Inside the Billionaire Shadow League Funding American Tennis

0:00Welcome to Pablo Torre finds out I am Pablo Torre and today we're going to find out what this sound is You can look at someone like Francis Tiafo Making the semi-finals of the US open winning tournaments and you can say I help make that happen right after this It's not surprising that tennis on some level I should say is like a Sport for people with money. It's a country club sport by reputation of course and history and history Yeah, but even like the US open this year which I've been going to every day How many has it been Matthew butterman and thank you for being here again by the way. Thanks for having me How many has it been I started going to the what is now called the Billie Jean King National tennis center When I was nine years old opened in 1978 old Louis Armstrong stadium in terms of covering it

1:04I don't know. I've been a sportswriter for 25 26 years and Pretty much every year. I try to go every year and part of the thing about it is that this feels like kind of the people's open There is crowd noise There is cheering there is booing there is the city of New York almost as this character the audience feels Participatory in ways that are not wimbledon or French opening yes a hundred percent the US open is the only grand slam and it's I would say the One of the rare of the big tournaments many of which take place in like huge diverse cities Where you walk around the crowd it's slum what resembles the city that it exists it takes place in a public park Publicly owned facility owned by the USDA national governing body of tennis in America They're all about

2:04Accessibility supposedly but this US open has Tested their definition of accessibility In ways that I think a lot of people didn't anticipate it is hard to get a grounds pass There is a level now of out of control Pricing when it comes to something that is meant for broad popular consumption Yeah, I would say this year what has really struck me about the US open is that I feel like I Am in an airport you can very easily see that in an airport There is part of the airport for wealthy people who don't wait on lines hangout club hanging out in the lounge and There is the airport for everyone else who is you know like fighting for an outlet and waiting in like the 26 deep Starbucks line. They are currently building nine New hospitality clubs to entertain the all the new club seating they have they actually moved a lot of the seats down from the

3:09Mid-level into the lower level through this $800 million renovation they're doing on authorized stadium So they did the thing that's supposed to be impossible, which is they created more beachfront property Which they can get the most amount of money from and the feeling I have gotten is that like this Non-profit organization which is holding a signature event in This public park is suddenly like somehow fitting in with the larger story of America of Income inequality and like the top 3% or whatever it is who can afford $4,000 to take a family forward to the US open If they're having all the fun and everyone else is just sort of like fighting over the scraps but the moment that This all came to mind Wasn't this year it was last year it was July and What is I think very safely described as one of the strangest tennis matches that

4:13Anyone anywhere has ever seen So he may have noticed that we do like following the money here on ptfo and today's trail Actually takes us from New York City just for a minute here and back to the great state of Rhode Island For a professional tennis match at the Hall of Fame open a small but dignified tournament in Newport Happens to be underway These are people who are playing who are trying to get to the major leagues of tennis There are rankings points on the line not that many there is some money on the line not that much But right now on this July day in question there is something big at stake Because three of the four players on the court are elite professional tennis players Bernard Tomic and Omar Jaseka on one side He recently retired Jack Sock on the other all of these guys still in their late 20s or early 30s

5:14But the fourth player Jack Sock's partner a Gentlemen dressed in all white is named Bill Ackman and Bill Ackman has never played professional tennis before Turns off his competitive Tennis experience I think it's safe to say that pretty much ended at Horace really high school in Westers County in New York did not play college tennis. He was a rower at Harvard He's hitting the ball right into the net Errors happen in tennis even the best players hit a lot of balls in from the net But I think there's like a lack of familiarity a lack of velocity on it Which in fairness may also be because at the time of this match Bill Ackman is 59 years old And then you get to his surf I

6:17Can tell you it's not a serve that really belongs on the court in a professional tournament Which makes all 67 minutes of this match inexplecable Until you realize perhaps that Bill Ackman also happens to be a hedge fund manager worth 11.7 Billion dollars. I try to have a conviction based on the facts and a kind of a key thing if you've done a lot of work on something and you Made your bet and then facts start to emerge that are inconsistent with the original thesis You got to rethink the bet I'm negative on New York if on Tommy's elective, but I'm positive on the country You know clearly we have the most pro-business president we've had in a very long time always been a big free speech advocate It's important for me to be able to share by points of view and The power of X is that you can reach a very broad audience of people I have you know approaching 900,000 followers and a lot of them members of media or CEOs people in government

