So Alex, Jay is a multi-hyphenate in a lot of ways. This is a guy who was a superstar college athlete, has a massive accident that sort of takes him outta the NBA and completely reinvents himself to the point where we know him from ESPN. We also know him really as one of the leading athletes turned entrepreneurs. He's a very good guy. And you know what? He has an incredible appetite, very inquisitive, and is building a big business. And I think he's a fascinating guy. And I think you'll find his interview very, very good. And very intimate and very revealing. There's a vulnerability that you showed and that he showed that was pretty amazing to witness. So, without further ado, Jay Williams. Alright, we like to start every show, Jay. Oh my gosh, I just introduced you myself. You introduce yourself and tell us who you are.

How do I do that? However, you take your time. Jay Williams, on-air personality, I own a media company, I invest. I followed him for a very long time. Kind of geeking out to be here with you guys and just excited for the opportunity to chat. And where'd you go to college? Oh, Duke University. Played for Chicago Bulls. And we have a great common friend, obviously much closer to you than to me, but I'm a big admirer of Coach K. Coach K, yeah. Which we'll talk about later. Definitely. Yeah, we're definitely, we're gonna get into all of this. I feel if we're doing TV I should have done a better job of introducing myself. You want take two? Do it again? I messed up, it's small. Yeah, no, that's good. That's good. People like it a little rough. I do wanna ask you, I mean, we're gonna talk about a ton

of different things, but one of the reasons I know Alex and I were so fascinated to talk to you is, given everything you just said about what you're doing, what you have done, it does feel to me like something new and different is happening in sports and media and culture right now. Do you agree? And why do you think it is? So I'll give you guys some context to how kind of, and guys like Alex, I think have really helped me expand my mind and how I think about this. I started holding company when I first got into TV, just called Clandestine Ventures, right? And my mom, who just passed away a year ago, God rest her soul always again, why such a negative connotation word? And that was always because at ESPN, I couldn't let ESPN know about investing. I couldn't let ESPN, I invested in a procurement company for sponsorships 'cause it always got used against me, right?

Like I wasn't focused on my craft. And I just think now we have people that are unapologetically themselves and this conversion between sports, finance, media, you could talk about your portfolio on air. You can talk about my relationship with Adam Silver and obviously our Duke connection and how it gives me different insight into team ownership and the CBA. I think now it's way more appreciated because there's a, the bandwidth has extended, right? And now it's just not about polarizing conversation or about the game itself. It's about how you're providing color to the commentary. Do you feel that way too? 'Cause I feel like, I mean, as Jay said, you were on the front end of this in terms of, you tell the story about, going into owners' offices in your cleats and seeking advice. But like, that wasn't the norm. And so does it feel different to you as well?

No, I agree with Jay. To me, it was like a taboo to do anything else besides your core business. And as a little bit, you had to do it in the shadows. I started my real estate portfolio in my early twenties, but it was like a dark secret. And it's funny, the most grief I ever got in my entire career, far more than the PD suspension and all of that, which we'll get into later, is my contract 252. Yeah. In the year 2001. And the contrast between that announcement and Ohtani? Ohtani was a hero. He was celebrated. I was a villain, you know, 101, it was like Darth Vader. So it was interesting how far things have gone. A lot of it, I think, is social media now. The power's gone to the athletes 'cause now they have a platform where they can fight back. Mm. And back 25 years ago,

owners ran everything. I was gonna ask you because I feel like there's this missing gap, Alex, that's happened, right? And you've been able to close that gap. But I see a lot of other athletes that are trying to focus on that and celebrities from going to becoming, you're the asset, but how do you become the principal? How do you navigate doing TV while also now being in a position to be an owner, right? Which is how people, they may take that as commentary. Like how do you kind of play neutral in that regard? Yeah, that's a great question. I mean, it helps that I commented on baseball and own in basketball. Yeah. That's a big help. I think for me it's really thinking about it long term. I think the biggest mistake I see young players is they become very transactional and they want it now because that's how it is in basketball, right?

You go to Duke for one or two years, and boom, you got a huge contract. In business, I thought about it: how do I build a business over the next 50 or 60 years? So it's allowed me to discipline what I call the 10-touch rule. So I won't ask you to be my partner or Jason until we have at least 10 touches. Mm. Now touches can be a nice exchange of emails, it could be coffee, it could be this, it could be going to a game together. But after 10 touches, that's enough time where we've built a relationship, and now we can maybe start thinking about doing something together. And it keeps you away from the one-and-done like, Hey, I met you. Can you invest in my business? It kind of gives you time to breathe. So it's more transformative than transactional. For sure. For sure. Because I find there's a lot of that in my industry.

