Episode 394: Navigating Multiple Exits Across Tech's Evolution

Corey KupferRaj Singh is the VP of Product at Mozilla, leading new zero-to-one product initiatives. He joined Mozilla in 2022 via the acquisition of his startup, Pulse, which developed AI meeting summarization models. Previously, Raj has been a repeat consumer-focused startup founder. He was co-founder and CEO of Tempo AI, a smart calendar acquired by Salesforce in 2015. He also co-founded All the Cooks, which became the largest recipe community on Android before acquisition by CookPad. Earlier in his career, he served as VP of Business Development at Skyfire, a mobile browser acquired by Opera. Prior to this, Raj co-founded and exited startups in the ringtone, live video, and college dating categories. He writes about AI, product management, startups, and VC on Twitter and LinkedIn, and holds a BS in computer engineering from Cal Poly, San Luis Obispo, and is based in the Bay Area. Raj, welcome to the DealQuest Podcast.

Raj SinghThank you, Corey. Thank you for that, comprehensive intro.

Corey KupferWell, I gotta tell you, if anybody has any questions on why you're on the DealQuest podcast. That bio alone, certainly answered those, not that anybody would, but, boy, what a background in entrepreneurship, in growing and exiting businesses, and we're going to get into all that. But before we do, I want to take you back to when you were a little kid growing up, maybe 8, 10, 12 years old. What did you want to be? Because I'm guessing a serial, founder, and, entrepreneur, and somebody who's had a bunch of good, successful exits. Probably wasn't it back then, but you tell me.

Raj SinghI was really into computers. I don't know what triggered it. I had the Apple IIe, maybe when I was 9, 10 years old, around there, and I just started taking things apart, and putting them back together. I wasn't as interested in coding, to be frank. There was, Basic, and QBasic, and I'd play with it a little bit, and I was like, oh, that's kind of cool, but it was, tinkering with the hardware, and then, trying to overclock it, and trying to make it faster, and play with the RAM, and my first side hustle. Probably not my first, but before going off to college, one of the things I did do was go and install the network cards in a bunch of my, buddies and other folks that needed it before they went out to the dorms, because they had, Ethernet hardwired. Most people's desktop computers did not have this is the pre-laptop era, for the most part. Most people's desktop computers did not have an Ethernet port, and so I would go and buy a bunch of these, Ethernet, cards, from Fry's Electronics, which was, the mainstay back then. Unfortunately, they're now defunct. But, and then I would, charge, and I would basically install it, set up the drivers, make sure it works, so that when they go to the, when they go to college, they can just kind of plug in the Ethernet cable and it would work. So, it's just funny, it's funny how these things play out. You never know, but in some ways, you choose your career arc, and then sometimes the career arc chooses you.

Corey KupferI love that. It's funny, because, I have a brother who's 5 years younger than me, and so, everything that you talked about in terms of, taking things apart, putting them back together, whatever, I had zero skill in that. My skills were in other areas, probably, why I ended up becoming a lawyer, and but my brother was like you, although he didn't end up going the tech route, he ended up going more the architecture route. But he had this, literally, he's he and I are I'm definitely older than you, he's older than you, I'm sure. And, back in the day, he would literally, have a transistor radio, and it would break in the house, and he would take apart the transistor radio at 8 years old, and put it back together, and it would work, and I'd always be like. How does he do it? I couldn't even conceive of how to do that, and he had a natural ability for that, and that led him more onto the side of, being interested in building stuff, and designing stuff, and he was into photography for a while, and, so he was, he had that kind of outlook like you did, and I never had any skill in that area whatsoever.

Raj SinghIt's funny to I would say, ignoring all of that. It still took 20-plus years before you kind of figure out, what you actually enjoy, and what you're actually good at, and what you're not good at, and it's, you don't really know, in your 20s, your kind of approach is almost like, hammer and a nail, I can do everything, I can solve everything, I can learn everything. And you quickly realize that's not really optimizing on both time and ROI. But certainly, asking what I was doing at 8 to 10, I was playing computer games, and I was taking apart my computer.

Corey KupferYeah, yeah, love it. So, you mentioned your first hustle, but one other question, looking back, what was your first deal of any type, whatever you consider as a deal. I don't know if it was in one of the early companies, or maybe even before that, as a, for you.

Raj SinghYeah, I'm not gonna count my summer internships, because I feel like my summer internships I was just really an I was an individual contributor, and just writing code. I will say, my first startup, out of college. First substantive deal was an acquisition.

Corey KupferOkay.

Raj SinghBy another, it was and basically, it was like a net-zero acquisition, just to be clear, so nobody was really making money. But it was during the dot-com crash, and it was an acquisition, by another company that was, real early in the video codec era, this is, 2000, so, DivX and things like that, and people probably don't remember that stuff, but it was very difficult to play video online in those days. But, yeah, how to, had a contract, how to put that together. It's like a whole different thing. And, it's fascinating, looking back at that, and I sometimes joke with myself. If I knew what I knew now, it would have been, worlds of better outcomes in different points in time, but, you're again, back then, I remember, I think it was a professor, I had asked, I said, hey, I want to start a company, I'm doing my master's, I'm like. I want to start a company, I don't want to do my summer internship. How do you do that? Literally, and he goes, why don't you go to the Chamber of Commerce and buy this book? And it tells you how to register and start a company, and, you don't really know, we didn't have internet for the most part. There was no resources, there was no incubators, you kind of just had to know people. So it's really wild, looking back, and then, thinking about where we are now, and effectively building a business is like honestly, walking through a wizard, at a box you could buy at Costco. It's so easy now.