7:22I follow him I regret to inform my audience He sounds off on all sorts of public policy The master of their education 5,000 word tweet is Bill Ackman this guy But the reason that I wanted to cover billionaire make-a-wish tennis as I have come to understand this is that This was not something that lots of people in real professional tennis were cool with when they saw it like actual professional tennis star Andy Roddick on his podcast the job of the Hall of Fame is to preserve and Celebrate excellence in our sport. This was the biggest joke I've ever watched in professional tennis There was exactly one person on that court Trying as hard as they could and the match where it looked like four players were in the bag. It was a disaster and Martina never to Lovah no less than Martina posted on

8:23Blackman's favorite platform X quote apparently you can buy yourself a wild card oh to have that confidence and Quote But immediately the tournament organizers said no no no Quote in no way did bill by his way into the Hall of Fame open They proceeded to explain that Bill Ackman and his partner Jack Sock they had this wild card spot Quote to bring further excitement to this year's tournament. Well, there was excitement about it We can deal to his charge. I was excited. I'm I remain excited by the fact that this ever It's crazy to be at tournaments. There are spots reserved for the tournament just to hand out usually they go to players who Might attract the crowd. I mean Serena Williams and Venus Williams, you know, they got a doubles wild card into the US open Yes, this year usually these people have some resume of accomplishments in the sport and

9:27That's not what happened here and that's why we're doing this episode is because I've been laughing at this for a variety of reasons One of them how Bill Ackman defended himself on Twitter when he said in parts quote What people are missing is that the whole thing worked out perfectly my poor play dramatically increased the virality of the event Driving massively more coverage than if I had played well and Quote the excuse making continued Quote Jack also chose the ad side and I have been playing the ad side for the last year I was also serving into the 130 p.m. Sun with a shot clock friend this is a new experience for me and Quote and that's of course before we then get to the whole thing about how the other side was actually taking it I mean kid gloves is not even an appropriate descriptor of how how soft How pillowy these these serves were at times well tennis actually has a word as a phrase that encapsulates this is called customer tennis

10:32It's what happens when you're on the other side of the net from someone who's not as good but Might be paying you to play with him or it might be you know beneficial for you Not to make them feel bad or uncomfortable But the concept of customer tennis which I did I know until just now that is the theme here This is transactional Tennis and it's not supposed to be the case that the tennis hall of fame or perhaps tennis itself writ large is In the position of the customer I mean what happens is that four days after the match Bill Acman announces on X that he is giving them the hall of fame a 10 million dollar endowment and That he would quote manage it for free To which the hall of fame says After some deliberation we cannot accept your 10 million dollars

11:34Because then it would create this perception of impropriety Which is a remarkable thing to have to say That we're at a point where this has been so embarrassing that for you to give us 10 million dollars looks like this is customer tennis of An even grander scale that puts us all to shape Yeah, it looked like a quid pro quo happening During an actual During an actual event that sparked a bit of outrage in Crossed a line and this is where we should point out that Bill Acman is not just any billionaire tennis enthusiast who thinks you can play professional sports He is particularly Important in the world of tennis as yes, the flow of money is concerned Yeah, he's been a huge benefactor. He's given millions of dollars to the junior tennis champion center Otherwise known as a JTCC in Washington DC which produced players like Francis Tiafo and Robin Montgomery both players that he has personally

12:37given money to an article help launch their careers and He's been a benefactor of the USDA foundation He went so far as to bankroll the professional tennis players association. Yes, Novak Jokovic six years ago was launching a player group That was supposed to sort of be a ballast against the control by management the ATP. It's a union It's basically a union And then also with a for-profit entity a whole magilla that led Bill Acman by the way to say things like quote I understood the plight of the player And quote, but the point here is that Bill Acman loves tennis funds tennis Is all over the sport in ways that someone like you has seen Everywhere every time I turn my head there's I feel like there is acman involvement and he has by the way Discussed openly that he plays with all of these

