Building a Fantasy Sports Empire | Adam Wexler founder of PrizePicks

By late 2017, no investor wanted to touch this industry with a 10-foot bowl. No investor would give me a shot. And I had just people telling me that I couldn't do things. I wrote down the smatchers and doubt me, please do. Adam Wexler, founder and executive chairman of PrizePix. One of the largest sports gaming companies in the world. 2015, fantasy sports industry was white-hot, but then, draftings in Fandall went overly aggressive. NBA Gs came after that and said, "Paid fantasy sports. Everything going on here is illegal gambling." And so the bottom of the industry fell out. What did you guys get right that others didn't? A lot of people didn't even necessarily believe me when I said, "We want to see you win." The advice that I used to get in my early 20s was, "Do what you love." But I think it's actually the reverse of that, that is much better advice, which is, "Make sure you love what you do." You may not have a terrible amount of cash to dish around. What you do have, one of your better currencies is equity. And you know, how can you leverage equity to build the right team as a founder, you're like the ultimate generalist? Do you think it's possible to build an extraordinary company and to be great without sacrificing your mental health? If I was interviewing you at 18 years old, and I said, "You're going to build one of the biggest sports technology businesses in the world, would you have believed me?" Probably not. You know, I don't think anybody in the right mind would be able to say, you know, yes, with a straight face. You know, at 18, I'm not sure I knew what I wanted to do exactly. I remember specifically going into school and one of the first majors that I explored was actually physical therapy, because I was always getting injured as a basketball player. Realized that that was in the school of education. So quickly I was like, I don't want to be in the school of education. Eventually, you know, before you know it got to business school, I think there was a lot of entrepreneurial related thoughts as a teenager watching my dad with his business and always thinking that he could be doing things differently. And then just during school, like a number of entrepreneurial thoughts as well. And it was unfortunate that when I was in school at the University of Georgia, like we didn't have an entrepreneurship program. It was created a couple of years after I left. And I would go speak to that class that, you know, while I was still living in Athens. But no, the answer's no. When was, when you say it was the first time where you knew you were special? Where you knew you were going to do something big in this world? When did that finally click for you? I'd say, you know, as an upper classman, knew that I thought a little differently than the average show, knew that I really, you know, there was a mantra, you know, when I was a, I want to say what I was a senior. And I had just people, you know, telling me that I couldn't do things or whatever. And I wrote down the smatchers, doubt me, please do. And that was just, you know, something that I definitely kind of lived by, you know, largely in my 20s. And little parts of my 20s, you know, gave me the feeling that I could get there. But it wasn't until, you know, this last ride with PrizePix that it really popped. That's interesting to say. Would you, is that what drove you initially was getting into entrepreneurship a way to kind of prove yourself to the world? Was it like I got to go out there and prove people wrong? Or what was the initial impetus that catalyzed you jumping in? I just feel like I have a lot of entrepreneurial traits, you know, not only was my dad, not your partner, both of my grandfather's who I never had a chance to meet, but both of them were entrepreneurs. One of them actually in commercial real estate in Miami, is one of the fact that my dad's dad moved, his part of the family to Atlanta, which is obviously where I was born and raised. And basically bought a chiropractic practice. So, you know, through different stories, and obviously firsthand with my dad was just exposed to a lot of entrepreneurship over the years. And what happened was when I was in school, you know, I was a real estate major, and I was a real estate major because my dad was reporting on commercial real estate, but I figured that he was actually a real estate professional, which was a wrong assessment. He was actually in the journalism school, which makes more sense, because that's the kind of path that he went down. In my case, became a real estate major, and more than anything what I learned from that is that I didn't wanna go into real estate. And so I did two certificate programs that I really kind of really gravitated towards more, more than that, one being a leadership program, the other being a music business program, and conveniently enough that we had just started up a music business program at UGA, and there was a digital music revolution going on. You know, there was Pandora was coming out, Shazam was popping, and I said, man, I really love this little industry within the industry, and I wanna go do stuff within this. And my first technology startup was actually a music discovery website, so. - How did that go? - Depends on how you wanna look at it. I mean, financially, not great. (laughing) - Music startups are the hardest to get working. - They absolutely were back then. But I mean, great experience, great exposure, great learnings, hustled my ass off. And I think a lot of that wisdom that I kind of garnered over that experience, like kind of showed up again through this experience with prize picks being in the entertainment space again. - Prize picks is like your big home run. It's household brand now. You guys are absolutely killing it, but there was a series of steps to get here, right? And you're talking about, I had to do these things to get the experience to then eventually allow prize picks to come into fruition, right? Can you walk me through just a couple points? What were some of those early businesses and pivots that you made that ended up leading you to prize picks? - I really enjoyed the art form, I'd say, that was B2C and the notion that you're trying to hit grand slams. - With B2B, it's more of a kind of like a linear kind of growth curve. - Right, 'cause you can build a big business with 1,000 customers and B2B. And B2C, it's about scale. - But B2C's hockey stick. - If you catch lightning in a bottle, you can hit that hockey stick. With that experience, the one kind of, one of the more memorable parts of it was, we had kind of like a month over month experience where we went from a while of grinding and we were getting, you know, these numbers sound small, but like we were getting 5,000 people a month