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Travis
You're listening to the Travis Makes Money podcast presented by GoHighLevel.com for a free 30 day trial of the best all in one digital marketing software tool on the planet, just go to gohighlevel.com travis what's going on, everybody? Welcome back to the Travis Makes Money podcast where it's mission to help you make more money. On this episode of the show, we have a special guest and a new friend, Lee Steinberg. He's a legendary sports agent, entrepreneur and chairman of Lee Steinberg Sports Entertainment. Widely regarded as the real life inspiration behind the film Jerry Maguire, Lee has represented more than 300 professional athletes across football, basketball, baseball, hockey, boxing and golf. Over his career, he's negotiated over $4 billion in contracts, represented the number one overall NFL draft pick eight times, and helped direct more than $1 billion to charitable causes worldwide. A best selling author, nationally recognized speaker, Lee's appeared on major programs including 60 Minutes and even Larry King Live. He is one of the most influential figures in sports representation and athlete branding even to this day. I'm stoked to have him on the show. Lee, how's it going?
Lee Steinberg
Thank you, Travis. Going great, Great.
Travis
Love to hear it. I want to go back in time, Lee, Remember all the way back in the day, first dollar that you ever made that got you excited, something that shocked you that you're able to make some money doing this thing. What was it? Tell me the story.
Lee Steinberg
So back in 1975, I was a dorm counselor in an undergraduate dorm at Cal Berkeley and they moved the freshman football team into the dorm and I had just graduated from law school and the quarterback, Steve Bartowski was one of those students. He ended up being the first pick in the overall in the NFL draft and he asked me to represent them. But representation was very rudimentary, Travis, that the teams could just hang up the phone and say we don't deal with agents. And all of a sudden, first time out, we negotiate the largest rookie contract in NFL history.
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What
Lee Steinberg
was sort of a stunning event. Although the number would be paltry today. So I realized that this field could grow and I could profile the type of players I wanted. And my love for sports then dovetailed with being able to have an economic return from it. Wow.
Travis
So it was almost one of those that, like, the opportunity fell in your lap type of a thing, and you just took full advantage of that opportunity.
Lee Steinberg
So it's been 52 years, and I did 64 first round draft picks in football, 30 in baseball. And football exploded as a support. So did baseball. So growth of the television contracts fueled growth in franchise values, growth in player compensation, and it's a brave new world.
Travis
Did you have any idea that this is how you were going to use your law degree?
Lee Steinberg
No, Travis. I was probably going to take a job with the Alameda county da. And I had traveled for a year after law school, saw the world, and I had a series of job offers, but they were either in traditional law, litigation, or criminal law. And some people thought I might go into politics, but I ended up doing this. And here we are all these years later.
Travis
Yeah. Were you, were you shocked at all that you were able to marry, like, two things that mattered to you at that time? Especially at a time when agents weren't really a thing to your. To your own recognition?
Lee Steinberg
No, they weren't. And it. I sort of tried to figure out what I love to do in life and turn that into a practice. And so I like to write and I've written four books. I like to. I love movies. I've been technical advisor on a series of them. I love making a positive difference in the world. So we have all our athletes retrace their roots and go back to the high school, collegiate, professional community, community. And I just tried to find the things that excited me in life and cobble them together and call it a practice.
Travis
Yeah, it seems like it went pretty well for you, I would say. But how, how long were you running this from that? From that very early on, first client, until you realized that this was going to potent, like have the potential to turn into what it's turned into today.
Lee Steinberg
It was not the second year, but it was the third year. And the third year I could see that Football, for example, had one game a week. An event grew up with television. So all the camera angles and the innovations made it much better. You had contact, which people loved. And I thought, this sport's going to supplant baseball. And in baseball, I thought, they're so traditional, if they could figure out how to stimulate ancillary revenue streams, stadiums that had experience to them jumbo Scoreboards, naming rights in football and NFL Network, a memorabilia, merchandise. The thought of fantasy sport. And I could see it all coming and realized that representing athletes was a good way to go, but then also putting together entrepreneurial businesses. So back in 2000, I thought up something called Athlete Direct. And this was in the rumination period for the Internet. But we put the first athletes we signed, Michael Jordan, Ken Griffey Jr. Who were the big players at that point, and had them go online and do a weekly diary, talk about their charitable foundations, do lifestyle stuff. And it, we owned it and sold it to venture capitals for amazing multiple. And I saw that we had the ability to create businesses that we could, we could do sports theme motion pictures, television, books and all the rest of it. Yeah.
Travis
So able to find multiple monetization points beyond just the initial signing of a contract.