13:38excellent tennis players quite regularly on Axe going to say quote I regularly play with mid 20 year old D1 college players and recently retired pros On a familiar court with no audience which is to say that Bill acman is living a life that I Totally underestimated. I think what's so interesting about this experience is that While it was so crazy to you Tennis exists in this universe where we've talked about the intersection of Of wealth with the sport where the system is set up And is so institutionalized so that this was not so crazy to Some of the people who were involved in the decision-making the part about this to me that I didn't quite realize until we started talking is that

14:38There are more Bill acabas. He's not alone. There is what appears to be This entire like shadow league of tennis of wall street guys these masters of the universe Who are seemingly constantly surrounded by these elite tennis players these actual former pros these collegiate stars and It makes it so that the world of Finance and tennis are So much closer than I personally ever realized and in ways that you didn't ever realize Either I think people are used to the idea that tennis is a wealthy person sport and they like it But I don't think most people realize how much Hangtime there is between wealthy people who are not star tennis players and never were and people who were really good former NCAA champions, tour players

15:41All of that to the extent that Those wealthy people sitting in those low seats at the US open paying tens of thousands of dollars for those tickets guys who are playing on the courts that they are watching Sometimes within months sometimes within a year or two are on the other side of the net from them If You're the kind of sports fan who needs to go beyond the stats and if you're the kind of sports fan for whom when that whistle blows You need the deeper story Then you've got to join the athletic live on YouTube to hear more about all the sports stories You just cannot stop talking about Ungame days you'll watch the biggest matchups alongside some of the athletics biggest and best reporters You know the ones who kind of know everything going on behind the scenes

16:44And you can even become part of the show thanks to the interactive chat The athletic live is presented by Google Gemini check it out now starting September 8th and subscribe now on YouTube The New York Times app unlocked Everyone knows you need to subscribe to the times to access all of the reporting But what if you could explore the times for a month for free without putting in a credit card Now you can when you download the New York Times app for the first time your first month in the app is free A month to go behind the paywall to see what time subscribers get every single day If you don't already subscribe to the New York Times download the times app today and get free access for 30 days We're using you man as a guide into a world that I did not know about a subculture a corner of tennis That seems to explain What we are seeing when we're watching tennis now on television

17:47But it's happening like not far from here. I mean it's sort of originating On Wall Street here in downtown Manhattan and the ways that the ultra rich Are connecting to all of these elite tennis players It brings us to a particular Wall Street figure who's sort of like the nexus point of this world And his name is Jeff Powell Otherwise known as the mayor of New York tennis AKA the guy responsible for why Bill Ackman Is somebody that I've been thinking about for the last year My name is Jeff Appell. Thank you for having me today I started playing competitively since I was about nine 10 years old I've been exposed to a lot, but I'd have to say that Is good as a tennis player or some people think I am I think I'm better off the court and sort of my contributions to the sport is what is Jeff Appell's day job Matt he runs an investment fund called JDA funds management

18:49I think he'd be the first to tell you he's sort of on the back nine of his finance career He's really into tennis and really into tennis players getting into finance He's the guy whose bio when you find it lists that he's advising these spacks And arranged an eight hundred million dollar merger and yes Yeah, all these eight figure transactions for VC funds and litigation finance companies and all of that But that's not why he's the mayor of New York tennis No, he's the mayor of New York tennis because Every week sometimes more than every week. He's organizing tennis matches on Randall's Island with Some of the best tennis players in the city people who were Top players in college some of them play professional tennis and there's this intermingling of quality club players, but also actual former pros Which is precisely how one bill acman gets involved in this world in the verse place

19:50Acman is invited by Jeff Appell to this Sunday morning game To play with him and a player Kyle Clegerman I sent Bill an unsolicited email inviting him to play tennis, you know talking about my tennis background and Kyle's background and coincidentally He responded two hours later Bill had picked up a racket since high school. We didn't know it so his skill It seems to me is that he is an expert matchmaker. He is the matchmaker that is bringing together Wall Street Titans and Terrific tennis players who may one day become Wall Street Titans Which brings us now to something called the finance cup Excellence determination and work ethic all key elements required to excel in finance and tennis And The two fields joined together yet again for the 2023 finance cup as the action starts now at the Miami Beach tennis center

