Bruin Capital's George Pyne - how to raise money, then spend it, build businesses up, then exit with grace

14 Jul 2026 · 50 min · 25 chapters

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In short

George Pyne, CEO/founder of Bruin Capital, explains how to invest in sports “second-level enablers” (pipes/picks-and-shovels) rather than teams/leagues: raising capital, deploying it, adding operational value, and executing “elegant exits.” He also discusses global investing, AI’s impact on sports vs entertainment, and how Bruin supports management teams and investors through planning and board processes.

Guest backgrounds

George Pyne is a sports investor and operator. He was NASCAR COO (mid-1990s heyday) and then IMG President (2006–2015), where he helped create and grow IMG College. He founded Bruin Capital in 2015 (investing since 2013).

Key claims

Raising money is harder than deploying capital. Bruin targets high-cash-flow, low-capex, liquid businesses where value can be added. He prefers empathetic, experienced management teams and low risk tolerance. Elegant exits require management finding an excited long-term partner and all parties succeeding.

Notable examples

Bruin investments/exits include Two Circles, Delta Tray, On Location, and current holdings Box2Box and Matchroom Sport (with Barry/Eddie Hearn). He cites Full Swing’s reported $530m acquisition by Versant as an example of Bruin’s exit approach.

Written by AI. May contain mistakes. Listen to the episode to check what was said.

Chapters

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George Pyne's Background and Bruin Capital Overview

0:41 to 2:26

George discusses his career journey and the founding of Bruin Capital.

“heyday of the series in the mid-90s as chief operating officer.”

The Challenges of Raising and Deploying Capital

2:26 to 4:50

George shares insights on the difficulties of raising money versus deploying it in investments.

“George, it's a pleasure to welcome you to London on what I hear is a fairly regular stopover for you.”

Investment Philosophy: Second Level Enablers

4:50 to 7:22

An explanation of George's investment focus on second level enablers in sports.

“when I started, that wasn't really the case.”

Navigating the Investment Landscape

7:22 to 9:06

George discusses the nuances of investing in less glamorous sports businesses.

“That can come in opening markets, but also helping CEOs manage growth.”

Reflections on Successful Fundraising

9:06 to 11:15

George reflects on his most satisfying and creative fundraising experiences.

“I just think if you talk to anybody that does what I do, they're going to tell you raising money is hard to do.”

Management Team Attributes and Challenges

11:15 to 14:03

Discussion on the qualities George looks for in management teams and the challenges faced in deals.

“So when we invest in something, the notion that it won't work out is never really there.”

Insights from NASCAR Experience

14:03 to 17:29

Learn how George Pyne's NASCAR background informs his current investment strategies.

“whether you still lean on that experience of being, you know, in the thick of it, on the front line at an organisation like that, even given the distance now, the sort of, I guess, 20 years since you left NASCAR.”

The Importance of a Global Outlook

17:30 to 21:53

Discover how having a global perspective enhances business opportunities in sports.

“which was enormously helpful to me where I apprenticed internationally and, you know, worked in 30 countries.”

Navigating the Art of Exits

21:54 to 26:12

Understand the nuances of exiting investments and ensuring success for management teams.

“If who you work with matters, we're pretty, we're pretty attractive option.”

Managing Investor Relationships

26:13 to 28:00

Explore how to effectively communicate with investors and prepare for exits.

“So we're always, you know, every company, when I'm speaking to an investor at a board meeting, we say, hey, we're looking to exit at this time.”
Show all 25 chapters

Understanding the Role of Bankers in Sports

28:00 to 28:45

Learn how engaging bankers can provide valuable insights for sports companies.

“And as you get closer, we spend more time with the bankers.”

Financial Literacy in the Sports Industry

28:45 to 29:49

Explore the financial literacy of sports teams and leagues amidst a changing landscape.

“Do you, you know, is there work to be done there in your experience in terms of the people who run teams, run leagues, to understand how this wider world of finance works?”

The Stability and Evolution of Sports Capitalization

29:49 to 31:08

Discover how conservative capitalization in sports presents unique investment opportunities.

“Well, I think when you look at sports, the capitalization of sports has been pretty conservative and that provides opportunities for investors that may not be in other segments.”

AI as an Enhancer of Sports

31:08 to 32:59

Understand how AI is set to enhance the sports experience rather than disrupt it.

“Flesh out what you said just there a little bit more for me about AI will enhance sports because that's probably a statement that some people listening might raise an eyebrow to.”

The Unique Value of Live Sports

32:59 to 33:56

Explore the irreplaceable nature of live sports in the entertainment landscape.

“And I think that's why it has been so successful over time.”

Investment Insights from Non-Sport Specialists

33:56 to 35:03

Identify common pitfalls for investors entering the sports industry without experience.

“Well, I don't want to say we don't make mistakes because we do, but I think, I just think, you know, not everyone's going to be successful and not everything's the same, Right.”

The Future of Sports Documentaries

35:03 to 36:11

Discuss the evolution and future potential of sports documentaries in the industry.

“behind the scenes documentaries might have peaked?”

Investing in Matchroom Sports

36:11 to 37:50

Learn about the investment in Matchroom Sports and its global market impact.

“Actually, thinking about it, Have you ever pitched the idea of having some cameras in your board meetings, sort of inside the sports investment firm?”

The Challenges of Boxing Promotions

37:50 to 39:40

Understand the unique challenges of investing in boxing-related promotions.

