, “Hey, buddy, you don’t look so good.” And I’m thinking, wow, how did my life get to this point? What happened? Then I collapsed outside a McDonald’s, and the homeless guy’s telling me I don’t look great. And so I pull out my iPhone 3GS, and I text one of my teammates, Lee, and I’m like, “Yo, Lee, I think I might be dying next to McDonald’s. Can you please come rescue me?” And he comes racing out of the office, and he finds me, and then he picks me up, and he hoists me over his shoulder, and I’m onwards to Safeway. And he kind of just drags me the next two blocks to Safeway, I buy some medicine, because I’m having this major acid reflex episode. So, I buy some antacids, and like an idiot, I go back to the office, and I keep on working, and I work the rest of the day. And I wake up again at three o’clock in the morning with this major intense abdominal pain, really, really bad, lower left abdominal pain.
And by the way, if anyone’s feeling that you should be worried, this may be appendicitis, that is a go to the hospital situation. So, I call my dad who is a doctor, and he was like, “This may be appendicitis. You should go to the hospital.” So, we were new to the US, me, and my two co-founders we’re all British. I didn’t know how any of this works. I’m like, do I even have insurance? I think I have insurance. I wake up my co-founder, like, “We need to go to the hospital.” We could barely afford an Uber. Taking an Uber was considered extreme for us. We would always take public transport, but we splurged for an Uber. We get to St. Francis Memorial Hospital. And I remember the nurse interrogating me. She was like, “Okay, so can you describe your day?” And I was like, “Well, like what do you do?”
I’m like, “Well, I’m a founder.” She’s like, “How’s it going?” And I’m like, “Oh, yeah, it’s fine. We’re crushing it.” Remember that time when was Gary Vaynerchuk crushing it? We were definitely crushing it. And she was like, “No, really?” And I’m like, “Well, honestly, it is pretty stressful.” And she ticks something on her clipboard, and she was like, “Do you do any exercise?” And I was like, “I think I exercised sometime when I was like 15.” And she was like tick. She was like, “What do you eat? Do you have a good diet?” And I was like, “Well, for lunch I have a bagel, and a brownie. And then as a team, we go out for dinner every night.”
And she was like, “You have a bagel, and a brownie every lunch?” And I was like, “Yeah, I’ve had that for the last two years.” She was like, “Okay, so what do you have for dinner?” It’s like, “We will have a pizza, or a burger, or we’ll go to 21st Amendment, we’ll have some beers.” And she sighed, and tick. And then she had another question that I don’t remember, and she said, “Okay, so here’s the thing. You have a hiatal hernia.” It’s a hernia right here amongst other things that are probably going wrong and that is irreparable short of surgery, which actually doesn’t really work. That explains the acid reflux. We don’t really know what’s going on with the rest of you, but your insides are basically way older than your outsides. You need to stop living like this or you will die quickly. I know that that might be harsh to hear, but that is just the truth.
Turner Novak:
I mean, you’re going to die if you don’t. You need to hear that.
Rahul Vohra:
I know. I now say this, I have given this story so many times to younger founders and then sadly to not so younger founders. I know people doing this in their 30s as well. Honestly, I’m a little worried about this whole 996 thing because you know what, if it works out, freaking great, cool. You make $100 million and you sail off into the sunset and that’s good for you. But if it doesn’t, you might die early. You might get a hiatal hernia. You might have these irreparable life problems. Now I’m at least glad that the younger generation is drinking alcohol way less, but they’re doing other stuff and we don’t know what that other stuff is, what the long-term implications of those things are going to be. Anyway, why am I telling you this story? This all happened simultaneously with the late 10 acquisition.
I will tell you, coming out of that experience, I was in hospital for a week. I was in recovery for about four weeks. My aunt and uncle very lovingly took care of me at that place in Sunnyvale. I had to learn how to eat again. I was eating little tiny bowls of rice every day, liquids only. Slowly my... I think the level of system shock was just... Basically everything shut down. I actually learn how to move again and walk again and eat again. It gave me this profound appreciation for my health and for my body and for my level of stress. And that is a superpower. That is a true superpower when you don’t give a fuck in fundraising situations or in M&A situations. Because just a few months before when the Series A investors were mistreating me, which they did, not Greylock, but the other firms or when the potential acquirers were mistreating me, which they did, I used to get really wound up about it.
