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Hi, I'm Jason Kelly.
I'm Alex Rodriguez and on this episode of The Deal, Jay Williams, 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 out of 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 in 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 win.
So, without further.
Ado, Jay Williams, all right, 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 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 an opportunity to jut And where'd you go to college? Duke University?
Play 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, which we'll talk about later. Yeah, we're definitely we're going to get into all of this.
I feel like we're doing TV. I should have done a better job of introducing that.
You want to take two? Yeah, No, that's good. That's good. People like a little rough. I do want to ask.
I mean, we're going to 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 I kind of 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 Cleindestine Ventures, right, and my mom, who just passed away a year ago. God wrestler soul always like you know, why such a negative connotation word, And it 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 because it always got used against me like I wasn't you know, I wasn't focused on my craft. And I just think now we have people that are unapologetically themselves in this conversion between sports finance media. You know, 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 in 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, because I feel like I mean, as Jay said, like you were on the front end of this in terms of, you know, you tell the story about you know, going into owners offices and 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 court business.
And it's a little bit you had to do it in the shadows.
And 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 two fifty two, the year two thousand and one, and the contrast between that announcement and Otani. Otani was a hero, he was celebrated. I was villain, you know, one on one. It was like Darth Vader. So it's interesting how far things have gone. A lot
of it, I think is social media. Now the power has gone to the athletes because now they have a platform where they can fight back and back.
You know, twenty five years ago, you know owners right and everything.
You know, I was, I was going to 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 your asset. But how do you become the principal? How do you navigate doing TV while also now being a position to be an owner, right, which is how people they may take that as commentary. How do you kind of play
neutral in that way? That's a great question.
I mean it helps that I commented in baseball and own in basketball. 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 felt about it, how do I build
a business in the next fifty or sixty years. So it's allowed me to discipline what I call a ten touch role. So I won't ask you to be my partner or Jason until we have at least ten touches. Now, touches can be a nice change of emails. It could be coffee, it could be this, it could be going to a game together. But after ten 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 problem into my business?
It kind of gives you time to breathe. So it's more transformative than transactional, for sure, because I find it it's a lot of that in my industry. Like even in looking at some of the deals that other athletes have taken and like, okay, well what's your long term plan? It seems more like instinct cask grabs instead of actually having a brand strategy.
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 twenty years and my mom was a guidance counselor. So I used to watch her go back to school and receive multiple master degrees while I was in school, so you can imagine being in daycare playing different sports, and my mom's you know, 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 wins or not over and over again. Because you you prepare for the job you want, not for the job you have. Right, And Ken Channault was the first black CEO that I've ever seen, yeah, as a little boy. So like I'm you know, 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. Back to AMEX. Then when I came to Duke, which is great, Coach had me think that way. We started sending letters to Fortune five hundred executives that had graduated from Duke, and we started inviting them down in North Carolina, 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, right, So within all that entails, so all these guys will 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 altern So with that in mind, I love the comparisons in Duke and Yankees because everyone that watches us you have an opinion. It's not like you're in different Yeah, either lover us or hater 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 sixteen 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, you know, I just want to 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 Okay, like, Jay, you could be a first round draft pick. Like I went from not being on the draft boards all of a sudden that summer being a first round draft pick.
And then I just started averaging twenty three twenty four 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 this was I was gonna be a four year guy. But then I just started receiving calls from like agents, financial advisors, accounting services, and then my father and 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 going to start like, what's the limited liability corporation? You know,
what does this actually mean? What do we want to name the LLC? You know, who are the members of the LLC? Are we going to have an agent that's going to be you know, handling your accounting services as well, like you know, And we just started having those real conversations and frankly, that onboarding process. While it was in my season, it felt overwhelming, but I think the more I did it, it became part of my routine, you know, 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. I don't know, if you dealt with this that people say, well, the more you focus on that, it takes away from your focus on the field, like that used to always happen to me. Yeah, yeah, for sure, for sure.
And I saw it just as a compliment to my work, right, And I made it to a point where I said, you know, for every one hundred thousand dollars that I make or every two hundred, I can buy a million dollars worth of real estate because you got eight hundred of debt two hundred of equity, So you kind of make it simple, right and you kind of building 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, piece from her, and now I have what I have for me. That person's Magic Johnson, that was a big mentor to me, started said, sat down with me almost thirty years ago and kind of created the foundation of my company today. Do we share magic as somebody that you look for it as well?
Because he's obviously the go I wore thirty two all the time. I couldn't wear in college because Christian Lady had it, so literally I took twenty two, which is just tenas off and 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 fought very well known agent.