20:59This is the sort of full flowering of These Sunday morning games uh that are happening in New York the idea is essentially a finance world writer cup of tennis the US versus Europe Your best bankers and former pros against our best bankers and former pros. I I'm so perversely interested in what this is like I would say one of the ultimate networking events given That Many of the people who have come through the finance cup beginning when they are right out of college Or shortly thereafter have gone on to run like major major Wall Street institutions and hedge funds as they alternate locations between the US and Europe this June by the way Marbella Spain At Rafa Nidal's Academy this whole thing has a trophy

21:59Have you seen the trophy? Yes, pretty nice trophy In fact, it's crafted from English Oak according to the Instagram page I found for it and it's also though A bear and a bull fused together Into this like almost mythological creature that speaks directly to yes the the provenance of Bear and bull markets and in 2025 it turns out this event happened to be hosted At the tennis hall of fame in Newport, Rhode Island 10 years in You know, we got to look like a real company It's a special event. You know there aren't that many opportunities In 59 where you get to go hang out with a bunch of wonderful people For a long weekend playing an amazing sport. We're all incredibly passionate about and people from all the world Come to this spectacular city. Newport is amazing. Who thinks Newport's amazing Now it's all coming together now, isn't it where we began our story

23:03Except we didn't mention when we began our story that It happened to also involve a Gatsby themed black-type event at the historic marble house mansion in Newport That's tennis, isn't it This is what makes this point different from all other sports. I would argue How would you describe actually that if you were to sort of give us a taxonomy of wealth and sports What does strike you as like texturally distinct to tennis as a matter of how they are Moneyed. I would say it's the participatory aspect of it. What do you mean in tennis? I think what happens because it's it's one-on-one It's because you need a partner. Mm. There's a situation where the illusion can get created that like I'm actually playing with this guy. We're a team. We're a team or we're hitting partners and I'm hitting balls and I'm hitting Hitting well today and He's moving me around and I'm moving him around a little bit and

24:06That thing that we mentioned before That whole concept of like customer tennis that can be forgotten Well in the finance cup to that point One of the regulations that governs who can participate is that you got to work full time in finance Which is to say that all of these elite players that you've referenced are all finance guys though. Yeah Yeah, they are actually on these teams in a corporate sense Yeah, ringers don't Exist you can't rock up there with Patrick Mackinrow No, you could be a former ATP number three But you got to actually earn your corporate sleeveless vest your fleece vest you earn that And Jeff Appell doesn't only put you in games He and a couple of other people become your mentors and nurse your career and it's why You want to keep showing up in those games on Sunday morning and it's why you want to play in the finance cup

25:10You don't play tennis all day You also do a lot of networking and I just feel like that People don't know this but Andres Pedrosa the most successful coach in college tennis in 2005 He worked at Bear Stearns. Okay. I know Andres from when he was still playing on tour And had a hand in his Brief and successful Wall Street career Jared Donaldson's another great example someone I've been involved in since he's 19 years old He didn't like hanging out with the tennis players. He liked hanging out with business people and just like business I went back to school after three knee surgeries He was at Fortress now. He's starting at Valley Asni In the capital markets Jared Donaldson by the way the guy who made five grants lambs was ranked as high as 48 in the world in 2018 Yeah, but not that into it apparently He always wanted another career you find that with like tennis players. I think I've done it maybe you know 150 times Of opening up some doors and coaching them in terms of

26:12What's the right fit for them and their comparative advantage right if someone's a A big personality and doesn't have a long attention span They're more better geared toward wealth management or The capital markets as opposed to the deep analysis and and the perhaps perfect example of this that I want to focus on with you now Is Milo's round. It's so how much tennis are you playing now Milo's not much Former Wimbledon finalists one of the scariest serves in the game Well for many years the last guy you wanted to see Next to your name on a draw sheet early in a tournament because he could literally take the racket out of your hand and now He's taking the money out of someone else's because he works at Goldman Sachs I knew I always wanted to do something very different after tennis and then Got this opportunity here at Goldman and Jumped on it right away and I was very excited about it and it's great because I'm learning a lot

27:16So now I sit on the external investing group on the private equity focus team and it's been a few adjustments along the way But it's definitely like exactly where I want to be and I'm getting close to that path. He isn't alone It turns out just last week at the US open former world number six Dale Monfie foreshadowed his own life after retirement So far to be honest, I have A new chapter Come in the next year. I will work in finance You know, I I already signed to be to work in the worst management in the Swiss company so my next chapter looking at more In the office and working in finance What did tennis players specifically have to offer The world of Wall Street do you think tennis is not easy right? Tennis is it is a grind That has always sort of reminded me of like boxing