Corey KupferOh, yeah.

Raj SinghIt's, complete night and day difference.

Corey KupferYeah, listen, I remember when I, when I started so, I started my own law firm, 6 years out of school, because I just was clear I wasn't meant to work for somebody. I was that was my early understanding that I was unemployable. And so, back then, when I first thought of my own law firm, it was, 1992? Okay? So. The amount of investment, the amount of time, we had to have somebody come in and wire an office to a server, computers to a server. No internet, no, I don't want to have this whole back-of-the-day kind of thing, but it was like, there was a lot, you didn't, and then even, 15 years ago. When I split up a partnership, and started, no, it was, let's see, Yeah, it was 10 years ago. Actually, 10 years ago, when I split up a partnership and restarted a firm, we had, a few laptop computers and about 500 bucks a month in cloud programming. And we were and we were up and running, so, it's such a different ballgame now. The, the barriers to, obviously, there are other barriers, but the whether it's, logistical technology, support, any of that kind of stuff, the barriers to entry have come so far down, and the access to information, which is, a point that you have, and the ecosystem to support entrepreneurship and growth and capital raising and whatever. It's, it's a whole different ballgame now.

Raj SinghAbsolutely, and people, just access to people. In pre-social networking era, it was just difficult. Email was emerging, text messages cost money, so people wouldn't do that. So it's like, these it's crazy to look back, and then it's gonna be crazy again to look back in 10 years and imagine what life was like before AI. So, I feel like each of these moments in time, whether it's internet. Mobile computing, AI, transformative events, and self-driving cars will be one of them, too, when they're actually realized for the masses.

Corey KupferYeah.

Raj SinghYeah.

Corey KupferSo, so talk to me about, obviously you had this, I don't know if it was, nature or nurture or both, but you had this way about you when you were, in the beginning, this natural thing about taking things apart and building them. And then obviously, you're in school, you're already asking about how to start a company. What do you think? Because you went on to, do multiple companies and have several exits, and, we'll work our way up and talk about what you're doing now. But, what do you think it was? There's this conversation sometimes about whether somebody's a born entrepreneur or, whether entrepreneurs can be made. I happen to think that there are national entrepreneurs, and there are situational entrepreneurs. I was certainly one of these people who was just born to be an entrepreneur. What where did it come from for you? Did you have models when you were growing up, in terms of family or friends, or, do where it came from?

Raj SinghYeah, sorry about that, I'm coughing here a little bit. I don't of course, nobody knows where anything precisely came from, but what I would say is I would say early in my career. Particularly, college era, when I was thinking about building my own stuff. It was mostly just out of seeing other people being so successful at the dot-com era. I was a little bit younger, and I remember there was a student from high school who's a year older than me. That had built a company and grown it to an exit, and I was like, wow. And again, at that time, the difference of 1 or 2 years made a difference, because the dot-com era, either you caught the tail or you graduated into it.

Corey KupferRight.

Raj SinghI was like, wow, so-and-so can do this, I could do this too. And so, part of me went down that, can I it's kind of almost proving it to yourself. And you have to understand, I went to a high school that was extremely competitive, and I probably was maybe in the top 20%, but definitely not better than that. There's a lot more smarter kids, and so you're constantly with this chip in your shoulder, oh, you're just not good enough, you can prove it yourself. Then the funny thing is Now here I'm building stuff. Working for somebody, working for a startup at one point, this is, 2001, 2002, And I'm like. Just this desire to, kind of do my own thing. And I think it's just because In part, I think I realized that I'm not the best coder in the room. That was a big aha moment for me. So, I'm coding, and I'm like, wow, there's always somebody better than me. I'm maybe the number 3 coder in the room, and when you realize that and actually accept it, you're like, whoa, okay, I need to find something where I'm the best in the room. Like and so, started building that way, and then the funny thing is, if you kind of continue down this arc. There's a natural self-selection when you think about how companies hire. Companies tend to hire people like themselves, and so they look for people who've had latter careers. People who basically worked for a company and then jumped to another company. They don't tend to hire people who've been building stuff on their own. They're considered, higher risk. Cultural, integration, risk of departure, boredom, anyway, harder to manage. There's always this joke about managing founders, very difficult. Sure. Because we say it like it is. We're more authentic. In some ways, we're the most too authentic. And so I would argue that, later in my career, independent of whether I wanted to build something or not, the career chose me, meaning that became the arc. There was just no other path. I needed to make money, and, finding a job, was not an option because nobody would hire me. So I had to start a company. And now I've hit a point, ironically. Where starting something new, as counterintuitive as this may sound, is the easy path. And historically. I like to choose the harder path, because the easy path, historically, for most, would be do a ladder career and follow that your whole career. And a lot of wealth is created in Silicon Valley doing that. Being in tech. But I chose the hard path. I kind of have a map career, I jumped around, I did my own thing over and over again, and sure, plenty of wealth creation along the way, but, questionable would have outperformed or underperformed me when, I was being pinged by Google, or Facebook, or Uber, very early era. 05, 06, What were those?

