Knowing When to Sell: Lessons from Two Very Different Exits with Superhuman + AngelList

Alrighty, how's it going?

Good, good.

Everyone hear us?

We're good.

Everyone? All right, well, I guess I don't need to do the intros. I had it all prepared and everything, but I'm excited for this chat. You've obviously been through two very different acquisitions, almost 10 years apart, 11 years apart, with Reportive and Superhuman. And what I'm actually hoping we get out of this is we can take some of the learnings and actually give it as a framework and a playbook for folks here that are looking to sell their own company. So maybe to get started, I'd love to split the conversation into how do you know when to sell, how deals actually happen, and then most importantly, how you don't screw it up. So we'll go back to Reportive. When it was your first acquisition, what did you not understand during that time when you sold Reportive?

What did I not understand?

Yeah. Like you agreed to it, your first acquisition, and you look back on it and you're like, wow, I had no clue.

Oh my God. I mean, basically everything. What did I not understand? Uh, so there were, I think the biggest lesson from the first company, and this is less about acquisitions and more just about the practice of running a startup, is we didn't have a strategy and stick with it. Mhm. You know, some days we would chase user growth, some days we would chase revenue. Sometimes those were alternate days and we would just flip between what we were doing every which way. And that made it difficult to sort of build a robust company over time. It made it difficult to tell a fundraising story that made sense. Now fortunately, we'd still built a product that people love. We still built a a brand that people fell in love with. It's probably older than most people here know, but just to give you an idea, this is back in 2010, and we'd built the first Gmail extension that had scaled to millions of users. Right there on the right-hand side of Gmail, you could see what people look like, where they're based, their recent tweets. You could click out to their LinkedIn pages, their Twitter, their Facebook, and all of that. And we'd somehow managed to amass most of LinkedIn's daily active users onto this one product. I actually didn't know that at the time. Had I known that we'd done that, we would probably have sold for a lot more money. It was ultimately LinkedIn that acquired us. So we'd amassed all of these users and people really loved the product. Now beyond that, we didn't really have a strategy, and that was the, the main thing that looking back I'd wish we had. But we ended up selling for a great premium to the right company. Mm-hmm.

Yeah, I actually remember when you sold, and back then I actually heard of Reportive. Because I was using the product and I heard you sold and I was like, wow, that's amazing. And it was actually something I aspired to. I don't think I told you.

I don't know if you know this, actually, we were one of the very first companies to raise on AngelList.

No, no way.

Before AngelList was a platform, this was back when it was a mailing list.

Yep.

Nivi and Naval sent it out to like 20 angels and I think 5 of them invested from that email blast.

That's amazing. I love how everything just comes back and it connects. So let's fast forward 10 years later. Uh, you're selling Superhuman. What changed? Like, how did you approach this differently than you did Reportive?