28:17There's an appreciation for the soft skill of athletes that doesn't necessarily show on A resume, but there's just like that intensity that comes with it the resilience just also being okay with like Failure and getting up again and trying again and in addition to the extent that like the world of finance can become something of a jungle at times and rather combative Tennis is very similar in the sense that it is non-contact combat But there's plenty of battling I think the one mistake you can make is thinking like just because I was a good tennis player I'll be good at the next thing or I deserve an opportunity and it doesn't work that way I took 342 meetings with different people all unique meetings To like get in front of as many people as I can learn as much as I can and see where I can get an opportunity to like get a shop and

29:18Trust me out of a hundred three hundred and forty two. There's a lot like hey We think we were interested or we think we can help you But then when it comes push to shove it's like a different thing right somebody the jobs that used to exist for former tennis players in the financial world Where you just kind of hang around and you get trotted out to play with clients and right show up It like a mask show up at dinner and let hand yeah Those jobs don't really exist anymore And I think me let's be the first one to tell you that because he had a lot of doors Closed he had all those meetings, but he only got one job I like that he remembers that he had three hundred and forty two of them Yeah, nothing hundred and forty six. That's kind of like how every wide receiver does how many players were drafted ahead of him Yeah, right he's hanging on to like how hard it took to get to the finals of Wimbledon 2016 He's got the receipts for it and the symbiosis of how these skill sets sort of

30:18Clyde and then swap sometimes I'm thinking of how These bankers also fancy themselves tennis scouts In some ways yeah because they are solicited For help for really promising tennis players Who might not have the means to afford was incredibly expensive sport I mean tennis if your kid is gonna cost you like fifty thousand dollars a year to develop right as a top tennis player so what happens is People like Bill Ackman gets solicited at times and say can you help out this kid happen to Coco Gough when the USDA foundation was able to Send some money to her family in order to get her and extra trainer and Ackman famously funded the early stages of careers like Francis Tiafos and Robin Montgomery too It's a funny that even just so you put it though being an early stage investor in Francis Tiafos is

31:22Almost literally investing. Yeah, it doesn't pay financial dividends. That is not what they're in it for There are parts of the world where that happens when it can get a lot of players into some trouble Especially when they aren't able to fulfill and pay back those investments That is not this at all This has a different sort of payoff you can look at someone like Francis Tiafos Making the semifinals of the US open winning tournaments and you can say I help make that happen That was a great guy You know he's done so well in life and the fact that he wants to give back to Young young athletes like me. It's some blue he gave me I mean he he's done so much for me. I mean he gave me a chance to play around around the world and not worry about Any any finances at all You can be text buddies with him for the rest of your life. You can be on email threads Jeff Appell and The accumen and Robin Montgomery are as we speak

32:23Talking about you know her progress wins a match you send her a notice support Benefactors. Yeah, you're the benefactor. It makes it you know, and that happens in all walks of life Um, I think it probably happens more in tennis than in just about any other sport that I've ever seen And in this case what you're saying is that accumen um He is generous in real ways And exchange he gets To hang it's one of those both things can be true As I think is often true with any kind of philanthropy. Yes. Yes. Yes. Yes. It makes us feel good about ourselves You know we get something out of it. Humans get something out of being charitable It's the curbing your enthusiasm episode in which Larry David is wondering about being an anonymous donor Is like oh, why would you do that? And in this case by the way what bill acumen and His colleagues who have estates and we're here talking about venture capitalists like Michael Loeb

33:25We're talking about Julia Koch and the Koch estates being of the complications of philanthropy here We're talking though about hosts hosts of actual tennis matches On their properties Yeah, practice tennis matches in the case of you know the Koch estate where I've been to interview players and Watch some practice matches. What's that house like Henry Morse sculptures jacke a medic sculptures. I mean really just You know one of the grand properties in south Hampton This is one of the things that happens like the week before the US open on the highest level where You know you can go out there and you know y'all like sinners staying in bridge hampton and Tommy Paul's and south Hampton and It's funny because there's only a handful of courts that have Enough room in the back court to be able to accommodate these professional players

