Episode 44: Paul Wachter - Founder and CEO of Main Street Advisors

0:00This week on Generating Alpha, I sat down with Paul Wachter, one of the most powerful and influential figures in sports, entertainment, entertainment, and business. Paul is the founder and CEO of Main Street Advisors, the elite advisory firm that represents some of the biggest icons in the world, including LeBron James, Arnold Schwarzenegger, Jimmy Iovine, Drake, and Billie Eilish, among many others. For decades, he's operated at the intersection of talent, capital, and culture, structuring landmark deals, shaping careers, and quietly influencing entire industries. In our conversation, we talked about how Paul built Main Street into a trusted partner for the world's most elite talent, which separates enduring icons from short-term fame, the lessons he's learned advising generational figures at the very top of their fields, and much more.

0:43If you enjoyed this episode, please follow the podcast and rate it 5 stars on Spotify, subscribe on YouTube, and share it to anyone who might find it valuable. I really enjoyed recording this with Paul, and I hope you guys enjoy listening. Thank you. Thank you, Paul, for coming on. I really appreciate it. You're welcome. Good to talk to you. Well, I'd love to start where I always do, the beginning. Tell me a little bit about your childhood, your upbringing, and what the environment was like. um i grew up in manhattan um i grew up in a european family um who were all i was first generation um so our we were very europe oriented we spent all our summers and all vacations really in europe we never kind of went west of new jersey basically i think a couple of times later We went skiing in Colorado, but we never been to California or anything.

1:38So, you know, it was kind of a very Manhattan upbringing. I was, you know, I was not poor. I was relatively privileged. I went to private school in New York called Riverdale, which I'm sure you're familiar with, Amir. And, you know, and so that was it. But it was all good. You know, I had two parents and they were good parents. And, you know, I was lucky enough to have a good education, had a good relationship with my brother, you know. So can't say that was horrible and it motivated me. And on the topic of good education, you went to Warren and then Columbia Law School, practiced law briefly at a couple of firms and then moved into investment banking where you worked at, if I'm correct, Kitter Peabody and Schroeder and Company.

2:32So I'm interested if you could just give me and my listeners a brief overview of what your career looked like before Main Street Advisors. Yeah. How you think that kind of gave you a unique perspective on advising entertainers? Well, I think you left out Bear Stearns, which is actually important. Because Bear Stearns was, in a way, it was kind of where I belonged. So I was at a, I clerked on the Ninth Circuit, which is not a law firm. It's a, you work for a judge. Yes. And you write opinions, you help the judge, you draft opinions for the judge, basically. And then I went to a very big, good New York law firm called Paul Weiss, which is still a big, good New York law firm.

3:15And I really, I was a tax lawyer, the pace of it was too slow for me. It just was, maybe if I had waited it out, I would have liked it, you know, in the long run, but it was slow for me, a lot of research. And, you know, my the judge I worked for always said I should be an entertainment lawyer, which I probably would have liked better. But I didn't I didn't listen, unfortunately. And I also moved back to New York from California. So California was the clerkship was how I got to California. So I moved back. And anyway, I didn't really like it. And I was lucky enough to get a job at Bear Stearns.

3:53um and it was a very wild kind of crazy firm it was not like goldman sachs is today or or morgan stanley it was a entrepreneurial boutique the partners were constantly fighting sometimes literally fighting like you know just fighting screaming at each other and it was fun it was fun and everyone basically liked each other and the guy who ran it was this kind of legendary Wall Street guy named Ace Greenberg, who's who you're nodding your head. So maybe you've read his little book of sayings, but he really was a legend and he was great. And so it was a lot of fun. And it was it was it was a good fit for me.

4:42Unfortunately, there was some personal lack of fit fitting there that led me to leave eventually which was a pity because I do think I belong there and I ended up at Kidder and then Kidder I went to Wertheim Schroeder and I was Kidder I was I can't say was my happiest time although I spent six years there but Wertheim I really liked it was it was a great bunch of people and I kind of found one of the things I learned, which is maybe if you're going to ask me for tips for kids and students and stuff later, you know, I never at the, it's like, I always tell this story because it's so me. Like when I was like 10 years old, I was playing baseball at camp and I got hit by a ground ball in the carotid artery and knocked out.

5:37So it's actually very serious. And I was out cold. I was in the infirmary or whatever for a couple of days. And because of that, I always wanted to play shortstop, even though I was scared of ground balls. And I was actually a good outfielder because I had a good arm and I could catch. It was stupid, but I had to prove to myself, like I can catch ground balls because I'm scared of them. And I was like that very much at the beginning of my career. Like tax law was a thing I wasn't really interested in, but I got a show that I can do it. And then eventually I figured out by the time I got to Wertheim, maybe even at Kidder, the second half, I had a really good boss at Kidder who helped me with this, is like, play to what you're good at and what you like and what you know.