Corey KupferStock option's been worth.

Raj SinghRight, yeah, and I've had many opportunities like that. And so, because I knew all the people, and the reason I knew all the people is because they all were startup people working alongside me at one point. So, And so, it's, it's interesting. Now, if you look at today, yes, I'm at Mozilla, I came in through acquisition. But, I would think most people would look at my background and be like, hey, I don't know if he's employable, he came into acquisition, he's been Is he just, is he just gonna start something new? And so the easy path for me is to go start something new. And ironically, the hard path would be to go join something, and it's not necessarily my choice, it's, as I said, it's the career has chosen me. So, it's kind of funny how these things play out.

Corey KupferWell, let's jump to that. I want to come back and fill in, we mentioned, All the Cooks, and Tempo, and Skyfire, and you had, real, those were all real acquisitions, buyers, Salesforce. Opera, compared to Japanese public company, so I want to go back to those. But let's, because you brought it up, I wanted to get there anyway. Yeah, it's interesting, because tell us a little bit about what you're doing now as VP of Product at Mozilla, and also, you have to delve into it a little bit, because listen, there's a lot of stories of founders selling companies Right? And then either they only work at the, at the acquirer because they have to, right, for a period of time, or even if they thought maybe it would be good, then, they don't last long. Because of all the reasons why you talked about it. But, you seem to be, everything we talked about in the past, like. Maybe it is the harder path in a way, but it's also the path you've chosen, and it's working out great, and, you're doing some great stuff with Mozilla. So, tell us a little bit about, that journey of that Sale 3 years ago, and then, a little bit more about what you're doing now, and why it's working for you.

Raj SinghYeah, it's interesting. I look at my different acquisitions, and by no means this acquisition by Mozilla was a life-changing event, but I've had exits in the past that were substantially larger. And, I think about those moments in the past, and for various reasons, either the way the deal was put together, that I wasn't necessarily part of the deal, and so I was there kind of for the transition period, sometimes the buyer doesn't want the CEO. They're harder to manage, they have a specific strategy of how they want to integrate this, there's already a leader, whatever it might be. Or, you're kind of a ironically, probably a very helpful trait in 2025 with AI, but at the time, you're a, master of nothing, but you just know a lot of stuff. I kind of joke with people, either a lot about a little, or a little about a lot. And CEOs know a little bit about a lot of stuff. And so And so it just always ultimately fell that way, interestingly. And I remember, here at Mozilla, kind of landed here, and initially in my head, I'm like, hey. I know the earn-out is a certain amount of time and whatnot, but we'll see how it goes, and maybe I'll take some time off, and, that's what I did last time, I took a few years off, and let's start something new. And I've really enjoyed my time here, and I think part of it is I think because it's new. It's like actually working in an operator role, which is a little bit different. And I have a team, and we're having fun. And so, I like to tell people, and, we just had a big team off-site, and I talked about this a little bit. People leave companies for various reasons, and often, sometimes it could be something just lucrative thing came up, or whatever, fine, I get it. But, sometimes they don't like their manager, I get that too, but a very common reason people leave is just that they feel like they stopped learning. So not feeling challenged anymore. So, that's something I always think about, once a year I kind of go through this, am I still learning new things? Am I feeling like I'm challenging myself in some way? But, I would be remiss to say that on a longer arc, of course I'm going to start something new again. I don't know when. And, I don't know what that's going to look like or whatever, but, yeah, so, and I guess to answer your other question. Mozilla, Firefox, browsers, super hot category. It's crazy. It was probably an extremely boring category for 15, 20 plus years. Yeah. Nobody was thinking about browsers. Probably if you, change the scaffolding UI, whatnot, you wouldn't even know what browser you're using. However, in the last year, we're seeing just a super emergence of AI-focused browsers, whether it's, like. Atlas from Sorry about that, excuse me, Atlas from ChatGPT, or, Perplexity with Comet, or, I think Opera Neon, Brave is doing stuff here. Chrome, Edge, whatever. And All of a sudden, it's like this super hot category, and so, we're right in the middle of it, because people are talking and thinking about what the future of web browsing's gonna look like. That being said, a lot of our revenue, it's public information, comes from Firefox and Search and our relationship with Google. And so it's always been a priority for Mozilla to diversify, so we don't have that dependence. There's a lot of unknowns, whether it's antitrust up and search and what all that future might look like, and so As part of that, I'm focused on a whole bunch of products for small business. To help drive that effort to diversify revenue.