34:30I think that all billionaire tennis courts are created. Not all billionaire tennis courts are created equal One of the advantages of the Koch estate is that there is enough room Not surprisingly behind the baseline so that The best tennis players in the world can hit the kikiest kick serve and the guy on the other side of the net will not run into the back fence. I I am looking at photos of the Koch estate and They got a room for all sorts of things Including a nice big tennis court where some of the best players in the world hall of fame members Have played and stayed and yeah, I mean if you want to talk about tennis benefactors. Yes, Julie Koch is right up there also one of the things that the JTCC does Every year is they bring some of the really promising kids from their academy out to the east end of Long Island

35:32So rather than Montgomery, I was speaking with her after she won a doubles match at the US open and I was asking her About what it was like being a kid because she was one of those kids who got brought up to the east end of Long Island As she grew up in Washington DC in a one-bendroom apartment with her mother and a grandmother and she told me of going Up to the Hamptons for a weekend to meet some of these people and sort of show People who donate money to organizations like this like Where their money was going and she recalled like being in a car and driving around there and with her friend being like thinking like Why are these driveways so long? I mean it was a completely different world of anything she had seen Frances Tiafou was one of the kids who made that trip He told me he just described it as just a complete eye opener. He had never seen or kind of imagined houses like that and to be on their properties was

36:38yet, you know a crazy experience for him In his words and he met Ackman and changed his life Which is all to say that when you understand where Bill Ackman's money in part is going Which is to fund the pipeline of American youth tennis This is something that American tennis in general really relies on Like he's important to the premise that we're even competitive as a country Because would separate America from most countries is These sports federations they don't receive government support They have to raise money themselves in order to fund their operations It is why one of them Got to play in a professional tennis match At the tennis hall of fame one might argue in Newport road island. Yeah, it's a big reason

37:45So I have to admit that in my Delight at how horrific Bill Ackman was in his lone professional tennis experience You have pointed out that actually Bill Ackman scouting report is not quite as I have conveyed it. Yeah, I mean to be clear He's pretty good tennis player by all accounts His favorite partner is guy named Richie Rennenberg Richie Rennenberg I spent 13 years on the professional tennis tour from 1987 to 2000 former pro US Open doubles champ good player There is a version Of Richie Rennenberg that Bill Ackman Can legitimately Hang with On a tennis court especially if he's his partner bills a very good play is very good technique I would say that he likes the faster courts, you know, so the grass courts suited him pretty well I remember seeing him at an event. I didn't know him probably 20 years ago There are these Michael Milken programs and he was okay. He wasn't great to be honest and then

38:49He worked at it and he plays a ton So I'd say the strengths of his game where his serve is very good his neck game is exceptionally good He covers a lot of court. He's a big guy And his ground steps like all of us, you know, he can days where he's hitting really well over turns and days where he's not But then I asked people like Milo's round edge who is played in this finance cup and has been across other tennis courts With Bill Ackman like what he does and I was like, you know, are you bringing the fastball? You kind of learn this ability to just adjust to make sure everybody's having as good of a time as possible Sometimes the fun part is people do want to get ace right people do want to see that big serve in kind of get the feeling of How quickly that passes by so sometimes that's a fun of it's the other times it's hey People if you're playing with somebody for an hour and a half they don't only want to do that Sometimes they want to get into some rallies. They want to get some exercise out of it And I asked Richie Rennenberg like who has You know for 30 years played with wealthy people originally they brought him into the finance world

39:54Ken Brody who had had been a top advisor to Bill Clinton He was Richie Rennenberg's entree into finance and I asked him like well, what do you do when you're playing a guy like that? Who's really into tennis? One thing you do is you try to put the ball in a good spot You know you're not hitting heavy top and throw a bet throwing him up against the fence. You're not doing that But so you know what you come to understand Is that idea of levels the idea of customer tennis and that you know the delusion that can take place And so do the people in Bill Ackman's life were they supportive of the experiment? Do they want him to do this? I asked Francis Tiafo who has hit with him not in a while I said ask him what he thought of it and he said he actually really wanted to play that match And I said why and he just had a big smile and I said why do you want him to see you know what the actual level was like? He wanted Bill Ackman to find out. Yeah, and he just had a big big smile