to kind of use our resource that we had built. And then one month later was 50,000. - Wow. - And that was like a revelation, but at the same time, we realized that we were still not making any money. And so it's like there's no business model here. It was not very easy to raise money out of Athens, Georgia, where we started the business, which is a music kind of mecca, but not music tech mecca. So at the, around this time, you know, I mean, in my early 20s, I wanted to move out to San Francisco. That was where, that was the place to be. I didn't have the financial means to kind of make that move happen. And so for a number of reasons, kind of abandoned that project. And it was the same week that I told my dad, I guess I'm gonna go get a nine to five, was the same week that I came up with my second venture, which was a B2B SaaS, described it as like a CRM for micro influencers. - Okay. - This is 2011, definitely ahead of the curve when it comes to influencer marketing software. But we knew we had something. It was actually inspired by what I was doing by hand to get the word out about my music discovery website. So we basically just productized a lot of that. Also a very interesting experience, you know, essentially became a social media expert at the time. I'm going around the country speaking at a lot of conferences, talking to social media directors, selling into social media directors. And we were at the forefront of having to help them value what these influencers were doing. And in our case, you know, I'm talking influencers like me and you, all the way from, you know, Kanye and Kim to, you know, down to that person who's got 500 people that follow them. But they follow them for specific reasons. And we're helping brands figure out who to go engage and, you know, interact with them one to one at scale. And we knew we had something good with that business, but, you know, because it was difficult to quantify the value that we were bringing, we, you know, it was difficult to kind of charge what we wanted to charge and build the big business that we thought we could build. And so that was like, you know, a good, had a good three or four year run with that business. Eventually that was a part of a couple successive acquisitions that landed with Sigeon, who people may know from their, their owners of PR, newswire and stuff. So that was my first exit, you know, and eventually I think it sold in 2018. But by 2014, I had already kind of gone off and kind of that's when I actually entered the fantasy sports space. But it was actually around that time just to show you that I'm a bit of a serial entrepreneur. I kind of came up with two, I planted two seeds at the time. One was another B2B SaaS play, but the other was scratching my inch to get back into B2C. - And you were building both at the same time. - I was building both at the same time under the same roof, had co-founders for each of those businesses. - What was your thought process there? Like, because normally you're like, hey, pick one thing, go all in. But you're like, am I gonna try to build these two, see which one gets more traction and then go on and that? - I think it was something along those lines. And that's kind of what happened. You know, this is, you know, 2015 rolls around, fantasy sports is super hot. - Yeah. - You know, fandall draftings are raising up. - What was that business called? - This business at the time, it was incorporated as side prize. Side prize would eventually become prize picks. - Okay, so that was the beginning and then it formed into prize picks later. - And then the other one was called Trust Fuel, and that was a B2B SaaS business. The quick background on that was, we knew that the best source of future customers for the previous business, which was in site pool, was through our happiest customers. You know, it was better than going out and doing cold calls, you know, cold emails and stuff. And we said, well, how do you identify your happiest customers? Or let me say it a little differently. The best source was through references and referrals, but how do you identify those is through your happiest customers. - Got it. - And so we built software that helped you identify your happiest customers. - Oh, interesting. - This was a category that was kind of emerging at the time there were companies like Gainsight and customer success was another one. Both of these companies, you know, were able to raise money in 2015 and had opportunity in front of them, but because, The fantasy sports industry was white hot. I told my co-founder, I gotta go full time on this. And I was just more passionate about B2C and it was scratching my own niche. - I think that's an important thing too when you're thinking about what to build as a founder. You do have to scratch your own niche. Right, like I think founder, market fit is pretty critical. I'm curious what you think though. There's like this advice where it's like, follow your passion, right? But some people, they're passionate about something where they just, they don't have an edge in it. They don't have some sort of competitive advantage. So how do you think through that advice too? Like, follow your passion, but also just choose something you're already naturally good at. How do you reconcile that? - Yeah, so something I feel very strongly about is that the advice that I used to get in my early 20s was go do what you love. And that was like kind of, I think a lot of common advice that's still be and told to this day. But I think it's actually the reverse of that that is much better advice, which is, make sure you love what you do. And I think that kind of relates to what you just said. You know, if everybody out there is gonna go do what they love, everybody's gonna be in the sports industry. You know, nobody's gonna be doing all these other things that we need as society. But if you actually find something that where you can love it and love it on a daily basis, what you're doing, that you can love all the different kinds of industries and different roles and different kinds of industries and find a lot of opportunities. So, you know, I think of like, you know, for example, people in my network that got into the waste management business, like, you know, is that them doing what they love or ultimately when they, you know, find a very successful opportunity, is that them loving what they're doing because it allowed them to be successful in that group. - It's a great point. I think about the phrase, don't worry about making the right decision, just make the decision right. It's like, it's your perspective on what you're doing, right? It's the person who's building a brick wall or someone who's building a cathedral to honor their God or whatnot. It's what's your perspective on the thing you're doing because you can find love