“around the world that, you know, we've looked at a lot of boxing businesses over the last 12 years.”

Navigating AI in Sports Investments

39:40 to 42:02

Explore how AI impacts investment decisions in the sports industry.

“Not a day goes by when Eddie Hearn is not appearing in an extended interview with one of many boxing YouTube channels.”

Advice for Aspiring Sports Leaders

42:02 to 43:16

Learn key advice for those aiming for leadership positions in sports.

“you really you know part of the thing is do no harm right and so I think being mindful of how AI is going to affect a particular investment, I think will guide us a little bit going forward.”

The Importance of Personal Branding

43:16 to 44:10

Discover the significance of building a personal brand in the sports sector.

“I think makes yourself more valuable, gives you a better understanding of the business.”

Concerns in the Sports Industry

44:10 to 46:28

Explore key concerns and insights about the current state of the sports industry.

“Yeah, I think we like to show thoughtfulness and that we're thinking about the industry, we're thinking about these ideas.”

Building Authentic Relationships

46:28 to 48:08

Understand the value of authenticity and relationships in business.

“I think you always have to be cognizant and mindful of your core fan and never forget that.”

Future Plans and Transition

48:08 to 49:13

Listen to George Pyne's thoughts on his future and plans for transition.

“So like, if you're, if you're in there with me and we're fighting together, you know, I'm, I'm kind of always on your team.”
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Transcript

Automatic transcript. May contain errors.

0:03Welcome along to the Leaders Worth Knowing podcast, the sports industry show from Leaders where we talk to the people worth knowing in the business of sport this week. I'm David Cushnan, content director here at Leaders and George Pyne is with me on the show today. George, something of a pioneer when it comes to sports investment. He was, as he tells it ahead of the game, investing through the Bruin Capital business he set up in 2013, way ahead of the curve before institutional investment in sport became as commonplace as it is today. A bit of background on George. He was at NASCAR for a long period during the heyday of the series in the mid-90s as chief operating officer.

0:47In 2006, he joined IMG as president, beginning a nine-year run there, a run which included the creation and growth of IMG College, amongst many other successes. In 2015, though, he went his own way, creating Bruin Capital, which has gone on to invest in companies like Two Circles, Delta Tray, On Location. Those three have resulted in successful exits as well. Bruin's current portfolio includes the likes of Box2Box, the sports documentary production company, and Matchroom Sport, where he's working with Barry and Eddie Hearn. And rather than investing in teams and leagues, the focus for Bruin has always been on what George calls the pipes or the second level enablers, the company's one layer beneath the headline rights holders.

1:33On the show, George talks about the challenge of raising money, of deploying capital, how to work with management teams and the art of the elegant exit. And we at the start of July. That was just before news that Versant, the US media company, announced it was acquiring Full Swing, the golf simulator business from Bruin, for a reported $530 million. And given that Bruin acquired Full Swing in 2021 at a reported valuation of$160 million, that feels like another one of those elegant exits. George was keeping shtum about that pre-announcement, but hopefully this is nonetheless a useful and interesting guide to sports investment, the story of Bruin and how it's all evolving.

2:21So here is George Pine, the CEO and founder of Bruin Capital. George Pine is here. George, it's a pleasure to welcome you to London on what I hear is a fairly regular stopover for you. Yeah, I love coming to London. I'm here, you know, once a month at least. We have five companies in London. So, you know, it's really the hub of operations for Bruin. You're doing the rounds this week. I'm sure we're going to get into some, if not all, of those five companies during the course of this conversation. You have been around, I'm hesitating to call you a veteran, George, but you have been around the sports industry for quite a while.

3:02And I wonder in various guises, and I wonder how now, I think in the 12th year of Bruin Capital, how you might describe yourself to somebody, to a stranger at a high level swanky dinner party. Yeah, well, we're a sports investor, and our point of differentiation really is that we're more operationally focused, that we're not necessarily going to be too financially structured. And the other thing that's unique about Bruin is that we open up markets for what we'd call lower middle market companies. So, you know, what's kind of crazy, it's hard to believe is, you know, we have nine companies today, 4 ,000 employees, 24 offices on the ground, 24 countries, over 100 offices, and we transact in 103 countries.

3:54So we're very international. 80 % of our capital is invested outside the United States. whenever somebody says something like that with lots of big numbers it makes it just makes me think how are you how are you dealing with the how many emails are you getting a day and how you how do you deal with your you know incoming traffic and information we have a lot of really great people i mean we the companies we have great ceos and we have a great group you know growing group of people at bruin 17 or 18 people and uh we've got great great great people so you count and trust on the team around you, which were, you know, just what I do.

4:32Can you believe it's nearly 12 years since you set this thing up? No, I mean, I really can't. It's been quite a journey. I mean, I have to say people, it was a big risk at the time, right? People just sort of, what are you doing? What is he doing? I don't understand it. And, you know, today now everybody's investing in sports, but, you know, when I started, that wasn't really the case. So it's been fun. It was probably a big risk for me. You know, I was 48 years old and I was like, hey, when am I going to take a shot now or when I'm 60? I go, this is my one chance to take a shot. I did. If I knew how hard it was going to be when I started, I'm not sure I would have done it.

5:10I think ignorance and stupidity were a real asset for me. What was the hardest bit? I think the hardest. So far, I guess. Well, I think, you know, it's been pretty consistent. I think raising money is hard. It's just a hard thing to do. And so, you know, and what I do, you have to raise money, you have to deliver for people, you have to manage the companies, you have to find the companies, you have to build the companies, then you have to sell the companies, and then you have to do it all over again. So staying on top of that is a full-time endeavor. This might be a silly question. I'm not sure.

