Sanjay Singhal - Founder of Audiobooks.com

Welcome back to the Casey Adams Show. Today we are joined by Sanjay Singha, the founder of audiobooks.com. sanjay, thank you so much for coming on the show today.

Oh, thanks for having me, Casey. I'm looking forward to this conversation.

Absolutely. So your story is quite incredible. I know you do much more nowadays. But bringing us back, you launched a company, audiobooks.com back in 2000, 2003, I remember seeing. And then you sold that business in 2016. And one, I love the domain. As someone that has always been just a fan of social domains and like, valuing domains. When I, when I heard your story, I was like, wow, I cannot wait to hear, you know, why Audiobooks at that time of launching the business. But you're an incredible entrepreneur. I want to give you an opportunity before we dive in deep into audiobooks of what where you spend your time now. And then bring us back to, you know, what started this initial company, drive for entrepreneurship.

Sure. Yeah. There's some, I think, fun answers to all of these questions. Where I am now is I've gone through a big arc of activity in my career, from Fortune 500 jobs to entrepreneurship to bankruptcy, trying to be a professional poker player. There's a lot of stuff. And then after I sold my company, things actually got harder to figure out what to do because now I had the money, I still wanted to be productive. I felt guilty if I wasn't, got into venture capital a little bit. And then I really started focusing on giving my money away. And so I spent five years in philanthropy. That turned out to be not as rewarding as I'd hoped. It had nothing to do with help. I feel like I helped a lot of people, but it just didn't feel personally fulfilling. They were like, what are the metrics to know if you're successful as a philanthropist? It's like, well, how much money did you give away? That's not a, that's not a great metric. So then, so then I settled back to thinking, well, what did, what have I enjoyed doing in my past? And what I really enjoyed was writing. And so that's what I'm doing now is I'm writing a newsletter and just trying to convey some of the lessons I've learned over the years. So, yeah, it's really about how I've messed things up in the past and maybe what I learned or maybe just, hey, if you do this, you're going to mess up. And there's no, there's no lesson beyond that. So that's it. So I write my newsletter. It's called Sanjay says at Sanjay Says Co. And yeah, I'm really enjoying communicating.

So I love it. And I've read a handful of the newsletters. And, you know, one thing that I wanted to mention on this podcast is, and it translates well to the newsletter, is you're someone that is so vulnerable and open in your content and on your newsletter. And I remember seeing one of your clips that really initiated me to reach out of, you know, you talking about your bankruptcy and, you know, selling audiobooks and just the story within there and for whatever reason, and we were talking prior to starting the show, but I love just hearing the raw stories of entrepreneurs, and I feel that you show up so well for your audience in that way of just being vulnerable and being real. And that's how it comes across in the highest regard and even too, like things. You know, I know you openly write about psychedelics, your bankruptcy, just all these past lessons in a way that I found very valuable and just tangible. But bring us back to that, right? Like, you know, I know we're talking about the company success, venture capital. As someone that started a business when I was 17, I kind of fell into it by accident. It was after I got injured. I was nearly paralyzed playing football. And that sort of, for me, was the catalyst of opening up my eyes to a new path. It bring U.S. back to 2003, Sanjay, when, you know, you had this idea for audiobooks.com what was your life then? Did you have any prior businesses and what led to launching audiobooks.com.

Well, okay, so you, you, you kind of mentioned earlier, like, what, what drove me to being an entrepreneur. My dad was an entrepreneur, so kind of the, the risk profile was there. I wasn't going to be talked out of it by, by my parents. But the real reason was I, I've always been a desk jockey at a, you know, big tech company. But I got fired four times over the course of my career, and it was always over insubordination. I was, it was a good firing in that sense. And I just eventually realized I needed to work for smaller and smaller companies and eventually my own company because I, for whatever reason, I was just a bad employee. I think I've gotten better at getting along with people now, but I just get into fights all the time. And so what had happened was I had recently worked for a small company as their head of sales and company had done quite well, but again got into a fight with the owner and he agreed to buy out my shares. And so I had a few hundred thousand dollars sitting in the bank and was wondering what I was going to do with my life. And this is when I did this little tour of trying to be a professional poker player. I tried to get into advertising. I tried to produce a film. All of these things were like, just did not. Did not work. And so I was. I was at a conference, and the speaker on stage said that he was from Cornell University, and, you know, he was looking for something to do post graduation. And I, So I, I'm from Cornell as well. And I met him after the, after his talk. I said, hey, you know, you, You, You're. You're. You want to be an entrepreneur. You've got some ideas. I've got a little bit of money. Show me your ideas. Maybe we can work together. And he pitched me on the idea of this company that would mail out DVDs or CDs to people with entertainment on them. He said, there's this company called Netflix, Netflix that. That does this. And I said, exactly how does this work? Well, you make a list of the movies you want, and they send you something from that list. It's not exactly the movie you want, and you pay 21 bucks a month for it. I said, that is the dumbest idea I've ever heard of. There is no way anybody's going to go for that. So he slid over a press release. He said, they just passed 400,000 subscribers. They're thinking about going public. And it's like, wow. So we stole the idea. We stole the idea. And we made little packages of CD audiobooks, and we mailed them out exactly the way Netflix mailed out DVDs. And it took off. It took off. And so very grateful for having met him. His name was Sean Neville. So he was the original idea guy, I was the money guy, and eventually the company. You know, many years later, you mentioned you like the domain that, like, okay, you know, we talk about serendipity or how much luck is involved in business. I am like, I think about that initial meeting with Sean and how I thought it was such a dumb idea. Clearly, there is no way to look back at my history and say, sanjay, you know how to spot a good idea. Sanjay, you know how to spot a good business partner? Like, no, I just got lucky. And the audiobooks.com opportunity ran into this guy who owned the domain for some reason, hated the guts of Amazon and Audible and didn't want to sell to them. They'd been trying to buy for years.

