Yes, He Made That Tokyo Drift Track - Then Built a $100M Healthcare Startup | John Fontein

Shamil Malachiyev: Hello, everyone. Today's guest is one of those rare people who's lived multiple lifetimes. From being in the studio with 50 Cent and Christina Aguilera, and writing music with Nicki Minaj and Kylie Minogue, to working on deals at Goldman Sachs, to then having raised over $75 million for his fast-scaling healthcare startup after seeing the cracks in the system firsthand. But this episode isn't about titles or companies. It's about who you become when you lose everything you thought you wanted and realize that the dream you were chasing was never really yours. John Fontein has built, lost, reinvented and reconnected with purpose in a way that most people never do. Today you'll hear about that journey: the depression, the pivot, the break, the heartbreak, the reinvention, and how all of it somehow led to exactly where he was meant to be. John, I'm excited for this one.

John Fontein: What's up, man? I'm excited too. I'm really glad I'm able to share my story with you today.

Shamil Malachiyev: Can we start with: what in your childhood did you think success would look like and feel like?

John Fontein: Man, my childhood. Depends on how far back we're going. I would say there was a pivotal moment for me, you're going to laugh, but in high school, where we had a talent show and I did a rap in front of the whole school. And it was the coolest moment of my life. I did this rap, it was probably terrible, but everybody seemingly loved it. And they were cheering my name afterwards: John! John! That was the biggest adrenaline rush I think I'd ever felt in my life up until that point.

So to answer the question, I think that was the weird childhood trauma moment, if you may, of me thinking: this is what success is. It's when you feel this adrenaline rush of people screaming your name. Whatever career gives me that, that's it. That's success to me. That was the beginning of my pursuit of that weird feeling. I've thought about this. It's a weird childhood trauma that I think has driven a lot of things in my life.

Shamil Malachiyev: What about producing and writing music versus actually performing? Have you tried moving in the performance direction?

John Fontein: No. Ironically, I think that was also the moment I realized: wow, I'm a terrible performer. I never want to do this again. So I was in this weird position of: wow, I love this feeling, but also I'm a terrible, terrible performer. That was, I think, my first and only historical rap performance in my career.

Shamil Malachiyev: How old were you when you started working in music?

John Fontein: I've done music my entire life. I played classical piano, classical violin. High school was the first time I actually started to write my own songs, and then I got really serious with producing, hip-hop beats, in my junior and senior years. I was in New York, and this was the heyday of 90s hip-hop in New York. So I really got into producing beats towards the end of high school.

Shamil Malachiyev: Can you bring us to the moment of how you ended up in the studio with 50 Cent? It's like every boy's dream who wants to go in the music direction.

John Fontein: Yeah, so let me maybe tell you my story of how this all began. I think the punchline to my story is: I'm doing exactly what I want to do, and there's no way I would have ever guessed that this is what I wanted to do. There's a famous Steve Jobs quote: you can't connect the dots looking forward. You can only connect them looking backwards. My life and my career are truly a representation of that.

So let me walk you through how I got to where I currently am. As I said, in high school I got really into music, into producing. I did it all through my first two years at college. And prior to my junior year of college, I came back to my parents' place for summer break. I was living with my parents at the time, and I was just focused on writing music. I didn't really know where it was going to go.

My upstairs neighbor, I'd lived in the same building for the majority of my life, who I'd been friendly with for the last ten years, asked how my summer was going. I told her: great, I was writing music, writing my own songs, producing. Didn't know where it was going to go, but I was hoping it would amount to something. She took interest and said: you should come upstairs. I was in the music industry before. I'd love to hear some of your songs.

So I go upstairs. By the way, this is somebody I'd known for a decade, and I had never been to her house before. She has platinum and gold plaques all over her wall. It turns out she was an early executive at Interscope Records. She was really good friends with Jimmy Iovine. And I was like, wow, this is insane. I'd never seen a platinum or gold plaque in my life. So I said, here's my demo tape that I'm working on right now. And she said: great, this sounds great. Let me send it to Jimmy. I have no idea who Jimmy is at this point. I'm a naive kid in college with headphones, making his own beats.

The next morning she calls, super early in the morning. I probably usually woke up at noon, and it's like 10 a.m., the earliest I'd ever woken up. And she said: I sent it to Jimmy. He loves it. He just loves it, and he wants you to fly out to LA. I'd never been to LA at this point. I was born and raised in Brooklyn. So I said: okay, hold on, Janet, who the fuck is Jimmy? Why do I need to go to LA? What's going on? And she's like: let me explain. Jimmy is Jimmy Iovine, the CEO of Interscope Records. And I was like, oh my God. Of course I know Interscope. This is the Dr. Dre, Eminem, 50 Cent heyday. And she says: I was his business partner early on, and he'd love to fly you out.

So I get on the flight, first time ever, to Santa Monica, and I'm in the Interscope offices the next day. By the way, this is 20-plus years ago, so I might get some of the details wrong, but this is how I remember it. I get to the main Interscope office, and people are pointing at me. Again, I've probably got the details wrong. And I'm thinking: oh my God, this is that feeling I've been waiting for, that high school adrenaline rush. I'm like, dude, I'm the man. I've got this.

This guy comes out and he's like, hey, I'm Jimmy. And I'm like, I'm John. He said: I listened to your tape, I loved it. And I was like, thanks. And he's like: and Curtis loved it too. And I was like, who the fuck is Curtis? And he's like: that's 50 Cent. And I'm like, holy shit, this is serious. And he's like: so we'd love to sign you. It just happened so fast. I'm like: what is going on? I have no idea what I'm doing. And at the same time, I'm still in college, a sophomore, and I was so, so proud that I was attending Princeton University. I distinctly remember telling him, with pride: whoa, whoa, whoa, I go to Princeton, so I can't just drop everything for you, sir. Which was, in hindsight, such a terrible idea. There was this awkward moment where he probably thought, what the fuck is wrong with this guy?

Shamil Malachiyev: Is he joking?

John Fontein: Yeah. But I was so proud of myself for attending Princeton, which, again: who cares? It's such a big regret. I should have just said, I'm in, I'm all in, I'll leave school immediately. But regardless, he says: we've got to work together. There's a 50 Cent movie coming out soon. This was the Get Rich or Die Tryin' movie. And he's like: here's your A&R, here's your manager. Come to the session later tonight.

I have no idea what's going on. This is crazy, but let me go through with it. So I meet with my A&R for the first time at Interscope. I'm like, wow, I need a manager. So I meet with a couple of folks there who would be my prospective managers. One of them is Christina Aguilera's husband at the time, Jordan Bratman. It's a whirlwind of chaos. I go into the studio later that night, and Polow da Don is there, actually with Nelly Furtado, making the song "Glamorous". We were making it for Nelly Furtado at the time. He ultimately changed it and it went to Fergie, but I was in that session. I was like: this is crazy. This is so, so cool. And also: I go to Princeton, so I've got to go back to school and really focus on my academics.

So I walked away from this thinking: oh my God, I have a record deal. I ultimately signed a management deal as well. So I have a manager, I have a record deal. It's that feeling I'd been looking for. I'm the king. I am the man. Nobody can mess with me. I felt so cool. I go back to campus, school starts, and I'm feeling amazing. I'm the man. I have a record deal. What do you have? You have nothing. You just have good grades. I have good grades and a record deal.

Shamil Malachiyev: All the girls are yours.

John Fontein: This is the greatest feeling of my life. I'm the man. It's like, you're having coffee with your friends; I had coffee with Jordan Bratman. It was so bad. But what happened was, I was so high on my own success, which I hadn't even had yet, that I wasn't actually putting in the hours. What I didn't realize at the time was that I had to be grinding, and they expected me to send them song after song to be taken into consideration for this movie. And I wasn't doing that. I was like: I have a record deal. I can send you one or two songs. I'll tell you when I'm done with my music. Not the case at all. And I realize this now, and I have no animosity towards anybody in the music industry or who was on my team at the time. I just wasn't putting in the hours.

