Transcript of What Jay-Z, Will Smith, and the Olympics Taught Him About Winning in Business | Ep 312 with Samyr Laine Co-Founder and Managing Partner of Freedom Trail Capital New

So, Samir, I mean, what a history you have had from the Olympics in 2012, Harvard, who hasn't heard of Harvard law school to working with Rock Nation? I mean, Jay-Z. I want to know, what the heck is it like to work with Jay-Z? I mean, you've worked with Will Smith, but I want to know, or maybe even let's hear the two of them. How is it to work with the likes of Jay-Z to then working with someone like Will Smith?

Yeah, it's a good question. It's a great question. I think they're very similar in a sense. At some point, you get people who, of that ilk, who are at the top of their field and have been for a long time. There are always going to be similarities. As you know, any high performer in almost any field, one to one, there are things that doing to get to that place, and they're similar. With Jay, I think what a lot of people say is spot on. Very thoughtful, very introspective. I think they both are. For Jay, he's a great, great, great, great listener, and Will is a phenomenal listener as well. But I think with Jay, he's a man of a few words in most instances, right? But when he speaks, he's very poignant and very thoughtful. Whereas Will is a storyteller. Will is a storyteller. If you read his book, if you hear the audio version, you know he's a phenomenal storyteller. But he's also a great listener because he's listening and then he's giving it back to you through story and connecting with you in that way. But from a performance level, what's gotten them to where they are is discipline, is understanding how to connect with people, understanding how to communicate.

They're both tremendous communicators through different mediums. I learned a lot by working with them in different capacities, being in their presence in some ways, having a front row seat at how they've achieved what they've achieved, Both experiences were tremendous learning experiences for me.

There's a saying, you never want to meet your heroes. When you were able to meet these people, one, was it what you thought it was going to be? Then two, were you nervous to then also give them feedback, and were they open to it?

Yeah. For me, the idea of never meet your heroes is salient if you've put people like that on a pedestal because they can never live up to the image that you have of them. And so I was fortunate enough to not do that. And I understood that I'm at Rock Nation, Jay's is my boss. And same thing when I'm at Westbrook and Will's the boss. But I think my anticipation of what they were like, what was spot on. Because again, from the outside looking in, I understand that they're tremendously successful. When Jay's says, I'm not a businessman, I'm a businessman, he told you what it was. And then when you get with them, that's accurate. You're asking questions about a business or a brand that we've worked on, and he's fully read in, but he's fully invested, he's giving you great ideas and so on and so forth. But you also understand that working with people like that, a lot of it is just being very, very, very, very clear in objectives, in what they're trying to achieve, and also clear in how you're going to go about achieving what they've asked you to do.

For me, for example, one of the first things I did at Roc Nation, I think literally my first or second day was the idea was, Hey, we want to launch a book publishing division. No idea how you're going to do it. Go launch a book publishing division. It took a little time to chat with the different legacy publishers, and Simon & Schuster and the Hachet books and a Pingo random house, and you're figuring out joint ventures. I've never published a book myself, let alone launched a JV with a big international book publisher. But the idea was, this is what Jay wants to do. This is his objective. And for me, I've got to be very clear in how you want to do it, when you want to do it, why you want to do it. Do you have particular non-starters? And then for me to vocalize to him, this is the path I'm going to try to take. Are you okay with that? You want me to pivot anything else? And for anyone like that, anyone of that vein, not because they're famous, but just because they're high performers, communication is key. You want to communicate.

You want to be as crystal clear as possible. Ask questions. There is such thing as a dumb question. Not dumb, but annoying, right? So if there's something you can figure out without taking their time, do it on your own. So if you come to them, you're very to the point. But yeah, communicate with clarity and concision. Those two are very, very important, and they were for me in that time.

No, I appreciate that. I think it's like you almost would get nervous depending on who you're around and who you're working. If you do put people in a certain place in your mind or a place in society, but if you don't do that, then people are just people. I think back to myself, I'm a huge proponent of working somewhere to gain skills, to gain knowledge and connections before becoming an entrepreneur. How was that for you now that you started your own thing, Freedom Trail Capital? What did you take away from all the things you did before?

Wow. You hit the nail on the head. For me, in my resume, in my education, a part of it was the path I took as an athlete. But then in my career, I've always tried to make sure that I was beyond reproached to some extent. If it was something I wanted to do, if I hung my own shingle and I wanted to be an entrepreneur, that I checked the boxes before from a pedigree standpoint, from a skillset standpoint, then I could be as bulletproof as possible. You're always going to have some weaknesses. No one knows everything. You make sure you align yourself with teammates and partners who can be the yin to your yang. But in my career, I was always, hey, I'm going to this stop because I want to learn these things. I'm not strong here. I want to get stronger here and so on and so forth. And so for me, and now I went to law school and I practice law a little bit. And then from there pivoted and grew as an operator. And I was able to understand what it meant to build a brand, build a business, build a marketing plan, tweak your supply chain, improve your margins.