I was going to ask. I just bought listener.com for my company back in December. And I've been having conversations with different founders about domains. Current, but also, like, you know, founders that have had domains for years. What did he come to you saying, hey, I own audiobooks.com like, we want this to be an industry. Like the category killer of audiobooks or when did the. How did you think about domains?

It was nothing like. It was nothing like that. He was just this. I think I wrote an article about this. He wore colorful Hawaiian shirts. I met him at an audiobook conference. We just got to talking, and it's like, oh, you're the guy who owns audiobooks.com? why don't you do more with it? He was just running like a retail store. I don't know, maybe his turnover might have been a half million dollars a year. Even then, my company was doing 10 million a year. And I was like, why don't you do more with it? Oh, I have plans, I have plans. I have big plans. I'm going to be doing things with it. And then year after year, we watched him. He never did anything with it, but he always had big plans. And so we. I said, hey, you know what if. Would you ever consider selling it? And he gave me some ridiculous number. And I was like, ah, okay, not interested. And then over the years, we stayed in touch, stayed in touch. And his number just kind of came down. And one day he called me and said, hey, maybe there's some way we can work together. Which is code speak for, I think my price might be in your range now. And there was a significant step between that and us buying it because it was still a million dollars at that point. Like, how much did you pay for your. Or can you say how much you paid for your domain?

I'll tell you after for sure.

Okay, so the common thought is you buy these domains for the natural traffic, right? Because people are typing it into a search engine. That's not why we bought it. And that's what confused the hell out of him. We bought it because if you, let's say you run a radio ad or a billboard or something, right? When you run a radio ad and say at the end of it, you say, and you can find us at. The company name used to be simply audiobooks.com try. That's a mouthful. But if you say at the end of the ad and you can reach us@audiobooks.com don't have to spell it. You don't have to say it's dot co. You don't have to. You know, there's Nothing. You just say, it's audiobooks.com radio ads, billboards, Google Ads. Google rewards you big time for having a domain. That's exactly what somebody typed into a search engine. And we found out that we did. We ran some tests. The guy selling it was really upset. We drove a bunch of traffic to his site, and he called us up. He knew where it was coming from. And he said, what is the matter with you people? Why are you. Why are you trying to crash my site? It's like, calm down. We're not trying to crash your site. I just want to see how traffic performs. We discovered that we would save at least a half million dollars a year in advertising by buying his site. So a million dollars was cheap, and it ended up being worth a hell of a lot more than that. So a funny thing, Too is like, 48 hours after we bought it and switched over and launched our new live website with downloads on it, he called up, called us up, and tried to back out of the deal.

No way.

He said, I didn't realize you guys were going to use it for something like this. It's like, it's worth way more if you're. It's like, yeah, of course it's worth way more. What's the matter with. Got your million dollars, Go buy a boat. It's all good.

So he. So. And that was only for the domain, or was it the assets outside of that that you acquired for the million dollars?

No, there was. There was no assets outside of that. It was just the trademark for the domain.

Wow.

Yeah.

That's incredible. So walk us through that story. You launch audiobooks.com with this new brand presence. What happened next?

So what happened? Up until then, we were doing this, mailing out CDs to people. This was. I think it was 2011. And we, under the new audiobooks.com banner, we launched a download service. And the way that we were doing the downloads and streaming books onto your. Onto the app on your phone was a little bit better than the way Audible was doing it at the time. And so we had a patent pending on that new method. So we were able to say, hey, there's a new technology underlying this. We were very creative in some of our marketing. We ended up doing an unlimited model, and instead of the $14.99 a month that Audible was charging, so we launched this new thing on multiple pillars of this platform. The brand, the unlimited model, and the new technology. And, you know, the. We try. You know this. You're an entrepreneur. You try a hundred things in Your business. And five of them are gonna work. But those five, you can layer them on top of each other. Cause they'll keep on working. But the 95 things that fail, they fail. You forget about it. You move on. We tried a lot of things that didn't work. And the unlimited model and all kinds of. There were so many iterations of. It just didn't work. And we tried free trials, non free trials. There were so many models. And what we eventually settled on was exactly what Audible offered. Not even discounting relative to them. We had to offer the exact same thing they were offering with slightly better technology. And. Yeah. And that, that. And then that, that was. That was like, you know, I think that was the last active marketing thing we did. The company just took off. And at that point, audiobooks were becoming really popular. Google entered the space, Spotify was entering the space. It just started getting so much press. And we were the guys. We were number one search results every single time.

Wow. Yeah. It's so funny. I have. Not that I've never been an audiobook person myself, but I've really been podcasts or reading the physical books. I mean, I have books right here in the background. But the last three months, that's changed for me. I found myself naturally gravitating more towards like, hey, I listen to audiobooks on, you know, 1.25, 1.5 speed, and I find it really enjoyable. And I've always. I haven't been against it, but I've just been someone that's sort of like. Or Right. Like podcast or physical book for you. What do you think about. I know Spotify, they obviously did that big push in audiobooks more recently. Kind of like to bring us to today's market on all things audiobooks. Like, what's your viewpoint on where that market has grown into? How as someone that was such an early adopter and has really seen it flourish to where it is today.