based on how you perceive it. And I think if you're just playing a game, right? It's like, play a game you love. Anything even building a waste management business. It's a game in itself, right? So you can fall in love with the game of it. I'm curious for this because now we're in price picks now at the early stages and there's some big decisions that have to be made and you got some big, big competitors out there. It's a pretty saturated competitive space. We talked about, I think, draft kings raised a billion or more in equity, right? You guys raised sub 10 million and you're going up against this juggernaut. What was your thought process on raising so little funding and competing at that level and hindsight? Was that the right move? First of all, you know, so I got into the fantasy sports industry in 2014. When I say I scratch my own itch, I was a season long fantasy league, fantasy football league consumer basically. And so the problem that I identified as a consumer was every year, 12 or more friends to get together. They all pull a little money to make things a little interesting. Somebody's got to collect the money from their friends. Nobody wants to be that guy. And so we built software to make the commissioners life a little easier. Quickly realized that was a very seasonal business, seasonal problem that we were solving. Quickly pivoted to the second product, which was, we're playing each other this week. Let's put some money on it to make it a little more interesting. Or even I'm not going to beat you because you're the best team in the league. Let me put money up against all of y'all. I can beat all of y'all. That was the second product called Side Prize, which is what the business was founded, the name that we kind of founded it under. Did that for a couple of years. But I referenced 2015 was, fantasy sports industry was white hot. But then draft kings and fandals went overly aggressive. You could argue. And the AGs came after them and said what they're up to are paid fantasy sports. Everything going on here is illegal gambling. And so the bottom of the industry fell out. And so I knew that fantasy sports was not going anywhere. This is something that we love to do as consumers. I knew with the numbers where there's tens of millions of people playing throughout the country. And so I'm like, I got to stick this thing out. I got to get to the other side of this. And it's going to be a bloodbath. And I know a lot of-- Did you knew that? And I knew a lot of entrepreneurs were not as DNA entrepreneur as I am. And so literally and figuratively. And so we're also just not going to be as resilient as I was going to be and just try to make ends meet. I knew how to bootstrap. I knew how to stretch this thing out. I just needed to get to the other side. And so 2016 was a huge struggle. 2017, middle of the year, the same week, ironically, again, that I say we decide we're not coming back with side prize that fall was the same week that the Supreme Court says we're going to take up the New Jersey Sports betting case. And with that development, I basically said, OK, wait a second. So 20 states have legalized fantasy sports and put those laws on the books. 20 states where you can operate with paid fantasy have not collectively got 40 or more states where you can operate. It's a pretty nice size map. It includes some of the biggest states in the country. So what could a product look like within the new laws that have been put on the books? And that's what ultimately birthed prize picks. So it was fall of 2017. I had a couple different formats that I was still kind of toy and with as football started. By week four or five landed on the one that would eventually become our core format. I mean, it's Balzi to go up against the company that's raising that much capital, that much fuel. And then you're a relatively bootstrapped incumbent. So yeah, so let me let me speak to that. So yeah, so I think it was important to kind of give that background. Yeah, definitely. By late 2017, no investor wanted to touch this industry with a 10 foot bowl. Really? Yeah, they thought it was the same. As it was in 2015, there was no line of sight to it being a big category again. It was still-- no investor would give me a shot. So it was in 2018 that mostly I raised money off of people that had known about my entrepreneurial experience. They had seen me with my last business, which was a business that showed it could have been a much bigger business. But at the very least, they saw me do my thing there. And so mostly it was able to raise from people out of Atlanta where I was building another business. And the other thing about this business is we had just inherently a very strong business model. And just these unit economics were just incredibly strong out of the gates. And so between the game profits that we were generating between angel funding and equity capitalization from people largely that knew me, not that they were betting on space. Not institutions, but just people who were betting on you. And then over the years, we also were fortunate to come up at a time when creative debt financing was coming of age. So what was called revenue-based financing, RBF. We actually had a couple partners over the years that allowed us to-- these groups were primarily focused on the e-commerce space where your customer acquisition costs, you basically pay it back in a matter of a couple months. We had a very similar payback period, very fast break even start to profit before you know it. It was just a model that worked very well with us, too. And we had some really amazing partners in a group called RevUp and ClearBank, or rebranded as ClearCo. And it was because of groups like that, we were able to-- even though at times we wanted to raise more equity capital, it was never easy because there was always this regulatory overhang that people were always questioning. And a lot of investors try to talk themselves out of an investment ultimately. Was that advantage, you think, like operating with constraints? Sometimes when you have too much capital, you start throwing money at problems. But operating with constraints actually can be a superpower. Do you in hindsight think that that actually helped you guys? I think it's a great question. And I think there's a very valid case to be made that it did. You just have to be so much more resourceful. And like I said, I've been learning how to bootstrap businesses since I started my entrepreneurial journey. And I think that's one of the hidden advantages of starting it in a place like Athens, Georgia, and eventually move my entrepreneurial pursuits to Atlanta. I didn't have the luxury of sitting on a lot of capital like they do in Silicon Valley, where they're quick to kind of abandon things. No, I'm going to stretch this thing out. And