5:43You tell me. Is it harder to raise money in your experience than to deploy it to identify where it goes? Yeah, I think the raising the money is the harder of the two. I haven't done it now four times. It's just, it's hard. Deploying, you know, nothing, I was thinking about coming in today, nothing's easy. I would tell you that there's nothing I get up and say, boy, that's easy to do. But I think the raising the money is certainly the hardest part. You mentioned it at the start there, and I think it's been described, and you have described it in various ways over the years, where and how you invest.

6:22Second level enablers is a phrase I've seen used. I've seen the pipes being used to explain how you do what you do. Just explain what that means and why that has been central to your whole approach, your whole thesis to sport and sports investment. Yeah, when you think about data centers, right, we're not building the data centers, but we're providing the cooling system for the data centers. And so the second level enablers was kind of a fancy way of saying, hey, picks and shovels and infrastructure. And that's really what we've focused on, the kind of the businesses that underpin the sports business.

6:58And they typically have good cash flow dynamics, high cash flow, low capex, high cash conversion, very liquid in businesses that you can add value to. And if you think about it, I think I'm a pretty talented American football family, but I'm really not going to add value to the New York Giants. But when we invest in a company, we can help add value. That can come in opening markets, but also helping CEOs manage growth. because when we get involved, you know, you got to grow. So, you know, you're going to be growing company three, four, five times the size of when they grow. And I think we're good people to be with for that journey because everything doesn't work perfectly.

7:40And when it doesn't work perfectly, like who do you want to be in the boat with? Somebody that's actually done it before and is empathetic. You know, I always tell people I've been fired by a client, I've missed the budget and I've failed miserably. So when things go bad, we're great guys to be around. Now we love the top line. Last night I was in Milan on a sales call for a company that we own. I go on sales calls for every company we own. We love driving the top line, but at the end of the day, you know, it's, it's wide ranging in terms of operations. When you talk about raising money, um, I wonder, is it, is it, is it more of a challenge given that you are looking for maybe the more slightly more under the radar organizations in the sports industry and not necessarily the the glitzy shiny teams leagues is it a different conversation no you know actually it's interesting you know teams are great investments right they've been great for 30 years you know the double digit CAGR growth they're very steady but they're not they're not often liquid right and you can't really add value and so there are a lot of people that will not invest in things that are illiquid and really where there's not value.

8:54Some people will, but a lot of people like the high cash flow, low capex, high cash conversion, certain liquidity. So actually, it's actually been a good niche and it's more traditional from an investment standpoint. I just think if you talk to anybody that does what I do, they're going to tell you raising money is hard to do. We're going to, I wanted to get your reflections on some of the deals that have been important to you. And I've devised a small format to be able to do this. So not necessarily in quickfire form, because I'd love to get into a few of these. If you had to pick out the deal you have done that you found most satisfying, what would that be?

9:37You know, if you look at it, again, I think it's the raising, if you ask me at Bruin, it's probably raising the money, you know raising 250 million then raising 675 million then raising 300 million and then a billion dollars like doing that that's really a validation of a lot of good work so if you said to me what's most satisfying probably that and when you've done that and when you get to the the third round and the fourth round is that a you know difference between first and fourth time you've done it. Did it feel like a much more refined process? Did each time have its own particular challenges of period of time, moment for the world, moment for the markets?

10:22We're getting better at it and we're more at ease with it. And of course, raising a billion dollars, that was a real validation of a lot of good work of a lot of people. So I think we're more comfortable at it today than we were when we started. What about the most creative deal? most creative deal you know for us we do wide-ranging things so but we but financially we're pretty basic and you know we we'd like to take 60 or 70 ownership partnering with management to owning 20 to 40 it's typically kind of down the down the we're kind of down the middle guys so i guess we're not too creative um we're kind of more straightforward uh riskiest deal riskier steel.

11:07So far. So we don't, we don't, I don't look at the, you know, we don't invest if we think it's very risky. So we have a very low risk tolerance. So when we invest in something, the notion that it won't work out is never really there. Now where, where there is risk is like, we expect to be successful. How successful we're going to be is always kind of a question. Some of them you feel, Hey, I'm going to be very successful. And you know, when we look at something with saying, hey, do I believe that that business can generate a 25 % asset level IRR? That's the first flip list. And the second is, can we add value to that business?

11:46And third being, do we believe in the management team? But in terms of risk, we're pretty uninteresting. We're not too risky. What do you look for in a management team then? What are some of the skill sets or the attributes of the leaders of organizations where you go, yeah, this is going to work for us and we are going to be able to work with them. And we've kind of evolved. I've involved my own thinking. Initially, I really want to find someone that has drive, determination, that really wants to be great and wants to go along for a journey of growth because we're going to get a 25 % IRR, you're signing up for a journey of growth.

12:26But I think as we go on, you're really looking for someone who has vision, someone maybe who's done it before, and somebody who's not afraid to bring in the best people and surround themselves with the best people possible to grow because this is a growth journey. What about the most challenging deal so far? Yeah, I find them all to be challenging. I don't think I've ever said, boy, that was easy. I think different deals have different challenges. You know, sometimes, you know, we've had a situation one time where we did diligence and we invested kind of in a notion of a line of product and that line of product didn't work out.