Like even in looking at some of the deals that other athletes have taken, I'm like, Okay, well what's your long-term plan? It seems more like instant cash grabs instead of actually having a brand strategy. Yeah. And so how did you start to think about being a business person and when. Is that something that like you're talking to Coach K about? Are you talking to your parents? Like how does that start? So I got lucky. My dad worked at American Express for over 20 years and my mom was a guidance counselor. So I used to watch her go back to school and receive multiple master's degrees while I was in school. So you can imagine being in daycare, playing different sports, and my mom's going off to night school. But my dad would bring me into the city because I'm from New Jersey all the time. So I would take the train with him, and I would see him do his Windsor knot over and over again.

because you prepare for the job you want, not for the job you have. Mm. Right. And Ken Chenault was the first Black CEO that I've ever seen. Yeah. As a little boy. So like even watching like Kamala Harris now run for president, like my two daughters see somebody that looks like them running for president. Like that's a monumental thing for what that could do for your psyche. So just knowing that my dad worked for a Black CEO, I kind of became enamored. Wow. With Ken Chenault and Amex. Then when I came to Duke, which is great, coach had me think that way. We started sending letters to Fortune 500 executives that had graduated from Duke. And we started inviting them down to North Carolina. Wow. Similar to how you did it with the Yankees, right? I mean, there's a lot of commonality here because Duke was always called like the Yankees of college basketball.

Yep. Right. And all that entails. I know, right? So all these guys would come down and we just kind of picked their brain around what businesses they were in, how they scaled those businesses, how I should be looking at utilizing like my name, image, and likeness. What businesses should I be thinking about investing in? And how I should handle my approach to the NBA. It was life-altering. So with that in mind, I love the comparison between Duke and Yankees because everyone that watches us, you have an opinion. It's not like you're indifferent. Yeah. You either love us or hate us, which is kind of cool. But my question to you is, at what point did you start crystallizing what a holding company would look like? What was your education behind it? So probably going into my sophomore year, we lost in the Sweet 16 to Florida and I kind of got punked on the court. And it was one of those moments for me where I had a choice.

I could have gone back home, spent some time with my friends back in New Jersey, but I'm kind of a competitive prick, Alex, in a lot of different ways in life. And instead of going back home, I was like, I just wanna stay here. So I went to summer school, I started overloading in all my summer courses, and I just worked out every day, got a chance to play USA Basketball, made the team. And I had this one game against Jason Kidd and Gary Payton, where I not only held my own, but I did really well. And all these conversations just started with, Oh, okay. Like Jay, you could be a first-round draft pick. Mm. Like I went from not being on the draft board to all of a sudden that summer being a first-round draft pick. And then I just started averaging 23, 24 points a game. And people were saying you could be

the top pick in the draft. So, I think during that time, we had never really prepped for all that stuff around finance. We thought I was gonna be a four-year guy, but then I just started receiving calls like agents, financial advisors, accounting services, and then my father, my mother, and I, which is always tricky. I was gonna ask you how you started dealing with that. Like when your parents are kind of at the forefront of those conversations, and it's like, All right, well we're gonna start like, what's the limited liability corporation? Right. What does this actually mean? What do we want to name the LLC? Who are the members of the LLC? Are we gonna have an agent that's gonna be handling your accounting services as well? And we just started having those real conversations. And frankly, that onboarding process while I was in my season, it felt overwhelming. But I think the more I did it, it became part of my routine.

Mm. And I didn't feel as disturbed thinking about, Okay, this is my business, basketball is my business, but this is also my business. I shouldn't let that take away because I dunno if you dealt with this, if people say, Well, the more you focus on that, it takes away from your focus on the field. That used to always happen to me. Yeah, yeah. For sure. For sure. And I saw it as just like, as a compliment to my work. Right. And I made it to a point where I said, for every a hundred thousand dollars that I make, or every 200, I can buy a million dollars worth of real estate. 'Cause you got 800 of debt, 200 of equity. So you kind of make it simple, right. And you kind of build it one block at a time. And then any role models that you had, who are some of those people that you've looked up to say,

You know what, I like what they're doing. I can take a piece from him, a piece from her, and now I have what I have. For me, that person's Magic Johnson, who was a big mentor to me, sat down with me almost 30 years ago and kind of created the foundation of my company today. Do we share Magic as somebody that you looked up to as well? Of course. 'Cause he's obviously the GOAT. I wore 32 all the time in high school. I couldn't wear it in college 'cause Christian Laettner had it. So literally, I took 22, which is just 10 off. I got that. But definitely Magic for what he's been able to do real estate-wise. Real estate is actually still a part of my portfolio I haven't really tapped into yet. And also kind of Michael's entry point, Jordan. Just, I grew close to David Falk. I didn't go with David Falk; I went with Bill Duffy.