I used to get super stressed about it. It felt existential. It felt like my entire life was at stake here. But something changed. It really just felt like a change in aura. I literally stopped caring. I just did not care anymore. Zero flex left to give. I was in those meetings and the moment I sensed BS, I was like, “Cool. Right. We’ll be in touch. Nice conversation.” And you know what? That changed the dynamic of every single conversation I was in. They could feel it, they could sense it. Suddenly everyone started chasing us. It is weird how much aura plays a part in fundraising and M&A, but it does.
Turner Novak:
So you almost died and almost dying completely just changed your really just mindset and your perception to the point where you just didn’t give a shit about the immaterial, material things like, oh, what term sheet do we get? Whatever. You’re just like, “I almost died. I don’t give a shit. Whatever you can throw at me. I’ve seen the worst of this.”
Rahul Vohra:
Yeah, exactly. I was reminded what actually mattered. I still cared about making the company successful. Here’s a crazy fact. We sold the company with two weeks of runway left, two weeks. You can imagine that. At a premium, there’s a great exit. Some of our investors made 20x that money, most of them made 3 to 5x that money, two weeks left. At the end of that I was like Zen mode. There was just something about the aura where I just didn’t care anymore. I knew it was going to work. My reaction was, I’m going to make this work no matter what. The thing that I lost patience for was being mistreated. When people would mistreat me and give me BS answers or the run around or ghost me, I was like, “Yeah, I’m not dealing with it.”
Turner Novak:
You mentioned two other things. LinkedIn pulled a term sheet or something with the acquisition. And then also the two weeks of runway before you landed this. Tell me about those two things.
Rahul Vohra:
We signed a term sheet with LinkedIn on December the 11th of 2011. There are two ways you can do M&A at the small scale. At the small scale is often an acquisition of talent just as it is roadmap and future roadmap. For us it’s kind of a mixture of all of those things. Because we were only five people including me. So you have a choice of doing the interviews before signing a term sheet or after. There are pros and cons either way, of course.
Turner Novak:
Interviews, this is when they meet the team?
Rahul Vohra:
Meet the team. For a team size of five, they’re going to meet the whole team. For Superhuman Mail I think they met maybe I want to say 5, 10, 15 people max, more like 10 people, but for Rapportive it was the entire company because we were only five people. So they are going to meet the people at some point. Sooner or later, any acquirer is going to want to peak under the hood and do the due diligence and say, “Okay, every founder says they have the best team in the world. Are they actually?” Way more due diligence happens here, by the way, than VCs do. VCs I found just generally roll with it. They’ll meet your co-founder, maybe they’ll come to the office, but that’s very rare these days.
Turner Novak:
Some of them don’t even meet the co-founder. They’re just like, “Ah, Rahul seems great. The chart’s going up.”
Rahul Vohra:
Which is shocking. Most VCs do not meet the CTO. It’s crazy.
Turner Novak:
I’ve changed my initial decision based on meeting other co-founders, whether it’s I actually do end up investing or I don’t based on meeting other people on the team. It’s usually not like I met the CEO, I hated them, but then the CTO was great and I invested. It was more of like, man, maybe there’s something here. I just always meet both the co-founders and you meet the CTO, you’re like “Oh this person, they’re a really good engineer or really there’s definitely something here.” Then you go back to the CEO and you’re like, “Okay, now I kind of get this.” I think that’s really so important, just meeting everybody as many as you can.
Rahul Vohra:
Yeah, I couldn’t agree more. LinkedIn met everybody. We disagreed about this. There’s perverse incentives here because the company is always trying to acquire UFS. I think people are literally incentivized on that. I think there are people in the organization whose job it is to acquire UFS. We agreed a price at the term sheet. This is me and my naivete. I thought, “Cool, end of negotiation.” That’s BS. That is not the end of negotiation. That’s the start.
Turner Novak:
It’s the beginning.
Rahul Vohra:
That is the first 10, 15%. There’s going to be a bunch of re-trades and re-prices all along. Do not be surprised if you end up anywhere from 50% of what you thought you were going to sell up to... maybe you trade a heck of 10, 15% below whatever that price was. But I didn’t know that. They met the team. There were two or three people where they were like, “Some of your engineer are fantastic. Some we don’t think they’ve met the bar that you’ve sold us.” I was like, “That’s BS. These people are fantastic. They’re great. You don’t know them. They actually are phenomenal.” And went on to have incredible careers at LinkedIn. So LinkedIn was wrong. I was right.