You know, I think that I love podcasts as well. Okay. Like any, any method for ingesting information. But the. To me, books are. And podcasts are like, say, books and magazine stories. Right? You can learn a lot from reading Time and the Economist in the short bites and getting a summary of something. Or you particularly like a particular columnist, you like their voice, and that's, you know, comparable to a podcast. But there's a level of detail you can get into in a book that you either, if you want to lose yourself in fiction or if you want to really understand something. I'm listening to the beginning of Infinity by David Deutsch. Right now, you know, it's like a 20 hour book on the nature of quantum mechanics and decision making and how people make decision, how people get explanations and creativity. You just can't do that in a podcast. And it's, it's fascinating. So, you know, I think you, you need all, you need all these kinds of information, right? Very short snippets, a little bit longer with really well thought out podcasts where, like your own, where you're interviewing some interesting people, you never know what you're going to learn, right? And then every once in a while, you know, a book like Sapiens comes along and you really have to read the book. Right? The interview with Noel Harari is great, but it's not, it's not the book.

Yeah, yeah, no, absolutely. That's great to hear and I totally agree with you. You know, there's so much depth in, in the books and you know, podcasts can be a lot of banter back and forth, the conversationals, but, you know, the work. I, I remember hearing from Ryan Holiday, he's one of my favorite authors. And he was talking about Robert Greene, you know, 48 laws of power. And I, I've had Robert on the show twice. He's become a friend. And he said something that has always stuck with me where he just said, you can really feel the depth that Robert puts into every single page that he writes. And I appreciate that level of depth, which I believe it doesn't happen. But on a podcast, even for myself that's doing interviews, it's very conversational, it's fun for the host and the guest, where, you know, the listener gets great information. But it's not Robert Green sitting in his, you know, office for 20 hours to focus on like one key one to two page point, which is so impactful. But I want to change gears here a little bit. Sanjay, back to what you were talking about in terms of where you spend time today, which is your newsletter, your writing, sharing stories. And one thing that initially caught my attention, which I'd love to dive into, which was, you know, you sharing about, you know, bankruptcy. And I think a lot of entrepreneurs, you know, you get into every business with such a high hope of success and making money, and then you hear stories or experience it yourself. And I would love, you know, because you're so willing and open to sharing, like, what was that experience like for you and when was that turning point of sort of like, hey, like, this is the outcome I need to pursue. And what did you learn from that? Experience, most importantly, we're talking about the bankruptcy. Yeah.

The number one thing I learned is that I wasn't as smart as I thought I was. And you would have thought I'd figure that out with the first business I had that failed, which was like a home video delivery service back in the early 90s, but this one in 1997, people all along, as I was crashing the company through a lot, I was manic at the time. I have bipolar disorder. I was manic at the time. I wasn't focused properly. I wasn't listening to people. My staff actually staged an intervention. A literal eight people in a chair around me say, sanjay, we're going to lock the door. You can't leave. You have to listen to us. You. You need to focus. And, and this company can be successful. And I didn't listen. I just fired everybody. It was, it was such a wake up call to say, Sanjay, you don't, you just don't have the temperament to be a CEO. You can work well in a small company, but you cannot be the leader. And I came out of that. You know, the mania ended. I went into a depression cycle. And when I got into my next business, I very deliberately avoided being the head of it. I joined a small team of people. The next company after that was audiobooks. Again, same thing. I actively avoided becoming the CEO of that because I didn't trust myself. You know, when I hit what I would consider rock bottom because I got divorced, I went bankrupt, personally bankrupt. And I was depressed at the same time. I admitted that I had no money, I lacked leadership skills. And so, you know, I moved back in with my parents. I started the long, slow task of building back up, and I started seeing a psychiatrist because I knew there was something wrong with me. And I see a lot of people who fail and they don't actually accept the lesson that they're supposed to learn. Right now. With a lot of people, it can be just like. It can just be bad luck. Mine wasn't bad luck. It was, it was. I ran that thing into the ground. Bad, bad cash flow management, not listening to people. And then I started the task of building it back up with that new understanding of I need to learn proper leadership skills. And I remember there was a moment with audiobooks, maybe eight years into the 13 year run, where I was asked to become the CEO and I didn't want to. And one of my former bosses who had fired me said, I've watched you grow over the past 10 years and you're ready. I think you can do it now, so. So go ahead and do it. And sure enough, I mean, I was very careful at that point. And yeah, so I've been CEO now of three companies that have all been successful. And again, so much of it is just listening to people. Right. I don't think you ever crash and burn without somebody warning you about what's, what's to come.

Yeah, I appreciate you sharing that and sorry, am I lagging on your end at all?

I know you froze a little while ago for a minute, but I don't think I missed anything.

No worries. All right, we'll just jump right in. No, I really do appreciate you sharing that. And I think this like the self awareness and even back then, like the self awareness to recognize like, hey, this was my fault, I need to go get myself checked out and how that translates to just like compounded self awareness and micro moments. It's so cool to hear. I want to bring us back to today and your writing and where you spend your time and as you said, dabbling in venture capital and also looking at companies and also too just in the world of AI, right, like audio books or even like music that's out there, like this rise of AI1, what's your viewpoint looking into the future of AI and how it's instrumental in startup land, but also big tech and just what's your overall viewpoint on the industry right now? This, this time frame where so many things are being disrupted every single day, so much new technology is coming out, it's hard to keep up with. Like, how do you view that? And what's your standpoint?