David Falk, a very well-known agent. Yes. From Michael Jordan, helping obviously with the Jordan brand, everything. So just watching the way Michael, but also kind of hearing that story, I think for me there was always this challenge because my father was so involved in business and my mother was participating in my business. See like, can I be vulnerable with you guys? Please. Of course. So you start finding out about all these things that got, and it's weird, it would've probably crystallized different for me if I had played 15 years in the league. But when I got drafted, you want to give back to your family, right? So when you start learning that, hey, you're gonna get gift-taxed, anything you give over a certain threshold. Like okay, just let me put my family on the payroll. Right. So my dad was a CFO, my mom was a CMO.

You give people random titles, not that they're actually responsible for those titles, but we were trying to figure it out. And I think when you start going through that process where you're paying your family, I had a lot of conversations with Magic early around how do I take more ownership in knowing that this is my business? How do I delegate some of those responsibilities to my mom and my dad? Which when I got drafted, that changed for me. They were my business partners while also being my mom and dad, which was a really weird, that's a lot of red tape... Yeah. ...involved in that, right? 'Cause a lot of people that are coming to you from different angles and I don't know how to properly vet deals. I don't know how to properly vet people. I never had a lot of practical experience in that. So I think leaning upon Grant Hill was another one because he played at Duke, what he's been able to do

with his businesses, a part owner of the Atlanta Hawks. I tried to lean on those guys, but also my career was cut short. So, my life took a different turn very abruptly after one year. So I didn't get a chance to really lean into those relationships as much as I wish I would've at the earlier stage. I did that later. Yeah. Jason, I don't know about you. It's interesting, we have a great threesome here of people where you have African-American, White, and Dominican. Right. I grew up with a single mom. Dad left at 10. And this changed my life, Jay. She had two jobs, secretary in the morning, she served tables at night. And we go into Publix one day and it's like a $75 bill. And she pulls out 55 bucks and then we're short about 20 plus bucks or whatever. And she goes into this other little zipper and she grabs like 25, but it's not green, it's like red.

And I was like, Mom, what's the funny money? And it was government money, food stamps. And I said, Oh my God, I have to like be the alpha, I have to be the leader of my family. But going back to your mom and dad, I can give my mother, a Dominican mom, any title, but she's still gonna be my boss. That's a little bit of- She'll say take those three letters and you know where you can stick 'em. But that's the thing about inheriting money, right? And I always see a lot of my other friends, a lot of the financial conversations that they had with their parents who were more successful and their competency was way higher than me. So now I was being thrusted into this lifestyle where I was with the rich and the famous, but I didn't really learn about the underground, underlying business of how to actually sustain that.

So we were, everybody was being onboarded to wealth in a crash course. And I think as my parents and my career started to build, a lot of that stuff, they often say when you make money, it reveals more of the challenges and difficulties, more money, more problems. And a lot of those family dynamics kind of started to play into the business as well. So that raises a really interesting thing about some of the work you're doing right now. Name, image, and likeness has changed everything in the college sports world. You see it right down the street from you at University of Miami, I feel like writ large. You're doing a lot of work around this, got a new show coming out, you're working with the University of Alabama quarterback. Now all these conversations that you're talking about that really only happened in a fairly limited way for a small number of people, they're happening across all of these sports,

across college football, even at the high school level. So, what's the advice that you give, having known what you know but also seeing what you're seeing now around NIL? I think first goes to the point that we were just making mention of, right? When you start, like, let's say crazy competitive, I wanna work out for eight hours a day and I sleep for eight hours, there's still eight hours left in your day. I'm like, how do you start building your competency in finance, at an earlier age? Like, you should know what an LLC is and all for these kids now, they're having a chance to make money. Like, Jalen Milroe is making over a million dollars a year in NIL. Now, as a 19, 20-year-old young person, that's a lot for you and your family to handle while you're handling a new coach coming in. Right. Replacing Nick Saban while you're now learning how to work

with the collective, which essentially is like acting like the front office for the school and negotiating rates. How do you keep the main thing the main thing when the main thing is actually the money and the revenue that's being driven off of all this conference realignment, TV, media deal rights? And it's all the Wild West, you know? So for me, I often start the conversation with, let's create a flat line. Let's understand what your business is. Like, your main thing is the main thing, but this is also part of your main thing. Right. So let's give the main thing in this totality the time and the attention it takes. Because if you want to be a billionaire, right? If you wanna go from asset to principal you need to put in the work. And by the way, reading two to three hours a day is putting in the work. Asking questions is putting in the work, having curiosity.