Well, it's such a different acquisition. So when we sold our first company, we were 5 people including myself. We'd raised $1 million. Uh, if it makes anyone feel better, we'd raised $1 million on a pre-money valuation of $3 million, which is just how much times have changed. I, I can't imagine anyone doing that now. Uh, and when we sold Superhuman, well, Last year we were about 120 people in total. We'd raised about $125 million. We were acquired by Grammarly for an undisclosed sum, uh, but I'm extremely happy with the exit. Uh, and now Grammarly has rebranded as a company to become Superhuman again. So we sold Superhuman to Grammarly, which is now Superhuman, and we've gone from building the fastest email experience in the world to doing that but also building the full AI-native productivity suite of choice. So it has Superhuman Mail, which is the fastest best email app ever made, but it also has Grammarly, which is the world's most trusted writing assistant. It has Coda, which is the best AI hub for teams, and a new product that we're building called Superhuman Go, which you can think of as a proactive AI companion that works everywhere that you work. Now, the two acquisitions are very different, both textbook examples though, and examples I hope that we can learn from here. So the first acquisition, the, uh, reportive sale to LinkedIn, was a classic example of a product integration. And it's a product integration that went really well. And this is the textbook definition. I think almost every company can do this. So the way that this one came about, we were a Y Combinator company back in the summer of 2010. And we were unusually, back then, one of those companies that had actually raised our money before Demo Day. And I remember PG and Jessica asked me, they were like, well, do you still want to present? Like, you've already raised your your, your seed round, what are you going to do? And I'm like, yeah, I'll present just for the practice of presenting, and we can start to think about our Series A story. So I was thinking about fundraising, but it turns out the actual value of that presentation was in the audience. There was this person, Emily Choi, uh, who now runs almost all of Coinbase, and she at the time was running corp dev for LinkedIn. So she comes up to me and she's like, hey, a really great presentation. The head of product for LinkedIn, Adam Nash would love to speak with you. I'm like, okay, great. So I go into LinkedIn, and if you think about what the product was, you're, you're in email, and on the right-hand side we try and show you that person's profile, basically their LinkedIn profile. The way that we were doing this back in the day was with a different company called Rapleaf. Now Rapleaf was a great company founded by Oren Hoffman, except what Rapleaf was doing was they were scraping LinkedIn as well as a bunch of other websites and literally just selling that data. Through some lenses, you may consider this to be theft. I didn't think it was. I thought it was a very cool business. LinkedIn certainly thought it was stealing their data and then monetizing it. So we were paying rapidly for this service. So we go in, we, we see LinkedIn. Adam is like, this product is amazing. We love that you're doing this. We love that you're giving the LinkedIn profile the recognition that it deserves outside of the platform and bringing it into email. However, you need to stop buying this data off Rapleaf. And I said, well, if we don't get it off Rapleaf, there's nowhere else to get it. And we entered into this negotiation where we reportedly got access to the secret API. So it turns out LinkedIn has an API, but don't bother trying to ask for it because they won't give it to you. Whereupon you could give them an email address and they would give you a LinkedIn profile. And it's very, very rare. I think about 20, 25 different companies have this. And over time, as LinkedIn's ambitions grew and grew and grew, and obviously now they're ginormous as part of Microsoft, the set of companies that they would contemplate giving this to shrank over time. And this is just a good example of being in the right place at the right time and saying the right things to the right people. And I'm so glad I was part of Y Combinator and I did the pitch and I said yes to Emily and I went to see Adam. I had leverage actually in that conversation, which is all of the technology influencers in the Valley were using my product. So if they just turned it off, they would have pissed everybody off. I didn't really realize that at the time, but there was some leverage in the conversation, which is how we got this API. The amazing thing is once we got the API, they never gave it to anybody else ever since, any other competitor at least. They did give it to other companies, but no other competitor, which didn't stop other competitors trying to come in and copy us, but they were obviously never able to get the data integrity that we had. So what did I just describe? A product integration. And now in their company, there is a PM that's assigned to us, there is a corp dev person that's assigned to us. I go in every quarter, we do like a quarterly business readout. And there's lots of lessons from this, which is you need to maintain a high say-do ratio. Say-do ratio. If you are saying you're going to do something, you should absolutely do it. Like, pretend like you're working for them, because everything you say or do is going to be transmitted back to the executive team. And it wasn't long, about a year later, maybe even less, before the M&A conversation started happening. And the way it actually started was I went out to raise a Series A. I pitched Greylock. If you don't know this, Greylock is one of the main investors behind LinkedIn. Uh, Reid Hoffman and David Searle were my main partners at Greylock. They're also on the board of LinkedIn. And as I'm pitching them for the Series A, they were like, Well, we can do this in one of two ways. We will happily write you a Series A term sheet, or you can be acquired by LinkedIn and we can promote your product and the one that you want to build to 250 million users, which is how many people LinkedIn had at the time. So that's how that acquisition came about. But the, the second one, the Superhuman one, was, was completely different. But I'll pause here depending on which way you want to take it.

Yeah, that's a great story. I love it. You basically put yourself in the right moment. So there was something about you were pitching at Y Combinator, and you had a series of random collisions from Emily Choi to Adam Nash. These are all names I actually know, because they've all gone on to do amazing things. And that's actually really fascinating. If you were to compress that into framework, how people can get themselves in that position, what would you recommend? Hmm.