Lee Steinberg
Yes. And to. We call them special projects. So we put together a white label athlete marketing group that any agent in the country could use, but we owned it and that had a liquidity event also.
Travis
Wow. Who are. And I, I recognize that this question might be really difficult and it's sort of like choosing between your favorite children, but who, who are some of the athletes that you've signed over the years that maybe you're most proud of? You're proud of like the career that they had, the work they did, the human beings they became.
Lee Steinberg
So Warren Moon came out of the University of Washington in 1978 and at that time there was a certain amount of doubt about the ability of a black quarterback to play the position. And so he sort of got downgraded and went to Canada for six years and was the most valuable player up there. Came back, signed the biggest contract ever for an NFL player and played 17 more years and became the first African American quarterback in the modern era to be inducted into the Pro Football hall of Fame. So that was exciting. Steve Young signed with a brand new football league called the usfl. And his contract at that point was stunning people to support $42 million and it made headlines everywhere. Troy Aikman won three Super Bowls and that was exciting. Lennox Lewis, the boxer I worked with, and then thought, you know, he shouldn't have a promoter. He should be the promoter himself and be the owner of the promotion company and. And eliminate 40% of the money going to a marketer, a promoter. And so different sports, many great experiences. The high point is the millions of dollars that the athletes have raised for charity. So somebody like Warren Moon has sent hundreds of kids to college on his scholarships or worked on the running back just put the 220th single mother and family into the first home they'll ever own. So the high points really are watching lives be changed and having athletes go back to the high school, community college and pro community and set up programs that enhance the quality of life with
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Travis
can you talk about your personal philosophy on money versus impact? I find, I find this sort of like battle that exists between the two of them and in reality with the people that I've talked to who seemingly have had the most social impact on the world around them. Money's always a factor and you can't, it's really difficult to, you know, extract one from the other. Can you, can you talk a little bit about your overall philosophy about that?
Lee Steinberg
Yes. So I had a father who raised me with two core values. One was treasure relationships, especially family, and the other was make a meaningful difference in the world and help people who were in pain or couldn't help themselves. So I looked for impact. I had a partner who in Jeff Morad, who was great at monetizing everything. So the irony is I didn't think about money when I was signing clients. I thought about domination of the field and how we could do that better. But it worked out the same way because we by focusing on Impact, I was able to find projects in different areas of the economy that were going to blow up, whether it was television or stadiums or again, every marketing concept. So thank goodness for my partner because he ended up making us exceptionally profitable. And as I said, it wasn't my permanent motivation, but it worked out and it enabled me to fund all sorts of interesting programs.
Travis
Yeah, seemingly. Tell me a Little bit about the. About Jerry Maguire, the film Jerry Maguire, and, you know, from inception to the project. Tell me. Tell me a little bit about your involvement or lack thereof.
Lee Steinberg
So the director, writer Cameron Crowe, called me up back in 1993 and asked if he could shadow me and pick up atmosphere for a film that would be based on a sports agent. And so for about a year and a half, he went a whole slew of places with me. He came to the NFL Draft in 1993, where I had the first pick, driver Drew Blood. So he came to the press conference for Drew with Bill Parcells. He came to the league meetings out in Palm Desert, where I was showing people off. He came to football games with me, to our super bowl parties. And I told him stories, lots and lots of stories, basically about my life and. And what he was saying. And then I was technical advisor. So he went off and wrote a brilliant script. So you. I had to vet the script to make sure the willing suspension of disbelief that holds you in the motion picture, that you didn't think the look was phony, that you didn't think the dialogue was silted, and do that. And then he assigned me some actors, like Cuba Beating junior who won the Oscar for Best Supporting. And I took him down to the super bowl in Phoenix and made him pretend he was a wide receiver client of mine all week so, you know, with Desmond Howard and Amani Toomer, and had to. Had to pretend he was a wide receiver. And so it's been 30 years, and this is the anniversary this year. And every time I walk through an airport or go out to dinner, someone inevitably comes up to the table and either says four words or asked me to say him. And they start with, show me the.
Travis
Yeah, man. Did you have any idea the impact that that film would have when that guy's shadow. I mean, a year and a half is crazy for somebody to be following you around. That's a lot of research.
Lee Steinberg
But he. He was easy to be with, and I introduced him to owners and to all sorts of different people. No, the fact that 30 years later it still runs on some form of television virtually every day was not expected. I think that it humanized the concept of sports agents and gave people a feeling that there was real caring there. And I think the fact it had a love story to it also brought a broader audience. Yeah, yeah, sure.
Travis
That's what. That's what the best script writers do, right? Lee, I'm curious to get your perspective on the changes in NIL for the ncaa. Tell me A little about your thoughts on that.