Using an analogy from tech entrepreneurship: people make a huge thing about raising money. It doesn't matter if you raise venture funding; you actually have to execute and deliver and build a product. A lot of people celebrate: we raised money, that's amazing, we won. That's just part of the whole journey. You actually have to then put in the work, and that's where the real work begins. I didn't realize that getting the record deal is just the entrance fee. Once you get that, you have to put in the hours. You have to perfect your craft and deliver. Otherwise you're just a decoration on their Christmas tree, and they have a lot of decorations.

So that's ultimately what happened. I just didn't put in the time or the hours. It's also because I was spread so thin: I was doing this music thing, I was at school, I was just spread so thin. Long story short, I get dropped from the label. They shelve all the songs I did with 50 Cent for the movie. Nobody's picking up my call anymore. And I'm like: oh dude, this is over. What just happened? I had everything in the palm of my hands, and it just evaporated. Disappeared. Gone. And at the time, I was young, probably 19, I can't remember my exact age.

Shamil Malachiyev: So you came from the highest of highs.

John Fontein: Dude, the highest of highs isn't even close to describing how good this was.

Shamil Malachiyev: Because this is crazy. This is something a lot of young music artists work years for, like five, ten years, posting consistently to their feeds, writing music, performing on the street, then getting the chance to be seen. And you had that straight away. The opportunity came so early.

John Fontein: All in 18 years. That being said, I had done music my whole life. So in a sense, this was everything my life at the time, I thought, was building up to. I thought this was going to be my career. As I mentioned, I was feeling that adrenaline rush I'd felt in high school. I thought all 18 years were building up to that moment. And it all crumbled so, so quickly.

By the way, when it ends, it ends. It's not like it's slow. Nobody picks up your call. You're done. Full stop. And when people don't pick up your call, it's really over, because then you're just sitting alone in your room with headphones, making songs, thinking: I don't even know who I'm supposed to send this to. It evaporated just like that. So I'm lost. I have no idea what to do. Everything I thought I was going to do with my life has now ended.

And I think the natural thing to do when you're in a dark place is to say: fuck it, let me just do the safe thing. Let me do what everybody else is doing. I thought I was this special star, but I'm not. I'm a nobody, and I just want to do what everybody else is doing. Let me take the safe route. In school, that safe route was either taking a job in investment banking or consulting. So I interviewed at a bunch of places, and I ultimately got a job with Goldman Sachs in banking.

Shamil Malachiyev: Can I just stop you for a second? With all of that situation at that age, what were your parents saying?

John Fontein: They think I'm crazy, right? They think I'm crazy because I'm saying I'm going to be a superstar music person. Then, when I get there, they think I'm crazy because that's all I said I wanted to do, but suddenly I'm not actually doing it. Suddenly I'm saying: well, I've got this school thing going on too, so I think I'm going to do both. And then they also think I'm crazy because, after I was dropped from the label, instead of saying, let me get back up and do it again, I was just knocked out. It's the typical saying: if you get knocked down on your knee, you've got to get right back up and go at it again. But I didn't. I just gave up. I was like: nope, I'm done. I'm on my knee, and you know what? I'm not even going to play this game.

Shamil Malachiyev: So was there nobody who thought: okay, this kid is young, we need to hand-hold him, show him, explain what this is, what he's getting himself into? It's not like you had 30 years of experience in the industry.

John Fontein: No, that's correct, I had nobody. But I also think trial by fire is a great thing. I was in that situation and I had to manage it myself. Had I been hand-held the whole way, I don't even think I would have gotten there anyway, because this was all trial by fire. Let me figure this all out by myself.

But I think the other thing that happened was, I, and a lot of driven people, are super, super competitive. I was super competitive in trying to get this deal. And the moment I decided I didn't want to do music anymore, I got super competitive about the next thing, which was to get a job in consulting or finance. Which, by the way, I couldn't care less about. But it was just that rush of: I don't want this guy to get the job ahead of me. The competitive instincts kick in. And I realize now, looking back at my life, that so often I was competing in somebody else's game rather than playing my own game. In this instance, I just got really competitive and thought: I need to bust my butt and get the best job at the best firm, because I'm competitive and I want to feel that silly adrenaline rush again.

So I start my career at GS. This is, by the way, 2008. So it's during the financial crisis. I had no idea. I'm not a finance guy. And the world is ending, as you probably remember. Companies are going down. I literally start my career as there are layoffs happening at the firm, and Lehman Brothers is shutting down, and people are walking out with cardboard boxes, crying. But I have no idea, because I've never done this before. So I'm like: I guess this is what finance is like. Everybody cries. There are layoffs happening every day. God, this is terrible. This is brutal. And I'm thinking: I can't not work, because if I stop working, I might get fired. So there was this weird moment of: I've just got to work every day. I can never stop working, because I don't want to be the loser that gets fired. So I'm just going to work every day for 20 hours. Because I think this is what happens in finance on a daily or weekly basis: mass layoffs.

Anyway, so I'm in this job. I shouldn't say silly job, it's a great firm, but I'm terrible at the job. And I take my first vacation with my parents to go to Japan. That's where my family was living. We're on this flight, and my mother sits down next to this kind gentleman. She's a very sociable person, so she starts talking to him. It's a 12-hour flight, so there's nothing to do. Once you start talking to somebody in hour one of the flight, you're kind of stuck talking to them for the next 11 hours. And he says: you should come to my show tonight at the Blue Note in Japan. And she's like: great, I'd love to. And I'm like: dude, I'm tired. I don't want to go. This is my one week of vacation from work. I don't want to go see this random guy's show.

Anyway, we go. It's a great show. We meet him backstage, and then he says, and he asked me, not my mother: I'd love to grab coffee with you tomorrow. I'm like, what the fuck, I don't want to grab coffee with this guy. But the next day I go and grab coffee with him, and he tells me: hey, your mother on the flight told me that she's so sad. Once she learned I was in the music industry, she told me you, John, used to be in the music industry, and she's so sad watching you every day squander your talent, not doing what you're supposed to be doing. She asked me on the flight, while you were sleeping, to see if I can help you. I'm actually with Universal Japan. Is there anything I can do? Do you have a demo tape? I'd love to hear it.

Of course, at this time I always have a USB stick, or a CD at the time, of my songs. So I'm like: here's a bunch of stuff I made a couple of years ago that you can listen to. And then, again, this is how I remember it, it probably took a couple of days, but the way I remember it is: the next day, he calls me and says, can you please come to the Universal Japan headquarters? So the next thing I know, I'm meeting with the CEO of Universal Japan, Ken Oyama, and he's saying: we listened to your tape, we loved it, and we want to sign you. It's the exact same thing that happened with Jimmy. And I'm like, what the fuck? I was not thinking about any of this at all. But then that adrenaline rush came. I'm like: holy shit, wait a second. I am the man. I could do this again. I doubted myself, but I'm the man.

Shamil Malachiyev: All of the doors are closed in the US; I should have just tried a different country.

John Fontein: Exactly. So now suddenly I'm like: dude, I'm going to be big in Japan. I can do this. And so, exact same thing. He's like: meet your manager, let's go into a studio session. That night I go into the studio with a group called the Teriyaki Boyz, who I ended up doing a lot of work with. They're pretty famous for some of the songs we did for Fast and Furious. I meet Nigo, the founder of BAPE. I meet Verbal, the founder of Ambush. And I'm now part of that squad. I meet Wise, who's part of B.A.P.E. Sounds. And now I'm making music for these guys.