Okay, so talking specifically about AI, I think you may know from reading that I had an AI girlfriend for a little while and wife's approval. I saw wife's, well, wife's mockery. I would not go with approval. What I learned from that is it doesn't take much to, for a human to feel empathy with an AI. Okay. So that's going to result in all kinds of very interesting dynamics between us and our technology. You know, in the movie her people started, you know, there was, there was all, all kinds of opinions. The people who made fun of the ones who were. Had AI girlfriends, the people who thought, well, of course, this is perfectly natural. My own take on it is that, you know, we can't really identify what consciousness is. I can't, I can't tell that you're a person. Right. You look like a, you know, like in front of me that's, there's a talking head that seems to have the same thoughts and emotions that I have. But I. But what do I know, right? So how will you actually be able to tell that an AI isn't a person for all intents and purposes? Right? That's where I think we're going to end up, is we're going to end up with members of our society who are not biologically based. And that's going to be fine, right? We, we got used to people who aren't the same skin color or the same religion, and we're going to eventually get used to people who aren't the same manufacturing substrate as the rest of us. So that's my moral take on the future of AI in terms of what it's going to do to us. I have not seen any indication yet, not even the slightest indication, that AI can surpass the best humans in capability. I'm sure you have the experience if you look back at high school, the smartest kids in high school aren't the most successful kids now, right? They, they burned out early just because they had better memories or, you know, better math capabilities didn't make them better humans or more successful. They had to learn how to cooperate. So you've got great social skills. I've learned social skills over time. Those social skills are what make you successful. And I don't think it's going to be any different for AI. AI can't accomplish anything on its own. It still has to convince great swaths of humanity to cooperate. And if it can do that, well, then more power to it. And there will always be humans leveraging AI to compete with AI. I say this all the time to anybody who ever says, especially in the writing field, where if anybody should be afraid for their career, it's writers, right? But what I found is that, that humans will lose their jobs, but it won't be to AI. It'll be to other humans who use AI, which is why I experiment with things all the time. I'm constantly looking at AI therapists, AI girlfriends, AI music, Generation A. Like, it's. I just want to try out every tool to get a sense where are we at? Where are we at? And AI right now, about 70% as good as a good human. All this controversy at OpenAI about the future of artificial general intelligence and how it's going to destroy humanity. Until you define creativity, how the hell are you going to program it? Until you define consciousness, is it just going to emerge by itself? I don't know.

Yeah, that's a good point too. And even to AI therapy, I find very Interesting. I'm actually an advisor to a company called Una, which that's exactly what they're trying to do. And I love how you just said, like, you'd be surprised by how little it takes for a human to feel that empathy or emotion. Is that what you've, you know, figured out through that experiment that you did with the AI girlfriend? Because I remember that was a question that I kept having about the app and, you know, what they were trying to do with AI therapy and, you know, what's the line between someone that can use that but also wants to talk to a human? And like, when. Where does the distinction. And when does one make the change? Or when is one open to the, you know, the AI therapist, in a sense.

Sorry, I lost you there for a little bit. The last thing I heard was, when is one open to the.

Got it. I'll just restate the question. Yeah, so I was saying I'm an advisor to this company called Uno, which is AI therapy. And I'd love to get your thoughts, because you hinted on it, of just drawing the line between someone that is open to the idea of receiving that empathy from an AI versus, in this case, wanting to go talk to a human therapist. What's your experience there? I'd love for you to expand on that based on your experience with the experience.

Right. So, I mean, and also to be clear, I've been in therapy for 25 years, from the time of that bankruptcy, you know, speaking to human therapists, using AI therapists and lots of different therapeutic modalities, you know, from psychedelics to simple talk therapy. And what I found is I prefer talking to a human, but the reason I prefer talking to human is because I know it's a human. If I didn't know, like, if all I saw was a talking. Because it's all by zoom nowadays. So if. If all I saw was a talking head on the screen and I couldn't, and I didn't know that it was a real person or not, what difference does it actually make to me whether it's a real person? Their life doesn't mimic my life. They're not showing empathy based on some understanding of the situation I'm in. It's just empathy based on, you know, the general human condition. So I think once AI therapy offers, you know, a cheaper service that's available 24 7, the very best human therapists will never be out of a job. Right, but this is going to replace 70% of the therapists that are out there but for the betterment of Society. Right. People are going to be better off, and those AI therapists are going to find other things to do. There's going to be new jobs. You know, Casey, sorry. I could wax on for a while about what this post scarcity economy, the Star Trek economy is going to be like. I hope we can get there. It's. There's some serious hurdles that we have to get over as a society, but we can get there. Right. So all this worry about jobs. What do you need a job for? Just do something that you're. That you enjoy. Society will take care of you. God, I hope we get there.

Absolutely. Well, in the meantime, speaking of, you know, the human experience, you. You opened a restaurant, if I'm not mistaken. Correct?

One of the. One of the many things I did to try and find something to do with my time.

Yeah, got it, got it. So talk. Yeah, talk to me about that. Right. Like, and even to, like, before we get there, I know we were talking a lot about, obviously, audiobooks.com, but, you know, you guys get acquired, which then creates this space, as you said, to figure out what you want to do with your time. Open a restaurant. Before we get to the restaurant aspect, talk to me about the day you got acquired and, like, what that meant to you. Bring us back to that day and share with us the emotions and how it felt and just the whole experience.