Lee Steinberg
Overall, the system evolved because athletes were on college campuses living at a lower standard of living than their non athletic peers because they couldn't work their during the school years supplement income. So they felt ripped off. They felt like their jersey was being sold in the student store. They saw the big TV contracts, they saw the filled stadium and they said what about us? They could have fixed it really easy, easily by taking athletes who had need and supplementing their income. Travis, they could have given them $5,000 per player and they'd have been in heaven. Yeah, yeah. But instead it's broken out into a system that now takes money as a motivational factor and is like free agency for high school players going to college and then a second bite of the apple and the transfer portal. So to show you how this works, the quarterback at Michigan now originally enrolled in LSU and was going to be paid $4 million there. So along comes the big Michigan offers him $14 million and before he ever plays at LSU he goes to Michigan. So it's free agency, the highest bidder. And what you're going to see is four conferences. The super impact conferences are going to elevate and leave the rest of college sports behind because they have the big alum groups, they can afford the Nils the most money. A couple years ago for Nils went to Ohio State and oh incidentally they won the national championship. So. And they're going to ultimately get rid of the ncaa. The big conferences will negotiate their own TV contracts and put together their own rules so they really don't need the ncaa.
Travis
Hmm, interesting. So you think that NCAA as an organization is going to be not like unnecessary.
Lee Steinberg
It will be necessary for the remainder of collegiate sports. But not those conferences with, I see with the Ohio States and Michigan's and Alabama's and sbs, those athletes will play at a different level. And so there have been three big changes. Gambling is an existential threat to football because if people start to feel like an athlete is revealed inside information or shaded performance in conjunction with gambler on prop bets and influence it, then people may look at sports wondering whether they're played on an even playing field. And you could have sports treated like wrestling, like an exhibition, so that's a danger. And then conference realignment. I went to Cal Berkeley. When you walk across the campus, you look at the Pacific Ocean and now Cal's in a conference called the ACC that looks at the Atlantic Ocean. So you know, so much for being a student athlete when you're traveling, you know, cross country, the Whole system's out of control. And the problem is their NCAA is not regulating it. So you've got politicians passing bills, but the field really could use some guardrails.
Travis
Yeah, for especially for a fan experience. It's ultimately going to make it worse for everybody. I saw a little bit of that happen too with the weird stuff that went on with the Pac 12 recently. Right. They're going under a big restructuring because of some television deal that went south or something like that, Right?
Lee Steinberg
That's exactly right. The they bargained too hard to Pac12 on a TV conflict and then went away. And so a conference which been around for, you know, 100 years came apart because SC and UCLA went to the and then Oregon and Washington to the Big Ten and Cal and Stanford to the ACC and Arizona and Arizona State went to another conference and they were left with virtually nothing.
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Travis
Yeah. Yeah, that's, that was a wild move to see something like, like you said, an institution that's been around for a really long time and now, you know, desperate trying to fill teams so that they, like you said, it's kind of crazy to expect student athletes to travel across the country for, for football games and then still expect them to be, you know, exemplary students and graduate with honors and get good jobs if they can't somehow, you know, have a professional track. That's why I was like, I, I, I appreciate you that you offer another perspective there because I, I, that's how I felt as a fan. It was like it, I, I could see that it was sort of unfair to the student athletes where it's like some of these universities are raking in cash based on the performance of these guys on the field or on but like you said, there probably could have been some sort of a happy medium that would have, that would have worked for both parties and still protected the fans. Still protected. The institutions have been around for some time, but it seems like they, they went the opposite direction.
Lee Steinberg
Well, I worry about continued fan support because they've really priced out working people and younger people from the games. Yeah, it's supply and demand. And the pricing, well, you can look at the World cup, you can look at a Super bowl, you can look at the NBA tournament now where though it's 10,000, 15,000, $20,000 for tickets on Nick game.
Travis
Yeah, yeah. It's crazy. I saw some. There was like a quarter million dollars for the finals at Madison Square Garden.
Lee Steinberg
Crazy. Yeah. So I've always thought if they would just save a part of the stadium, maybe 10,000 fans who they let in under reasonable pricing, you could build the future of the sport. And. But if someone hadn't played the sport live or they don't have them played live or gone to a game live, you know, hopefully they'll be. Be able to sustain interest.
Travis
Yeah, yeah. And you have companies like Ticketmaster too, that are doing some questionable, maybe even leaning toward predatory practices when it comes to taking more than their fair share with their surge pricing and all this other stuff. And it's like, even concerts, like any event anymore, seems to be like, oh my gosh, like about if we're going to take, you know, me, my wife, a couple of friends, we're going to get some food, some drinks, like this is $1,000, you know, outing for an evening for something that used to be 100 bucks.