Corey KupferLove it. So, some people, talk about entrepreneurship versus intrapreneurship. And, and being in a place where you can bring some of that, entrepreneurial spirit and talent and independence and, creative thought and that kind of stuff in environments, and obviously there are companies where entrepreneurship is not really supported and encouraged in others, where there are. And it's it's sounding to me, like that's that's maybe the place you're in right now, right, is developing new products, doing similar things to what entrepreneurs do, but within a bigger organization. Is that an accurate read?

Raj SinghYeah, and that's accurate, and I will say there's vast differences. There's certainly pros, and there's certainly cons. And, it's probably a whole other talk on its own, just kind of going through the various differences of building on your own. People who build on their own, they're a special breed. They're taking a lot of risk. They have nothing to lose. The highest likelihood is failure. You're going all in. It's a different kind of risk model, it's a different way of operating. You're not as worried about, over-optimizing on legal and brand. Brand impact and things like that, because you're just trying to make it. You're just trying to survive. The types of talent that come to a larger company is different. Often, they've had a latter career. They've not had a map career. And so, they're not necessarily comfortable being wrong in public, which is very common in a startup, or dealing with, lots of different, loud voices around the room with very different opinions, and not being the shiny object this week anymore, or whatever it is. And so, there are some fundamental differences. Obviously, there's things around how it's financed. The, equity and return, and all that stuff, and how it's supported. But, there is a big difference, and of course. We do the best we can, but I will also say there's a lot of culture you can bring in. It'd be foolish to say that many paying companies today aren't moving as fast as some startups. Very impressively. And so. That doesn't happen, overnight. That's deliberate and intentional, cultural things and processes and the right people and whatnot to kind of make that stuff happen. They're probably still not moving as fast as a startup, and they're probably definitely not playing in as many gray areas. But they're certainly moving a lot faster than when we think of, old school, Microsoft from the 2000s. Very slow-paced. So, lots of lessons and things to be learned.

Corey KupferDo you think that's, a big part of that is the, AI arms race, so to speak, and, the speed to market, and the fear of being left behind, and all that kind of stuff?

Raj SinghI think anybody in tech, I don't care whether it's individual or company, should be running through some kind of analysis of, are you existential, or is the company existential? And Gen AI is, an incredible productivity booster, but it can be extremely disruptive, depending on what you do and where you spend your time and how you think about things. Now, tech has been through many moments like this.

Corey KupferTech is a very unique.

Raj SinghSector. In tech, people who work in tech know that we have to constantly relearn, and learn new things, because the programming language you were using 10 years ago is completely different, the framework's completely different, and the design tools that you're using yesterday are not the same as you're using tomorrow. And so, you kind of learn and adapt. I do worry more about other industries. There are plenty of industries, maybe even including the law profession. Accounting, finance, etc, where the way things are done is still the way things are done, 10 years later, 15 years later, and that's really hard, imagining you're an IC, or imagining you're even a leader in that kind of organization, to suddenly say, hey, we need to completely revamp our workflow. And what you're seeing as a result of this Is if you look at tech. They're just simply branching out even more. It's like, there is basically no territory that Google does not want to enter. No space. And where there may have been more natural boundaries between the hyperscalers. You're seeing them play on everybody's edge now. You're seeing OpenAI launch social networking tools, like Sora. That's competing with Facebook, you're seeing OpenAI launch shopping that's competing with Amazon. They're playing on every edge. And you're seeing Amazon, Build Cloud, which is competing with Google. So it's just fascinating, thinking about how these edges will continue to blur, and I think, in part, this is because the aspirations have changed. It's no longer sufficient to be a billion dollar company. People want to be $10 trillion companies, and so when you start thinking that big, it's a completely different game.

Corey KupferYeah, love it. All right, so I want to go back to, some of these exits that, we mentioned. In my experience doing m&a deals for over three decades, the journey to each one is different, and the deal structuring is never quite the same twice. Take us through a little bit, I know there's at least, three of the, most successful ones we talk about in the bio. The journeys on those, did you get to a point where, were you just approached on some of them? Did you get to a point where you decided it was time to sell and, hired a bank around a process? What were the journeys to exit, on those? And then also, along the way. Had you raised capital in all these companies? Did you have capital?

Raj SinghYup.

Corey KupferWhat was the journey?

Raj SinghEach, I always tell people, what worked yesterday doesn't work today. And each of these journeys was completely different. And each of them was a product of its own circumstances, its own timing and market. And arguably, if the window shifted 6 months, may or may not have happened.

Corey KupferRight.