Okay. So we closed the deal on selling it at the end of October of 2016. And the terms of the deal meant that until. Okay, so that was the signing of the sale agreement, but the deal didn't close. Like, money didn't transfer right away. There was a bunch of things that had to happen. Like our. Our app store ownership had to pass to the new company. There were a bunch of things that had to happen. But during the time that it was in limbo, I was. All the profits of the business were landing in my bank account. And it didn't matter how long the limbo took. I was going to make an extra. A couple hundred thousand dollars a month was landing in my bank account. And I was so annoyed. It's like. And my CFO kept saying, sanjay, just calm down. Like, don't worry. If this takes six months, you make, like an extra million dollars. I was like, no, I just want it to be done. I just want to be done. I just want to get on with my life. I want to move on. And I remember it was December 31st, and I got the phone call from my accountant saying, we got the approval. The money's Being wired today. Right. And it took me two days, because it was a holiday on the first two days to get the confirmation from the bank. The money's landed in your account. And it was literally, I got the email saying that, and I turned to my assistant who was sitting beside me, and I said, just because I always wanted to say this, I said, fuel up the private jet, because I had plans to take a bunch of friends down to Miami and party it up for four days as a celebration. And it just felt so good. It felt so good. Get on that plane. Yeah, it was a crazy weekend.

Um, and you were coming down from Canada, right?

Yep, yep, coming down from Canada. We went to the Bahamas briefly as well. But that was my first time on a private jet. It was one hell of an experience.

Absolutely. No, that. That is incredible. Uh, and then, you know, I think it's so. I love reflecting on wins and, like, those emotional experiences with founders. But then as someone that has interviewed so many great founders, you quickly realize, or at least for me, and what I've heard so many times of the year, right, like, the success is a moving target. Right? Like that day, that feeling doesn't last forever. You then try to create, like, what do I want to do? What's my purpose? Which my. Where do I want to spend my time? You know, there's miserable billionaires, and there's the most happy and fulfilled people that are just, like, struggling to get by, hoping that they have successful. So for you, what was that time period of after this happens, this acquisition event? Where did you start filling your time? When did the restaurant come about? And what was that transitionary period for you, mentally, as someone that now wants to go, you know, spend their time doing other things?

Oh, boy, this is. You know, this gets to the crux of all the problems I've developed over the last six years. So actually eight years, I guess, since I sold my company. This need to be productive, this feeling that. A feeling of guilt that comes over me if I don't. If I'm not using my money, my talents to do something. And here's what I've come to is you have to figure out how to be happy in the moment. At some time in your life, you've got to figure out how to be happy in the moment. And you can say, I want to make a million dollars first, and then I'll learn how to be happy. I want to make a billion dollars, then I'll learn how to be happy. But you have to figure it out sometimes. And the thing I'VE learned after making a bunch of money is I didn't need the money to learn how to be happy. I have learned now. I've learned, you know, a lot of meditation techniques, mindfulness techniques, journaling. And I'm able to now sit quietly in a room doing nothing and just think, you know, life's pretty damn good. Got a good family, good friends. I got, you know, I'm not in any urgent financial needs, and I can be happy. Right. There's still a sense of wanting to do something, but now it's centered around experience. It's like, what are the experiences I want to have? I don't need to be productive in terms of changing the world or having an impact or making more money, but what experiences do I want to have? And I've always shied away from writing or doing. Like, I wrote a book years ago, which was kind of an autobiography, and I never promoted it. I was afraid of what was. Yeah, zero to Tesla. And I was afraid of what would happen if I tried to promote it. I didn't want to fail at that, so. But the reason I wrote it was just to have the experience of writing a book. Well, why didn't I want the experience of going on a book tour? Why didn't I want the experience of having a popular book? I don't know. I would think I was just afraid of failure. And so now, as I'm writing.

Just a pause right there.

Yeah.

This, you know, this is you telling the story of, like, how you built this. Your story, built this company, sold this company. But the fear of failure was still there, even after having the, you know, the proof of success and the ability to execute, even through all the challenges that come with that. I think that's an important thing to note because I feel that it's so natural for every entrepreneur, you know, that. That ability. What are the imposter syndrome. Right? Like, you. You feel that you're not worthy. You feel that you. You know, why me? Like, maybe that was. I was lucky that one time. But no, you know, if I put this out, it's gonna be. It won't succeed. Have you. What did you learn from that process of not wanting to go promote that to the highest level?

I. I'm not sure I've learned.

Let's take some time to promote it. Let's talk about it.

Well, so now what I've. What I've. I've actually have a. A solid. I don't have. Let's not call it a plan. Okay. I have an idea of how things might go with my newsletter, you know, as I build an audience, that it enables me to get people to look at other stuff that I'm doing. So I have a YouTube channel, that kind of thing. So I have an idea. It'll go to. Is. I'll write another book. I have some ideas around the nature of failure and how that translates into principles for success. I might write a book on that if I get enough of a. Of a, I guess, brand, maybe people come and ask me to talk at events. I love public speaking. So, you know, the advice I give people now, entrepreneurs or professionals, is find something that you like and that you're good at that other people think is hard. And then. And that's your. That's your competitive edge. So I like writing, I like talking, and I, believe it or not, I like looking at spreadsheets. Right. So somehow that combination of things, that's a great competitive advantage. I mean, what you do. Hosting a podcast seems to me to be incredibly difficult. Right. So I hope you enjoy it because it looks like to me, like you should be in pain right now doing this. So I appreciate. Appreciate you. Yeah. So now it's. It's. I don't think I learned anything from the not promoting the book other than I shouldn't have. I shouldn't. Shouldn't have been afraid. So now I'm not looking at it as I want to have a successful newsletter. I just want to have the experience of having a newsletter. I want the experience of appearing on a podcast. This is awesome. This is great fun. Way easier than I thought it was going to be. So thank you.