Well, I think there's a lesson right there that isn't even about M&A, which is just generally say yes to things, right? If we as entrepreneurs, as founders, increase our surface area, increase our opportunity for luck, we're doing the right thing. All of you here today, you're doing the right thing. Now, this may not generate value in and of itself, but perhaps there's a conversation you have today or a co-founder that you meet or a product idea that you or a feature request that you hear about, that is exposing your surface area. But more importantly than even all of that, it is just turn up, right? And I actually learned this lesson when, as you can probably tell from my accent, I'm not from the US. I grew up in the UK. I went to the University of Cambridge. We had an entrepreneurship society there. And I remember hearing from folks like myself, founders and CEOs who were maybe 10, 15 years ahead of me, about how the biggest thing they could possibly do was actually just turn up. And there was this— I forget the name of the company, it may have been Sophos Antivirus— and how the founder, the CEO, just, just got on the plane and flew to Silicon Valley and met with the right people. And it was such a— it was such an impactful story for me that it inspired me to do the same, which is actually how for my last company we ended up migrating. We were 6 months in the UK and then for the next 1.5 years we moved to the US. And I actually, in total, I've moved about 21 people from the UK to the US.

Oh wow.

Just by, just by pulling people out and everyone's done fantastically. So, so that's like, that's not even an M&A lesson. That's just a general life lesson. When it specifically comes to M&A, I think there's a few things that we can do to make it way easier, way more likely. So thing number 1 would be Get angel investors into your company. Give people skin in the game. You should be able to map out the cloud of potential acquirers for your company, ideally very early. Figure out who the CEOs— the CEO is, who the founders are, who the executives are if it's a very big company, and then get those people to angel invest. You might think it's a conflict of interest. I say, uh, without conflict, there's no interest. So just get those people involved. If they have to recuse themselves from the decision, they will, as appropriate and at the right time. So that's obvious. Do that. And you can do that when you're raising your next round of financing. The next thing I would do is product integrations. I think we've done— oh, and by the way, before I move on, an obvious example of that for me was my second acquisition, Superhuman. So Shashir, who recently, a year ago, became the CEO of Grammarly, was an angel investor in Superhuman. I also was an angel investor in Coda, his last two company— sorry, his company and my company. Did that make any impact on the acquisition? Probably not. I don't think either of us would say that was the reason this deal happened, but you know what it did create is over the 7 or 8 years where we were mutually co-invested, a good excuse to hang out, talk strategy, talk about productivity, talk about collaboration, He's a pricing guru, so he would give me a ton of pricing advice. I'm good at product and design, and I would give him product and design advice. And we developed mutual trust along the way. So that's a good example of get angels into your company. The next, I would say, is build product integrations. We talked about that with LinkedIn and my prior exit. After that, I would say stay in the press. I think there's a lot of people who are unnecessarily bearish on the amount of work that it takes to be in the press, and some investors will actually tell you it's a waste of time. I am hard in the other camp. I think it is challenging to do well, and so few companies do it well that if you can do it well and it is very doable, you'll just immediately stand out. So be the darling in your category, be everyone's favorite company, and be journalists' favorite company in your space. Very doable. The next thing I would say is do not wait until the last minute. These are relationships that have to be created well in advance. With Shashir, I created that relationship 7 or 8 years in advance of selling Superhuman. And there's actually a fun aside to that, which, which I'll tell, uh, in, in just a second. But then the, the last point here is you need a good why now. So when it eventually becomes time to sell your company, you need to explain to the acquirer, and they need to really feel why now is the right time. And the best possible why now is you have another company that's going to buy you. So if they don't put a bid in, this will be the last opportunity. Like, you are gone for good. The worst possible why now is you're running out of money. You don't want it to be that. And a good medium one is you have an incoming funding round, so you're going to be at least 3 to 4 times more expensive tomorrow than you are today. But the best possible one is you have another bid. Now, I promised I'd tell a little aside. Which is to— so, so not the why now, but what was the one just before that? It was do not wait. Right. So an example of this in action was when we were selling Superhuman to Grammarly. Let me tell you how it came