Raj SinghIf, it's hard to predict. And so, let's, if we just want to go through the last three, looking at All the Cooks, I remember this exact discussion. All the Cooks was accepted into Y Combinator. This is, 2010-ish time frame. And there's a three-day window at the time before you, decide whether you want to accept to join Y Combinator, and Paul Graham used to manage all of it directly. And in that 3-day window. One of our advisors had introduced us to CookPad, which was a company in Japan, and they wanted to branch into the U.S, and they basically came in with an 8-digit offer, all cash, we had raised no funding, and said, hey, can you become the U.S. Office? And we almost didn't take it. There was a lot of deliberation. Right? I went back and forth, back and forth. We're like, and part of what was running through my head, my own calculus, was I had spent a lot of time with, not leaders, but or maybe, product management leaders at companies like Epicurious and AllRecipes to understand their business model. And realized at the time, and of course you could argue it's very different today, but at that time, their businesses were primarily ad-driven. So it's basically, he had sales teams, and they're selling sponsored ads, on those sites, and AdSense was growing, but it wasn't as sophisticated or as didn't pay out as well as it does today. And they were not valued like crazy. Now, these might feel like small numbers, but at the time. These were, big numbers. So they're valued, $100 million businesses, like IAC valued Epicurious, or AllRecipes, I forget which one they own, at a $100 million business. And so we were like, okay, we have this 8-digit number that's not bad, it's not 100 million, but it's not bad. We're kind of doing this, and we're like, it's gonna take 10 years to build this, large organic traffic funnel, because ultimately, in the recipe universe, it's an SEO game. Because you just gotta rank high. And so, in the end, decided to take that offer. And so, that's kind of how that materialized, and of course, that's doing a transaction with a Japanese, public company. Very different, very trust-driven, Not as many attorneys involved, substantially more straightforward, very fast close, less than 30 days. It's nuts. The whole thing. So, very interesting experience. If you look at the, and I say this because there have been moments like, for example, I had a ringtone company in 2005, And I had a I had a, mid, 7-digit offer, for that, all cash. And I didn't take it. And I was, and I was doing, almost a million ARR, and I was a sole founder. Sole founder, 2005, I was 24 years old. So, so I was like, okay, why should I go sell this thing for 5 million bucks? It's like, it's not Now, I look at that, and I'm like maybe the right call was to sell it. The ringtone category drastically changed over the next couple years. Pretty with the iPhone and whatnot, you could just install the ringtone directly. You can no longer sell it. And I also think about why I didn't, because I had offers not for a lot at that time, but two, three million dollars, fundraising, basically take the money and then just go bigger. Because there were some ringtone companies that grew to $100 million revenues. Now, I don't know if their outcomes were great, because once you take funding and you run all the math and no longer have control, etc, it's a completely different game, but in any case. I think about that, it's like, oh, okay, that was a offer missed, that was not my only offer missed. So I have other stories like that too. So you can't hard to predict these things. Anyways, fast forwarding to that second exit, if you're talking about the last three, so I had a calendar company. And it was a very popular calendar. It was, a top 10 app in the productivity category growing like crazy, but very hard to monetize. We had raised quite a bit of money, 10, 12, 13 million dollars. It feels like nothing today, but this is 2013 era. And, we still have 4 or 5 million in the bank, and I'm, scratching my head, I'm like, how do you monetize this thing? Like. It's just, like. Really, difficult. And, consumers don't pay for calendars, and at the time, businesses, they're paying for, Office, they're paying for Google Apps. It comes with all of that. They're not willing to just go pay for a calendar on its own. And so, this is, a real issue challenge, how to turn this into something interesting. So. Basically came into a board meeting, and I was like, I think we should consider, possibly finding an exit. We have a growing consumer thing, but I'm struggling with how to, I had $4 or $5 million in the bank, but I'm like, I'm struggling to figure out how to monetize this thing. And, they ultimately were very founder-friendly, and were like, it's your call, Raj, we support you. Now. The funny thing is, during that time, I put out a few feelers to people I know, and ended up spinning up multiple offers. I'm not gonna go through the different companies. We had, now, the way these things, work is, some of them don't issue the term sheet until you kind of agree, verbally, or agree at least over email or text message. So, I don't necessarily have, and, often when they issue some kind of LOI, there's a period 24, 48 hours before it expires, and so they don't like to issue those things until everything's agreed. So, so we're doing this, and during this process, one of our advisors, said you should go talk to Salesforce. And I said, hey, I don't really, I don't really, what do you call it? We don't really do enterprise. We're, very consumer-focused, bottoms up, never talk to Salesforce. Anyway, so they connected us. And it turns out they needed what we were building, because they were specifically looking for this. They just weren't aware that we existed. And they came out with a very good 8-digit offer. Everybody made money, investors some many investors doubled their money. And so Most investors double their money. And so, we took it, and then there was a huge, earn out on the other side as well. I didn't stay for the whole thing, just the way it worked out. But it, that's kind of how it landed, and that was, that was fascinating. Lots of I probably think, I think they spent, $2 million in legal fees. For the transaction, it's 60, 70 attorneys in the deal room on Box. Just nuts, the whole experience. It's very stressful, I tell people. Going through acquisitions, if you think fundraising is hard, acquisitions are substantially hard. It's crazy. And the way they think, fall apart. The smallest of things, just, someone's opinion changes, a leader just doesn't think it's worth it anymore. Who knows. It's all so stressful. And, and of course, and then the emotions for the founder. Like, I actually have a whole thing I describe to people, the four emotions, like the day of, relief, once it's officially closed. You instantly see, some crazy number in your bank account? In my case, it's like going to SVB, at the time. But yeah, you see, just. And they're like, whoa, okay, and then, and then, And then, within days, you're entering regret.