another thing that it teaches you along the ways that hey, you may not have a terrible amount of cash to dish around, but what you do have one of your better currencies is equity. And how can you leverage equity to build the right team? And there's a lot of people, especially people that are earlier in their careers that are willing to take, especially if they believe in the concept that are willing to go on a low salary. But what could be a material amount of equity? And I'm super happy that those people that made some of those decisions early on are going to get rewarded after the day. What was your lightning in the bottle? What was that like aha moment where you guys just, that inflection point where you guys just started to take off? Like what did you guys get right that others didn't? Having done a B2B SaaS business right before, I would look at these at our numbers on like a literally a per customer basis. And it reminded me of a B2B SaaS business that was focused on like-- L2B, CAC, all that. It reminded me of a company that was focused on the SMB market. And I'm like, if I just think of each one of these customers as a small to medium sized business, because we're making some real money off of our customers that are playing our game every day. But there's real revenue that we're looking at here. But at the end of the day, and I want to be clear about this, we were an entertainment provider. So it's imagine like you're spending money to go watch a baseball game or go to the movies or whatever. At the end of the day, think of us in that category. So I would hope that people, they May 1. win, they may lose some, but they're having fun. That was also the thing. So everybody's winning in the grand scheme of things because we're entertained. But we got to build a business at the end of the day. And so before the pandemic, even at a small scale, I knew these numbers were promising. But then the pandemic hits, sports around the world turn off. We're not VC backed. All of our businesses largely built off of game profits, some angel funding, creative debt financing. We don't have much to go off of spring 2020. But it was in 2020 where we kind of hit the reset button. We just kind of reset the team. We reset kind of like what we were doing right, what we were doing wrong. And then as we were kind of turning the corner into 21, that's when we were finally ready to kind of hit the gas. And I think as we started to hit the gas that spring, we never really looked back. But we had built that foundation over a couple of years prior. And I think what did you guys compete on that made you guys so asymmetially successful? Was it like you guys just had superior product that you have some secret when it came to marketing or what specifically did you guys do to just take off? Yeah, you know, I think for starters, like we were at the forefront of what we call the DFS plus category. This is not DFS 1.0 where that was really oriented around what's called the salary cap format. That was where kind of draft kings and fandom will kind of made their living and kind of you know, started their businesses. Just to put it out there like I loved the concept of daily fantasy sports. Fantasy sports you could literally play on a daily basis. I really disliked the way that they had just executed. It was not a very mainstream appealing game. I'm a casual. I'm not like I just want to be entertained. I'm not trying to you know, research every little thing about every player as well as everybody I'm playing against, which is what kind of salary cap required you to do. Got it. So we just wanted to kind of create a basic variety of daily fantasy sports that could appeal to the masses. And we were not the only ones to kind of start in this category of DFS plus or so what some people call pick them. There were companies in you know, 2017 that were you know, toying around with similar you know, concepts. We were one of the first two to hit any meaningful level of scale. And then you know, we've become the clear market leader over the last couple years. But I think what it comes down to is it was all this this this category always had a very strong business model. And once again, it had the ability to have mainstream appeal. And that's not what previous iterations of daily fantasy really had. So you saw that and just capitalize on that gap. And you kind of yeah, you made it more mass consumer. Yeah, exactly. Take me back. I don't want to glaze over what you just said because you're in COVID sports came to a halt. You have very little funding. Was that like an existential moment where you thought, hey, maybe like maybe we won't make it? I would say yes, but no, because you know, at this point, I'm you know, a decade into my entrepreneurial journey. I've already been through one of these, you know, similar developments from 2015 with this business when the bottom fell out of fantasy sports, you know, just the industry. Now now the bottom is falling out of the sports industry at large. And so, you know, in terms of the kind of core team that we had to assemble, like I wasn't I'm seeing Tony Robbins unshakable right behind you like, you know, I was pretty unshakable. Like I'm like, we're we're going to figure this shit out. That was your mindset. Like you just you didn't waver from that. Sports are going to come back. We were quickly, quickly ratcheted down our burn. Like right then. And then it's like, Hey, we don't know what the future is going to look like tomorrow. We don't know the future is going to look like in a couple weeks, months, whatever. But it's not like sports are not going to come back. My world's not coming to an end. Like we just got to stick this thing out. It's the same mentality that I had in late 2015 all the way through 2016 into 2017. If we got to stretch it out for a year, we'll stretch it out for a year. And so I wasn't so phased by it. But there were definitely some people around me that that were a bit phased by it. And I just had to make sure that they were in the right mental space. And, you know, obviously as a leader, you got to make sure that, you're rallying the troops and we're going to get through this. That's the mindset, man. I guess in thinking back to those times to sitting where you are now, if you were to operate with 2020 hindsight, were there any big decisions you would have made differently or anything you would have changed and how you built the company? We had a, there's one thing I'd call out, which is we had a decision to make right when we came up with price picks. So understand that I had been in the industry for a couple of years, but I teamed up with one of the early engineers from my previous business, the one that was in the B2B space to basically create price picks. And the only thing that came over from 2014 to midway through 