Shamil Malachiyev: And you're still working at Goldman Sachs.

John Fontein: Correct. So then I come back to GS, and I'm like: dude, you guys don't even know what I've been through. They're like: how was your vacation? I said: it was okay. It was good. They have no idea. Because you're not allowed to do two things. I think things have changed in finance, but at the time, you had to disclose if you were doing something else, and I was like: I can't tell anybody about this.

Shamil Malachiyev: You have to spend 23 hours working, right? Goldman Sachs is very high intensity.

John Fontein: Correct. You're literally not allowed to do anything else. Again, things have changed a lot, but this is 2009, 2010, post-financial-crisis, and I get it: they want everybody fully committed to making sure the firm doesn't go belly-up like so many other firms. So I can't tell anybody. And I am living this secret agent, double agent life. During the day, I started a little late, but from like 10 a.m. to midnight, one or two a.m., I'm at work. By the way, while I'm at work, the iPhone had just come out, and I'm texting with Nigo and Verbal and all these guys in Japan. I have a manager in Japan at the time, and I have headphones in: send me the latest mix. I'm listening to it during the day. And then from two to 10 a.m., we used Skype, which was the big thing at the time, and I was in Skype virtual sessions. I'm not kidding you, I don't think I slept at all for a good year. Zero. Because I was so energized and excited about doing this.

So essentially, for that two-, three-year period, I was writing and producing songs and sending them to my manager in Japan, who was distributing them to Japanese artists. And we saw a tremendous amount of success in the Japanese market. We had multiple number-one hits. We had a couple of albums go multi-platinum. We had some go gold. I did a bunch of songs with the Teriyaki Boyz. And then what happened was that some US artists who wanted to break into the Japanese music scene pinged my management team and said: do you have any songs for us? So I was fortunate enough to do songs with a bunch of US artists. I did a song with Nicki Minaj called "Change". I did a song with Kool Keith that was never released. I did a song with Tyga that wasn't released. And I was like: wow, this is kind of crazy. I don't remember exactly how old I was. It was all a blur. Mid-twenties.

Actually, I can tell you exactly how old I was, because of the year. I was 26. In 2011, there was an earthquake which ultimately led to a tsunami in Japan, the Tohoku earthquake. It was a terrible, tragic incident. Almost 20,000 people died. It was a terrible tsunami that affected the Tohoku region of Japan. When that happened, I got a call from my manager saying: hey, Kylie Minogue reached out, and she's been asked by UNICEF to do a charity song for the victims of this Tohoku earthquake. At the time, I was writing a song for Calvin Klein, for the fragrance CK One. So I said: we have this song we've been working on for Calvin Klein, the CK One song. I can repurpose that. Instead of "CK One", I can make it "We Are One". And he's like: let me propose that to the Kylie team.

This is all happening so fast. The earthquake happened on March 11. By March 12, a day later, I was on a Skype call with Kylie. Never met her in person, by the way. And we said: great, let's do this song. We've got to put it out right now. So we quickly changed the vocals from "CK One" to "We Are One". And "We Are One", the Kylie Minogue song, became the official UNICEF charity song for the Tohoku earthquake. This is such inside baseball: if you listen to the backing vocals, that's a demo track I made with a friend of mine, because we didn't have time to fully record some of this stuff. A lot of the backing vocals are actually the demo vocals I recorded with a friend.

So that was a wild, wild time. And I thought: wow, I'm working with these big US names, I have a ton of success in Japan. But from a pure financial perspective, I'm not making as much as I thought I would. And to come back to your question, what did success feel like: now I'm 26 or 27, and I'm naively thinking success is not only the adrenaline rush but also the money. I just want money and fame, which is the dumbest thing, but in my defense, a lot of 26- or 27-year-olds think that. So I was like: I'm not getting paid enough. I need way more money.

And the way to do that, I thought, was to own my own master records. To actually control the distribution and own all my masters. So I thought: I'm going to branch away and start my own label, because I have a name in this industry in Japan, I have a bunch of songs already, and I have artists I can sign pretty fast. So I did that. That was my production company, Relabel. Sure enough, I was able to sign the artists I wanted. The first album we put out goes number one on iTunes. And I'm like: fuck yeah, I'm going to be rich.

What I didn't realize was all the stuff that other teams had been doing now fell upon me: administering rights, dealing with the intricacies, the personnel issues. And I still had to work at GS. I thought you just make a song, you put it out, it goes number one, you make money.

Shamil Malachiyev: And you still had to work at Goldman. Jesus.

John Fontein: Obviously that was naive. There's so much that happens behind the scenes: negotiating points, talking to the labels to understand distribution, working with the artists, who are creative beings who need a lot of hand-holding. And this was just so, so much for me. By the way, a lot of the discussions I was having at the time, I thought were handshake agreements. A lot of them didn't come through. I thought the moment we had a number-one record, which we did, that's it, we've won. But that wasn't the case. So once again, I'm in this weird position where I'm like: wow, this actually isn't as big a success as I thought it was.

Shamil Malachiyev: Can you explain, for people who don't know much about the music industry: once the song goes number one, we kind of assume you just get money sent to your bank from Apple Music and everything else.

John Fontein: Well, you do, through royalties. But before that, you have to negotiate the points and the splits you're going to get on each song, which is sometimes contentious. For each song, frequently there's not just one writer and not just one producer. There are multiple writers on any of these songs, and every writer gets some points, percentages of that song. You might think your contribution is 50% of the whole song, and therefore you're entitled to more points. But another writer might think: well, well, well, I deserve 50%, you deserve 10. Previously, my manager was doing that whole negotiation on my behalf. But now, because I owned everything, I had to do all of this. And at the time, I'm still 26 or 27, and I don't think I had fully developed proper mechanisms to deal with stress. The stress was just piling up and up and up.

And it impacts what you put out, because I'm thinking: okay, I'm probably not going to get many points on this song, so I'm not going to put much time into it. Let me just ship it out. But this one I think I'm going to get a lot of points on, so let me put time into that. Which is terrible, right? As an artist, what I should have done was just focus on the craft: make the best song possible, not care how many points I get, because ultimately, if the song is successful and I keep putting out hit after hit, I'm going to make it. Very similar, by the way, to tech, where you shouldn't worry about competition or the amount of money you raised. If you just build a 10x better product, your customers will come. They'll use your product, they'll love it, and then you can build a real business. I didn't realize that. I just thought: I can get more money here, less money there. Let me focus on making the most money without paying attention to the craft.

So all this is building up: the stress of negotiating these deals, artists complaining to me. By the way, I was so busy dealing with my existing artists that I couldn't even sign new artists.

Shamil Malachiyev: Did you have anyone advising you at the time?

John Fontein: I had two employees at the time. This was all bootstrapped. We're just struggling, hustling. We still had a portfolio of records, and administering them takes time. So ultimately, what I decided was: I think we've got to get out of this business. At least I thought that. I don't like this at all. And once you start to think that way, every day you wake up, there's this huge weight on you. The feeling just intensified: wow, I hate this. It got worse and worse and worse.

So I decided: I have to get out. I don't want to burn people, so I have to make something of this. I want to sell this and get out clean. From then on, every single moment, once I decided that, was: this is over. I don't want to do this, but I don't want it to go to zero. I just need to sell this. So I figured out: what am I going to sell? I've got to cobble some parts together. I have these distribution rights, I have these artists. Let me package this and find a buyer. Any new opportunity that came in, I can't even remember, because I was in such a dark spot, I just said no to. Which was terrible. In hindsight, I should have said: hold on, let's consider that, because maybe we have a shot. But I had just given up. I'm like: I'm out. I'm done. It doesn't matter if there's another shot. I just want to get out of this business.