Lee Steinberg
And then there's Uber and Lyft with, with their variable pricing that take a big event like that and, you know, charge multiple. So that adds to the cost.
Travis
How do you perceive a company like the Savannah Bananas and what Jesse Cole is doing over there with the banana ball? How do you look at that from a fan experience?
Lee Steinberg
Entertainment. It's just a picture of Patrick Mahomes with his kids at Banana Game and he thought it was really entertaining. Remember, you had the Harlem Grove Trotters for years. Who did that? We're in the entertainment business and sports is just another form of it. As a matter of fact, not only is Pro Football by 2 to 1 the most popular sport in the United States, it's the most popular form of televised entertainment. Wow. Percentage of the top rated shows now are not American Idol. They're. They're an NFL football game.
Travis
Yeah. And now a lot of those are going to streaming and stuff like too. What do you think about that?
Lee Steinberg
I've got some skepticism about that. The reason that a sport like football is so popular is if you have a couple hundred dollars, you can buy a TV with rabbit ears and get a bunch of games on, college games on Saturday, a bunch of pro games on Sunday, you know, just over the air. But all of a sudden, you start to cut the package into pay streamers who charge individually for the package. And then if you have a time with economic challenges like today, you start to lose. When Amazon or Netflix does a game, you start to lose that audience because it's not universal anymore. The reason they have those massive TV contracts is the fact it's a loss leader. And you can advertise as a network and promo your Monday through Friday programming on a Sunday afternoon. So you may not make money on the package, but you'll make money on the popularity of your network.
Travis
Yeah, there's a lot of interesting things happening in that world. Lee, I appreciate you coming on and be willing to share a little bit about your story and some perspectives on those. There's just. Just some. Some con. There's some like, you know, dinner party conversations I've been having recently. So it's great to get an expert. Oh, yeah, of course. Yeah, I was going to ask about that before we took off.
Lee Steinberg
So it's called the Comeback. And it. It is about how life sets us all back. It could be economic, it could be health, it could be marital or relationships, or it could be, in my case, it was alcohol. And the point is, inevitably, we're going to face these challenges. How do you come back? How can you be resilient? How can you see life at the end of the tunnel? So it's a subject line and it tells stories, not only my own experience, but of Patrick Mahomes and Steve Young and Warren Moon and Troy Aikman and a number of other athletes who face adversity.
Travis
What do you hope people take away from that book? What do you hope the impact is?
Lee Steinberg
If somebody's out there struggling, despondent, depressed over problems with addictive substances or anything else? What I hope is it gives them hope that you can find light at the end of the tunnel, that you can come back from challenging circumstances to build a fulfilling life. And if it impacts just one person out there who's struggling, then it's. It's been a success.
Travis
The Comeback. Go pick up a copy of Lee's new book.
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Travis
You guys know I tell you this all the time on the show, when we mention a book, just go buy it, okay? If you're driving right now, you know, pull over. But other than that, go pick up a copy of the book immediately so that you do not forget to go through. I mean, people like this spend their lives building amazing careers. All the failures, the obstacles, the wins, the successes, the losses, everything in between. And then they take the time to write it and put it in a book that's 300 something pages that you can digest in a week or two. I mean, it is, it is a net positive in your life to go pick up a copy of the Comeback from Lee Steinberg before you forget about it. So, Lee, I appreciate you coming on the show and sharing a little bit about your journey. I do not take your time lightly. I know you're a busy guy. Everybody else tuning in. Remember, money only solves your money problems, but it's easier to solve the rest of your problems when you got a little bit of money in the bank. So let's start there here on the Travis Makes Money podcast. Thanks for tuning in, everybody. We'll catch you guys next time.
Host: Travis Chappell
Guest: Leigh Steinberg (Legendary Sports Agent, Entrepreneur, Chairman of Lee Steinberg Sports Entertainment)
Air Date: June 18, 2026
This episode features a deep-dive interview with Leigh Steinberg, renowned sports agent and the inspiration for the character in “Jerry Maguire.” Travis and Leigh discuss making money through building relationships, balancing financial success with making a social impact, pioneering innovations in sports and athlete branding, the evolution of sports business, and personal resilience. Steinberg shares insights from a half-century at the top of the sports industry and previews his new book, “The Comeback.”
Leigh Steinberg’s story is one of following passion, shaping an entire industry, focusing on value and meaningful relationships, and using business success as a platform for positive change. His insights into sports, money, philanthropy, and resilience provide a valuable blueprint for anyone looking to combine financial gain with lasting impact.
Action Step:
Check out Leigh’s new book, “The Comeback,” for more on overcoming adversity.