13:07So we were able to, we had a pivot that was challenging. On other situations, you might have industry trends against you. And so you're going to have to pivot as well. And then I think the journey of the growth of really taking an organization and trying, increasing it. You know, we go try to go from 10 million to 50 million or, you know, 25 million to a hundred. And that, and that journey of transformation, you know, is not easy. So I, I have yet to find something that I'd say, boy, that was really easy. I think they've all been kind of challenging, but challenging in different ways. You touched on this earlier, but in a, in a previous, um, life, uh, previous part of your career, you spent a lot of time at NASCAR, as, I think, chief operating officer through the mid-90s and well into the 2000s.

13:57And I just wonder, even though you are not investing in rights holders in sports properties themselves, whether you still lean on that experience of being, you know, in the thick of it, on the front line at an organisation like that, even given the distance now, the sort of, I guess, 20 years since you left NASCAR. Is that still a valuable experience? Does that still sort of inform what you're doing now and how you're thinking about, particularly when you go into some of these organizations you've invested in and are working with the leadership teams? 100%. I mean, when you look at NASCAR and IMG, having done that for 20 years gives me enormous perspective on what's possible in an industry.

14:44And we can really see the potential of companies, not only initially, but during the journey. And what makes us, I think, special and attractive for somebody is like, we know what's realistic and we know what's not realistic. And that gives us a real firm foundation of what decisions to make and how to approach things. And if I didn't have that background, I don't think we would be as effective as we've been. I'm interested in what somebody like you consumes um not in terms of food George in terms of um information and you know paint us a picture of how you gain the information and insight that and intelligence that is is useful for you is it is it part sport part the markets parts sort of macro trends geopolitics break it It really is all, what you said, you know, every day I get up, I read the Wall Street Journal, Financial Times, New York Times, a little partial in New York, New York Post, Bloomberg, CNBC, every single day.

15:51And then, you know, all the, all the various, you know, Sports Pro, all the different various. Sports Business Journal, George. Sports Business Journal, sorry. Yeah. all of the trade publications. And you are right because you have to understand what's going on in the world and how it applies to what you're doing, specifically us when we're on the ground in all these countries. I mean, so for us, understanding the world, understanding economics, understanding sports, understanding the whole situation and how it relates. I mean, interest rates affect us. how companies do affect us, how the sports industry is going affects us.

16:37And you have to kind of weight all that into your decision making. And as an American, it is often said of Americans in general, frankly, but some of the American sports industry that is still a little bit insular and is not necessarily looking internationally outside of the sort of geographical boundaries of the US. But in terms of your role, your position, you talked about the trips to London and the international businesses that you are deeply invested in. Is that something that has changed over time? And do you, you know, would you encourage more US sports executives to have that genuinely sort of global outlook?

17:21Well, I think having a global outlook makes you better irrespective of where you are. I mean, I had the unique background of nine years at IMG, which was enormously helpful to me where I apprenticed internationally and, you know, worked in 30 countries. And today at Bruin, you know, we have 15 advisors around the world. So we have one degree of separation from almost any kind of information, which is enormously helpful. And I do think, you know, you have to understand how to relate to people. And I think, There are different people in different cultures and understanding that your strengths and weaknesses as an American, you need to understand that and you have to understand other people's perceptions of you and you have to be able to work collaboratively.

18:04And I think that is a real skill set in terms of an American going to other parts of the world or vice versa, a European going to America. And so we've been able to straddle that really well. And yes, we are very international, but a lot of our companies really do. What we do is open up America for those companies, which can be a daunting task for a company making 10 or 20 or 30 million of EBITDA. Going to America is a daunting task. We make it less daunting. But again, you really have to have the human skills to work with different people from different backgrounds and understand your background may not apply in a different situation and have the willingness to do that.

18:46I always remember there was a guy named Doug Isabel, Irish. She was the chairman and CEO of Coca-Cola. And when I was early on at IMG and I had a staff meeting and not everyone was very differential. And after the staff meeting, I went to my, I said, gosh, I'd hate to be a diplomat. I go, how do you manage all these people? And I remember sitting with him and he told me, he gave me great advice. He goes, you know, you're going to be in a different territory and somebody is going to want to go from point A to point B and they're going to want to do it differently than you are. And you got to let them do it.

19:16and that is how we roll. You know, we have really, like you said in the beginning, how do you manage all this? Hey, we have great CEOs and we're there to support those guys and work with those guys. But in the end, they're charting their own course and we've got to back them. And kind of having the soft hands of doing that, I think has been important to our success. You talked about sitting in on sales calls at all the organizations that you're invested in. And I imagine you sort of pick and choose clients to sort of lean in on, I suppose. I just wonder in terms of what you personally are bringing to these organizations, what you regard as your biggest skill and whether that has evolved or changed over the period you've been doing this.

20:03Yeah, well, certainly opening up markets. With the network we have, and we're very strong in Europe as well, Australia. So we have a great network, those 15 advisors around the world. So we, we, you know, we opened doors at the highest levels for our companies to, you know, doors that they couldn't open on their own. And that's a real value, but also, um, so that's attractive, but we're also very good in terms of we, the way I've always, how did a guy whose wife taught him how to drive a stick shift and never change motor oil in his life, end up running NASCAR and rules reported into me. And you know, how that happened is I had a very detailed three-year planning process.