So I think that's the start. Number one, you also have to own your IP. So I think that's really big right now for him. So him and his teammate, Terrion Arnold, last year, they started this whole thing around LANK, Let A Naysayer Know, which I thought was really smart, right? And it turned into the school's rallying cry. So they filed for trademark the name. Hmm. And I've never seen this happen before where players have filed for trademark, for a name that the school then kind of backed because Nick Saban was talking about, Let All Naysayers Know. And it had this virality moment last year with Pat McAfee on game day, where it just went everywhere. So they did a merchandising deal with the school, right? So that sets precedent. So now they're sharing that rev with the school. And now we kind of create a digital diary series around that.

because I want him to be able to talk firsthand person around how do you navigate owning a name like that, dealing with the school? But also, trying to win a national title, competing for the CFP, having the greatest coach of all time that is no longer there. Right. So how do you, not that you can control anything, Jay, but like how do you think about like what is your narrative and how you're seeing this and how do you stay in alignment with what the school is doing, but how do we make the world see who you are a little bit as well from a leadership perspective? And we own that. And we are working with the brand now, Beast, which is actually gonna be a sponsor of the show. So we're able to tie his endorsement deal into the content, which is smart. And I just like that medium. And it's a proof of concept for us to see how do you work

with the collective, how do you work with the school? And also, at the same time, how do you build his own individual brand? And like, how do you personally engage him? I mean, are you talking to him most days? Like what's the, how do you build that rapport where you become a trusted advisor to him? I think I'd be curious to see how you talk to Anthony Edwards. Right? 'Cause I've known him for a while too. I think it's more of a Big Brother approach here. Okay. As it like, okay look, if we're gonna do content, I don't think that answer puts you in the best position with the media. Probably wouldn't say it like that. Maybe how about this? Or when he gets frustrated about something, I don't understand why this deal works out. Okay, let me explain the nuances of this to you to a degree. I think it's more of that relationship

and helping him navigate. I'm not his agent. Yeah. I'm not his financial advisor. We're working with him on the media side and working with him on brand- You're a partner. Yes, I'm a partner with him. So Jay, if we zoom out and you said the Wild Wild West, I think that's exactly what it is. The NIL genie's outta the bottle, they probably never come back in. But a few questions: How do you feel about that, kind of pros and cons? And is this something that is ultimately better for college sports? I do think it's better for college sports. I still get frustrated at it because, whenever people, I hear them talk about NIL, the natural proclivity is to say, Well, okay, now athletes are gonna pay. Well actually like, can we talk about rev share? That's different, right? So now we're starting to engage in that conversation.

And whenever you talk about rev share, Arod, then you start talking about, Okay, like how about workers' comp? So just to be clear, what you're differentiating between is NIL where it's like they're getting paid by a brand or a collective or a company versus rev share where they are actually a real partner and employee ultimately of the school or the team. Do I have that right? You already see Dartmouth basketball trying to do that. Right. And also like, so USC, UCLA, they go to the Big 10. Now you tell me how that fits the geographical footprint. It doesn't. It fits the financial footprint of the Big 10, right? Which I understand, but it's no longer about academics. Like that travel schedule alone from going from SoCal to Columbus, Ohio and then back, like you're gonna miss multiple days- And then back to Maryland and then back to New Jersey and yeah.

Come on. Alright. So, I understand that. But with that comes a lot of responsibility. So, when you start having these types of conversations, then I go, Okay, well, the university has representation, the leagues have representation, the players are allowed to have representation when it comes to branding and endorsement deals. But who is sitting at the table for the players? You need a union. If you're gonna become unionized, that means you're going to be an employee. So, you have different employee rights, benefits. And I think that's the next step in the natural evolution. Especially when you look at basketball and football. They generate the most revenue, and look at what happened to the Pac-12. Like, it's, there's no longer the Pac-12. Right. It's disintegrated right in front of your eyes. Improbable. We didn't talk a lot about it, but that has been a really interesting,

I feel like a new version of what media can be and is going to be. What's your vision for that? I think it's one that's constantly morphing. I think it's like anything; I think when you go into it, you think it's gonna be one way, and then you have to pivot a thousand times, and it starts to take on a new shape and form. I think originally, at first, it was okay, as we look at Giannis, who I think is one of the biggest athletes in the world, touches three continents between Africa, the United States, and Europe. How do we capture the value in the production and creative aspects along a lot of his endorsements? 'Cause you're seeing a lot of those are just outsourced to third parties. Right. Right? And I think once you kind of become integrated into the storytelling aspect of it, it allows you to build longer sustainability with that actual client. It's not a cash grab.