2017 was me and kind of maybe what I gathered through the industry. There was no code, there was no team, it was just me. So the question is, is this the same business, or is this the, you know, is this a brand new business? And for a number of reasons, we decided to make it the same business that dated all the way back to 2014, but I had to creatively give us room to breathe and room to grow because fortunately, like I alluded to before, well, became price picks had a good business model on day one, but had the old investors, you know, caused too much of a fuss, we would not have been able to kind of get to the other hump or we just said, hey, we're just going to start a brand new business and deal with the consequences at a later date. There's a lot of people that, you know, develop, you know, expertise in a certain domain, whether it's the healthcare space and they start a brand new business. It's like, you know, they'll keep starting businesses in the healthcare space. This was essentially a brand new business, but I brought the cap table from the previous part of it, the journey along for the ride. And it's ironic because so many of them have literally told me they thought they thought they had a zero. And for this to not only have basically been an investment they were excited about in 2015, in some in 2016, to something that they viewed as a zero in 2017, to then become arguably the best investment they've ever made. Like that is, you know, that is, I mean, I take great pride in that. And hopefully, you know, they'll all be appreciative of this crazy journey that we've been on, you know, together, but we had a real decision to make. And I hope that that's appreciated over time. Yeah, well, that's big man. Are you, you know, as you were, because you're a hardcore founder, like you're just a builder, you can solve problems, run through walls, like you just have that in your DNA. But I've experienced difficulties making this transition myself, but I'm curious for you, going from founder to CEO, I know your chairman now, you operate as a CEO at the business for a while, right? But I think founder and CEO are two very different roles. What was that like for you evolving into the CEO? Like what did what did you have to develop and how did you have to evolve to go from founder to CEO? Yeah, I think it's a as a founder, you're like the ultimate generalist. Take up whatever is in front of you and you know, every day is a new day. Yeah, I think as the CEO, I think one of your biggest responsibilities is building out the team and finding those specialists, finding those people that are smarter than you, making them buy into the vision and where we can take this thing. And then, and obviously, you know, every year, I think you're kind of leveling up the talent side of it. You know, we're only able to recruit so seasoned of people in the early years, but then by the time, you know, we had built the business to where it was, you know, for example, in 2022, 2023, I said, our biggest, there was a lot that happened in 2023, for example, you know, we're managing through all the tailwinds, where we're one of the fastest growing companies in the country, but we're also dealing with these headwinds because some of our competition was a little anti-competitive. And then, you know, we're just dealing with a lot of things, but the best thing that we did, the biggest accomplishment I thought from that year was we built this super strong layer of director to VP types. And we were able to attract them because of the brand that we had built and the growth of the business and just everybody, you know, just wanted to be there. And so, we were still very light at the very top on the C suite, but we had this really strong layer, kind of right below. And that I think really put us in a good place. Yeah, it's funny because I think when you're the founder, you kind of build this identity around I can do everything and I can do anything like just give me whatever task nothing's beneath me. I'm just going to run through walls and make it happen. And then you realize at a certain level of scale that doesn't matter if you're a super human, you run out. There's you just can't you have no leverage to move a bigger boulder. And so it's just all about the team you built. But for you, I'm curious on the recruiting front. I mean, that is a never ending process. I do this all day and I've done over a thousand hires myself and it's still hard, right? I'm curious for you as someone who's building a team and recruiting top talent, like from the time you started the business to where you're at now, like, what have you learned if you were giving advice to other founders CEOs, building their teams, with the lessons you've learned, what would you want to impart to them? I mean, one of my favorite things that I, in Atlanta, a number of us come from the School of David Cummings. David's probably one of them were successful tech founders and investors and one of the faces of Atlanta technology. And I think one thing that I got from him that I'm a big believer in, actually two things that relate to what you said. One is cultures the most defensible thing that we have. I'm a huge believer in that and so I'm very protective of that. But then as far as recruiting more specifically, I think I got it from David about the notion of a canoe test. the premises, okay, this person checks all the boxes that gone through the interview process. They've created a good impression with the people that have interviewed them. And then they get to me. And the biggest thing for me is especially in the earlier days when it's a core group and we're gonna all be brushing shoulders and seeing each other every day, especially with the in office culture we had pre-pandemic, do you wanna spend the whole afternoon and a canoe with this person? And if the answer's no, or you're even hesitating, like, you may not wanna bring them in. They may be just a stud at everything else, but if they don't have the right personality for your team, that you've built in every organization a little differently. Is this the right person for that? That you wanna spend time with and it's something that, I think is less important now, 'cause I think we're at a point where, a lot of people that we're hiring bring families to the table and whatever. But in the earlier days, it's like, no, we're gonna grind this thing out together and that's gonna be nights and weekends and through breakfast lunch and dinner sometimes. So especially from the earlier stage, I'm a big proponent of that. - I like that mental model, 'cause a lot of people, "Hey, would you wanna grab a beer with this person?" But if you're drinking a beer, you're gonna have a good time no matter what. So. - And that's probably like an hour long, you know? - It's an hour long, but