Yes for Michael Jordan Helpen 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, you know, can I be vulnerable with you guys? Of course, So you started finding about all these things I got,
and it's weird. It probably crystallized different from me if I played fifteen years in the league, but when I got drafted. You want to get back to your family, right, So when you start learning that, hey, you're going to get gift taxed anything you give over a certain threshold, like okay, just let me put my parents, my family on the payroll. 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, right, But we were trying to figure it out, and I think we 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 and 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 involved in that, right, because you know 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 par owner of the Atlanta Hawks. I tried to those guys, but also my career was cut short, so you know, 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 have 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 ten, and this changed my life. Jay, she had two jobs secretary in the morning, she served tables at night. And we go into public's one day and it's like a seventy five dollar bill and she pulls out fifty five bucks and then we're short about twenty plus bucks or whatever, and she goes into this other little zipper and she grabs like twenty five but it's not green, it's like red. And I'm 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, she's still going to be. Yeah, that's a little bit. You take those three letters and you know where you can stick on you. But that's the thing about inheriting money, right, it's and I always see a lot of my other friends, a lot of the financial conversations that they had with their parents, you know, who were more successful and their
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 were everybody was being onboarded to wealth and a crass course. And I think as my parents and my career started to build a lot of that stuff. You know, they often say when you make money, it reveals more
of the challenges and difficulties. You know, 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 iminjin. 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 RI at 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 firstco's to the point that we're just making mention of right when you start like, let's say crazy competitive, I want to work out for eight hours a day and I sleep for eight hours, there's still eight hours
left in your day. Like how do you start building your competency in finance at an earlier age, Like you should know what LLC is and all for these kids now they're having a chance to make money, like Jalen Moro is making over a million dollars a year and nil right now as a nineteen twenty year old young person. That's a lot for you and your family to handle.
While you're handling a new coach coming in replacing Nick Saban, while you're now learning how to work with the collective, which essentially is like acting like you know, the front office for the school and negotiating rates. You know, how do you keep the main thing the main thing when the main thing is actually the money in 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 flatline. 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 want to go from asset, the principle you need to put into work. And by the way, reading two to three hours a day is putting in the
work asking questions. It's 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 Terry on Arnold last year they started this whole thing around link let a Nay say or no, which I thought was really smart, right, and it turned into the school's rally and cry. So they filed for trademark the name.
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 they sayers know and 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 you know they're sharing it at 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're working with the brand now Beast, which is actually going to 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 prooful 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, And because I known that for a while too, I think it's more of a big brother approach here as it like, Okay, hey, look, if we're going to do content, I don't think the 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, Like, 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 your partner. Yes, I'm a partner with him.
So, Jay, if we zoom out and you say the wild world West, I think that's exactly what it is. The nil genie is out of the bottle. They'll 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 you know, whenever people I hear them talk about nil, the natural proclivity is to say, well, you know, okay, now athletes are going to pay. Well, actually, can we talk about rev share? That's different, right, So now we're starting to engage in that conversation. Whenever you talk about revshare, Hey, Rod, you know I think you start talking about okay, 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 revshare, where they are actually a real partner and employee ultimately of the school or the team.
Do I have that right?
I already see Dartmouth basketball trying to do that right. And also, you know, like so USC UCLA they go to the Big Ten. Now you tell me how that fits the geographical footprint, Yeah, the Big Ten. If it's the financial footprint of the Big Ten, right, which I understand, But it's no longer about academics. Like that travel schedule alone from going you know, from SOCAW to Columbus, Ohio and then back like you're going to miss multiple days.
And then back to Maryland and then back to New Jersey and Yemma.
Yeah. Right, So I understand that, but with that comes a lot of responsibility. So you know, 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 going to 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 is supposed to look at basketball and football, they generate the most revenue. And you know, look at what happened to the PAC twelve. There's no longer the PAC twelve. It's to sintegrator 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 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 I you know, it's like anything. I think when you go into it, you think it's going to 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 Yannis, 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 because you're saying allow those or just outsourced to third parties, right, And I think once you kind of become integrated in the storytelling aspect of it,
it allows you to build longer sustainability with the actual client. It's not a cash grab like I think a lot of players look at endorsements as okay, Like I have a five year deal worth twenty million dollars. That's great, and then when you get into you know, 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 going to sit at the creative table, We're going to keep all the metrics in the data, we're going to show you how we're adding value to your brand. And then I want to get I want to pierce the conversation because I really think it bleeds into the portfolio from an investment opportunity. Once again, it goes to
deploying capital. Then could we deploy capital and co invest alongside that athlete, take a stake in what that entity is principle principal, right, and then help scale it as well. I mean, similar to how Ryan Reynolds has built Maximum Effort. You've seen them do that with Aviation Gen. You've seen them there with Mobile, You're seeing to do that with Wrexham. So I think having the pipes right to amplify to brand,
but then also having the capital to deploy. I think having a seat at the table with the right board of athletes, and then I think inevitably getting athletes to buy into this thing of shared economics, like I'm watching Steph do it and he's doing it successfully and very well on Lebron Stephan Curry. Once again, first thing basis, I'm sorry Steph probably, but like you know, how many
things can you scale by yourself? Right? So you know, as an athlete, I think I'm built to say, hey, I can't win a national championship without Mike dunleyby or without Carlos Boozer, or without a rod. So then you know, how where is there a world for lack of better terminology, Like you know, like a multi family office in which five or six guys are coming together and they're saying, Okay,
how do we add value? 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 is just saying hey, I'm at the table with capital. I think to me, that's where you receive compound interests over time and you're creating enterprise value.