Corey KupferYeah.

Raj SinghBecause you're like, why did I sell it? I could have sold it bigger. It could have gone bigger. I did Superhuman invented, basically consumer subscription for productivity. Nobody had really done that at the time. I'm thinking about it, I'm like, man. We should've just done that. We should just throw a subscription on. But people weren't doing that in the App Store at that time. We were probably a couple years just a little too early. So, you go through regret, and then you go through this, I call it inspired, where you're like, hey, I'm gonna make this the best acquisition they ever had. And of course, you realize very quickly you're, a little cog in some large. Conglomerate, and I don't mean that in a negative way, but, just the reality. You're a big company, and you're just you're a tiny piece of this. And so you don't have the influence or impact that you might think you will. And so, you got you start slowly get beaten down, just kind of through that process, and then eventually you hit what I like to tell people. Is apathy, where it's not like you don't care, but you're kind of like it's not like you accept, it's acceptance. It's like, it's not my company anymore, it's their company, they control its destiny, its journey. I'm gonna do the best I can, but I'm just an employee in this company. And so it's like, it's really interesting, those emotions, and I often share it with other founders who've been through acquisitions, and they resonate with those different phases.

Corey KupferThat's funny. Yeah, I love that description. So, in that deal, for Salesforce, it sounds like it was a classic, they had to build by, build by choice, and they decided, once they, so you were out there, they're like, all right, rather buy this and build it. So many company acquisitions come down to that build versus buy decision, and it changes the whole tenor of the m&a negotiation once a buyer has made that call.

Raj SinghYeah, no, they took our whole team, which was, the whole company. 30 of us, and then they what I mean by whole team is they actually then issued offer letters to all the interns we had issued offer letters for in the summer, so we had, 6-7 interns that also joined, and then all of them got full offer letters. Which is wild. So I was just like, wow, it's like 40 people.

Corey KupferLove it. Love it. So listen, this is, considering how many startups you've had, how many exits you've had, and whatever, this is such a broad question, that, we could spend probably 5 hours talking about lessons and whatever, but, is anything, you I guess one of the things that's fascinating for me, and you pointed out, which I love. Is that you've been doing this for a while, and you've done this at various stages of the market, of the evolution of tech, of, all these things, and this concept that the game's, always changing. So maybe lessons in that area, because, listen, I see, you see it all the time where, a founder, maybe they have one big success, and they think they can recreate it. And they don't, and maybe part of that is that they don't recognize that things are different. The way I evaluate deal value on strategic deals today looks nothing like how I did it fifteen years ago, and that evolution matters. Or you see situations where, folks just don't like, maybe they don't you talked about, for example, timing of exit. I've had clients where I'm like, they're in an unbelievably hot market, they get a big offer. And, and I say to them, you're not gonna sell, and they're like, oh, what would I do? I love my company, whatever. And then, listen, you have examples on the other side where people were offered huge amounts of money, it seemed at the time, and they held out, and they, and they got 10 times or 100 times that. So there's examples on both sides, where they missed the boat, where they didn't. So maybe, any lessons on That conversation about, when you sell, how you understand how the market's evolving, how you evolve yourself.

Raj SinghSo, I like to tell people there's windows. You can't say, oh, I'm gonna have my company for 7 years, and I could sell it any year I want. And obviously, it's always better to be bought than sold. So, we should make that clear up front. There are windows, and you miss a window, the next window might not emerge for 3, 4, 5, 6, 7, 8 years. And so That's something you have to really think about, and I think the hardest question in all of it, and this is the thing I think you really have to internalize, is how tired do you feel?

Corey KupferFair.

Raj SinghAnd I say that because the number one reason companies' startups fail is they run out of money, but the number two reason is the founders get tired. Yeah, because it's exhausting, and it's stressful, and you're wearing your company. And everywhere you go, you're thinking about work. You may not be actually working, you may not actually be at a desk, but you're always thinking about work. And so that, it's not easy. And so, and so I think if you're, in a situation where there's a window. And you feel really tired, you have to ask yourself, can I can I pull through and, hold this out for another 5 years or not. And so In my opinion, others say, oh, Raj, you've been successful, you exit all these companies, and I always tell them. Selling is not necessarily success. To me, success is like, can I take this and IPO this thing, right, and make it a big standalone public company that's, like. Creating a lot of, having a massive economic impact, and creating jobs, and all that kind of stuff. And so, I don't look at it that way. I look at it like it's fine. I've created liquidity, I've made, pretty much all my employees are millionaires, across the different companies. Sure, I've done that, but But they all got acquired, they didn't survive. That's not, the outcome I necessarily wanted. And.

Corey KupferBut it is the outcome that far more companies actually end up with than actually IPO. Everybody.