about. So all the way back in 2017, 2018, I was— we were like maybe 10 people at Superhuman, and I was grinding away trying to get to product-market fit. We'd raised a bunch of money, but we were probably 2-ish or maybe 3 years in at that time. And the last thing I wanted to do was spend any time on networking, building relationships, any time that wasn't hiring or building the product. And I just got the invitation to go to this conference called the Lobby Enterprise. Now, this is, if you haven't heard of this thing, it's a great conference. Pretty tricky to get to, you have to be invited. I think there's like 100 or 200 people. So, it was companies of note, founders who were, people thought were doing interesting things. I got nominated to go. And it takes place in Hawaii. Probably would've eaten the entire week. And my immediate reaction was, "Fuck that." I'm too busy. I've got a company to build. I don't have time for a boondoggle off in Hawaii. And my co-founder, one of my co-founders, Vivek Sodero, who interestingly was also a co-founder of Rapley from prior in the story— funny how it all swings and roundabouts— he said, no, Rahul, you have to go. We'll take care of the business whilst you're away. But there will be amazing people there. And I can't tell you how or why it's going to be useful, but you have to go. And we had this big fight, we had this argument. I was like, it's a waste of time, I'm not going to go. Eventually he just pushed me out of the office, bought my plane ticket, and said, at the very least, just go have a vacation, go enjoy yourself. So I was like, fine, I'm gonna go, go do this boondoggle in Hawaii. So I get there and I'm actually slightly early. I'm like, if I'm gonna go, I may as well enjoy it. So I get there a day early, the other delegates aren't there, and I'm just chilling by the pool I order a margarita. There's one other guy there, it's a brown dude. We, he also has a margarita and we're just chilling by the pool and it turns out to be Shashir. And we start having this conversation and, uh, he, I, I ask him, I'm, I'm like, okay, who are you? What do you do? He tells me he's a founder, his career. And it turns out the very first tech job he ever had was working at Microsoft. And it turns out the thing that he was doing when he was working at Microsoft was working on Microsoft Outlook. I said, well, boy, do I have a product for you. So I give him the whole Superhuman demo and he loves it and he's like, can I have that? And I said, yes, in fact, I can onboard you right here, right now at the pool. So I onboard him onto Superhuman right at the pool, which is super fun. You can imagine just us two productivity nerds nerding out. And then the very last thing we ask people to do when, uh, when we're done with the onboarding is close their Gmail tab. So he's moving his mouse up over to the Gmail tab, and he closes it. And I see next to the Gmail tab is this favicon that's like a little K. I'm like, I usually know most favicons. What's that K? And he said, oh, that's my company, Krypton. And I said, well, I just gave you a demo. Can you onboard me onto Krypton? Show me what Krypton's all about. And he gave me, legit, the best product demo I'd seen that year. Because it was a document, it was a database, it was a spreadsheet, it was a collaborative system, it was an application builder. And like, maybe today that seems obvious with the likes of Coda and Notion and Airtable, and there's a bunch of others. But I tell you, back then it really blew my mind. I had not seen anything like it. I was like, wow, this is incredible. Can I invest? He said yes. And I was like, would you like to invest in Superhuman? He was like, yes. And so we like immediately co-invested. At that point. And that started what became, as I mentioned, a friendship all the way since then. Now wind the clock forwards until it's the end of last year, the end— sorry, the end of— not last— the end of 2024. And Grammarly is announcing it's acquiring Coda, and Shashiya publishes a blog post about how that acquisition played out.. And there is this sentence that he posts in this blog post where he said, and as, as the deal was done, I sent an investment memo to our team titled the AI Native Productivity Suite. And he goes on to outline his vision for what an AI native productivity suite actually is. And it turns out to be exactly the same thing that we were pitching internally as well. And so I immediately sent him a text. I'm like, hey, it's been a year, but first of all, congrats. Secondly, we should hang out because it seems like we're on a collision course here in the best possible way. And this is December '21. He's literally just about to step out to a vacation with his family. We give him a call and I'm just like, should we consider merging? Because I feel like we could do this better together. And he was like, super interesting. I'm technically not the CEO until January 10th, so let me, let me first become the CEO, then let me figure out what's going on at Grammarly, and then let's have the conversation. And 6 months later we were acquired. So it's a good example of how you can't really predict where you need to be. And thank God for Vivek for pushing me out of the office at that time. You just have to turn up and meet the right people.