you're trapped in a canoe down a river with this person. Yeah, I like that mental model a lot. I do think a lot of the biggest screw ups too, you find impressive people that just don't assimilate in your culture. Like you can have a great receiver on the Patriots and they go to a different offense and just totally suck, right? So the environmental fit is so key. And you guys have built such an epic culture. And it kind of permeates through your brand as well. What was some of the, I guess the practices or the rituals or the things that you imbued to just build this high-performance winning culture? - You know, and I think a lot of it is definitely reflective of my personality. So, you know, I appreciate, you know, you say and things all those lines. Big part of me is like, I don't take myself or life too seriously. And so for example, I remember like, you know, when we were building out like the kind of like flow of what the consumer process looks like, you know, within the earliest iterations of price picks, like, there was like, okay, let's like, you know, in other, with other operators, it was very much very transactional. With us, we wanted there to be like, let's embed some fun elements of it. So like, you know, even when you lost, I remember we put a meme in there of like that water boy that you can do it, you know, you know, or better luck next time. So some gift me, we kind of really just embedded kind of meme culture in the other way. No operators doing that right now because, you know, they're a little too grown up and not, you know, a little too serious about the whole thing. And well, no, this is fun. This is entertainment, you know, look, you're gonna lose some, you're gonna win some, but just have fun like I said before. That's a big actual, it's, it sounds simple, but like when you're in this competitive landscape and you're going to war with people, like it can get very serious, but I think products and cultures that just think about, how do I delight the customer and just, I think that goes a long way, but I think fun, when I think about it, like winning cultures just have fun. And like, because they have fun, they win more. It's like this self-propeptuating loop. And one thing I'd also add on that was very different when we got into the space versus everything that was remotely close to us was, there was always this, you know, we, like, a lot of people didn't even necessarily believe me when I said this, but I was super sincere. Like, we want to see you win. Like, the closest example that you would find in like a Vegas culture is actually the Blackjack dealer. You know, if you were to compare the Blackjack dealer with a traditional sports book, the traditional sports book and the consumer have an antagonistic relationship. Consumers like, I want to take down the house, I want to bankrupt the house or whatever. If you look, if you go over to the Blackjack table and you understand kind of the dynamic there, well, you say, should I, should I hit right here? You know, in the Blackjack dealer says, you know, the book says blah, blah, blah, blah. And then you actually hit 21, you're high five in the Blackjack dealer, you're tipping them or whatever. There's a bond that you have. And so we kind of wanted to, you know, hit us over time if that's the kind of dynamic that we had kind of been creating. And it's just funny that every one of those games inside of a casino has kind of a different dynamic. But the Blackjack dealer, I think, is one that I thought was very relatable to kind of the kind of premise that we took. - That's so interesting. That's a really cool way of thinking how you built the product. From your side, I'm curious, you know, as you've gone through this journey, there's a lot of founders listening and people that want to start companies eventually as well. It's a never-ending growth journey, right? Like even now you're chairman, you have a different role. Like it's just a never-ending series of obstacles and I'm just curious, reflecting back for you. What was one of the bigger insecurity shortcomings or just inner battles that you had to overcome? 'Cause I know you have this kind of ruthless, dog and mindset in this self-belief. And I have to imagine that that was probably cultivated in some extent over time, versus just like one day you woke up from a slumber and you just mutin' entrepreneur. What was something that you really had to overcome to be in the position you are now? - You know, some days I wake up and I'm like, especially in the earlier days when I was in the CEO seat. Man, I'm, I mean, I think I'm a really good CEO. Like other days I'd wake up and I think the exact opposite. (laughing) I've never run a company this big, you know? And so just like that constant kind of inner battle that you kind of think about, just like, well, when I was thinking I was really good, I was probably thinking about certain aspects that I'm very strong at. And then it was the opposite. You know, when my weaknesses are pronounced, you know? And so just really kind of just wrestling with that. And, you know, I only, I wish I had done it earlier. I only joined a peer group maybe about a little over a year ago, maybe a year and a half ago, the 10X CEO program. And ironically, they're primarily for venture backed. We were talking about this. They're for venture backed, you know, founders. And in my case, we weren't venture backed. But, you know, I think just, you know, being able to kind of, you know, talk to people that are at similar stages and just, you know, deal with similar stuff, I think, and I, has always helped. - I definitely experienced the same thing. And I feel like it's just about what you're focusing on in the moment. You're like, okay, well, revenue could be up that this product blew up or something happened here and like, I'm terrible or I had to fire this person. But it's all, it's all where you're focusing. One day, you can just see all the things that are going well and you're like, wow, I'm killing it. The next day, you're just focusing on your problems. You're like, I'm a shit CEO. Like, look at all the things that I'm screwing up. So at the end of the day, entrepreneurship is really just about controlling your focus. - But I also think it's about, you know, just, you know, delegating and I'm not, you know, one thing that I think I've done well over the years is that I'm a big believer in leaning into your strengths and then kind of, you know, supplementing for your weaknesses. So like finding people that can are really strong in certain areas that you're not. I think some people try to cover that up, you know, themselves. And I'm the first to admit areas where I'm not very strong. - That awareness is key. - Yeah. - I'm curious, what are one or two habits that you've adopted that have had a really positive