So I want to take, as we all say in our collective business, a hard pivot here 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 because it changes what your job is going to be. I would love to know how it changed
you as a burgeoning business person. Is who as how you defined your Yeah?
Well, first off, I think it gave me no pun intended a real crash course in how hard and cold business could be. I've been a part of a lot of deals since. Sometimes when you have money in the deal, you just you're forced to look at things way more objectively, right, because your money is 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 Comrich, 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 appeal for me to swallow. That was 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 is to ask 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 wanted to understand basketball and the CBA and
how it worked. And it actually it led me down the 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 going to pay for these thirteen plus surgeries? Right? So the bulls chet 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, because 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 business is associated with basketball more importantly, and I really started studying the cbauder a guy named Charlie Grantham, I tried to become an agent. I thought that was like my first step into the world because I wasn't going to play anymore.
And then, you know it, just things became difficult because you realize when you're actually working for an agency, you spread a lot of money out to five oh one C threes, which are essentially AAU programs, 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 they associated with the agency, that we have paid Kevin Love's AU team, And it was just one of those things where I was like, Okay,
how am I going to do this? Like I you know, I've 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 and that's what I really I was like, okay, like now I see how media works. I see how this one article came out, how it affected me. I frankly started the process of writing my book. Then I was like, Okay, I'm going to change this narrative.
I'm no longer going to be the victim to my motorcycle accident. I'm going to start thinking about how I use my accident to build off of and kind of lean into what I want to become business wise. And I think I was the first step, like in it's PR it's like crisis management and kind of starting that step. And media working for ESPN making thirty five thousand dollars
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 because this is something else we have in common. And I was telling Jay.
At fourteen, I served the year's 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 twelve years of therapy. I continue to be in this huge part of my life. But I had built this incredib doble career and I was almost forty. It was so scary to have to think about, oh my god, am I gonna have to scratch everything and start all
over again. That I was below like 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 re engage, you know, because there's a version of this certainly for you.
We're just like, all right, I'm good.
I'm gonna go live on an island or do whatever I'm gonna 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?
Like, J 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.
In 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 coming to field. 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 on earth the na 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 scary thing to be in a place where you've builded and now you're 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 and hm so. And I also felt like there was millions of kids out there that don't have, you know, 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 you know, I want to go back and play baseball, or I want to go back and go to the Hall of Fame, or I want to go back and build an empire. It was really about like, I know, I have another chapter. I don't know what that looks like, but I'm going to give it a go.
How'd you learn how to tell yourself a different story? Because I know that was you're playing at Duke similarly playing the Yankees, like you're 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, like that's that's Jay. It's like number two pick in the draft place for Chicago Bulls. He's on I nineties on the billboard. He is Michael Jordan's locker. So as that looked me
like are you okay? Like it was it was completely It was a different entry point. I were even sit down to business meetings and like some of these higher level executives start the conversation for there, and I feel like I have to drag myself out of the basement to get to the lobby level. How do you deal with that? From a storytelling perspective.
I just started leading with the worst. I started leading with them, righting them to it, them to it, beat them to the spot right. And it's kind of what you started 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. And if you want to throw me out of the meeting, let's just do it in the first ten minutes. That way, I
don't waste your time, you don't waste my time. 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 that 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, we sign a big contractor you're that number two pick
from the Bulls or the Yankees or whatever. Self awareness decreases, an ego increase. And I wake up every morning with two prayers. I want to 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 a namor with sea level executives, as I've always wanted to be one me too. And it's amazing how many people I talk to that have gone through challenges within their businesses where filling for bankruptcy or losing
money for investors. I think I recognized while I was riding 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, are more public than others. But maybe that's a place to actually build the 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?
You know?
I mean, so with all of that in mind, you're doing work on yourself, but you also have to.
Do the work.
You know, you have to figure out like who you're going to be and what you're going to do and candidly what you're going to contribute, you know, I mean we talk about this all the time in terms of like what your what your mission is going to 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. So, yes, Coach K is on the respective.