Yeah, I love it. Love the stories. It seems a lot of it comes down to putting yourself in the position as much as possible and then focusing on very specific ways in which you can integrate with companies and integrate with companies that could be future acquirers. Is that the way to compress all of it? Show up and focus on potential integrations to increase your probability of potential acquisitions? How would you compress it?

Um, well, there's a bunch of things. So show up to all the things you can. Obviously use your judgment. Integrate where you can. Again, use your judgment. It shouldn't take over your product roadmap. It should genuinely be useful for your users. In our case, it was the point of the product. Be in the press. Don't leave it until the last minute. And then there's some other frameworks that I've come up with which are more about judging the— so those are all ways to make the acquisition more likely, but we can also figure out how to judge the quality or the likelihood or the sort of score the success of an acquisition. And so one is what I call the sort of the three axes of M&A. And I would say axis number one is, are you being bought or are you being sold, right? And you can have an order or two magnitude on outcome size. Startups that are trying to sell themselves are less attractive. Startups that are being bought are going to command the premium because then you can go run a competitive process. So that's axis number one. Axis number 2 is the urgency. Like, where is the urgency coming from? Is it coming from you, the company, because you're running out of money? Bad. Don't do that. Don't wait until it's then. Or is it coming from the acquirer because they desperately need to fill a strategic hole in their roadmap? Good. Great. That's actually the best possible acquisition. And then axis number 3 is what is the stage of the company? Is it— and there are 3 possible ones. There's acquihire, product by and business by. So in an acquihire scenario, usually 5, 10, 15 people, maybe you haven't yet built a product or you haven't yet built a product that anyone uses. It is just a team of highly talented, passionate people who know a domain really well. This was in vogue back in 2014, 2015, then it kind of fell out of fashion. Now it's in vogue again as the, the largest AI companies have a lot of money to throw around. So you can do this. And you can do pretty well, especially because there's still a lot of upside left in their stock. But the second type, which is even better, is great team and a great product, right? We— I think that was— that's what I would classify my first company as. We hadn't really built a business. We'd made 14 cents of revenue in the entire history of Reportive. I think we tried some ads at one point, but we built a product that all of Silicon Valley was using, and we had collected all of LinkedIn's daily active users. And then the third category is you've built a real business, and you're making a whole bunch of money, uh, you're growing really, really quickly. And, and that was the case for Superhuman. We grew twice as fast in 2024 as we did 2023. In 2025, we were accelerating again. We were one of the large cohort of companies for whom, for whom AI was this massive accelerant. And so that's, that's the third axis, uh, so That's the way I would score it. And then one final framework that I think folks might find interesting— this is actually a framework that Superhuman or Grammarly used to score us as an acquisition— was the following 3 questions: should we buy a company right now? Number 1. Number 2, should we buy a company in this space right now? And then number 3, is this the best company to buy in this space right now? Uh, chances are your acquirer will be using a framework like that, so it's helpful just to think through these these things.

That's great. Um, I know we're coming up on time. Last question for you: if you decided not to sell Superhuman, uh, in 5 years from now you look back, what would make you regret that decision? And another way to ask this question is, um, how do you know it's the right decision to sell?

Well, it's a, it's a very, very complex question, so a few quick thoughts. Number one, as founder and CEO, you have a fiduciary responsibility, and it's super important to remember that, that you have to put the company first, you have to put all your shareholders first, and then all classes of your shareholders first. And this is probably the last thing you're worried about if you're in this audience, because, you know, it's like, get to product-market fit, build a company. But when you are in the fortunate position of people want to buy your company, you have to put what's best for the company ahead of what's best for you and everybody else. And so when these offers come in, it's tempting to say— some people might say, well, I'm just going to ignore all acquisition offers because I'm going to, you know, IPO or bust. It maybe sounds cool, but that is not a responsible way to run your company. If it is genuinely a real acquisition offer, you have the fiduciary responsibility to take it seriously. So every time an offer came in, we would take it seriously. And then the calculus that you as founder or CEO have to run is, is this the best outcome for the company? Is this the best way for us to achieve our mission? Is this the best outcome for the team? Is this the best outcome for the customers? And is this the best outcome for the investors? That's a lot of best you're trying to balance. And this is where it's going to be subjective. There's going to be a conversation on the board and then Perhaps the hardest to answer is, is this the best timing? Now, what was clear to me with Superhuman was towards the end of the year before the— towards the end of 2024, as AI was, I would say generative AI was picking up, not quite agentic AI. A lot of very large companies looked at their product portfolio and said, oh, we have an email-sized hole and a big hole in our product portfolio. We're going to reach out to Superhuman. It was very clear to me that a lot of companies were doing that outreach. And the stars were aligning, and generative AI was making that clear. And maybe agentic AI would have made it less clear. So in other words, the stars align very rarely, usually once every maybe 10 years in the history of any company. And who's to say your company's going to be here for the next 10 years as opposed to this 10 years? Uh, so we took the opportunity very seriously.

Yeah, well, I think that's a great note to end on. Thank you, and hopefully you all got some actionable feedback on how to create moments for your startup to get acquired in the future. Thanks, Rahul. Thank you.

Thank you.