20:44So the guy that ran the whole, owned the company said, I want that guy to do that for everybody. And so I'm doing the same process I did 25 years ago at NASCAR and at IMG that we sit down in the fall. I've sit down with every company and I meet with them probably three different times. And we really develop a strategy that's confirmed by the numbers. I think numbers are like cholesterol or blood pressure and they confirm the strategy. So if the strategy is good, the numbers are good. If the strategy is bad, they can't be good numbers, right? And we trace that month in and month out. And we kind of spend our time where the great opportunities are or great problems.

21:22And if we're not needed, that's wonderful too. But my experience over 30 years is that you never get too far away from a person. And you're close with the management team. They know that you're there to help and that if help isn't needed, you're not going to be there. Nobody here is looking to impose their will on anybody. So I think that combination of planning with that kind of combination of top line growth is attractive to, and we've done better with founders, right? If who you work with matters, we're pretty, we're pretty attractive option. And I think it's for both of those reasons, one driving the top line, opening up doors, but also being empathetic.

22:06Like I said, you know, I have failed, so I understand what it's like, or I've had my back to the wall and I know what it's like. And if you've run something and you're the CEO, you know, it's a lonely job. And so having somebody that's there for you, that's not flying the plane, but someone you can say, well, hey, when you went in a storm before, how did you sail through that storm? I think it's helpful. Let's talk in a bit more specific form about some of the organizations that you are currently invested in or have invested in previously. And it strikes me that the story of brewing is very much also the story of the sports industry.

22:43And I guess that, you know, you've sort of clearly anticipated trends and seen trends come and go over that period of time. And I wonder particularly about three of your investments, two circles, Delta Tre and On Location, which each tell a

23:03You've been through an end-to-end process in all three cases. The art of the exit, maybe just reflect a little bit on each of those and how you came to the decision that it was the moment to exit and actually what you left behind in terms of three organizations that are still, you know, absolutely at the forefront of the industry and flourishing. You know, it's funny because it was all new to me as well. what's happened with us on the exits is the management teams having experienced success really want to realize success so you would have thought the investor would have been the guy running to the exits in in each case which is great that the management team is like I want to realize you know what the the success we've created so um that's really kind of how that's played out and you know it's still playing out you know to this very day so you know people work hard.

24:00They're there for five or six years. You know, they want to, they want to realize their success. And of course I'm not a post that I'm a bit of an artist. Like I love the companies. I love building things. I hate selling them, but it's part of the job. Right. So, uh, and you know, look how you sell a company is important. What I've learned, you got to raise the money. You've got to find the companies. You got to buy the company correctly. You have to manage the company, but if you don't sell it correctly, it really, all the other stuff really doesn't matter. So how you sell a company, how you manage the exit is important.

24:32What can go wrong? Well, you may have not understood something about your company when you went to sell it that could be problematic. You may have overestimated an element of your company or you could always underestimate it. So you have a lot of human dynamics with the management team. is naturally, as I was at IMG, apprehensive about what could happen in the future. And so all that needs to be managed carefully to be successful. And on the flip side, what does an elegant exit look like? I think an elegant exit is when the management team finds a partner, a home that they're excited about after our journey.

25:24and, you know, financially everybody succeeds. And so far that's been the case. And I hope it stays that way. But, you know, when you work with these people for five, say Gareth Balsh at Two Circles, like I really appreciate Gareth. We're still friendly to this day. And, you know, I wanted a good outcome for him. And I think he hopefully wanted to have a good outcome for me. And so it's important to me that these guys succeed. succeed. And, you know, I'm happy to say John Piero at Delta Tray, he visited me the last time he was in New York. Gareth, I spoke to about a month ago. John Collins at On Location, I went to, he's running the Islanders.

26:03I went to the Islanders and, you know, it's your life. So far, it's a lifelong friendship. The exit is just part of that journey. And take us inside your world, let's say at the point of an exit of an organization like two circles or delta tray tell us a little bit about your role in terms of not just the the management team that you that you leave behind if you like but in terms of then who you're reporting into how you're communicating that the story you're telling to to the people you know our investors to your investors yeah so so we we we have a quarterly board meetings and we so we had a quarterly meeting two weeks ago and we talk about each company when we think we're going to exit we always say well we can't nobody can predict the future if they did we would be in macau or las vegas we wouldn't be we wouldn't be here but um so we kind of manage that with our investors to say here's here's what we think about the company here's what we think some outcomes could be and here's when we think those outcomes will take place and why and then that also ties So here's the different strategies within those companies.

27:17So we're always, you know, every company, when I'm speaking to an investor at a board meeting, we say, hey, we're looking to exit at this time. Now, of course, things change and, you know, that could, but that's the thought process. So that's important. And then also, you know, you have to hire, there are a lot of talented investment bankers. You have to pick a banker that you think will do a good job for you, and you have to work closely with the bankers. And what we've done at Bruin is we bring the bankers in a couple of years before an exit to give us a review. Hey, what do you think of this company?

27:57If you're us and we have two or three years left, what strategic direction would you take? What decisions would you make? And as you get closer, we spend more time with the bankers. So it does a couple of things. One, it allows us to get input from an outside set of eyes. And two, it educates the banker on the company. And three, it also helps the company to hear from an independent source about what's important. After hearing from us for five years, you might want to hear from somebody else whose job it is to sell. So, in fact, we bring our companies together once a year. and almost every year we'll bring in two or three bankers to present to the companies to talk about you know how they like to take a company to market about what's important and how they should be thinking about things so that you are right yeah you're managing the management team you're managing your investors and in a way you're managing yourself because you got to you got to land the playing and we are in a financialized era of sport now there are so many more investors of all sorts of types and there's nuances different types of whether it's institutions athletes you know celebrity fronted um groups are the are the what's your sense of the financial literacy of the sports industry as this financial world is sort of enveloping them?