And so 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 you know, really, all right, Q one, where are we Like? What are we doing? Like what the portfolio look like? And we go through that, but then we go into like me personally, what's the marriage look like with the kids? Like how
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 instead of just trying to go off and invest in all these different things, and like, all right, 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 entertaining community versus the business community. I love the way you reach out and you're not afraid get that from And you should be doing a lot more of that because you on TV and you 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 appatite, you know, like and it's like even when I reach out to I want to be an owner one day of a team. Right, So understanding you know 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 going to happen in Europe? The explosion of n W s L and their new media rights, the w n b A, which is an interesting entry point from an investor perspective, you know,
Professional bull Riding PBR, that League Sale GP. Like understanding where all these leagues are coming from and how to actually bet those opportunities, that's number one, Right, I think you are on point, and that goes just a closed loop on the story. I think when I was learning TV, I think I saw that gap and I did this show called The Best Shop and it was with Lebron and Maverick and it was when they were launching spring Hill.
Maverick Carterron James's business press.
Sorry, should be a little bit more right the script. Yes, you know, 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 right, And I also saw from my perspective, all of a sudden on the show, now I'm an executive producer and I'm talent, like, oh okay, I can eat on both ends. It was very fascinating. So then understanding that dynamic and how they worked, then I started working with Rich Climbing and Kevin Durant
when we launched the Boreroom. Now that was tricky because I had to sell the Boarroom to the company I was working for, Right, So that allowed me to have a lot of different conversations with Jimmy peterarro Connor show in ESPNS thirty for thirty with Rich and Kevin. But it was once again it just served proof of concept that I was with Serena hearing Williams about her venture firm.
Serena is one that you could just say, Serena, I don't know.
Some people you know, you gotta be first name bans you can't. But then I started sitting down with Steve Baumer and Josh Cronky 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 the 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 it 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 going to 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,
and the uncomfortable, especially sitting in that table. And I love the fact that you have quite honestly the we say the Cojones.
Maybe mock see.
Yeah, that's a Georgetown Georgetown duke.
I feel very much imposture right now, I have like Dominican University here, but Jay with you. I love that you can verbalize as part of it, and to say it first of us hard to do it in your mind. To say it in your mind, you're saying it publicly. I want to be an owner one day. That's awesome, But how does the J. Williams Holding Company look in five years if.
You had a year way? 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. 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 entity with a media, marketing, branding arm where I can look at certain investments and I can look at at their operating teams and effectively take shots at those type of
assets and scale that slowly. And I don't want to use the term private equity because that's just like you know, everybody I ever want to be involved in private equity, or every athlete once 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 saying, hey, Jay, you know, in five years, if this explosion continues to happen within the collegiate market, you know what's one of your port codes? I would say, you love to own a significant piece of Duke basketball? Mm mmm, 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 you know, departments are still very archaic, and now I think you're seeing the same way private equities entering the NFL conversations around areas and other PE firms right entering that market. I think that's going to happen on
the collegiate market. And you know, 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 I always love commentary, but I want to 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 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.
I mean, you talk about magic all the time, basically saying you can get in the room.
You know, 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 because 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 through, what's it like being at that home plate? And then you're in and then you prove yourself and the relationship begins.
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 my bye here 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.
You know, twenty percent of the athletes ask for the meeting, probably one percent of those twenty follow up in a real way. And you got to follow up right, and you got to 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 you know, Tiger or maybe Tom Brady or something that is just
one and done and you're good. But it's just who's going to 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 dot a rapid fire. Now I think you're going to be really good at this.
I think you're gonna be really good at all Right, I'll start in the view, and what are the rules that you keep it tight? Keep it just keep it tight.
Do I get a chance to ask any back to you guys?
No?
Yeah, 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 Rubuste.
I think you say, Jason, what's the best piece of advice you've received on deal making your business?
Never run? Always walk with pace? Same question? Was the worst advice you've ever been given? Worst advice came from an athlete? This is bad? Actually, successful athlete, Jay, The more deals the better. Oh, actually, so that's the best answer we've ever gotten.
That is what's your hype song before you go into a big meeting or negotiation?
This is this is weird Like I've been listening to a lot more classical orchestra. I'd like to try to be calm, pick the emotion out of any specific I'll go to old school, like a little Patti LaBelle.
A fun fact about yourself that your colleagues will be surprised to.
Hear about loyalty and transparency is very important to me because I don't I didn't have that a lot of my life. I had a lot of times where a lot of deals or a lot of people try 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, Shay Williams.
Thank you. I appreciate that good stuff. Guys, thanks a lot, Thanks Jay, Thanks man.
The Deal is a production from Bloomberg Podcasts and Bloomberg Originals. The Deal is hosted by Alex Rodriguez and Jason Kelly. Our producers are Anamazarakis, Stacey Wong, Lizzie Phillip, and Victory Veez. Original music and engineering by Blake Maples. Our managing editor is David E. Ravella. Our executive producers are Jason Kelly, Brendan Francis Newnham, Jordan Opplinger, Trey Shallowhorn, Kyle Kramer, Andrew Barden.
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