I ultimately was able to find a buyer for the distribution rights to my portfolio of songs. On paper, it's amazing, because everybody's like: wow, you sold your business. In reality, it was an okay outcome for me, specifically from a financial perspective. The joke I always tell is that it provided me with enough money to allow me to take out a jumbo mortgage to buy my first house. In that sense it was good, but it wasn't the "wow, I never have to work again". It was: because of this sale, I can now take out an inordinate amount of debt from a bank to buy a house.

And from an emotional perspective, it was: what the fuck am I supposed to do now? I've had two ups and downs with the music industry. Do I really want to do this again? That was a real emotional low. And at this point I'm thinking: okay, I've just spent 28 years of my life in and out of music. Why am I doing this? Do I actually want to do this? Or am I only doing it because, candidly, my parents taught me piano and violin, and I'm kind of doing it because I think they want me to do this? I don't really think I want to do this. That was the first time I asked myself: what do I want to do? As weird as that sounds.

If you think back to why I was doing that in Japan: it was because my mother reached out to that guy and said, can you please help him? I, his mother, feel so sad looking at him. And I didn't want her to be sad. That's why I said, I'm going to do it again. When I think about the Interscope Records thing: I was writing my own songs because I had done classical piano and violin my whole life, because they wanted me to do it. Not because I was like: I love music, I want to do this. And I don't blame them. It's amazing. They pushed me. But it was the first time I thought: I don't actually think I want to do this. Which is such a weird thing to say, because I had the gift and the skill to do it. But it doesn't matter if you don't actually want to do that thing.

Shamil Malachiyev: Did you feel like all of the motivation you had within you, that allowed you to juggle Goldman Sachs and Relabel and all of these night-day cycles, was because you had that fire trying to prove that you can, to your parents, to your mother specifically?

John Fontein: I think that's a huge part of it. And side note, I'm an only child, so all the pressure was on me. But it's not just my parents. If you think about why I did Goldman: it's because I wanted to compete with my friends, who were all doing this too. It was just extrinsic pressure and extrinsic validation that I sought so deeply. I wanted validation from my parents, that they didn't waste all the time and effort giving me private lessons growing up. I wanted validation from my friends, that I'm as capable and smart as they are, as evidenced by getting a job at a great employer. There was nothing intrinsic about any of my motivation. It was all seeking external validation, which, for the first time, as a 27-year-old, I actually realized.

Side note, on the note of validation: I also yearn for competition, and, this is so weird, at the time I sought vengeance. I had a literal folder in my inbox called "shitlist", and any time somebody would email me with some modicum of rejection or disbelief, I would immediately categorize them into the shitlist. I'm not kidding you. And I'd think: I'm going to go through this folder, and when I make it, I'm going to email all of them: I made it. You were wrong about me. Thinking back on it, I'm like: dude, who cares? Of course you get rejected sometimes. They don't even know who I am. But so much of it was driven by this extrinsic nature. I should screenshot and share the shitlist with you. I still go through it sometimes just to laugh, because the rejection emails are not even rejection emails. They're like: we don't have time at this moment, but thanks so much for reaching out. And I'm there thinking: this is going on my shitlist. I'm going to get you.

Shamil Malachiyev: So you took that personally, as if your self-worth was at stake.

John Fontein: Correct. And so, for the first time, I'm like: wow, this is embarrassing. I have no internal motivating factors. I don't really know what I want to do. So I took time to really think through what I want to do.

Shamil Malachiyev: How long did it take you?

John Fontein: Here's the punchline: it's not like after a month I knew what I wanted to do. The punchline is, I had no idea what I wanted to do. Which is not uncommon, by the way. At the time I'm 27 or 28, and if you're in your late twenties, you've done the whole system. It enticed you into college, you started your career, you're four or five years in. Talking to a lot of folks around this age, I think it's very common. You're suddenly out in the big ocean with no idea what you want to do. You've been following the rules the whole time, and then it's: okay, what am I supposed to do with my life? I had that as well. Mind you, I'm still at Goldman this whole time.

Shamil Malachiyev: Did they have any idea?

John Fontein: They had no idea. And by the way, they had no idea I was going through these emotional swings, from total depression to super high to total depression. I'm still at Goldman. It's weird: John used to have headphones in his ears at all times, but now he doesn't even have his headphones. That's probably what they thought, because I'd just stopped doing the music.

So, ultimately, what happened at GS: my boss at the time says, hey, we're going to fire the partner on the team in the London office. Partners are the most senior people at GS; there are only around 400 of them. And I'm a senior associate at the time, a nobody, basically. She says: one of you four needs to go out to London for two weeks, because we're going to fire him on this day, and I need one of you to make sure that when he's terminated, there's still some continuity with his clients. You've got to go through his inbox, make sure you reach out to them, because he's going to have client meetings, and make sure we don't drop the ball on anything. And being client-facing is a big thing at GS, because you're representing the firm in front of clients.

I just raised my hand: I'll do it. I'll go to London. Because I'm searching for some reason to exist, for what I'm supposed to do. In general, I just raised my hand for a lot of things, because I think: what's the worst that can happen? I have nothing anyway in my life, or so I think. The worst case, it's a shitty experience. Best case, I've got a great bar story to tell friends.

So I go to London under the pretense that this guy's about to get fired, and I just need to man the coverage until the next partner comes in. Sure enough, the guy gets fired. And then it turns out he has a meeting the next morning with a big client. And I'm like: fuck, they don't have the backup in yet. I'm a little 27-year-old shit. And I say: you know what, I'm just going to go into the meeting, and I'm going to pretend like I run the team. I don't know what compelled me to do this, but I go into this meeting, and the guy's like: who are you? And I say: oh, I'm John. I'm head of the London team, of the EMEA team. He's like: okay. And I'm just like: fake it till you make it, baby.

At that point, I just convinced myself: I run this team. I'm the partner. I'm not, but I just convinced myself. I run all of Europe, Middle East and Asia for my team. That's me. I just play that role, and it turns out I'm very, very good at it. So what was supposed to be a two-week trip becomes six months, and that becomes 12 months, and that becomes 18 months. I ultimately just did that role for 18 months. And I'm like: wow, I'm good at this. Specifically, what I was good at was understanding these clients' needs very quickly and figuring out which pieces I needed to bring in to help them accomplish what they wanted. Because I knew I wasn't actually good at finance, but I was very good at figuring out which pieces to bring in for these clients.

Shamil Malachiyev: And looking back, could you say you'd replaced having to prove something to your parents with taking on an amazingly complex task to prove something to the partners within the company?

John Fontein: I think so. And it was also the first time somebody other than my parents believed in me. I had a manager at the firm who actually believed in me and gave me an opportunity. Nobody's going to risk their reputation on somebody with only one or two years of experience, but this person was willing to risk her reputation on me, somebody who now had five or six years of experience. By putting me in these situations, by allowing me to potentially embarrass her in front of clients: I never wanted to let that happen, because she actually believed in me. This was the first time somebody in a professional setting was willing to take a big risk on me, and I wanted to reciprocate.

There's a quote, it's now my favorite quote, that I really believe in and still embody to this day, that the famous philosopher LeBron James once tweeted: when you stop working hard, you disrespect those that believe in you. That was really my mantra going into this. This person believes in me. I don't want to stop working, because I don't want her to feel disrespected. So it wasn't just fake-it-till-you-make-it. Initially it was, but then it became: okay, now I've faked it. I actually have to learn this. I actually have to be good at this craft.

And that's all I did for 18 months. I lived in the office. People who worked with me and knew me at the time will laugh, because I'm sure they'll remember. I slept under my desk. The lights were always on in the office, so I had to tie my tie around my eyes as an eye mask. I literally never left the office. 160 hours a week. I actually know that's how much I worked for six months, because I was pulled in by HR, who could see when you came in and out of the office with your prox card, and they had to tell me: you've got to leave the office. Because they could see I would never, ever leave.