Raj SinghSure. Well, and I think that's important to understand how the venture industry works. The venture industry will see a new hot trend. NFTs. Or, remote work tools during COVID, or, Gen AI consumer, and they'll be like, hey, okay, we don't know if this space is gonna work. We don't even know if it's a category or not. But we will contribute 1% of our total assets under management, which might represent billions, because, the venture industry is very large. And, we'll roll it for 1%. If it doesn't work, fine. And if it works, we have a play in this 1% that is going to become a new IPO-able category.

Corey KupferYes.

Raj SinghIt's very hard to predict. You look at the remote work tools category, pretty much 100% of the companies died. The existing companies got bigger, the Zooms, the Slacks, and whatnot. Right, the teams, but all the startups and the vast majority of them all died. There was, no ROI. But it only cost them 1%, but then sometimes they're right. Sometimes that 1%, turns out, this is a macroeconomic trend or what, and it's gonna become big, and a couple IPOs come out of it, let's say cybersecurity category. So They don't know. But it's okay, because that's how the model works.

Corey KupferYeah, yeah. Yeah, it's okay, because that's how the model works on the investor side. But on the founder side.

Raj SinghNo, yeah, no.

Corey KupferMuch more, it's not 1%, it's 150%, right, of what they're doing. So it's, it's fascinating. Yeah, from that perspective.

Raj SinghIt's, I tell people. The venture failure rate, and the stat is, 10 years old. I think it's 86%. So, 86% of companies post-Series A don't return the money in.

Corey Kupfer**Raj Singh** [00:46:42] That's a remarkable stat, because there's a lot of smart people involved. These are people managing other people's money, these are large investments. To not return the money in at that stage, with all these smart people involved, what's going on. So that one side of the coin, I look at that, and I tell people, as a result, there's always a 14% luck factor. Then on the other side of it, there are funds that consistently do better. Yeah.

Raj SinghRight? Now, what is it about these funds or these individuals? Is it just simply deal access? And if you look at a lot of funds, I'm an investor in a bunch of funds. I kind of stopped, because I ultimately realized it's better to just leave it in the market. But I look at, how they report and the data and whatnot. And one of the key metrics that they always look at is. It's not about whether, they invested in XYZ, it's whether they had the opportunity to invest in XYZ. And so it's really about showing I had access. Right? I may have made the wrong decision, but I did have access. And so, is it that the largest funds, or the most successful funds self-select? Because the founders themselves want those funds, and so they get more access, and so, I don't know. But there is, there is some truth, why is Founders Fund, always, returning as well as they are? Why is Sequoia, doing as well as they are. So, yeah, I don't know, but, as a founder. Yeah, the default mode is failure, and, one of the things I tell companies that I've advised or invested in or whatnot is, and this is so counterintuitive, is on day one, start thinking about who your 10 most likely buyers are. And why? Because it takes 3, 4, 5 years to figure out who the person is who could execute that buy. So, you want to basically identify the 10, you want to start pitching them, or not pitching them, but pinging them every 6 months and say, hey, I'd just like to show you what I'm up to. And no intent to sell. You're not selling. You're building your company. Right? But, you're trying to build a relationship, and the reason is it takes 6 months to a year to 2 years to figure out who could even executed by, because you need to have enough authority and whatnot, especially since 80-85% of acquisitions are CEO-driven, and they're almost done at a whim. So the 15% that are driven through logic, you have to make sure you're top of mind. And the reason you do this is in a downside situation, because downside situations come fast. You now have 10 people you can go to quickly to try to spin something up, because it's very hard to try to sell a company in a situation where you have no existing network. Then you pretty much have to do what I call spray and pray through corp dev intros. Which then just get routed to execs, and then if the timing doesn't align, it doesn't work. And I always tell people, acquisitions are all about timing. It's not that what you're working on isn't hyper-synergistic with this company, it's just not the right time. And if you look at the flow in how acquisition logic usually happens. Executive team has some kind of off-site, and during that off-site, somebody raises something, hey, we need to build this, blah blah, and somebody comes out and says, we kind of need that now. And then somebody will spin up, hey, Corp Dev, can we go see, who's in the space? We need this now. And so that's the timing. And if that timing doesn't align, you could be off by 6 months, either on the front or back side, it's not gonna happen. Right? And so your goal as a startup is just to make sure, if and when that happens in one of those meetings. That corp dev and or that executive sponsor. Thinks of you, and so you're at least in the mix. That doesn't mean you're going to be the one who's acquired, but it does mean if they're going to go talk to 3, 4, 5 people, you're one of those 3, 4, 5 people. Because the worst situation is there's acquisitions happening, and they didn't even talk to you, and you had a competitive product at equal revenue and whatnot. And that kind of just sucks.

Corey KupferYeah, but not only have you lost opportunity, but now you've got a bigger gorilla, in your, brought up one of your competitors. So it's a it's like.

Raj SinghYeah.

Corey KupferGlobal Wally.

Raj SinghYeah, sometimes, yeah, I often say when.

Corey KupferSometimes it's it doesn't, yeah.

Raj SinghWhen I say an incumbent decides to enter your category, it usually accelerates your startup in some ways, and I say that because they start spending a lot more money on educating the market, and so people really get to buy, and especially if you're doing something like enterprise is not winner-take-all. Consumer is very winner-take-all, but enterprise There's always multiple winners, because companies have to apply leverage for risk. So they have the option A, option B, and option C. So there's always 3 winners in every category in enterprise.