29:31Do you, you know, is there work to be done there in your experience in terms of the people who run teams, run leagues, to understand how this wider world of finance works? Or actually, do you feel like there's a good level of sort of mutual understanding? Well, I think when you look at sports, the capitalization of sports has been pretty conservative and that provides opportunities for investors that may not be in other segments. When you look at sports, just take a step back, go higher. Sports right now is the only thing that brings millions of people, in the case of the World Cup, billions of people together that are engaged around the subject matter.

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30:15and it's AI proof and actually AI is going to enhance sports. So as an investment platform in this world, that's pretty attractive, right? And so that is a backdrop. And then with the lower, more conservative, which for good reason, conservative nature of the capitalization of sports even makes it more attractive. I think sports is, I think the whole industry has done a very good job of managing through all this. I feel like it's been an evolution over 10, 11, 12 years. And I think the industry has got a good handle on it. Now, what hasn't happened and not everything's going to work. And so we really haven't been to that scene yet, but not every investment is always going to work.

31:03And so we'll see how that unfolds. That's normal, but we haven't really had to deal with that too much yet as an industry. Flesh out what you said just there a little bit more for me about AI will enhance sports because that's probably a statement that some people listening might raise an eyebrow to. How do you, big question, I appreciate that. How do you see the influence of AI impacting sports? Well, even take a step back, think about entertainment. Entertainment, in my opinion, has been commoditized by streaming, right? So to me, entertainment's a lot less attractive. Music actually was disrupted by technology as well, right?

31:47There used to be a thing called albums with records, and now it's on Spotify and others, right? We'll have to clarify that for younger listeners. That's right, that's right. I'm too old for that. So the reality of the situation is the only thing that hasn't been commoditized by other forms of technology is sport, right? Because sport is reality TV. There's winners, there's losers, there's people you like, people are villains, and it's unpredictable. And so it's become more and more valuable on the one hand, and now you have artificial intelligence where you can come in and create a song. You can come in and create very low budget entertainment products that look not so bad.

32:27So artificial intelligence is going to disrupt entertainment, could disrupt music, but it's not going to disrupt sports because it's live. You have to be there. You want to share with your friends. You big crowds come together. Sports is a statement of who you are and what you stand for, your community. It's not going to be disrupted. It's actually going to be enhanced because AI is going to bring sports to people in new ways. They're going to bring data available to people that they didn't have before. It's going to enhance it, not disrupt it. So that to me is going to make sports enormously valuable and enormously attractive.

33:04And I think that's why it has been so successful over time. You can't make up the drama. You're not going to be able to make up the drama of the World Cup, right? You know, you're just not going to be able to replicate that. Wimbledon will be, you know, all the, you know, whatever it is, the Lord Cricket Grounds, you're not going to be able to replicate that. And so because that becomes so unique. And because the following is so passionate, I think it's so far so good for sports. We talked a little bit about the different types of investors, institutional investors in sport. You're obviously coming at this with a deep knowledge and experience of working in sport.

33:40But I wonder as you sort of cast your eye across everything that's happening in terms of the finance world and its interest in sport, what mistakes or missteps you see from non-sport specialists who are looking, investing, coming into this world? Yeah. Well, I don't want to say we don't make mistakes because we do, but I think, I just think, you know, not everyone's going to be successful and not everything's the same, Right. And so not understanding those differences, if you're not deeply rooted in the business, you know, you could find yourself in places you really don't want to be. And understanding how the ecosystem works is, you know, is a skill.

34:27I want to talk about a couple of your current companies. Box2Box, a really interesting organization. Everybody listening will be very familiar with a lot of the work that it has done over actually many years now, but Drive to Survive and everything else that has followed since then. A, how do you see the sort of company outlook for an organization like Box2Box, are very much seen as a bit of a pioneer in that space. And actually more broadly, would you agree or disagree with the suggestion that maybe the brief era of sports documentaries, behind the scenes documentaries might have peaked? Yeah.

35:13I think they're very good at what they do. They're enormously creative and talented and have a lot of desire, which is very attractive to me. The key for box-to-box is to build out the other elements. So you are right, there's a, you know, through the streamers, there's almost been an unlimited demand for sports documentaries. And that will, I don't think that'll go away, but that can, as you, to your point, it can only go so far. So, but branded content, other forms of content, short form content, podcasts. There are a lot of different ways to create content that are relevant to people. Also, multi-year platforms, developing multi-year shows versus just a documentary.

36:02Formats, other types of entertainment platforms is really directionally where we got to go. That's the next phase. Actually, thinking about it, Have you ever pitched the idea of having some cameras in your board meetings, sort of inside the sports investment firm? We haven't. I don't know. We'll see if that comes along. Yeah. See if that gets through the quality control. I don't know if that's Netflix. We'll find that too interesting, but whatever. Maybe not Netflix, but one of the other lesser streamers, perhaps. We must talk about Matchroom as well, which I guess is your latest investment. investment.