Like I think a lot of players look at endorsements as, Okay, I have a five-year deal worth $20 million, that's great. And then when you get into four years and eight months, it's like, well, how do we start renegotiating that deal? So for me, I'm like, no, like we're gonna sit at the creative table, we're gonna keep all the metrics and the data. We're gonna show you how we're adding value to your brand. And then I want to pierce the conversation because I really think it bleeds into the portfolio from an investment opportunity. Once again, it goes through deploying capital. Then could we deploy capital and co-invest alongside that athlete, take a stake in what that entity is. Principal. Principal. Right. And then help scale it as well. I mean, similar to how Ryan Reynolds has built Maximum Effort. Yeah. You've seen them do that.

with Aviation Gin, you've seen them do with Mint Mobile. You're seeing to do that with Wrexham. So, I think having the pipes to amplify the brand, but then also having the capital to deploy. And I think having a seat at the table with the right board of athletes. And then, yeah, I think inevitably getting athletes to buy into this thing of shared economics. Yeah. Like, I'm watching Steph do it, and he's doing it successfully and very well. And LeBron, Stephen Curry. Stephen Curry, once again, first name basis, I'm sorry. Steph probably is another one. He's on the verge, he's on the verge. Yeah, he's on the verge. But like, how many things can you scale by yourself? So, as an athlete, I think I'm built to say, Hey, I can't win a national championship without Mike Dunleavy. Or without Carlos Boozer or without Arod.

So then, where is there a world, for lack of better terminology, like a multifamily office in which five or six guys are coming together, and they're saying, Okay, how do we add value? Mm. Maybe we have a pool of capital here that's not ours, but we can deploy capital from, we can then co-invest with that. But then how do we add value collectively with having the brand strategy and coming to the table with a vision? It's just saying, Hey, I'm at the table with capital. Right. I think to me, that's where you receive compound interest over time, and you're creating enterprise value. So I wanna take a, as we all say in our collective business, a hard pivot here. Okay. And go back to something you mentioned earlier, which is, I dare say, the pivotal moment in your life when you're in a terrible accident, right as you come into the league, and it changes the entire direction for you.

Tell us what that moment meant for your life, but also for your business career. 'Cause it changes what your job is going to be. I would love to know how it changed you as a burgeoning business person, as how you defined yourself. Yeah. Well, first off, I think it gave me, no pun intended, a real crash course in how hard and cold business could be. Right? I've been a part of a lot of deals since sometimes when you have money in a deal, you just, you're forced to look at things way more objectively, because your money's the asset in the deal. When you're the asset yourself, it's hard not to become emotionally tied to that. So I remember watching the Bulls draft Kirk Hinrich, who I just played the year prior at Kansas, and did work against him to replace me essentially in my hospital bed. Right? So having conversations with Jerry Reinsdorf,

understanding and hearing firsthand what their business strategy was, was a hard pill for me to swallow. And it's crazy like thinking about it like, it's one hell of a business strategy. I mean, it's the right plan, right? It's the right plan that all of us would do. But when you're hearing that as the asset on the other end in the hospital bed, that led me into a deep state of depression. I mean, I had two attempts at suicide that I've talked openly about, but I think that forced me all of a sudden to start over again after I went through a couple of years of depression. I really want to understand basketball and the CBA. Mm. And how it worked. And actually, it led me down a path with risk mitigation as well. Because when you start receiving all these bills, you're like, Well, hold on a second. How am I gonna pay for these 13 plus surgeries?

Right? So, the Bulls kept me on their insurance. I had some challenges later with disability that I had to work through, but it opened my eyes to risk mitigation in a completely different aspect, which kind of led me down the path when I made my first really big investment in an insurance brokerage firm 'cause I started to understand about wholesale, I want to kind of sit in between the middle. It really opened my eyes up to the under-the-table businesses associated with basketball, more importantly, and I really started studying the CBA under a guy named Charlie Grantham. I tried to become an agent. Hmm. I thought that was my first step into the world because I wasn't gonna play anymore. And then, things became difficult because you realize when you're actually working for an agency, you spread a lot of money out to 501 's, which are essentially AAU Programs. Right.

And that was still deemed illegal at that time. And a news reporter broke the story on Yahoo Sports that even though I wasn't the main agent, but associated with the agency that we had paid Kevin Love's AAU team. And it was just one of those things where I was like, Okay, how am I, like, how am I gonna do this? Like I've lost the ability to connect with players because if it becomes public, that's my mantra to a degree. And how do I kind of change that narrative about me? So I got involved in TV and that's when I really, I was like, Okay, now I see how media works, I see how this one article came out, how it affected me. And I frankly started the process of writing my book then. I was like, oh, okay. Like, I'm gonna change this narrative. I'm no longer gonna be the victim to my motorcycle accident.