But we got into this disagreement about this and they wanted to re-trade on the basis of interviewing the team. Then stuff happened internally and our executive sponsor went on a six-week vacation and this, that, the other, and they pulled the term sheet because they wanted to re-trade on price and we couldn’t agree on the re-trader price. I felt like it was just completely not within the spirit of how we were engaging. But of course they did end up buying the company three months later.
Turner Novak:
That is pretty common where they’ll say, “Oh, you owe back taxes. We incurred all these costs and you have to pay the costs and we’re going to back it out of the price.” Then also it’s like you might have had other conversations that you drop out of and they know you’re the only option or they know that they are now the only person you’re talking to. So you want to make sure... I’ve had that with portfolio companies before, is all those things I just mentioned have been things where they’ve been gotchas where the price is 30% lower than you initially thought and you have a month of runway and you just have to do the deal.
Rahul Vohra:
There are ways you can protect against this. I’m by no means an expert, but I think we handled this very well at Superhuman. We worked with, and I’m going to give a shout out to my new favorite M&A advisory bank, AXOM, A-X-O-M. They did phenomenal work, incredible work here. They’re all ex-catalyst, which means they have the Catalyst Playbook, the Precision, the Rolodex, the Contacts, the whole thing. It’s really, really, really great work. I don’t remember the term sheet exactly, but it’s things like, look, we both agree there will be no material re-trades. Now what is material? We didn’t define what material is, but at least there’s something to point to that we can start to have a conversation around if and when we need to.
We agree the topics that we will re-trade over. Sales tax is a class one. And that in super no, actually is happening in our case because most startups don’t pay sales tax in certain states. It’s just not something that you set up. That also isn’t a risk most acquirers can take on. So when an acquisition happens, it is expected that those states will come knocking and say, “Hey, you owe, us...” It’s usually not a bunch of money but you owe us some sales tax. To mitigate that, you’ll create these escrow funds or a holdback or things along those lines. That’s all completely normal. But you know what, 26-year-old me did not appreciate the extent of the re-trades that LinkedIn wanted to do.
Turner Novak:
I actually have to give a shout-out for speaking of sales tax. One of the sponsors of the show Numeral, they’re probably the best way to figure out your sales tax if you’re a founder. Just plug it in, start using it. They’ll figure that stuff out for you just as you go. The worst thing you want is to owe $10000, $20000 in a bunch of different states and you just weren’t keeping track of it. They’re a good way to get around that. You still have to pay it, but one thing you can do is you can actually... usually your customers will pay it. If you’re just like, “Hey, 4% sales tax on the invoice.” You can generally tack it on. You just got to do it. Because a year later you can’t really go back to your customers and be like, “Hey, by the way...”
Rahul Vohra:
Yeah, [inaudible 01:26:35] getting right.
Turner Novak:
Just thinking through, so when you first started Superhuman, you had alluded to earlier you did this personal onboarding. Could you just explain what that was? I feel like there was a Superhuman onboarding was a thing that people started to do. Can you just explain it and how it worked?
Rahul Vohra:
I’ve seen a lot companies, especially in the productivity space, get this wrong. I no longer believe in the traditional launch. Let’s say you’ve built a new e-mail app or a new task manager or a new calendar app. Now the surface area for these products is absolutely massive. It’s bigger than almost any domain you could think of, which means you also get a massive surface area for bugs as well as massive variability in how users want to use the product. Most companies would launch start-ups and because the demand for these products is so high, you quickly get tens of thousands of users as we talked about, that’s not harder these days. But guess what?
Those users will very quickly find thousands of bugs. Any company would very quickly get overwhelmed and they would simply not be able to fix those issues fast enough. So those users then become disappointed. They churn out and they tell everybody about their experience. That is the very definition of a net detractor. In my experience, it’s significantly better to do what we did, which is onboard customers at a measured pace every week. That way you have the bandwidth to fix any issues they find and you can focus on making them especially and particularly happy. So yeah, that’s what we did.
Turner Novak:
You have this sort of quantifiable product market fit framework. Does it fit in with that at all? Then I’m curious really quick, what is it and have you made any changes to it over the past couple of years? I feel like people are probably pretty familiar with it, but maybe have you had any changes in how you think about it?