6:25Like, don't try and like reinvent the wheel. So by the time I got to Wertheim, I was focused on sports. I was focused on media. I was focused on hospitality, which I really like, casinos, which I didn't love, but it's part of hospitality, you know, and I also learned that if you team up with other good people in your field, you're more powerful than always trying to do everything alone, which is what I was doing early on. So there, I've answered a lot of your later questions and your early questions, all with one answer. But anyway, I, you know, I really loved Wertheim. I was very happy there, But, you know, I had these I had met Arnold Schwarzenegger early, much earlier, 1981.

7:12We stayed friends and, you know, sort of in the early 90s, we started having this conversation like he asked me to help him with his Planet Hollywood deal, which was a very iconic kind of a thing. And then help him with with some movie stuff and help him with some real estate stuff he was doing. And so by the time I started Main Street, I'd already helped him with a bunch of stuff. And he felt like at that time he was the biggest movie star in the world and he was making a lot of money. He was kind of like, I can't because he's really good at business. But he's like, I can't do everything. I need someone to help.

7:49Plus, he said to me, interestingly, like he really loved real estate. But he said, I don't really know anything about the stock market. I don't know anything about that kind of stuff. I need someone who can like help supplement what I know with other stuff. And so long story short, eventually we agreed to do this. And I started Main Street, which was just really with him. Before we go back to the episode, I want to take a short break to talk about my sponsor, Roe. The Generating Alpha podcast is presented by Roe, the all-in-one banking platform for startups. thousands of startups like perplexity product hunts and more use row you get everything you need to manage your startup's cash fast banking setup cards with a two percent cash back and yield that turns company cash into extra runway all super important in the early days of launching but the thing founders really love about row is their team they're obsessed with helping founders disrupt the status quo and will go to the end of the earth to help them to do so and exclusively for Generating Alpha podcast listeners and viewers, you'll get a$1 ,500 statement credit, plus a ton of exclusive perks when you manage your company cash with Rho.

8:59Terms and conditions apply. To learn more, visit rho.co slash Generating Alpha. Rho is a fintech, not a bank. Checking and card services provided by Webster Bank, member FDIC. See reward terms for details. Thank you, and back to the episode. Incredible. And the reason I was nodding my head when you we're talking about Ace Greenberg is my 10th guest on this podcast was Alan Schwartz, who I'm sure you know of. And Alan has since become a close mentor, and he has a lot of incredible stories about Ace. But you started Main Street with Arnold as kind of your first client. Tell me about the early days, those first couple of clients.

9:33And over time, what do you think were the deals that most impacted the kind of firm you guys are today? Well, the first, the other two first clients, and I never know who was first. I could probably figure it out, but I've never looked, is Tom Werner, who's now chairman of the Boston Red Sox and Liverpool, but at the time was probably the biggest comedy producer in television with his partner, Marcy Carsey and Jimmy Iovine, who is pretty well known in music. And they were the next two clients. clients um you know honestly planet hollywood even though it happened before it's interesting two of the deals that are most important for main street happened before main street was formed one was planet hollywood because it taught me i think it was the first influencer deal the first sort of real celebrity deal that was organic it wasn't you know buy my rolex or you know my omega or whatever by you know arnold did a seven up ad in japan in the 70s it wasn't like that it was like we're actually coming together like hollywood lawyers hollywood producers stars we're coming together to start a company and to bring what we know to the public now it worked great and then in the end it didn't work as well for some reasons mostly probably having to do with the food and stuff, but the idea worked and I learned a lot from it.

11:10And Arnold was very smart about what, what you should do and what you shouldn't do. And I learned a lot from that. And, um, and the other one was an investment we made, um, again, before main street and a company called dimensional fund advisors, which is a major financial firm. But you know, one of the things about that company, apart from it's grown to be a gigantic, successful financial company, is just the quality of the people involved, like the sort of morals and ethics and intelligence of the people was something that really resonated with me. And I realized, you know, that's important to me.

11:53Like, I like working with people. I'm not looking for fast buck artists and slick people. I'm looking for solid, smart people who know how to build something and how to do something. Those were two deals before we even started Main Street that really influenced me. And then, you know, probably the most famous deal we did early on was when we bought two 747s and leased them back to Singapore Airlines. They became very famous when Arnold became governor because we didn't, I guess we didn't announce them, but they leaked. In fact, everyone swore it would never leak and it leaked maybe 20 seconds after we signed.