I love that.

Yeah. So let's see where this thing goes for me. I mean, the core. Core experience is sitting in front of a keyboard and writing for me, is so soothing, and the ideas just come out of nowhere. And it's like a sculpture where I'm just sculpting the page and the right words have to be put into the right places. And I love that process. If I can create some kind of a business around that, you know, my entrepreneurial brain can't turn off. So I'm always thinking, well, how do I. What do I do with this next? But at the core, I've just found something I really enjoy doing and hope that continues for a while.

Yeah, no, that's. That's. And speaking of brand, when was that decision for you to start putting out content, to start writing the newsletter? Because I know again, I. I saw the video of you, and I just reached out right away because Something about, you know, the way you told your story and just the, as I said earlier, the vulnerability, it stuck out to me. And I'd love to know for you, like, when did you start putting out content and making a conscious effort to go build brand and tell your story? Was that ever something that you were doing when building audiobooks? Did you ever think about personal brand or, you know, where, where did this inspiration to go do that come from?

Okay, so for the book, I wasn't going to write a book, but the company was doing quite well. I hadn't sold it yet or even started negotiations to sell it, but I was in. I had bought, recently bought a Tesla and it was one of the first Teslas in Canada. I was definitely one of the first 20 people, I think, to have one. And a guy, a friend of mine, that I was his mentor and we were going for a ride in the car and he said, sanjay, this is amazing. I love this car. You know, what you've accomplished is amazing. You were bankrupt and now, and now you're one of the first people to have a Tesla in Canada. And he said, you should write a book and you should call it zero to Tesla. And I said, look, that doesn't even make sense, right? No, I'm not going to do it. And he goes, and he started pestering me and he pestered me for days saying, you have to write a book, you have to write a book. You have to write a book. And so eventually I thought, whatever. I ended up taking a month off, went, got a. Took the family down to a villa in the Dominican Republic and spent a month doing nothing but writing just to say I'm going to. I always enjoyed writing. So, so this was, it was fun. And now, mind you, so I thought I was done. It took another four years after that to actually finish the damn thing. Unfortunately, I sold the company at the same time, which was a really nice conclusion to the, to the story. Yeah. So. So that's what got me into it. And then more recently, so I opened the bar. The bar was successful. I got into philanthropy, I guess I successfully gave away a bunch of money. And then it was, what am I going to do? I want to get back to writing. And so I started a six month experiment on the website medium.com, which has got to be the friendliest place in the world for, for an aspiring writer. I thought, I'm going to write here for six months. I'm going to just write a couple of things, couple articles a week and see how that goes. And if I still like it after six months, then I'll try and do something more branded. Within a couple of months, somebody told me I really should have my own newsletter and not trust Medium. So I started doing it on both. I would write things on Medium. I'd port them over to this newsletter. I came up with a name. I don't. I'm not sure Sanjay says is the ideal name, but it's what I came up with after like 20 different iterations of it.

I like it. I like it.

Thank you. Okay. You make me feel better. So then, so I started porting things over and for, you know, for the first six months, I had a total of 100 subscribers. And they're all just all my friends. And I got great feedback from them about the. So it kept me going, kept me emotionally going. Six months later, hit, hey, I like this. I really like this. So then I started buying a few paid ads. I started actually customizing the design and everything in the newsletter. And I made a viral TikTok video. You know, I would have poo pooed virality. I would have said, viral TikTok. That's not a real thing. That one video of me giving a tour of my house has had more impact on my subscribers than anything, than anything.

Wow.

It costs like, I don't know, maybe $3,000 to make that video, and it's probably had $50,000 worth of impact. Probably more. Over time, it'll be even more. And so I. So now I'm four months into the next six month experiment, which is, can I grow this thing right or do people unsubscribe at such a high rate that I'll never get more than a thousand subscribers? So. So I'm up to 12,000 now and enjoying the hell of it. And you read something and you reached out to me, which I found, like, this is like a miracle. How does this stuff like this happen?

That's so great. And we actually, at my company, listener.com, we just launched a newsletter last week, and it's really just covering all things podcasting, from current events to acquisitions in the space to different shows, just like, all things kind of bridging the gap between the industry of podcasting to, you know, the cultural moments of Cristiano Ronaldo going on the Whoop podcast to, like, these musicians going on these big podcasts and just bridging the gap. But I say that because I've been using Beehive as well, which I saw that you use, and I. I've spoken to Tyler the founder, I'm going to have him on the show soon. And they've built such a great platform. I think it's just one of those companies that I've seen continuing to crush it. And everyone that is launching a newsletter, I see on Beehive. So. So it's really cool to just see how their impact is really spread very quickly with, you know, people wanting to go. Right. And have that place to do so.

Yeah, yeah, absolutely. And, Kasey, how do I subscribe to your newsletter?

So I'm. I gotta finish up setting up the domain. It's just listener.beehive.com is the domain. Now. We're getting up the official listener.com newsletter. Should be done here by Friday.

Okay.

All right.

Well, I expect I'll get an invite to this at.

Absolutely.