Corey KupferYeah, it's a great distinction between, on the enterprise side. That has real implications for m&a strategy too, because the number of viable buyers shapes how m&a transactions play out. So, before I ask you my final two questions, is there anything, in terms of what you're doing now at Mozilla, some of those, products, or things you're working on, I don't know what's disposable at this point, but, anything you want to share about what you're currently doing before I ask you your final two questions?

Raj SinghSure, yeah, so, I have to promote Firefox, of course, go check it out, we're doing great things. We announced, today we have a new AI mode coming. I'm responsible for a lot of our small business products, so products like Mozilla Solo, which is an AI website builder. We have things like Postful for managing social media for small business. We have other tools coming as well, but just a whole suite of tools for the service provider, solopreneer, entrepreneur, it's a great community to try to democratize access. Be your own boss, business in a box, as we talked about. So, that's my quick, shout out, and of course, I'm I'm easy to reach me if you have any questions related to any of that, through Twitter and LinkedIn, as you said, at the, at the top.

Corey KupferWell, that actually leads into my second last question, which is, yeah, how can people reach you? Where should they find you?

Raj SinghYeah, so, I'm on LinkedIn, I'm on X, I'm on Threads, my email's public raj at rajansingh.com, you can ping me, I generally will reply. So, it depends, as long as it doesn't come across as spammy, I'll reply, for sure.

Corey KupferAwesome. Raj, my final question on the podcast is about my highest value in life, which is freedom, and for me, that means everything from freedom around the world for people from oppression, to why I've been an entrepreneur and haven't had a boss for decades. What does freedom mean to you, and how does it impact your life and business?

Raj SinghThis is gonna sound cliche, but I'm a big, Because I think this is such a common answer, but, freedom is, being able to choose where you want to spend your time. And I've been fortunate, I've been in that situation for some time. And so that means I can spend a lot of time with my kids, when I choose that's what I want to do. I don't fear, oh, I'm gonna lose my job, or, that's okay. Doesn't mean I'm not looking at prices, but, I will generally eat out where I want to eat out. If I if I want to travel somewhere. I am looking at prices, I'm like, oh, this is a little bit crazy, I'm not going to be stupid. But, I think that's I think that's freedom. Some people call that financial freedom. But, I've been very lucky that my two startups ago was acquired when my son was, 2-3, so I spent a lot of time with him for 3 years. And then this startup was acquired when my daughter was 2-3, and so I spent a lot of time with her the last 3 years, and so it's been, that's worked out great.

Corey KupferRaj, thank you for being such a great guest on the DealQuest Podcast.

Raj SinghThank you, Corey.

Corey KupferAll right, awesome. Alright, we're just gonna do a quick, promo video. I'm gonna say how excited I am to have you on an upcoming episode of DealQuest, and you're gonna talk about, the episode hasn't happened. I'm gonna ask you what are people gonna hear about on your upcoming episode.

Raj SinghSure.

Corey KupferQuick summary. Here we go. DealQuest community, I'm so excited to have Raj Singh on an upcoming episode of DealQuest. Listen, I'm not gonna list the multiple startups and exits, that he's had, but let's just say he's had a number of successful ones, and, it's led him to where he is today, and he's gonna bring a lot of wisdom. Raj, what are people gonna hear about on your upcoming episode of DealQuest.

Raj SinghIt's a blessing and a curse to have gone through multiple exits, so I can certainly share where every scar has come from, and if people want to take it offline, I can definitely dig into some hard truths about what that process is like, and how to drive FOMO, and all of that.

Corey KupferLove it. And, one of the things I know, because, I don't wanna, I don't wanna date Raj, but let's just say he's done startups over a number of years and decades. One of the things that's fascinating that I know we're gonna talk about, because we spoke about it a little bit in advance. Is this conversation of how the world, whether it's tech, whether it's, fundraising, whether it's, how deals are done, have changed over time, Raj. We're gonna get into that a little bit, you think?

Raj SinghOh, absolutely. Yeah, I joke with people, I had a startup venture-backed, through the dot-com crash, the great financial crisis, COVID, and so I've seen all three major recessions. You could argue we're probably in another well, I don't know if we're in one right now, but it is definitely a weird economy.

Corey KupferI love it, folks. So listen, if you wanna if you wanna hear from somebody who's, learned the hard lessons sometimes, but also has had a lot of success, throughout, all the ups and downs of the economic, entrepreneurial, and technological evolutions, definitely check out Raj's episode, coming up on DealQuest. And hey, if you're listening and you think you'd make a great guest on the show yourself, head over to [beaguestondealquest.com](https://beaguestondealquest.com/) to apply. We'd love to hear from you.

Raj SinghThank you.

Corey KupferAwesome, man! Appreciate you coming on, that was a lot of fun.

Raj SinghGreat, Corey, thanks for, doing that. Look forward to seeing it go live!