12:36But they were financial deals. They weren't tax deals. They were, you know, economic deals and they were really interesting. And no one had ever, no individuals had ever done that before. And I think both Arnold and I have always been attracted to trying to do things first or differently. I'd say in his case, he likes being first. In my case, I like being more less than first. I just like being different, you know. And I think that was a great example of both. And, you know, the Singapore Airlines CEO was like, like, what are you talking about? We can't lease an Airplug, a 747 to an individual.

13:18But he did it. He got incredible. I think he got a Terminator jacket. He got a picture. At least he got a picture with one. Are there any more examples of like those very unique or interesting deals in kind of the throughout the evolution of Main Street? So there's so many. I mean, I mean, Beats was well, Beats was later. I mean, Beats started really started in like 2006. But as I talk about in the Defiant Ones in the documentary, you know, one of the things that was funny about the whole beats thing was, you know, Jimmy Iovine had an insight that was really smart. And his insight was that nobody wants to pay for music anymore because that was during the Napster kind of era.

14:06He goes, but people still want music. They just don't want to pay for it. So the question is, how can you use music and the power of music to sell something where you can make money? And again, he focused right in on something organic, which was Dr. Dre and headphones, which was not a stretch. Right. It wasn't Dr. Dre and Corn Flakes. You know what I mean? It was something where it made sense. And so I think that, you know, always sticking to that kind of authenticity, which if you, I don't do many of these interviews, as you know, but whenever I do, I always talk about the same thing, which is authenticity, because, and I think we're living in a world right now where authenticity is definitely being challenged, you know, by the thousands of influencers who are all looking for brand deals.

15:00They can't all be that authentic. I'm not saying none of them are, but, you know, so we've always tried to stick to that. And, you know, so, I mean, I mean, we've done so many so many other things in the middle and in between all these things. But I mean, those are obviously deals that are all fairly well known and that we're well known for, you know. but even even lebron's nike deal which which i negotiated or led the negotiation for is is you know again it was it was very much about trying to it wasn't like oh let's just grind these guys and see what they come up with like lebron and maverick who's his business partner long-time business partner they had a genuine love for nike maverick had actually worked at nike and LeBron had turned down famously Reebok for Nike.

15:56So it's not like, you know, slash and burn. It's kind of like, how do you structure something that's good for everybody, right? How do you structure something that's good for them, good for LeBron, good for Maverick, good for Main Street, good for everybody, you know? And how do you really do that? Obviously, with the main thing focused on being good for LeBron, but also being good for Nike because, you know, if you approach negotiations with how can I win and how can I win and how can you lose, you'll have a short career. I mean, you might have a career and you might make some money, but you're not going to have a long career.

16:34And so it's not that hard to serve your clients well, but to also make sure that the people on the other side of the table don't hate you and that they actually maybe respect you and like you. And I think, you know, Nike was a good example they have a great relationship i ended up with a great relationship i did other deals with them but lebron got an incredible deal and i will if you ask them i'm sure they'd say they're thrilled with the deal nike again so you know it there's been so many of these things at different forms though like i said that wasn't an investment deal um planet hollywood was also less of an investment deal dimensional fund was an investment deal beats was really creating a company And we've created many other companies since then.

17:22We're continuing all the time to create new businesses, some of them with some of our well-known clients, some of them not. Depends on, you need an idea. And why do you think you're so comfortable kind of doing things that haven't been done before and going outside the box when building these interesting businesses with some of the top entertainers of the world? I mean, I don't know. I think the longer you're working with people like that, the less you see them as celebrities and the more you see them as people. I would think that having hung out so much with Arnold in the early years, I kind of became a little inured just sort of to the whole thing.

18:09It was just like, I would walk down the street with him and he would get mobbed and I would get so frustrated because I'd be like, shit, I forgot who you are, you know, because to me, you're just my buddy. And we're trying to go shopping, you know, and, you know, walking on Madison Avenue, there'd be 300 people standing outside the store. To me, it was more of a pain in the neck. But over time, you kind of get used to it. And you realize that, obviously, they're people, they're all different, everyone's different, but no more all different than other people. And so I just, I'm very lucky that I, that I have all those people in my life because every one of them is brilliant or a genius in some way, sometimes more than one way.