36:40So earlier this year, you took a healthy minority stake in matchroom sports, boxing, darts, snooker, Eddie Hearn, Barry Hearn, who are very familiar characters, and they are characters. Tell us a little bit about how that deal came together and what you saw in that company and actually how you see a company like Matchroom fitting in your overall thesis, as we said, the second level enablers, the pipes, because it is to some extent, at least a bit more of a forward facing organization. Yeah, it was a unique investment for us. I mean, when I look, I admired the company for a long time, and I've admired Barry and Eddie for a long time.

37:27They were a client at IMG. I was always aware of them. And then when you start looking at the size and scale of darts and the growth of darts has been phenomenal. And when you look at snooker being global and you looked at what the digital viewership was for the snooker championship was off the charts, very attractive. And, and also boxing, you know, they, they promote 40 fights around the world that, you know, we've looked at a lot of boxing businesses over the last 12 years. And, um, this was really well-run. These guys were well-run. So when you also look at through the prism of, hey, this is a global platform.

38:04They're in 25 countries. They're a global events company. It's just had a lot of really attractive attributes. I, you know, I've spent a fair amount of time with Barry and Eddie and the more time you spend with them, the more you admire and respect what they've done. You know, one little thing as a, again, a little bit of an operator, you know, they're great promoters, like the colors, the music, the introductions, the whole way they approach everything is just really, really good. So as impressed with them, as impressed with their sports that they're involved in, you know, again, like many of the companies, I think we can be helpful in America.

38:44And so I think when you think about the value add that we can have is, you know, events in America, sponsorship in America, and just also adding some of the, we might be able to add in some small ways to what they built, but just really taking with them. I mean, I just spent the weekend in New York. It was in Milan last night. It's Tuesday. I'm here in London. I was in New York over the weekend, but we went to darts at Madison Square Garden. It was amazing, just amazing. The crowd, the enthusiasm, it was incredible. I had one investor with me that came and was so taken by it. I told him about the championship here in London.

39:19He's coming. He said, I'm going to take my family. We're going to go. And then the boxing match at Barclays Center was thrilling. So the company's got a lot of potential. I think things that are global, global live event companies, you know, with global content is quite appealing. Any trepidation on your part in investing in an organization where, particularly on the boxing side, the sort of business dirty laundry is hung out on the Internet? Not a day goes by when Eddie Hearn is not appearing in an extended interview with one of many boxing YouTube channels. And part of the part of the sport is that sort of soap opera, the, you know, the business side, Eddie Hearn, Dana White, whoever he's, you know, arguing with, negotiating with, in combat with.

40:11Does that give you does that provoke any nervousness in in George Pine, the investor? No, you know, when I'm reminded that there's a great American media mogul named Ted Turner. And I saw him speak 25 years ago or so. And he said, early to bed, early to rise, work like hell and advertise. And, you know, that's, they're great promoters and being a great promoter is telling the story. And Eddie does a fantastic job, but I also would just tell you, having been around him and his father, they might be great promoters, but they're also very, very thoughtful and successful business guys. What, without getting you to give away the secrets of your next investment, where do you see the opportunity?

40:55to me. And you touched on AI. What are you looking at broad strokes at the moment in and around the sports industry and particularly keeping an eye on it? Maybe that's a particular sport. Maybe it's a particular vertical or area of the industry. Well, kind of falling on AI, I think as an investor right now, you need to be careful about being disrupted by AI. So now I kind of joke, You know, as I get older, I'm like, you know, boring things aren't bad. So, so, you know, I think really service businesses that are not disrupted by AI, I think have a real attractive nature as we kind of go on this journey as a, as an, as an industry or a world, AI is going to disrupt a lot of things.

41:38and so I think you really want to stay clear of businesses that can be disrupted by AI so that will influence how we look at things like we were looking at a great golf software company it's a terrific job but you know that could get replaced by AI and you know pretty easily and and like you said to I wasn't dodging the question I don't like to make risky investments you really you know part of the thing is do no harm right and so I think being mindful of how AI is going to affect a particular investment, I think will guide us a little bit going forward. So there's a bit of an AI sniff test for you now before you do anything with any business.

42:18I wonder, George, just as we come to the end here, be really fascinated to get your advice for, and you work with lots of, as you've said, founders, C-suite executives, but actually advice maybe for people working in the sports industry who are perhaps a level below that, but looking to make the move into the C-suite. And you talked a little bit about some of the leadership attributes that you value. What advice would you give to people in that position, the leaders of tomorrow who are, you know, maybe two, three years away from stepping up into the kind of leadership position where one day they might be talking to you as, you know, running an organization that, you know, is looking for investment or, you know, working with you, partnering with you?

43:05I think, you know, the one thing I would say is to try to get as wide of a background of experience to work in different parts of the sports industry. I think makes yourself more valuable, gives you a better understanding of the business. So try to broaden yourself out if you can and, you know, believe in yourself. You know, take risk on yourself, bet on yourself. I think when someone bets on their self, there's no better bet, you know, to make. And you know what? Everybody fails. Not everybody talks about their failures, but everybody fails. So when you get knocked down, just get back up and keep going.

43:39If you look at most successful people, they had great failures, but it wasn't the failure that defined them. It was their ability to overcome that failure. So I think being broad, taking calculated chances and not being able, not being afraid to fail would be the advice I would give somebody. And we just talked about Eddie Hearn. And I wonder how important, it's definitely a trend we're seeing amongst leaders, not just in sport, but elsewhere. This idea of, for want of a better phrase, executive brand building, personal brand building. and actually I wanted to ask you George about your your if I can call it a strategy your LinkedIn strategy because you have made even more of a name for yourself I think on LinkedIn over a number of years now by putting together some really detailed thoughtful analysis and I wonder why you decided to do that how useful that is for you or actually whether that's just a bit of a a thought clarifying process for you on any particular topic?