40:55So he was good with it for his own reasons and even his buddy Richie Ranemberg You know he understands That there are limits, you know And I think it's telling sort of like what his reaction is when we When we ask him about Ackman skill I remember not long after I got there his bills coaches Georgie and Olivia come over and say built They just get Bill and walk hard into the challenger and I'm like what? I actually thought that's kind of cool I mean I'm you know he's been talking about maybe getting a well-quent little challenger here a challenger there So we started talking about partners and people that he might play with and at one point he kind of said Would you want to play and I said Bill? No, I mean you need you need some you need somebody if we because with playing with me We could easily lose love and love so I said you need somebody who you can at least get a game So this is translate that though Richie Ranemberg literal 1992 US Open doubles champion Is like I am not good enough To help you stay on this court

41:55In a minor league tennis match This is where I just got a return of course to the everything app X Because a week before the match with Bill Ackman posted on July 2nd Quote We win I am pretty sure I'll be the oldest person in tennis history at 59 to win ATP points I am playing the best tennis of my life and Jack this is Jack sock his actual eventual doubles partner Jack is one of the greatest double players ever he won at Wimbledon and the at US Open and a gold medal in Olympics And we start practice this Friday so you never know And quote So we know what ultimately happened yes, and I think like one of the big questions hanging out there is like Would you ever do it again? That's even on the table What it puts on the table is like What was the learning experience for you? What lessons what was the lessons you took from these 67 minutes on

42:56the tennis court The thing about tennis and really all sports and really lots of parts of life is that your greatest strength can also be your greatest weakness so like Courage and bravado And seeing possibility where no one else sees it is probably like black man's greatest strength It allows him to make bets on things where everyone thinks he's completely crazy Right, right now building want to talk to us for this episode which remains very disappointing Yeah, I always want to talk to people I'm writing about Especially I'd imagine if that person's stated investing philosophy is once again This I try to have a conviction based on the facts And a kind of a key thing if if you've done a lot of work on something and you Made your bet and then facts start to emerge that are inconsistent with the original thesis. You got to rethink the bet So I had to ask his friends like what do you think he would do if he did it again?

43:56And I asked the guy who brought him into tennis in the first place In his adult life figured he'd know better than anyone since he's played within so much and talks to Molotime and Jeff a pal said Don't bet against it happening. I don't want to speak for Bill But he's not a man to back down from any challenge If someone had asked you to play that day would you have played Yeah Really 100% Unfortunately, I had a tear on my plan to fascia so I couldn't have played I've never said no to a challenge on the tennis court Even in that answer It's like if I hadn't tore my I'm just like oh my god Yeah, I was kind of amazed because I mean Jeff really does know About levels, but you know, it's that thing I guess that everyone wants to stand in the batter's box and see what a fastball Actually looks like could I hit the no one Ryan fastball? No, no, oh Course not no and you'd be lucky to get out of their alive

45:00I mean that's that's what's amazing to me, but this is what this story became all about How does the mind go to a place where it's okay to play this tennis match and it's all wrapped up in Money and philanthropy and the sport that has this intersection that I think doesn't exist anywhere else What is so reassuring? is the total Shock Bacteriality of there is a distinction In terms of what my money does not buy me Yeah, you probably shouldn't be on the court. It's the complete flaw of the whole 10,000 hours idea Yes, yes, which is that you know Is it nurture or nature like there's a lot of nature involved, you know, there really is I mean and you can get to a certain point when you're development if you're

46:02You know get help and taking lessons and do all those things, but you know You are different from these people you can fund the sport you could invest in the prospects You could enable the entire premise that America is a plausible tennis country On your giant mansion But the thing you can't buy is The actual ability to hang on a court with real professional athletes It's sort of the equivalent of you know Making a lot of jokes and there's people around you that are laughing at them all the time and You start to think that like wow, that's really be funny. Yeah You know what happened on that court in Newport, Rhode Island Is that person When to do stand up yes, and it didn't go so well What I'm here to tell you is that what I found out is that it was hilarious

47:12This has been Pablo Tore finds out a metal-lark media production And I'll talk to you next time You