18:55And I'm lucky because I get to hang out with those people. So instead of being like, oh my God, you know, I can't believe I'm with so-and-so it's more like, what can I learn from so-and-so I'm so lucky I can sit with, you know, whoever, LeBron. I mean, LeBron, you know, he's a really interesting guy. He kind of hears and sees everything. He remembers everything. He hears everything. He sees everything. You wouldn't necessarily know that if you just looked at him as a great basketball player. But when you know that and you're with him, you can learn a lot of things. Yeah. And in 2025, how would you describe kind of the structure and philosophy of the partnership you guys have with your clients?

19:39The structure and philosophy of - Just overall, how would you describe mainstream advisors and how does it interact with its clients? Because it's interesting because you do a lot of different things. But the thing I always tell people when they start here, and I try and remind them all the time, is we are a client service firm. Like first, second, and third. Everything grows out of it. Helping them build a business, whether it's Beats or something else, that is in the service of a client. We're not doing that for our own sake. We're doing that for someone else has an idea. We're there to serve.

20:13We will help them with anything. We'll help them with, you know, if they want us to help them buying a house or getting a mortgage, we'll help them with that. It's not our job, really, but we will. You know, if they have questions about, you know, schools, anything. Our motto is just be there for these clients. And so as a result, everything that we have has grown out of that. So we have sort of a private equity business. We have a venture capital business. We have, you know, this what we call incubation business. All of that grows out of serving clients, which is why if we're not, I wouldn't say we would never do something with someone who's not a client, but we don't look for that.

21:00And a couple of times we've tried to do something like an assignment, like an M &A assignment or something for a non-client. It never really works out. It's just not the right thing for us. And, you know, someone could become a client through doing something with them. And, you know, we have a lot of businesses now. So we, I don't know, I'm going to make up a number. Maybe 100 businesses were invested in. I totally made that up. I don't know. It could be 70 or it could be 120. I have no idea. But whatever it is, it's a lot of businesses, right? And all of those businesses potentially can use help in different ways, including from some of our clients or just from our relationships, whether it's with Wall Street or with law firms or our own ability financially.

21:52And so that's kind of what we focus on is sort of how do we serve our clients and then how do we leverage that to help the companies that we invested? So we're helping ourselves, meaning our clients and our financial results, but we're also helping these companies, which is why they then like us to be investors, which is why we get good deal flow. So it's all kind of a system, but it all grows out of serving the clients. And I know it sounds might sound like bullshit, but and I know a lot of people say stuff like that. But you can ask anyone who works here like that is all I ever talk about. It's all I ever talk about.

22:39Like, I just, you know, yes, we're I think we're as good at doing deals, M &A deals and other capital raising as anybody, honestly. I think we're good at all that. I think we're as good at private equity as anybody. But the thing we're better at than anybody is serving our clients. So that's where we focus. And you negotiated, as you said, LeBron's agreement with Nike and also negotiated the sale of Beats to Apple. What do you think makes a great negotiator? Well, it's kind of what I told you, you know. So, but again, and I don't want to act like I do everything alone because I, I am the lead negotiator on all these things.

23:25But, you know, in case of Nike, I had a great partner in there with Maverick because there's a lot of parts of that deal. Like the shoes, you know what I mean? And the design and how LeBron would work with them like someone else was doing it in the case of Apple. Obviously, you know, Jimmy and and other people were were talking to them about other parts of it that would be less in my area and more in terms of, you know, how are we going to work together going forward? All those things. Those are really important things. But from my perspective, you know, my my job, so to speak, is to try and come up with a really smart financial structure that works for both parties.

24:07I'm obviously trying to protect my clients and I'm trying to not necessarily maximize every dollar, but you're trying to have a really good financial result. And like I said, but my approach is always start with what the other side cares about, whether it's Apple or it's Nike or it's anybody. It's like, what do they care about? Because the minute you lose sight of that, it's going to get hard. And, you know, and I think people appreciate that, that, you know, you're like caring about what's important to them. And again, this is something as I say it, I probably sounds like bullshit. It probably people, other people say it.

24:49I really mean it. And you could ask anyone, like, it's just to me, the way I've always approached things. And I think, I think, I don't why, but I think that it feels easier to me. Like it feels like if I say to Nike, like what's important to you? Like what are your red lines in the sand? And they say, well, it's this, this, this. And you go, okay, well, let's live. Let's try and live with those. Now let me tell you what mine aren't. Let's see if you can live with mine. And then if that worked, you're 90 % of the way there you know so i would say that's it i would say i've said this many times i still don't believe most people do it i still think most people think that they're a good negotiator when they're crushing the other side and i just don't i don't necessarily buy it you know like i said a good result for everyone is great because there's always the next day there's always the next day that's why i say it's so important, like Maverick is, you know, figuring out all the ways they're going to work together successfully.