I'm gonna start thinking about how I use my accident to build off of and kind of lean into what I wanna become business-wise. And I think that was the first step, like, it's PR. It's like crisis management and kind of starting that step in media, working for ESPN making $35,000 a year, which is another humble kick to the gut. Yeah. And I started understanding media, working in media, and I started the process of writing my book. This is something else we have in common. And I was telling Jay, like in '14, I served the year suspension for PDUs and my whole world kind of fell apart. And I mean, I think it's very public now that I've done over 12 years of therapy. I continue to be in it as a huge part of my life. But I had built this incredible career and I was almost 40 and I'm just like, it was so scary to have to think about,

Oh my God, am I gonna have to scratch everything and start all over again? Like that. I was below ground zero, below ground zero for different reasons, obviously, than yours. But nevertheless, we had to build it back up from ground zero. I mean, you and I have talked about this a lot. I mean, one of the first in-depth things that we did was essentially me asking Alex a question of why did you even decide to reengage? Because there's a version of this, certainly for you, where just like, All right, I'm good. I'm gonna go live on an island or do whatever. I'm gonna remove myself from public. I'm not gonna play or I'm not gonna certainly get out there. What was your thought process? I mean, like Jay, very much depressed because you've worked so hard to this point, right? And you feel like you're now set up to win,

or reap the benefit of your great work and thousands and thousands of hours of commitment and dedication. But ultimately why I think Jay and I probably didn't go to an island is because we're both competitors. And I like that, competitoring prick. I'm gonna steal that because I mean, I'm a nasty competitor, almost too competitive. And I felt like I had something else, I had another chapter in me. And I was too young to just give up. I mean, it's not in our DNA to give up. I don't know if I had suicidal, but whatever the stop before that is, I was probably there. Because it's such a, a scary thing to be in a place where you've built it and now you are at ground zero, literally at ground zero, below ground zero. Like I felt like if I got up to the lobby, that was a win. Hmm. So, and I also felt like there was millions of kids out there

that don't have parents that are great mentors or single parents like my mother who don't have that. And I felt like I had a lot to offer for those kids to at least learn from my mistakes. And that was really the thesis of wanting to come back is to make an impact. It was too far away from, I wanna go back and play baseball, or I wanna go back and go to the Hall of Fame, or I wanna go back and build an empire. It was really about like, I know I have another chapter, I dunno what that looks like, but I'm gonna give it a go. How'd you learn how to tell yourself a different story? 'Cause I know that was, playing at Dukes and we were playing the Yankees, like, we're on TV all the time, right? So like before, when I would walk in rooms, whether that was business or personal, it would be like,

That's Jason, like number two pick in the draft, plays for Chicago Bulls. He's on I-90, he's on the billboard, he has Michael Jordan's locker. So all of a sudden, I look me like, Are you okay? Like it was completely, it was a different entry point. I would even sit down to business meetings and like some of these higher-level executives would start the conversation from there. And I feel like I would have to drag myself out of the basement to get to the lobby level. Like, how'd you deal with that from a storytelling perspective? I just started leading with the worst. I started leading with that. So beat them to it? Beat 'em to it. Beat 'em to the spot. Right? And it's kind of what you start to do with your book or your story. And I felt like, if you start with the worst, then we can get better from there. Hmm. And if you wanna

throw me outta the meeting. Let's just do it in the first 10 minutes. That way I don't waste your time, you don't waste my time. Yeah. But I feel like when you own things and then you talk about the lessons learned, at least you set the foundation to show that you have self-awareness. And I see this from a lot of young kids or just people in general that they make mistakes, but their self-awareness still hasn't gotten to where it needs to be. And what I sense is that when you win a championship or you sign a big contract or you're that number two pick from the Bulls or the Yankees or whatever, self-awareness decreases and ego increases. And I wake up every morning with two prayers: I wanna enhance my self-awareness and decrease my ego. And I think that's my happy spot. Yeah. That's one way that I did it.

Yeah. I think I learned that throughout that process. I've always kind of been enamored with C-level executives. Yeah. Because I've always wanted to be one. Yeah, me too. And it's amazing how many people I talk to that have gone through challenges within their businesses, whether filing for bankruptcy or losing money for investors. And I think I recognized while I was writing my book and having all these conversations, Oh, like everybody's had a motorcycle accident in some form or fashion. Everybody's had some kind of crash. Like ours may be more extreme than others or more public than others, but maybe that's a place to actually build a bridge between myself and people to actually not come to the room with more of my ego, but to be more self-aware and then to actually form more of a community. And so how do you start building from there? I mean, so with all of that in mind,