Rahul Vohra:
I think we’re talking about the product market fit engine that we built it Superhuman, which I believe is still one of the most shared entrepreneurship posts of all time and on first-round review. If you want to find it, search for Superhuman products market fit engine. It gives you a way to define product market fit. It gives you a metric to measure product market fit and it gives you a methodology to systematically increase it. The crazy thing is it can even generate your roadmap for you, and guarantee... This will make sense when you read it, guaranteed that roadmap will take you to products market fit as measured by this metric over time. It’s a very thorough process, which is definitely more than a 15-minute conversation. It basically revolves around one core question, which is how would you feel if you couldn’t use the product? Three possible answers, very disappointed, meaning they would love it.
Turner Novak:
They’d love the product.
Rahul Vohra:
Exactly. Somewhat disappointed or not disappointed. You measure the percentage, let’s say very disappointed and there’s a whole process for figuring out what to build to get more and more and more people saying very disappointed. And yes, we still use it to this day.
Turner Novak:
Interesting. It’s basically, I think if 40% of people are very disappointed, then you have product market fit. Am I remembering that right?
Rahul Vohra:
Yes. Although the caveat with all of these metrics and supplies to MPS and everything else is, the number changing over time is just as if not more important than the absolute number. Because there’s going to be some form of systematic bias in however you measure this. We do it by email. I’m sure we’d get different numbers if we texted people. But the question is how is it changing over time?
Turner Novak:
Interesting. There’s probably products too. Email might be a product that people naturally hate or love versus it might be another category that people love this even if it’s a bad product, just generally speaking, like the category. So I guess you could be biased there too. But that’s an interesting point of just do people over time get more and more disappointed if you were to no longer be able to use the product?
Rahul Vohra:
Or as you add new and new personas, are you able to maintain the high score that you hope to have? Is usually how we think about it.
Turner Novak:
When it comes to building the Superhuman brand. I know we talked about earlier you literally rebranded the top company around the Superhuman brand that you had built. Maybe it was just a coincidence because the name is a great name. Maybe that’s all it is. But how do you think about just building a good brand?
Rahul Vohra:
Well, I think there are two pieces to this. Number one, build something people love. Then number two, build something memorable. Even if you don’t love Superhuman the product, you can’t help but remember it. It’s just one of those names that piques interest. It’s intriguing. You didn’t know it was a mail. Like hey, what is this Superhuman thing? What does it mean to be sent by a Superhuman? What actually is that? So there was that. The other piece of this was I was deliberately back solving for a 100 year iconic generational brand, which still feels surreal because it just happened last week. I think will happen. I think that we are going to build this 100 year company. This dream that we had when we founded Superhuman all the way back 11 years ago is going to still come to pass, and that is incredible.
Turner Novak:
Do you have a personal productivity stack? I don’t know if I just used all the Superhuman suite of products, but what do you do, you think that’s unique in terms of being more productive? I’m assuming you got to have some tricks up your sleeve.
Rahul Vohra:
I do. Of course the Superhuman products are amazing, but this version of the question isn’t that. Outside of the Superhuman products, I’m typing so much less than I used to. More than half of my input is now voice. I use this app Wispr Flow. It Is incredible. I just hold down function. I just say what I want. They do things where they screenshot the screen in and around your dictation, so if there’s a particularly hard to spell name or a project code name that’s weird or unique, they’ll even get that. As you can tell, I speak pretty fast. I speak even fast when I’m dictating and it gets it right. Not only does it save me time, I’m less tired at the end of the day because I haven’t been tippy typing all day long.
Turner Novak:
Interesting. I’ve heard of people use that. I’ve never actually tried it. Any other tricks that you feel like you do or is that probably the biggest one?
Rahul Vohra:
That is the biggest one. Oh, the other one that’s huge, but this is just obvious. I constantly have ChatGPT grinding away in pro mode. I buy the most expensive ChatGPT, I can. I think I’m just going to always... if they had a $10,000 a month thing, I’d probably buy it. I don’t know what it would do, but...
Turner Novak:
Yeah, hopefully it’s good if it’s $10,000.
Rahul Vohra:
Well maybe it replaces an actual human assistant at that point, but I just have it constantly grinding away. I just turned 42, two, three weeks ago, and so I have very middle-aged dinners. My dinners are like, peptides, cancer screening, braille, full body MRI. That’s the thing that gets discussed tonight.
Turner Novak:
It’s like my back is kind of sore and my knee is like...