25:59It's really important that he gets that right, too, because then the next day, my part's kind of over. His part's just starting. Right. And then what about when something goes wrong in the deal and you have to renegotiate or there's a you find a problem or a mistake? Well, if everybody likes each other and I'm including me in that, because if I don't like me, then they're not going to want to see me again. But if everybody likes each other, then when something goes wrong, it's a lot easier to go, okay, okay, let's sit down and figure this out. You know, I mean, this sounds so obvious to me, but, and you're very young, obviously, and you're obviously very precocious, but it's, it's not as obvious as it sounds because most people just don't do it.

26:42I, I think that's a, that's, that's a perspective that I agree with. A lot of people say it, and I don't see a lot of people doing things to back it up. And you've had a track record of betting on clients quite early in their careers, if I'm correct. You first met LeBron in his early 20s. I'm interested in... 20, actually. You meet a lot of potential clients when they're very young and started their careers. What are a couple of red flags in clients that you don't necessarily want to work with? and what do you think made your successful clients stand out? Red flags meaning good or bad? Bad. The red flags for not great people.

27:25And then what made your client specifically stand out from you think the rest of the pack? I think in terms of the ones I want to work with, usually I can feel it. But there is a famous story, which honestly, I don't know if it's true or not, but I'll tell it to you anyway. I honestly don't remember. But according to certain people, When I met LeBron, you know, I wasn't a huge basketball fan and he was not obviously as famous as he is now. He wasn't, you know, he was basketball fans. He was famous, but I was a little more of an NFL fan. And, you know, I just didn't know that much. And I the story goes that I went home and I asked my 12 year old son, like I met this guy, LeBron James.

28:11Do you think I should take him as a client? And he was like, like, what are you, an idiot? of course you should take them um I don't know if that's true I will tell you that when I met Maverick and LeBron uh together I was super impressed with both of them and it's important that I was impressed with both of them because you know I knew I'd have to work with both of them and and they just both seemed so smart to me and you know I knew their backgrounds I knew they didn't go to Wharton and, you know, all that stuff. And yet I was like, wow, you know, they're just so just curious and naturally intelligent.

28:50So, you know, that's one thing you can look at. Another thing, you know, you know, obviously talent is really important. You know, when you, when you meet someone who's really young and you think they're really talented, you know I also I always do check with my kids you know when I first met you know Billie Eilish and her family like they were really young you know I think she was 17 or 16 and her brother was you know a few years older like their talent was like jumping it's like it was like screaming off the page so sometimes it's kind of obvious but I also asked my youngest daughter and she was like the same, like, of course, of course, this, these people are unbelievable.

29:36So, you know, and then I don't normally go ask a lot of people, but sometimes, you know, it's just, it's just clear. And then not everyone I've taken on has been the beginning of their career. I mean, Arnold wasn't, I mean, I knew him actually at the beginning of his career, but he didn't become a client until he was already a big star. And there are lots of examples of people who were already successful when I took them on what I hope in some or many cases I hope I've helped them to become more successful and help them to achieve more goals like clearly a guy like Tom Werner who was you know the uh like I said the most successful comedy producer television with his partner Marcy and you know they had eight or nine primetime shows on the air at that time And you wouldn't even know what that means, but that was that was normal.

30:32You know, that was not normal. It was incredible. And and he was the owner of the San Diego Padres. It was a very, very bad experience for him. So the idea that I was able to help him through a connection of mine, start trying to buy the Red Sox and then successfully buying the Red Sox, bringing in the money with him and some other people and then you know going on to buy Liverpool and all those things the fact that I could be helpful in that is it makes me feel great because for him he loved sports and and it was his dream you know and so but he was already a huge success I didn't help him become a comedy producer you know so I'm I it's fine either way I mean it's really fun to work with young people and if you could be a mentor you know as they're growing and you know um LeBron like said it's 20 20 almost over 20 years already and you know and I hope with Billy and other people it'll be the same like it's fun to help them grow but it's also fun when you find someone who's in the middle of their career and you can help them you know yeah Yeah.

31:48And you mentioned a lot of these names. There's also in this day and age, there's more and more kind of influencers and creators popping up and trying to build businesses. And a lot of them end up having a lot of hype, but then eventually dying down after a while. What do you think it is that this kind of generation of creators and influencers get wrong about building enduring businesses? I don't think it's about getting wrong. I think the problem is a little bit that there's a culture right now. So when I was, we talked about my background. When I was young, right, I went to high school and then I went to college and I happened to study business, but I could have studied English or whatever.