impact in your life that you wish you would have started sooner? - Well, okay. One thing I'll say is just sleep regimen. I mean, like I try to be religious about, at the very least, attempting to get at least seven hours of sleep, you know, I'm a night owl to begin with. So I think it's unfortunate that, you know, our society has been kind of wired on this nine to five kind of regimen. - Yeah. - When there are plenty of people who are early birds, and I'd love to know the percentage of the population that's a night owl, because I do some of my best work at night. And especially as a serial founder, you know, you want me doing that work, 'cause I'm not distracted by email. I'm locked in. I'm, my creative juices are flowing. - Yeah. - And so if I'm going till 2.30, 3 o'clock in the morning, don't bother me till 10 a.m. or don't have any issue with me not responding to 11, you know? - Right. - And I can only imagine how that would have been for me if I was on Pacific time. - Right. - On Eastern time and I'm complaining. That's a big one that I wish was just, hopefully we get better at that as a society over time. It's like, judge me on my output. Don't judge me on kind of the time that I'm clocking in and whatever, something like that. - Well dude, I think building a company, you go a little bit, you have to be obsessed. An obsession doesn't necessarily follow your regimens perfectly, right? Like you're gonna have these creative bursts where you're cranking for five hours to 3 a.m. But I think to some extent, I'm really curious to get your input on this because for me, I've typically found, if you wanna go build something big and change the world and make a mark, it just requires such a level of almost psychotic obsession where it just consumes your entire being and that comes with trade-offs and there's expenses and because of that, do you think it's possible to build an extraordinary company and to be great without sacrificing your mental health? - I sacrifice is a big word. Mental health is, I think incredibly important. Have I sacrificed it? No, but have there been instances where, I'm putting my wealth before my health, 100%. To me, one thing that I've definitely started to, especially with this transition, I was CEO for 10 years, now I'm executive chairman and special advisor to the CEO. So I'm still for- time, but just in a very different capacity. And so now it's like, I tell people, like, you know, I haven't had this much flexibility in a long time. Maybe since I was an early stage founder, but I'm still a similar amount of busy. I'm just trying to figure out where to kind of put my time and whatnot. But the other thing that I was going to say back to your question is like, this is definitely a year where I've paid for putting wealth before health. And I've got to get health ahead of wealth. Yeah. You know, I'm doing physical therapy right now. I'm, you know, for some ailments that I've had, you know, over the years. Just neglected. Yeah. And like, you know, my partially torn labrum led to issues in my ankle that have allowed me to or made it so that I can't play my favorite hobby being basketball. So I got to get back on the basketball court. And so whatever I got to do to prioritize that inside of my calendar at this point, that's my priority right now. Yeah. Because I remember when I started my company, for the first two years, it was legitimately 100 hour weeks every week, five, am till 10 pm, seven days. Maybe I took partial Sundays off, but it was legit, consistent 100 hour weeks for a long time. I'd be in and out of the hospital just from burnout, but I just had this desperation in me. Like, I was like, I have to succeed or die. And it was that intense for me. And then as I got a bit more traction, I'm like, okay, this is entirely unsustainable. Like, I don't want to kill myself because then I can't experience all the awesome things that I'm building anyway. And I started getting a lot more satisfaction and seeing, especially once you build traction, you can have a team. You really have to put a team around you so you can step back and get into your creative genius and actually find balance. But now I, you know, I play paddle multiple times a week and I refocused on my health and I feel like people demonize the work ethic, the hustle porn. I do think, I don't know what your take is, but I feel like it's necessary to some extent for a certain period of time and a certain season of the business. But eventually you graduate and you change your motivational fuel. Maybe it's not desperation or trying to prove the world wrong. And like, no, I just want to create a masterpiece or I want to do something different. But I feel like we do have to honor those seasons, right? Like, sometimes there are trade-offs and you got to decide if you want to make them. But to build something great, I think it does require some pretty intense imbalance for a while. But then you can kind of get back and find your center. But I feel like life's just always shifting priorities. But I've just never seen an example of somebody who's built something great who didn't go way to the right or left on something for at least a prolonged period of time. Yeah. And use the word seasons. I would use the word chapters. But yeah, 100%. I mean, like, you got to get, you got to put the grind in and, you know, I would hope that people always kind of, you know, put their mental well-being, keep it top of mind. You know, for example, another another way that I was going to answer the question is I go, my routine has always included like gym after work. Yep. And for me, especially getting on the bike and just catching up on texts or emails, whatever it may be, it's kind of, you know, I use it as a way to kind of decompress and just like, it's been as much mentally beneficial as it has been kind of physically beneficial now. Now at the same time, sometimes I wish I wasn't, you know, double-tasking. Sometimes I wish I was actually fully locked in on the work out and sweating more. But especially, you know, when the business, you know, doesn't have all the all is growing so fast and we don't have the personnel that we need. You know, I was definitely kind of having to multitask even at the gym, you know. Sitting where you're at now, I'm always very fascinated to understand people's self-perception, because you've built this incredible business. Yeah, I know you're so hungry for more. Like sitting here right now, do you, do you feel successful? Do I feel successful? I think, I mean, you know, I would love to see it when a definition of successful, you know, looks like, according to your own definition, like, do you, when you, do you feel successful? The way I'd break down is like, in my career, sure. I think we've accomplished things that a lot of people kind of, I'm very