Rahul Vohra:
That’s me, terrible for a long time. So I’m like, “Okay, I have to take this stuff seriously now.” But I’m not an expert. For the last week, basically nonstop... I’m sure I cost OpenAI more money than I pay them. I’ve had ChatGPT grinding away on coming up with a personalized health plan for me and for my wife that’s going to be this executive program and then this kind of peptide protocol over here and this other protocol over there. I’m constantly refining and generating the plan. Honestly, the kind of thing where I feel like I’m working full-time with a person. That’s what I’m doing to... In a way it’s more productivity, but it’s I think common to a lot of what we see with AI. It’s simply work I wouldn’t do otherwise. It’s not giving me more time, but it is letting me do something I previously would not be able to do.
Turner Novak:
Yeah, because just like it’s completing a job, it’s doing some digital labor for you. I’m sure you would love to have done all this research, but you would’ve had to search around and read some things. Now ChatGPT you can just summarize it.
Rahul Vohra:
Exactly. I’m just like, “Tell me what to do.” Obviously I double check. This is my health. But it does a remarkably good job.
Turner Novak:
I know you do a little bit of Angel investing too with my friend Todd. What do you guys like investing in?
Rahul Vohra:
We do a whole bunch. We’ve invested in 120 plus startups now. Check size is typically 300K to 500K. We’re investing out of fund three, seven unicorns. We have zip super base, high touch mercury writer next health placer. That’s a 6% ish unicorn rate as of today. We have many, many more to come. One that we’re particularly excited about right now is Loyal. Loyal, makes longevity drugs for dogs. You probably saw this...
Turner Novak:
Celine’s actually a prior guest of the show. I love Celine. She’s awesome.
Rahul Vohra:
I didn’t know that.
Turner Novak:
I don’t know the unicorn yet. I would’ve sworn.
Rahul Vohra:
No comment. It’s Celine’s comment.
Turner Novak:
Okay. Fair.
Rahul Vohra:
They received FDA efficacy approval in February making them the first company in the history of forever to receive FDA approval for lifespan extension, and people are sleeping on this. Do you know how big that is? That means the government believes and agrees that their drug is going to extend the lifespan of older, larger dogs. They have many tailwinds that will continue to compound, like longevity has become mainstream. We’re just talking about it. GLP-1s are normalized. The veterinary market is consolidating with private equity. That’s one of many examples that we’re currently very, very excited by. But yeah, it’s really fun to invest in startups alongside Todd. I think it makes me a better executor of technology and a better operator.
Turner Novak:
Talking about Celine, she was a solo founder. You mentioned you think there should be more solo founders. Because I feel like general consensus is like you get a bunch of people, everyone’s good at different things. It’s not as hard because you have help. Why should there be more solo founders?
Rahul Vohra:
It’s a question of timing. I have this thesis that if you double click enough on any co-founding story that you might come up with, it really was every single company, a solo founding journey. One person had the vast majority of the efforts and the wherewithal and the momentum and usually also often the idea to say, “Yeah, we’re going to go do this thing.” And they start marshalling the resources. They probably start putting in 12, 13, 14 hour days and not everyone’s doing that to begin with and nor should they. The other thing I found is, because I’ve tried to start many companies, two have worked, it is very easy when you have a group of co-founders and you don’t know what you are doing. You don’t have an idea that you’re all agreed upon, or you are operating in a bit more of consensus mode. Do we all agree that this is the idea?
I have never made that work and I’ve never seen it successful. What I’ve seen to be successful and what I’ve experienced is me like the guy at the start saying, “This is the idea. I’m going to will this thing into existence. It may sound crazy, but here I go.” And I do that for... Like in the Rapportive case I did that for the three months until we got into YC. And that was the point where I recruited co-founders. In Superhuman’s case I did it for nine months and raised the first $1 million of capital by myself, bought Superhuman.com by myself, built the first mocks landing page, and knew exactly what we were going to build. Hired a design agency, started creating concepts. And I used that momentum to bring on board Vivek Sodera, who was my operations co-founder, and Conrad Irwin, my CTO.
Turner Novak:
It sounds like there’s a lot more that goes into it than people might think for that kind of stuff.
This was a lot of fun. Thanks for coming on the show. This is awesome.
Rahul Vohra:
Yeah, absolutely. Thank you for having me. Great conversation.
Stream the full episode on YouTube, Spotify, or Apple.
Find transcripts of all other episodes here.