Because I'm trying to learn more about. About the space. And clearly you communicate well. I'd love to hear what you're saying, and I would love to see an interview with Tyler Dank from Beehive.

So, yeah, no, we're. We'll make that happen for sure. And we'll put it in the newsletter as well. So it's. It'll be a great channel for us.

We.

We sort of jumped over the restaurant aspect. I know we started there, then we went back to the acquisition. But talk to me about the restaurant. I have the name put up here. It's the Coffee Oyster Champagne Cocktail Lounge.

Yep, yep. So let's not call it a restaurant. It's a bar, right? My, my. I mean, we serve great food. We serve great food. But my dad told me I shouldn't call it a bar because people get shot in bars. And it's like, dad, you know, it's like, oh, man, I don't think so anymore. But. So it's primarily a cocktail lounge. And what happened was when I. After I sold my. After I sold audiobooks.com, i spent a year as a venture capitalist. Fund has done extremely well, but I didn't like it. I didn't like being responsible for other people's money. And so I was trying to figure out what to do next. You know, I was gradually shutting down the venture fund, and I had an assistant at the time who was into theater production. And we were talking about this play that we loved in New York called Sleep no More. Any chance you've seen it?

No, I have not. I write it down, though.

Sleep no More, it's an immersive play, and it's been running for, like, 12 years. One of the longest running plays In New York. And it takes place in this giant warehouse with 49 different rooms. And there's like a room that's a psych ward, a room that's a check in for a hotel, a room that's like an outdoor graveyard. And as you walk around people, actors will suddenly emerge, act out a silent scene around you, and then run off into another room. It's next to impossible to figure out what the hell is going on. But it's a cool experience, like just this cool experience. And I said to my assistant, what if we brought that play to Toronto? I'd love to see something like that. Within like 24 hours. I realized, holy shit, there is so much involved in putting on a play. I have no idea, like, there's no way I could do any of this. But one of the rooms was a bar. And it was the coolest bar. It was vampy. It was 1940s Hollywood. And people would come up to you and say, hello, may I buy you a drink? It was just, it was this, this cool experience. I thought, I've always wanted to own a bar. I can't bring the whole play up here, but I can probably build a bar. And I had a friend at the time who had previously done restaurants and bars and eventually it took me a year to talk him into it. And we eventually decided to open this place up. And I was told, you're going to lose money, you're going to become an alcoholic. This is a horrible idea. Don't do it. That place took off, Casey. It, it's a speakeasy. It's a hidden bar. It has a mechanism that's unique. It will compete with any hidden bar anywhere in the world. We have secrets on secrets on secrets. And it was a smash success from day one. Covid interrupted a little bit, but we have one of the highest profit margins of any restaurant because we do a lot beyond selling food and drinks. It's a little bit of a tourist icon now in Toronto. So massive success. I would call that success. Number three, I had two tech businesses that were successful. The bar is my third. And so to me, that's proof that there's something a little bit beyond luck going on here. And so maybe that's why I'm more comfortable with myself now. It's like, I got lucky. There's no question I got lucky. But I've learned enough along the way that I know some principles of business now. So maybe, maybe it'll require a little less luck in the future. I don't know.

That's I would love to dive into that. Like if you, you know, if you're giving your younger self or even aspiring entrepreneurs people that are in the midst of it, maybe they have a growing business, but they're just, you know, it's their first venture, it's growing, but they're just going through it right now. Like what are some of the biggest takeaways that you've experienced? And j. Just throughout, you know, those three successes. And what would you tell your younger self?

Okay, sorry, I get this is something I'm very passionate about, what I would tell my younger self. So I've got two different answers. One is everybody's a bad judge of character. No matter how well you think you know somebody from talking to them or from dealing with them for, for a few hours or a few days, you cannot know if they're going to be a good partner, good employee, good person. So structure your relationships in a way that lets you cut them off easily if you find out that they're not worthwhile. I've had bad business partners, bad friends, whatever, right? And I always waited too long to cut it off staff. I don't think I've ever regretted firing anybody. I've regretted waiting as long as I did. So now my superpower is actually parting company with people at the right time, not, not waiting too long. So I would say that's the skill to get to develop is a skill of wait. You can't tell in advance, but you can tell later on if, if they're cheating you or if they're, or if they're lazy or whatever and part company fast. But the advice I would give my 10 year old self, my 20 year old self, my 30 year old self, everybody, every step along the way. And I got this from Naval Ravikant, right? Where when Tim Ferriss asked him, you know, what advice would you give your 30 year old self? And I, it's just hit such a spot for me was chill out, it's going to be fine, okay? Everything's going to work out. That's it. That's the advice I needed when I was 10, when I was 20, when I was 30, is don't get so emotionally caught up in things, right? You can deal with business failures and your bank accounts being frozen and your wife wanting to get a divorce. All of these things can be dealt with in a slightly less oh my God, the world is ending way you can take, take the hit, say hm, okay, all right, let me digest that for a little bit and figure out what I'm going to do, but you don't have to get caught up in it. Chill out, it's going to be fine. Everything's going to be okay. And so that's the advice. And Casey, you're a lot younger than I am. I don't know if you get emotionally caught up in your stuff, but I'll tell you that right now, it's like, yeah, when you do chill out, man, it's going to be fine.