fortunate that a lot of people just kind of dream about what we've been able to accomplish with pricepix. In life, no. And there's so much left to accomplish in life. Where do you feel like you're not successful in life? I'd answer that a couple of different ways. Like, number one, you know, I want the right balance between health and wealth. Yeah. And it's been imbalanced for a while. The common thread between all of my businesses to date are, you know, the common Silicon Valley refrain was like, we're going to, you know, change the world, right? In my case, the common thread between everything that I've done is I'm just trying to make the world a little more fun. You know, that related to my music discovery website related to what we did with brands to engage, you know, their consumers through, you know, influencer marketing and social media and then naturally with everything we're doing with pricepix, like, yeah, just trying to boost the level of fun on a weekly basis, allow you to get away from the, you know, the grind in your own world. But, you know, there's going to come a point in time where I want to, you know, get bigger into philanthropy and, you know, just, you know, there's more, there's more that I want to do that goes that stretches well beyond, you know, pricepix. Yeah. And so, you know, I think as you start to think about more legacy oriented things, yeah, I'm not done by any means. So it's like, I'm always going to be that entrepreneurial type. That's just kind of once again, that's my DNA. But am I successful with pricepix? Yeah. I'm glad you recognize that because I feel like it's a, it's a trap that's very easy to fall in, where you're just never satisfied. I definitely fall into that quite often. I'm like, I haven't done shit yet. I need to go so much bigger. But then I realize, wait, I'm just, I'm just, uh, delaying my happiness unnecessarily. And if you just allow yourself to kind of feel the winds as you go, it's small or big, you generate more fun in your body and your mind and you just, in that ends up propelling you into more success. And, and, you know, this is something I'm just digging up off the top of my head. But like, I've never been attracted to the word retirement and just retire. That's Voldemort. It's, it's, I don't think I'll ever fully retire as it's been traditionally known. Yeah. There will come a, you know, points in time where I'm less focused on wealth creation. Yeah. You know, but, but retirement does not sound appealing to me. Yeah. Cause we're, we're creators. That's who we are as people, right? And we were, we're put here to create things. I, I, I describe it as I'm a producer not so much a consumer. I, you know, but I think you're saying the same thing in a different way. Yes, definitely. Yeah. And we can enjoy the productions of other people, but we have to have our thing that we're contributing to the world. I think wrapping up last question here, a lot of, a lot of builders, a lot of founders, a lot of people that are pioneering here listening. If you could just share one piece of advice or a message from the heart to everyone out there in the arena building, what would you want to leave them with? The adjective that I appreciate more than any other when people are complimentary of, you know, kind of everything that I've done over the years is just being resilient. You know, it's, it's the resiliency. It's like, you know, did I go to an Ivy League school? No. Was I the smartest kid in a lot of different environments? No. But you can't necessarily teach resiliency. I think you have to prove that. And it's something that a lot of founders do not necessarily, you know, you might, you may think you're resilient, but I think there's, there's levels of resiliency. And, you know, we've talked about it a little bit, but with what I dealt with when in the early depths of my career with my business that was seeing some traction, the business model did not follow to the next business that had enormous upside. And we just didn't achieve it necessarily to this business where, you know, in 2015, bottom falls out could have closed up shop right then and there, you know, a year and a half in kept kept going 2020 pandemic comes, you know, you know, other businesses around us and both of those instances closed up shop plenty of them. There was a lot of dead companies around us. But, you know, just staying the course and figuring out how to get, how to creatively stay the course and figure out how to get to the other side. And so that that's the, that's the word and the adjective that I really appreciate when people recognize and I think is a huge part of, of, of success in my career, in my wealth creation career, in my, in my kind of professional career today. I like that and two things I want to highlight there before we wrap. One is you've built your identity and your self-esteem not based on the outcomes of being this, you know, Forbes 40 or building x valuation of a company, but by a character trait that's in your control, right? So like that allows you to feel successful anytime you want because you relate to yourself as being someone who's resilient who will figure shit out and that builds a lot of self-esteem and pride for you. And I think that that's really, really powerful. And I think second, that is the message that I really capture from you is get creative, never give up. There's always a third door to look through. There's always, and there's always a way. And I like that about your mindset is through all the shitstorms you've been through. You're like, all right, we got to pivot the model. Do we have to pivot the business? Where's the opportunity in this? We're going to get through it. And I think that mindset, if you're listening and you embody that, that will take you as far as you could possibly ever want to go. But I do think that is probably the definition of an entrepreneur. Yeah, and one thing I'm reminded of right now and I haven't thought about it enough in an entrepreneurial context but every year I'm watching college basketball. Well, whatever. And that's the Jimmy V week. And don't ever give up. I would edit that to say, you need to recognize when certain businesses need to just call it a day. But I'd say don't ever give up on your entrepreneurial career if you want to be successful as an entrepreneur. Give up on ideas, but don't give up on yourself. I think that's a great way to put it. And then he also talks about a full day is when you would laugh, cry, and I forget what the third one is. But there's a lot of great stuff in that, in that one speech that I think he's talking about it in a sports context. But I think so much of it can be true in a business context as well. I love that, man. Amazing, dude. Thanks for coming on the show. This is incredible. Appreciate it, you have me.