you're doing work on yourself, but you also have to do the work. You have to figure out who you're gonna be and what you're gonna do and candidly, what you're gonna contribute. You know what I mean? We talk about this all the time in terms of what your mission is gonna be. So how do you hone that over time and who do you go to? I mean, is this something where you go to Coach K and I know Alex has sort of almost like a board of advisors that he- Yeah, Coach K scratched three copies of my book and told me, Bring this back when it's better. Yes, Coach K is on the respective board. And so how do you go about building that? Well, I did form a personal board for some people that I had admired that I reached out to in college and I get beat up. Like, it's like a real, it's like a real board meeting,

like, Really? All right, Q1, where are we? Like, what are we doing? Like, what's the portfolio look like? And we go through that. But then we go into, like me, personally, what's the marriage look like? Where the kids? How are we balancing it? Like, it's like I really get pushed and tested, which I very much appreciate. But just to go back before, like I really leaned into media because instead of just trying to go off and invest in all these different things, I'm like, All right, like what is my platform? Like basketball was my platform before, what is my platform? And I think learning media and studying it and then studying how to be effective at it, but also how to be different than what I saw on TV. One of the things I think you do well, which I think is a huge gap between kind of the sports community, entertainment community versus the business community?

I love the way you reach out and you're not afraid. Where did you get that from? And you should be doing a lot more of that because you're on TV and you're reaching out to be with great people, whoever you think those are, is the best way to grow your business. I think I just have an insatiable appetite. And it's like even when I reached out to you, like I wanna be an owner one day of a team. Love that. So understanding what teams are coming on the marketplace. Like what's happening in Las Vegas for the NBA? Is there a team in Mexico City? What's gonna happen in Europe? The explosion of NWSL and their new media rights, the WNBA, which is in an interesting entry point from an investor perspective, professional bull riding, PBR, that league, SailGP. Like understanding where all these leagues are coming from and how to actually vet those opportunities.

That's number one, right? I think you are on point. And that goes just to close the loop on this story. I think when I was learning TV, I think I saw that gap, and I did this show called The Shop, and it was with LeBron and Maverick, and it was when they were launching SpringHill. Maverick Carter was LeBron James' business partner, yeah. Yes. Sorry, I should be a little bit more- That's all right, that's I'm here. Yes. And I saw them building this media empire, but then also I saw how they were utilizing the media empire for a lot of their investments. And I also saw from my perspective, all of a sudden on the show, now I'm an executive producer, and I'm talent. I'm like, Oh, okay, I can eat on both ends. Yeah. It was very fascinating. So then understanding that dynamic

and how they worked. Then I started working with Rich Kleiman and Kevin Durant when we launched The Boardroom. Now, that was tricky 'cause I had to sell The Boardroom to the company I was working for, right? So, that allowed me to have a lot of different conversations with Jimmy Pitaro, Connor Schell, who did an ESPN 30 for 30 with Rich and Kevin. But it was, once again, it just served proof of concept that I was with Serena here, Williams, about her venture firm, right? Serena's one that you could just say Serena. I dunno, some people, you gotta be first name basis or you can't. And then I start sitting down with Steve Ballmer and Josh Kroenke, and hearing about all the teams they own and start learning about tax abatements and how to think about that when you're actually building a stadium in Inglewood, right?

Some of the challenges that come along with that. And then I would listen to high-level athletes who actually were pretty competent in business but still didn't sound as competent or still were somewhat a little bit afraid to sit at the actual table. Alex, do you still get that? Like with certain athletes, like who were, they want to be in the room and they could be in the room and they can listen, but they don't know how to take it to that next step as a business person. Yeah, I think a lot of it is because they're never alone in a room. Yes. I would tell athletes, get yourself in the room and go alone. That's the greatest advice I can give you. Because if not, inevitably they're gonna talk to your agent or your manager or whatever. Now it's okay to bring one person or whatever, but get in the room, get uncomfortable and feel comfortable in the uncomfortable, especially sitting at that table.

And I love the fact that you have quite honestly, we say the cajones. Maybe moxie? Yeah. See, that's a Georgetown word. See, Georgetown, Duke, I feel very much an imposter right now, okay? I have like Dominican University here. But Jay, with you, I love that you can verbalize, that's part of it. And to say it, first of all, it's hard to do it in your mind, to say it in your mind. You're saying it publicly, I wanna be an owner one day. That's awesome. But how does the Jay Williams holding company look in five years if you had it your way? Hmm. I think having capital to deploy is very important to have a seat at the table. So, I think what you might see is I'll always keep my foot within media, from an ownership perspective. 'Cause I understand that business and I understand where that business is going.

But I think the sports marketplace is really fascinating for me, Alex, right? Like being able to have capital behind an entity with a media marketing branding arm where I can look at certain investments and I can look at their operating teams and effectively take shots at those types of assets and scale that slowly. And I don't want to use the term private equity 'cause that's just like everybody, I don't wanna be involved in private equity or every athlete wants to have a family office, but a team of brand strategists and a chief investment officer in which we could look at different assets and then marry IP to certain athletes that I think actually want to work and actually want to have a seat at the table. Because I do see that correlation. I am able to have conversations with certain individuals where I'm like, I'll bet on you. Because I know that you will like to work. And also, we have access to so much stuff, right?