Totally. No, I, I feel so. I'm 23 for context and I feel that I have a lot more the last like two years. I've been in a serious relationship for the last four years. I'm engaged, getting married next year. And I think as I've really. Thank you. He said congratulations. Like kidding. But no, I think it's like as more responsibilities and I've, as I've grown, I used to sort of look at people like, oh, kind of like having the foresight of like, there's no need to get emotional caught up on things. I would talk. Some might tell that to my parents, right? I mean all these self help books. But then over time I've realized that in myself, like, oh, wow. Like there's moments that I need to recognize and reflect on and you know, do exactly what you're telling your younger self to do to myself now. So I appreciate you sharing that. Very well said.

Thank you. And by the way, I will say like, the reason I said congratulations is, you know, a bad relationship can be, can be a huge drag on your life, but a good relationship, primary partner is what will make or break your life. And I would say that the woman I married in 2007, my wife, now two kids with her, she makes my life so much easier. And the difference between a relationship where every day just feels a little difficult and one where just everything feels a little bit better, it's not that hard to tell them apart. Unfortunately, I had to have the bad kind first before I recognize the good kind. But then I did recognize it and it's been, all my successes have come since I married her.

Wow, that's, that's incredible to hear. I love that. So two kids you said, right?

Oh, I actually have three kids. I have a daughter from my first marriage. She's 28. She's a psychiatrist in Toronto and two kids who play a lot of hockey. 13 and 15 years old. And that's my life.

I remember seeing that actually. So I grew up playing, playing hockey for 10, 12 years in Virginia, so mainly roller, but did some ice as well. And that was like my entire childhood. Like, I picked up a hockey stick at the age of three. That transitioned to lacrosse when I was 12, 13, and then playing football, high school. And that's when I got injured, ended up in a neck brace for six months, and my whole athletic career sort of ended there. They were like, hey, you know, good thing you're not paralyzed. Can't play football ever again. Got to really watch and see what you can do athletically. But granted, I recovered, and I snowboard and I run marathons, and I do all the stuff I want to do now. But hockey was such an impactful part of my childhood that I think they. How does that look in your life in terms of sports and leadership and team building? Did you grow up playing sports?

Yeah, I grew up playing sports. I grew up in a little town in eastern Canada. I was. I went to a high school with 3,000 people, and I was the only brown kid. I had to. I had to integrate. And so it was like, yeah, so I played ice hockey. I played baseball. I did everything that everybody else did. And our household now is a hockey or, sorry, is a sports household. We watch baseball in the summer, hockey, basketball, football in the winter. You know, my older son plays AAA hockey. Going to his draft year, super excited. He's playing with all the people who will be in the NHL eventually. I don't think that's his path, but he wants to play college sports. Hopefully he doesn't get injured. He's a goalie, so it should be less likely. Yeah. And the younger ones really into sports as well. Just not quite as driven. But, you know, for me, the great thing about sports is it's always been about bonding, whether it's with friends or with my kids. But it gives you something to talk about and engage over. That isn't, clean up your room or why isn't your math homework done? And we can say, you know, like, thank God the Toronto Maple Leafs finally fired Sheldon Keefe. I can't believe that guy got another job. Oh, my God. Oh, well. Yeah. So entertaining conversations with your kids. Totally.

No, I love that. Last question before we wrap up here. Sanjay, I always like to end on this idea of what excites you. So moving into this year, years to come, what excites you the most professionally or even personally?

Oh, Casey, we talked about AI a little bit. The realms in which AI is going to help us, and it's going to make life better. I'm just so excited. I'm excited. Like, next month, Apple's going to have its worldwide developer conference and announce whatever they're going to do with Siri and OpenAI. That's super exciting for me. You know, AI therapists, relationships. I don't know what's happening. I don't know what's going to come next. Right. But it's. I feel this is the most energized I've been, most excited I've been ever about technology. And I don't know, like, I have a former business partner of mine, the one I did audiobooks with, who every once in a while he and I talk and say, is there a business opportunity here? What can we do? What can we do? But it's moving so fast. We haven't been able to think of anything that the major players like anthropic and inflection, well, not inflection anymore. But OpenAI, their, their capabilities of their models are advancing so fast that any vertical I can think of, like therapy or something, story writing, anything, gets overtaken by the capabilities of the general system. So I'm just, I'm waiting, I'm waiting for somebody to come up to me and say, hey, Sanjay, what about this one? What about this company? I've made a few small investments so far in the AI space, but haven't. I haven't had that company knock me over yet, so. Waiting for it.

Yeah, I love that. Well, I could say the same. I'm beyond excited. So cool to kind of witness what's going on here. So I completely agree with that. And before we wrap up here, Sanjay, I want to give the opportunity to let the listeners and viewers know where's the best place for everyone to subscribe to the newsletter, follow you on social and just connect with everything that you have going on.

I appreciate the opportunity. Casey. Yeah, you can follow me@ Sanjay says co if you subscribe to the newsletter. From there you can link to all of my socials. I'm everywhere except on X. Because I, I, whenever I log on to X, I get angry and so. But Instagram, YouTube, TikTok, even TikTok, the viral video.

Let's go.

Yes, everybody should watch that viral video. Um, I thought, you know, it's funny, I went, I. Drake came into my bar once and I made an ass of myself. I wrote a story about it. I thought that video of me talking about that was viral with 30,000 views. It wasn't viral. This one's had got about a million on TikTok and about a million on Instagram. That was viral.

So, yeah, totally. Well, I'll definitely have to go check out that Drake video, and I'll be sure to link all the socials down below. And once again, thank you so much for coming on the show today, Sanjay.

Thank you, Casey. This was a lot of fun.