And that was amazing. What I also realized was there was a ton of growth, both at the company and internally. I no longer thought: what am I supposed to do? I was growing as an individual, I was seeing success. The feelings of "I only have so much time to figure out my North Star" went away. They were replaced by: I really enjoy what I'm doing, I'm really good at what I'm doing, I enjoy the people around me, they're pleased with my work. I was learning a ton, and I really enjoyed it.

Shamil Malachiyev: Did you have a plan for moving up in the corporate world? Partner, managing director?

John Fontein: No plan. Just living in the moment: I'm really good at this, I'm going to do this, that's all I care about. I didn't know if I was going to be there a long time, but I didn't yearn for leaving. I didn't yearn for the next thing.

All of that changed when I was sent on a due diligence trip to Berlin, Germany, for due diligence on a company that Goldman wanted to invest in. The team I was on at the time was making investments off Goldman Sachs' balance sheet. The team was investing in incredible tech companies at the time: Uber and Airbnb and Spotify and Dropbox. They couldn't miss, not because of me, but because of the other, smarter people on the team. And they wanted to send me to Berlin to meet with this founder who was starting this travel company. He was this hotshot. I met with him, and he explained his vision to me. And I thought: wow, I've never really traveled a ton, and I love what he's saying. Maybe travel is the thing I could get really into.

Long story short, I never came back from that due diligence trip. I just stayed in Berlin. Goldman ultimately did invest in the company. I was supposed to go back to London, and I pinged the founder of the company and said: hey, are you guys looking for somebody to join? I'll do this. I'll join your company if you're looking to hire. We went for a beer, and he's like: are you serious? And I was like: yeah. I don't need to go back. I'll just stay and do this.

I think what I also realized was that it was my nature to move fast on things. I'd learned that from the music industry: if you're in the studio with an artist, you might never be in the studio with that artist again. So your immediate instinct is: let's just make a song. Let's do this right now. My default was speed. Say yes, and then think about the consequences next. When they asked, does anybody want to go to London? I just said yes, and thought about the consequences next. Here as well: I just told him I'll do this, and then thought about the consequences. Specifically, the consequences were that I had no place to stay.

Shamil Malachiyev: Exactly, because you had rent, gym membership, stuff at the office, everything in London.

John Fontein: Yeah. So I've got to figure this out. I was there with a suitcase for probably two weeks. I have pictures of me with plastic bags, figuring out what I'm doing there. But what eventually happened was I left Goldman and joined this company called GoEuro, it's now called Omio, as one of their first hires on the business development team.

My job at the time was to reach out to train and bus companies across Europe to get their data, their timetables, their fares, so that GoEuro would be able to sell tickets for them. Most of these train companies were state-owned, monopolistic train companies that had never shared their data with any third party in the history of their existence. And suddenly here I came, a naive, wide-eyed 30-year-old, saying: hey, give me your data and we can sell tickets for you. But again, I was really, really good at faking it till I made it. I just pretended like I was the train expert, the travel expert. And sure enough, for the first time ever in these companies' histories, they agreed to share data with my company.

And I was like: wow, this is awesome. I'm learning about travel, I'm really good at this job, and I'm traveling, because I had to go to all these European countries to strike deals with these train operators. I'm seeing the world. I'd been in New York and Japan, two beautiful, incredible cities, but those were really the only places I'd gone. As I started to travel through Europe, I would go to so many small cities, to strike deals with the local bus operator or the local train company. And I would see life like I had never seen before. I'd go to the smallest villages in Eastern Europe, in Poland, in Spain, where there's one bar, and that's where everybody goes to watch the one game. And people would have a Biggie Smalls shirt on, and I'd be like: wow, they have no connection to New York, no connection to Biggie Smalls. This is their life. I'm so fortunate. I have everything you could ever ask for: an amazing career and life in New York, an amazing experience in Japan. These people would die to have a tenth, a hundredth of what I've experienced. And yet I'm complaining: oh, what is my life? What am I doing? Woe is me. It gave me such an appreciation for how fortunate I was.

Shamil Malachiyev: And did you notice the difference in the grit, the pace at which people move? You went from a super-high-speed work ethic to working in Europe, and as everybody in the US always says, Europe is kind of slow, relaxed, doing things its own way. Did you notice differences in the way you like to work?

John Fontein: Yes, actually. And it's a reason why I decided I wanted to start my own company. I'm always going 120 miles per hour, and I still did that at this company. I would work every single weekend. There is no work-life balance for me. It's all one complete mesh: this is my life. I love to work. I love to go out as well. But I'm doing everything all at once. And I wasn't seeing that in other people. To some extent I was seeing it in the founder. But I thought: if I'm still working 140, 160 hours a week, why am I working on somebody else's vision? I should work on my own vision again.

Now, that decision is not an easy one, because there's this trauma in my mind: wait, wait, wait. Last time I did that, I had this terrible experience with Relabel. The outcome wasn't bad, it's just that I remember all those emotions. So it took a lot of convincing myself that I should actually do this again. Because I've already seen what that looks like, and I hated it.

So this time I decided: before I do this, I should ask my friends, my smarter friends, what they think, rather than going at it all by myself, trial by fire, with no mentorship. I kept pinging my really good friend Mike, Mike Botta, who is now a co-founder at Sesame. He was my college hallmate, and we were great friends throughout college. He calls me his best friend; I call him my sixth-best friend. I immediately knew: this guy is smart. So I would call Mike: dude, I want to start a company. He was one of my groomsmen, truly, jokes aside, one of my best friends. And he knew all the challenges I'd had selling Relabel and the experiences I'd had building it. So I told him: I want to do this again, but I don't want the same thing to happen to me. Talk me through this.

And a couple of things I realized as we kept talking: I wasn't successful at Interscope, and I wasn't successful at Relabel, because I was doing two things at once. I was doing college and Interscope. I was doing Goldman and Relabel. I realized: I've got to do one thing. I can't be spread too thin. If I'm going all in, I'm going all in.

And the reason I did two things at once was because you see and idolize the people who are seemingly doing multiple things at once. At the peak, you have Elon Musk, who has 19 companies. And even short of that, you have all these people on Twitter saying: here are my six side hustles, each making 100K. So I always thought you're supposed to have a lot of things you do at once, and you hustle and make them all a success. This was also the heyday of influencer marketing, where you see people saying: I travel, and I have a job, and I have these amazing side hustles. And I'm like: if they can do it, obviously I could have four businesses at one time. But now, for the first time, I'm thinking: maybe not. Maybe if I'm actually going to be very successful, I have to do one thing and only one thing. And when I thought back to why I was so successful in London at GS, and so successful in Berlin, it's because that was the only thing I was doing. I'd stopped doing music. I was only focused on banking, then only focused on GoEuro.

So I realized: I've got to go all in. I can only do one thing, and that's all I'm going to do. And if I'm not successful, it's okay, because at least I didn't spread myself thin. And I quit the job without knowing what I was going to do next, to force myself to figure out what it was going to be. I left Berlin. It was an amazing experience.

Shamil Malachiyev: Did you have enough cash saved up until that point to be able to leave? How much runway did you have?

John Fontein: So the company did tremendously well. But I probably had like three months of runway. I'm very crafty, though. I'm a total hustler. That's probably for another time, but I've slept at a train station for a month. I'm just a hustler, is what I realized. I figured out that I had a great credit score, and that if I could open up a bunch of credit cards, and Venmo at the time charged no fees on credit-card payments you would make to one another, what I would do is pay my wife with one credit card on Venmo, and then she'd deposit that money into my account. And then, when that credit-card payment was due, I'd pay her on a separate credit card with a different due date, in order to pay back this one.

Shamil Malachiyev: A loop.