44:47Yeah, I think we like to show thoughtfulness and that we're thinking about the industry, we're thinking about these ideas. And I think, you know, trying to be positioning yourself as a thought leader is a good thing. And so on LinkedIn, when you're coming out with these position papers, what better way to show that you're thoughtful by having a point of view on different issues. So I think that's why, you know, we kind of, that's part of our, what I would say our communication strategy is to go out and, and give good perspective on things that maybe they don't relate to us specifically, but relate to the, to the industry.

45:23I think for us, we want to be perceived, hopefully real perception is reality, but you know, thoughtful people when it comes to industry that we love and that we've made a living in for our whole lives. just a couple more quick ones one as you look across the the sports industry in general what gives you cause for concern at the moment what's what's worrying you about what you're seeing well you know someone asked me that the other um i was at dinner with muhammad el-aryan in the other day and he asked me what i worried about and i didn't have a good answer because i don't i'm not a guy that worries a lot worries a lot probably a good trait right i think you know right now, you know, I'm just talking, if you think about it, we had the financial crisis when I was at IMG, learned a lot.

46:09In the last six years, we've been through COVID. We've been through Liberation Day on the tariffs. We've been through the Iran war. I mean, we have been through some things here. So, and when you, you know, it's not that we don't have problems, but I just kind of don't, I don't really worry about them. I think, you know, if I took a macro level at sports though, I think you always have to be cognizant and mindful of your core fan and never forget that. There's always a temptation to go for the casual fan, but you got to always serve that core fan. And if you're always serving the core fan, everything else will work.

46:48You talked about some of the executives, the founders that you have worked with closely over the years. And I just wonder all the deals you've done, how confident you would be that everybody that you've worked with, partnered with, would work with you again. And actually how important or not that is to you in doing the job that you do. Yeah. You know, you try to be authentic and be who you are. I am really close with a lot of people that I've worked with, you know, over the years. when you look at our network of Bruin advisors, many of the people are people that I work with, or even some cases competitors.

47:28And so I'm proud of that, you know, um, is every person you're ever going to meet? Love you. No, if everyone does, maybe you are doing what you're, uh, you're not a good leader, I suppose. I want to show about leadership, but I think I value relationships and I value the people I'm with. And when I tell people that are CEOs like, okay, you know, I'm going to be here five years from now. And then I'll point to three guys that they know that I've been with for work for me, you know, five, 10, 15, 20 years ago. So I'm pretty sticky with people. You know, like when you're once a friend, always a friend, you know, the Americans leave no Marine behind.

48:07I don't believe in leaving any guys on the beach. So like, if you're, if you're in there with me and we're fighting together, you know, I'm, I'm kind of always on your team. And I think for the most part for me, that's worked out pretty well. So like I said, those three CEOs I mentioned, that's all true. One I went to a hockey game with, the other one came and visited me while I was in New York with his family. I mean, that's who we are, you know. And in terms of elegant exits, as we talked about earlier, is there an elegant exit somewhere in your future? How long do you envisage continuing to do what you do at Bruin?

48:42Yeah, no, that's a great question. And one I've thought a lot about. And for my own health and longevity, I want to work, you know, as long as I can. So, you know, I certainly at least 10 more years is kind of how I see it. But I think, you know, and obviously at some point down the road, there'll be a, I'll have to think about a transition, but you know, I'm kind of all in and reinvigorated. You know, my boys, two boys play American football and no more American football. So actually for me, I'm getting back I used to go watch my boys play football for 17 weekends a year. So I'm getting back 17 weekends a year.

49:21So I actually have more time right now to work than I ever did. But, you know, I plan to go at least for 10 more years. I think it's good for my health and well-being. And I love what I do. I don't hunt. I don't fish. I don't golf. I've been married to my college sweetheart for 36 years, have four kids. And really, for me, my life is work and family. I wonder what we're going to be talking about in 10 years. Who knows? Who knows? That's the beauty, I suppose. That's the beauty of it. George Pine, thank you ever so much for being with us. Thank you. It was a pleasure being here.

From the publisher

Investor George Pyne, Founder of Bruin Capital, joins the show to share his thesis for sport and his rationale for targeting what he calls 'second level enablers' - the companies a layer below the headline-grabbing team and league properties.

 

In a wide-ranging conversation, he reflects on 12 years of Bruin, the investment firm he set up following a career that including a stint as COO of NASCAR between 1995 and 2006, and then nine years as President of ING.

 

Pyne discusses the particular challenges of raising money - he's done it four times with Bruin - and then deploying capital; his approach for working with the management teams of the organisations he's invested in; and the art of the elegant exit.

 

He also reflects on some of Bruin's most memorable investments, including Deltatre, Two Circles and On Location, and a current portfolio that includes production company Box to Box and Matchroom Sport, where Bruin is now a minority investor working with Barry and Eddie Hearn.

 

The conversation was recorded in early July, shortly before news broke of Bruin's sale of golf simulation company Full Swing to Versant for a reported $530 million.

 

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Join us for The Summit, part of Leaders Week London at Stamford Bridge, home of Chelsea FC. For more information and to secure your pass: https://leadersinsport.com/sport-business/leaders-events/leaders-week-london/

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