So it's like somebody says, Hey Jay, in five years, if this explosion continues to happen within the collegiate market, what's one of your port codes? I would say, I would love to own a significant piece of Duke basketball, right? Would love to own a significant piece of Ohio State football. I think that's going to be a marketplace that's being tinkered around right now. But then also thinking about all these traditional athletic companies, athletic departments are still very archaic. And now I think you're seeing the same way private equity's entering the NFL, conversations around Aries and other PE firms, entering that market. I think that's gonna happen on the collegiate market and how could you help Duke generate more revenue and be more profitable, right? By having experts associated with Duke basketball from a branding perspective, from a content perspective, from a media rights perspective. So I think in five years, I think

that's the direction I'm going. And I think, similar to you, I think I always love commentary, but I wanna be insightful with my commentary. And I also think, similar to what we're doing with Jalen, I like telling things more from the player/businessman perspective instead of just the player. Yeah. Perspective. I think I'm starting to learn that that could be my sweet spot that doesn't allow me to ultimately hurt my relationships, but still be true to myself and what I see. Well, that's the, I mean, you talk about Magic all the time, basically saying you can get in the room, like you guys can do the thing that is certainly hard for a journalist, but like hard for an everyday person just to get into the room. 'Cause everybody wants to know exactly what you're talking about. What's it like? What's it like shooting that free throw? What's it like taking that three?

What's it like being at that home plate? And then you're in. And then you prove yourself, and the relationship begins, et cetera. Yeah, I agree with that, Jason and Jay. The thing is that I've studied so many of the titans, right? But what they are expecting is they're expecting for you to come in the room, be a nice guy, and take a picture and sign autographs. And then we say, bye-bye to you. Now we put you on your way. They're not expecting you to have a real team, and they're definitely not expecting you to follow up. And I think that's where most athletes, 20% of the athletes ask for the meeting, probably 1% of those 20 follow up in a real way. And you gotta follow up, right? And you gotta be long-term thinking because if most athletes come in with high expectations, one meeting, big deal.

It doesn't really happen like that unless you're Tiger or maybe Tom Brady or something that is just one and done and you're good. But it's just who's gonna be persistent to hang around, hang around, keep coming back and stay focused on what you really need and want, you know? All right. Let's do our rapid fire now. I think you're gonna be really good at this. I dunno how I feel about this. I think you're gonna be really good at it. All right, I'll start and then you pick it up. And what are the rules? Keep it tight. Keep it tight? You just keep it tight. Do I get a chance to ask any back to you guys? No? We'll see how it goes. Yeah. All right, at the end. What's one word to describe your deal-making style? Patient. What's more important to you, your instincts or data?

I really value data, but I think it's coming down to instincts and gut who people are. Who is your dream deal-making partner? I mean, it's David Rubenstein. I thought you were gonna say Jason. What's the best piece of advice you've received on deal-making or business? Never run, always walk with pace. Same question. What's the worst advice you've ever been given? Worst advice came from an athlete. This is bad. Actually, a successful athlete. Jay, the more deals the better. Oh, wow. Actually, no. Oh, interesting. That's the best answer we've ever gotten to that question. Tangible. What's your hype song before you go into a big meeting or a negotiation? This is weird. Like I've been listening to a lot more classical orchestra. I'd like to try to be calm. Okay. Take the emotion out of the deal. Any specific composer that you like?

I'll go with old school, like a little Patti LaBelle. Okay. A little Patti LaBelle. A fun fact about yourself that your colleagues will be surprised to hear about. Loyalty and transparency are very important to me 'cause I didn't have that a lot in my life. I had a lot of times where a lot of deals or a lot of people tried to pull the wool over my eyes. And I think I always try to operate from that space. All right. Well, this has been a huge treat for us. Thank you so much, Jay Williams. Thank you. Appreciate that. Good stuff, guys. Thanks, Jay. Thanks a lot. Thanks, Jay. Thanks, man.

How Jay Williams Reinvented His Brand After Basketball | The Deal

Bloomberg Originals offers bold takes for curious minds on today’s biggest topics. Hosted by experts covering stories you haven’t seen and viewpoints you haven’t heard, you’ll discover cinematic, data-led shows that investigate the intersection of business and culture. Exploring every angle of climate change, technology, finance, sports and beyond, Bloomberg Originals is business as you’ve never seen it.


How Jay Williams Reinvented His Brand After Basketball | The Deal

Scripts