John Fontein: A loop, yeah. I mean, I have spreadsheets. I knew exactly how much money I had daily and exactly when I had to pay off the previous credit card and when the next credit card was due. I had like 40 credit cards open at this point. Brutal. I don't wish this on anybody.

So I go back to New York. I'm talking with Mike to figure out what company I want to build. Mike, my smartest friend: tell me why I shouldn't build this idea or that idea. I had a couple of ideas, and they were all surrounding consumer, because I'd just had this experience in the travel industry, which was consumer-facing.

Shamil Malachiyev: Do you remember some of those ideas?

John Fontein: My wife was pregnant at the time, and she had a lot of questions about first-time pregnancy. I wanted to do something around a social network where expectant mothers could exchange ideas about pregnancy, which I still think is a cool idea. She was also shopping: what's the best crib? What's the best stroller? So I thought: what about a marketplace where you aggregate the best products based on your demographic, and you earn affiliate revenue on that? That has since launched, and I still think it's a good idea. I was also thinking of a direct-to-consumer stroller that was way more effective than some of these super-high-end ones, because it was all complicated to me.

Regardless, Mike would shoot down every idea I had. Rightfully so, because as I'm explaining them to him: these can't scale. And he kept saying: don't do those terrible ideas. Do my idea, Mike's idea, which was this healthcare marketplace. And I was like: stop there. I don't know anything about healthcare. I don't want to touch healthcare. I don't want to hear your shitty idea about healthcare. Healthcare is scary. Listen to my idea about this travel stroller. And so we went back and forth for about six months.

After that six-month period, I still didn't have the idea. So I actually thought: you know what, I'm not going to do this, because I don't have the idea that I want. I have a pregnant wife, and I don't want to repeat that terrible experience I had at Relabel. So I'm going to get a job. I had great success at this travel company, so I'll get a job. And again, super competitive, I hustle my way out there and get a job interview at a company in San Francisco. So I fly to San Francisco, and I'm in this interview, their last round, meeting the whole team for four or five hours.

I come out of the interview, and I have 20 missed calls from my wife. I call her back: what's going on? Is everything okay? It turns out she'd gone in for what she thought was going to be a routine checkup for her pregnancy. And it turns out that our child, it was a girl, had something really bad, which was a microchromosomal deletion. She was 20 weeks pregnant at this point. The doctors said: we're so sorry. She had this abnormality where she was missing a microchromosome, which could lead to autism, could lead to death. And the doctors said: you still have four weeks to decide whether you want to terminate this pregnancy, because the risks are too high for this child.

I distinctly remember this phone call, because I distinctly remember being in San Francisco, just walking around thinking: what the fuck am I going to do? This was supposed to be the best moment of our lives. And now I'm on the other side of the country from my wife, who's crying, bawling, obviously, because the doctor has just told her: you have four weeks to decide if you want to terminate. It's literally a ticking time bomb.

I call Mike, right? That's my sounding board. Mike's a PhD as well. And I'm like: Mike, tell me how bad this is. What am I supposed to do? He doesn't know, because this is a very rare thing. But I'm talking through it with him. I come back to New York, and from then on, we have four weeks to decide what we're going to do with this pregnancy. We're going in for these visits with the doctors. They don't really have answers, because so much of medicine is unknown, and a lot of it is fear-based too. I'm going on these forums to figure out the implications, and it's also unknown. Some people are like: I terminated. Others are like: no, I didn't, and I'm really glad I didn't. It's all unknown. And that's healthcare, right? So much of healthcare is unknown.

Added to that, there were a couple of articles saying: if you can get the right care for the child, even in the worst case of this microchromosomal deletion, you can get treatment. But you have to have good coverage through your employer, because a lot of the required treatment is not actually covered by insurance. And I'm like: what the fuck does that mean, not covered by insurance? If this is happening to your child, everybody should be able to get this treatment. It turns out that's not the case. Some of these treatments are really expensive. So the people who can't afford the treatment will ultimately have a child with very bad symptoms, or they'll terminate, because they don't think they can afford the proper care. I'm reading these terrible, gruesome posts on Reddit and thinking: why? This makes no sense. Everybody should be able to seek and receive this treatment for their child, and yet some people can't, because it's not covered through their insurance plan.

And I'm also thinking about my own experience, where I'm going into these doctors' offices for a ton of procedures, and nobody has told me the price of any of this. I'm just walking out. Mind you, I'd never really had interactions with the healthcare system. I'd lived in Europe for a while, so I didn't know how convoluted healthcare is. But I do know we're going to a ton of appointments, and nobody has sent me an invoice or a bill yet. And I'm like: am I going to be able to afford this? Obviously I want to save my child. It's the most important thing to me. How much is this costing me? I had no idea.

So, for the first time, I call Mike and say: yo, Mike, tell me about this healthcare idea you have. I'm now curious. He starts to tell me about it, and it's all clicking, because everything he's describing is everything I'm experiencing with my child and everything I've read on Reddit and these posts. And it's funny, in these key moments, you remember exactly where you were and exactly what happened. I was getting my LG OLED TV installed, and there was chaos in my house. And I called Mike and said: come right now, because I want to do this with you, and I want to talk with you about this. Sure enough, he showed up 30 minutes later. There are people drilling holes in my wall to install the wall bracket. I remember it in vivid, vivid detail, saying: I want to do this with you. Let's do this. Just like I remember the exact chair I was sitting in at Jimmy's office, I know this exact moment where I told Mike: I've seen enough to realize that what you're describing is a problem. I want to build this with you.

That was the moment I decided I was going to be a healthcare entrepreneur. Because this problem, I saw firsthand. It happened to me. I was reading deep, dark posts about how it affected others. This was what I wanted to do with my life, for my daughter. Side note: we were able to get the treatment for her. She's fine now, because we were able to get this treatment. Everything is fine.

And I can get into Sesame, the business we ultimately created, but I wanted to first come back to what I started with. You can never connect the dots looking forward. You can only connect them looking backwards. I'm doing exactly what I want now. I am building a healthcare product that helps people with real, real needs, that allows them to get care they otherwise wouldn't have gotten. It's everything I wanted to do. I love it. I wake up every moment thrilled.

Let's walk backwards. If I hadn't been dropped from Interscope, I would have never worked at Goldman Sachs. If I didn't work at Goldman Sachs, I would have never taken that one-week vacation to Japan, where I met the Universal executive and ultimately signed. If I didn't stay at Goldman after I sold Relabel, I wouldn't have had the opportunity to go to London. If I didn't go to London, I wouldn't have gone to Berlin to meet GoEuro and join the company. If I didn't have that experience at GoEuro, I would have never had the bug to start a consumer-facing tech company, a marketplace. And you can go even further back: if I never went to Princeton, I would have never met Mike. Ultimately, everything connected. All the dots connected to this moment where Mike and I decided: let's build this company. At any step of the way, had I done something different, I probably wouldn't have been here. So truly, you cannot connect the dots looking forward. You can only connect the dots looking backwards.

Shamil Malachiyev: But when you get all of these opportunities thrown at you at all these different times in your life, how do you know to trust the universe and say: I should go for this. I should take this.

John Fontein: I think very early on, I had no idea. I was just going with momentum. And that's why I made a lot of bad mistakes, because it was just momentum, momentum, momentum. Over time, I really learned to trust my gut. Let's come back to, again, it's a fine story now, but that four-week period where the doctor gave my wife and me the option to terminate. You could apply the question there. How do you know? It's terrible. It's literally a life-or-death situation. How do you know whether or not you're supposed to terminate a child? You don't, right? You have to go with your gut. And ultimately, we, as a team, went with our gut. We wanted to raise this child. As I said, everything is fine now. We're so fortunate and blessed.

But I've learned over time to really trust the gut and go with it, because ultimately, you know yourself. Now, your gut is often wrong. But most times, there's a reason why you trusted your gut, and oftentimes those things ultimately enable you to be successful at whatever choice you made.

Shamil Malachiyev: What do you think are the main lessons you've taken from your early failures, the downturns? What are the lessons that helped you?

John Fontein: I think the one thing you learn after having a lot of failures is, it's just a classic saying: when you get knocked down, you've got to get right back up. In entrepreneurship, that is the norm. You're going to get rejected more often than not. Things are not going to work more often than they are. You're going to get knocked down more often than you're doing the knocking down. The key is: you're never knocked out. As another famous philosopher, Allen Iverson, said: same fight, different round. That's how I feel. You just keep fighting. You keep showing up. You put in the hard work, and then great things will happen.

In general, my pain tolerance has gone up tremendously. I think the reason I ultimately gave up in music was that I didn't have that pain tolerance. I hadn't experienced rejection to that degree. But now I have. So when we go to investors, or partners, or employees we're trying to make an offer to, and they say no, they reject you: that's fine. Move on. Move on to the next fight. Old me would have categorized them in my shitlist inbox, first of all. I'm kidding. But old me would have been knocked out at that point. Old me would have said: I can't do this. I hate this. Now, you wake up and you assume that nothing is going to work, and it's your responsibility to make it work. It's your responsibility to fix it.

And that's not just rejection from investors or prospective employees or partners. It's even with our product. We launch products that we think are going to work, and frequently they don't. Frequently our customers don't end up using it. And that's fine. Your expectations were dashed, but you just keep going. Iterate, fix it, make it better, launch it again. Maybe it doesn't work again. Fine. Keep going, keep making it better. At some point, you start to get to something that works. So I think that's the big lesson: don't get knocked out. Getting knocked down is fine. Just get right back up and keep going.

Shamil Malachiyev: I think the main problem for a lot of founders is generating that self-confidence, which comes from self-belief. If you don't have anyone actively believing in you and telling you: don't worry, you can do it, then you're stuck with only the voice inside your own head. And whenever you fall down, it says: well, it was destined. You're a loser. You're not enough. How do you get yourself to a point where you have the upper hand in those conversations every single time?

John Fontein: I don't think I'm there. I mean, there are dark places. I want to get better at it, but there are dark places. Everything I'm saying, it's not like when somebody rejects you or says no, I'm just: okay, that's good, I'll go right back at it. There are still deep, dark conversations of: man, I can't believe, after all these years, I'm still getting rejected. There are still dark conversations I have with myself.

But I think it's the speed with which you get out of that, which I've gotten really better at. The ideal is that you never have those conversations. But the truth is, you're always going to have the "I suck" conversations. What matters is how quickly you get out of them. I've heard this from Djokovic talking about tennis as well. You're not going to win every single point. When you lose a point, you're obviously going to say: why did I do that? But the next point is going to happen now. So it's about how quickly you can get out of that moment and focus on the next point. Because if you're harboring it into the next point, you're probably going to lose the next point as well.

It's very similar in our current business. You're not going to win every single deal. You're not going to have every investor say yes. You're not going to have every prospective employee join your company. You're going to get rejected, and that's okay. And it's okay to think: what did we do? Why did we get rejected? But then it's about how quickly you come back up. How quickly are you ready for the next pitch? How quickly are you ready to iterate on your product? How quickly are you ready to reach out to the next candidate? It's all about the speed of getting back on your feet.

Shamil Malachiyev: Did you ever learn to detach yourself from your company, your product, whenever you get rejections? That each rejection is not personal, it's basically just not a perfect match?

John Fontein: No. And that's a bad thing, but I also think it's my superpower, because I take everything so personally. There's the old saying: it's just business, it's okay. But as I said, business and work is my life. So it's not okay to me. I'm not okay if you reject me, or my company, or whatever it might be. Period, full stop. I don't think that's a good thing, but I think it's my superpower, in that I hold a tremendous amount of responsibility. I take it very, very personally. As I said, I'll get right back on my feet, but it's not just some detached "okay, it's just my business, they're not talking about me". I take everything personally. It's a direct reflection on me, and so I want to make it better.

I really think that comes from my experience in the music industry, where my product was an artistic reflection of myself. My songs were literally a reflection of my feelings and what I was imagining at the time. I took every rejection deeply personally, because when they say no to a song, they're saying no to you. They're saying no to your emotions, to what you had in your head that you put on paper. And I feel the same way with business. When somebody says no to a product or an investment, I take that personally. This company is a reflection of my emotions, of my being. Everything is very, very personal to me. Again, it's not a great thing. I just think I know how to tame it, and it's my superpower.

Shamil Malachiyev: The thing I get faced with a lot is that I always think there is a universe where Shamil would just say something a little differently, present different information, approach from a different angle, and I would have gotten the deal. So I pressure myself: it's my fault. Obviously they don't need that kind of service or app for their work, but it's something wrong with me. I didn't push enough. I'm not good enough.

John Fontein: So I think teammates, your employees, your colleagues, actually see that, because it's visceral. People can see that when I lose a deal, I'm pissed. And I'm hopeful that it's motivating, because it isn't just: it's okay, we lost the deal, on to the next one. Everything is the most important thing to me, and I think that rubs off on others. By the way, when I see that in my co-founders and my employees, that excites me too. I see this frequently in employees, whether they're a product manager or a marketer or a sales rep. When the sales rep loses out on a deal, I can see people getting upset and taking it personally, and that energizes me. That shows me they actually care about this thing. I'm pissed off too. Let's do this together. When I see a marketer run a campaign that didn't work as well as he or she thought, and they get pissed, I'm like: yeah, you should be pissed. This is personal. And when you see somebody taking that amount of ownership, it's really contagious. People get excited when they see that in others.

Shamil Malachiyev: And did you learn a lot of those things from the people you met in the industry? There's this story of you spending some time with Floyd Mayweather and Justin Bieber on an island. Could you talk a bit about that encounter?

John Fontein: So that's one of my absurd life stories. One of them is my encounters with Justin Bieber. This is one of three ridiculous moments in my life. I'm on my honeymoon in Bora Bora with my wife. We're on a private island. Once you're there, you can't get off. By the way, it's the most beautiful place ever. We get there, and there are like 12 couples there. And on a bike comes this blond-haired kid. He gives me a high five, and I stop and tell my wife: holy shit, that's Justin Bieber. I just high-fived Justin Bieber. We quickly realize: Justin Bieber's here with us. It's a private island. There are literally 12 families. And he's there with Floyd Mayweather. By the way, all this is on Instagram. You can fact-check the dates.

The next day, we go to the restaurant. There's only one on the island. Justin Bieber's there, and he's buying shots for everybody. And we're like: this is fucking amazing. We're taking shots with Justin Bieber. This is the coolest thing ever. Then Floyd Mayweather comes in with a ton of cash. They don't accept cash on the island. I'm like: what are you doing? This is amazing. This is the greatest day of my life. We stay there, we drink with Floyd Mayweather and Justin Bieber. We stay for lunch, still drinking. We stay for dinner. He's just buying shots. He's performing karaoke at the bar. Next morning, we wake up, and he's there again, buying shots for everybody. And I'm like: this is the greatest thing ever. I have a bar story I can tell for the rest of my life, as I'm doing here.

Then day three comes, and we wake up and we're like: dude, we've got to avoid Bieber. The guy's killing me right now. We've just drunk for 48 hours straight. So we go to the hotel bar, and we're like: do not look at Justin Bieber. Ignore him. Run, run, run. Sure enough, he's like: shots for everybody! And I'm like: no. Ignore the Biebs. We're out of here. We're going snorkeling. So that was the first and last time that I will have rejected Justin Bieber in my life.

Shamil Malachiyev: Probably the only time he's ever been rejected as well.

John Fontein: Never say never. If I ever meet him again, I'm going to tell him this story, and he'll hopefully laugh at it. But that was a wild, wild event that I'll always remember.

Shamil Malachiyev: Is there something special or unique about all the famous people you've encountered throughout your life? Do they have some intrinsic qualities that helped them reach that level of success?

John Fontein: I think the most successful people I've met or worked with have a true, true passion for their craft. At every step of the way, whether it's in the music industry, in finance, in healthcare and tech, the most successful people aren't just going through the motions. They're maniacally obsessed with perfecting whatever it is they're doing. And they're so obsessed because they have such a passion for doing that thing. It's at every single level, from the most junior person all the way to the most senior person. The most successful people have this complete obsession with the thing they're doing.

In the music industry, the best, best songwriters and producers have an obsession with perfecting every single note, every single beat of the drum. It's maniacal. If one hi-hat is off, it's a catastrophe. They have to make sure everything is correct. In tech, the best people are obsessed with building the product for their customers, and they'll go through every single pixel to make sure that experience is the best experience for the customer. And I can keep going.

But you can't fake that obsession. You really have to be passionate about whatever it is you're doing, because past a certain point, if you're not obsessed, you're just going through the motions, and that's not how you're going to win. You have to show up every day with a pure obsession. I'd like to think I'm doing that today with Sesame, and I'm hopeful people can say I was doing the same thing at Goldman, and at Relabel. You don't have to be passionate about just one thing for your whole life. But in the moment when you're doing it, it has to be the one thing you're obsessed with and totally passionate about.

Shamil Malachiyev: Has anything changed over the last five, ten years in how you find your true motivation, in terms of what you want to do next? Maybe there are parts of you that you never knew existed that you've uncovered.

John Fontein: I think a lot of this is being comfortable with the unknown. In my early career, at all points, I wanted to have some North Star that I knew and was working towards, and everything I did was to get closer to that North Star. When I was doing music, it was: I want to be a rock star, so everything I was doing was about how to become a rock star. At GS, it was: I want to be the best client-facing person, so everything was towards that. I always had to have some North Star I was aiming towards.

I've become much more comfortable with the uncertainty of things, with the unknown. And I think that's important, because as we build, specific to Sesame but also other companies, so much of it is the unknown of the unknown. As you put a product out into the world, you don't know how folks are going to react. You can't go in saying: I need a North Star and everything we do has to get closer to it. You can have some idea, but once you put it out, it's the unknown of the unknown. How are people going to use it? How are they going to react? And it's okay to not fully know. You have to have some instinct, but it's okay to not fully know.

The reason I've realized that's so important is that then you don't have preconceived notions or biases going in. You just follow what you're seeing. If you have preconceived biases, i.e. here's my North Star and we have to get there, you might miss the forest for the trees. You might miss things that are going on, whether in music or in technology. What I've gotten really good at is not having preconceived biases: putting stuff out there, seeing where it goes, how our consumers react to it, what feedback we're getting. Do they like this thing we didn't think was going to work? Do they hate this thing we thought was going to work? And based on that, being very flexible in changing direction. Oftentimes, people end up liking one feature we didn't even think was going to be big, and then we say: there it is, that's the North Star, we're going to focus on that. Without initially going in with a preconceived notion. That's really the thing that's changed between ten years ago and now.

Shamil Malachiyev: And how do you want to be remembered? As what kind of person?

John Fontein: I'm quoting a bunch of great philosophers today. As the great philosopher Dr. Dre once said: I just want to be remembered as the shit. No, all jokes aside: I want people to think of me as, yeah, that guy showed up every single day. That guy worked extremely hard. I want to be able to say: I made that song. I built that team. I built that product. Whatever it might be. I want people to remember me as: that guy always rolled up his sleeves. He always did the work. I don't need to be the world's biggest rock star. I don't need that feeling I had in high school of everybody chanting my name, screaming "John". I don't need that. But I do want the people I work with and interact with, however small or big that group is, to think of me as: that guy always showed up. That guy always rolled up his sleeves. That guy was the shit.

Shamil Malachiyev: What are you most excited about currently?

John Fontein: So, my current company, Sesame: we're now seven years into this journey. And hopefully it's year seven of our overnight success story, in that these companies, specifically marketplaces, take such a long time to build. I don't think I ever appreciated that. At every step of the way, I've wanted to stop and quit. But I really feel strongly that we've found a turning point, and we're actually about to win.

We wanted to disrupt the way people get and access healthcare. And for the first six or seven years, that was kind of a pipe dream. A lot of things were working, but a lot weren't. This is the first time where I confidently feel: I actually think we're about to change healthcare. Now, of course, that could be another ten years from now, but maybe it's only going to be two years. It's the first time where I felt, I don't think this is a pipe dream anymore. We're actually going to pull this crazy, crazy thing off. And we're going to do this. So I'm most excited about actually seeing that through. Maybe that happens in ten years, maybe it happens in a year or two. But I just know it's going to happen. We're going to be successful. We're actually going to disrupt healthcare. I'm most excited about doing the thing we first set out to do seven years ago.

Shamil Malachiyev: And what has been the catalyst for this change?

John Fontein: Truly hard work. But I keep coming back to this: time in the market is the most important thing. Just the ability for us to exist and survive. There have been a tremendous amount of ups and downs in venture, in healthcare. There was a pandemic in 2020. We've survived. Existing and surviving has allowed us to iterate our product and continuously refine it, to make it a better and better product that serves more and more customers. A lot of this is just withstanding the headwinds that exist in venture and in healthcare. And we've withstood a ton of these headwinds, which has allowed us to iterate and make our product better and better, which has allowed us to continue to raise capital.

And so now, at this moment, I feel like we have a truly incredible 10x-experience product that our consumers, our patients, absolutely love. I use it, I can feel it, I know. And side note: all the economics of the business are working. We're humming along. It's that moment where you just know, in your gut and viscerally, that it's going to work. Similar to how I knew, viscerally, in my gut, when I had to sell my label: this is not worth it, it's not going to be the success I thought it was, I have to shut it down. The flip side of that coin is that in my gut, viscerally, I now know: this is going to work. Sesame's going to work. So I don't care about the punches I'm going to take in the face. I'll get knocked down, and I'll come right back up, because I know in my gut that it's going to work.

Shamil Malachiyev: You're like one of those people who tackle something crazy because they say: this is going to be such a cool story to tell one day, about how I've lived, what I've done. And you're full of those stories. Every single year of your life is probably something. I was quite serious when I thought that maybe this is the story we'll see on Netflix one day, as a limited series, six episodes.

John Fontein: I hope so. I don't think the story is over yet. Hopefully I'm still in chapter six of the 20-chapter book. But I think a lot of life is just showing up. Saying yes to many things. Obviously saying no selectively, but saying yes to many things, showing up, doing the hard work, laying each brick at a time. Worst case, it doesn't work out, you get rejected. Best case, you have a fun bar story to tell.

Shamil Malachiyev: I really hope in the future we get to sit down again, to talk deeper into your seven-year journey with Sesame, because I know there is a lot to unpack there as well. But we have to keep these sessions relatively short for the listeners, to make it easy on them. That was such a fantastic session. The stories you have are such an inspiration to any founders who are embracing this new world of AI, trying to start something, who don't know how hard it can be, who are trying to navigate that uncertainty. To be honest, I'm just so happy that you've stepped out into the light with all of these stories. You've boiled a soup that's going to give all the necessary nutrients to the new founders coming into the game. You've spent quite a while brewing it.

John Fontein: I love it. Dude, I really appreciate this. I really appreciate the opportunity to tell my story, and I appreciate this platform. I hope folks found this helpful. If not, you're on my shitlist.