So a lot of it for me to get to this point was taking positions, working with people, being at places where I could augment my skillset, where I could strengthen whatever weaknesses I could have, where I could learn, where I could grow. It was always about growth. I do take that from my time as an athlete. I was a triple jumper. So I'm always, how do I improve my speed? How do I improve my strength? How do I improve this part of my jump or that part of my jump? And it was really tinkering away at those so-called weaknesses. Exactly like you said, it's been the same in my career. If I'm not a great Excel modeler, great. Can I take a a role where I don't have to be the best, but I can learn as I go along and improve looking at Excel spreadsheets or making models or reviewing a PnL or over looking at a balance sheet and all that stuff. The things that you just don't do in law school. And you do to some extent, but you're not doing any of that in law school. And so for me, a lot of my career, even my education, even the classes I took in law school were about, I'm going to do this thing.

I'm not there yet from a knowledge standpoint. I'm not there yet from a skillset standpoint. I'm not there yet from an experience standpoint. How do I eventually get there? How do I take roles and have experiences that allow me, when I want to become an entrepreneur, to understand that I've minimized my weaknesses. You can't eliminate them. In some case, maybe you can, but they're tough to eliminate. You'll always have some weaknesses, but to minimize them, to make sure that you're as prepared as possible once you go out on your own.

I've always wanted to know, what is it like to be an Olympian? What's the feeling like? I was wondering I'm watching the Olympics this morning, and it got me thinking about just the amount of nerves. What does it feel like when you get up there to know that this might, A, be the only time you go? You might only get one shot in your life. You've been practicing most of your life. It's not just four years before or two. It's most likely your whole life running up to this moment, and you have one shot. It reminds me of the M&M song, right? Yeah, that's it. You got one moment, one shot. So mom spaghetti. What was that feeling? Tell me the feelings, what was going in through your head in that moment.

It's funny because for me, and I competed professionally throughout law school. So I competed in college. I was an All-American in college. I went to University of Texas. I used my last season of eligibility while I got my master's degree there. And then went to law school and competed throughout law school. And so in my first year of law school, I tried to qualify for the 2008 Olympics in Beijing. I didn't qualify. I didn't jump far enough. And then so when I did qualify for the 2012 Olympics, by then, I was top 10 in the world. And so a lot of it was relief, right? Because I tried four years prior, I didn't make it. And so I was relieved. But then there was a little bit of level of expectation, right? Because to your point, try to no wait, didn't make it. I'm working for four years. And in between, you got world championships and different competitions. But the Olympics, it's the pinnacle. And so I did four years, even more than four years, because I'd be competing for a long time. But when you get there, you're like, I did it. I've achieved something that I've set my mind to, my mind, body, and soul, too, to be honest.

And it was four years plus in the making, and it was everything you would imagine it would be. But it's also tough because you're balancing the idea of, I don't want to rest in my laurels because I got here. I feel like I could win a medal. I'm top 10 in the world. So you take the opening ceremony, all the fan fear, all the pageantry, the 90,000 people there. My parents were somewhere there. You can't even see them. And you allow yourself to feel the goosebumps. You allow yourself to get that sigh of relief and just appreciate how far you've come. And then the next morning, you're like, all right, now I have a job to do. And then you're absolutely right, because I tried to qualify for the 2016 games and didn't. So it was my one shot. Still have some regrets. I guess you can call it regrets. But as Jayzie says, you got to learn to live with But I put it all out there. It had tremendous experience, and it really was everything that you anticipated it be. And for me, that's from watching way, way back in Barcelona '92 and Atlanta '96.

Eventually, I've watched every summer games, and you get to 2012, you're like, This experience was everything I imagined it would be in then some. Competitively, it could have gone better, but just being there was phenomenal, to be honest.

How was it in the Olympic village? I've I've heard stories. But I imagine it, you probably are hyper-focused, and then afterwards, you don't have anything else to do. You're then like, I'm just going to let loose because it doesn't really... I don't have to eat certain things. I don't have to not sleep. I don't have to do all the things that made me get to that point now that it's over. Then what happens?

There's a little bit of that. There's a little bit. So a whole lot of partying, a whole lot of debauchery. I didn't partake. My wife was also Olympian. We were both competing at the same Olympic Games, so we had fun. We had fun ourselves.

That's epic, by the way. Yeah. Usman and wife competing at the same Olympics. Okay. Yeah.

So it was phenomenal. But It's funny because when I competed in my, and I think they flip flop for the 2028 Games in LA, the track and field portion was at the tail end. And then the men's triple jump was at the tail end as well. And then also, usually after the Olympic Games, there are some track and field competitions, international, that you have to. So I didn't get to, quote, unquote, let my hair down as much as a lot of people do, because after that, I went to Stockholm, and then Barcelona, and then Zurich. I had a few very big competitions after the Olympic Games still. But you're exactly right. It is a big party. After people compete, as long as you're not being at the tail end of the Games, you are letting your hair down. London was a phenomenal host because it's just a great city, especially in the summer, you've got phenomenal weather. And so after that, everyone's going out to the pub and into the city and having a great time. But yeah, the village itself was a lot of fun. It is very intense. There's a lot of anxiety in that first week or so.

And then as people start to compete and they're finished, you can also realize who's done competing, who's not. You can see them, and they're in line at the McDonald's in the cafeteria in the village. All you can eat free McDonald's. So So you can see, all right, I see you've had McDonald's for every day, every day for the last couple of days, so you must be done competing. Or I see you stumbling back into the village from the city. So you can always get a sense of who's done.

That's why I wanted to be an Olympian, just so I could eat McDonald's and I won't gain weight. What is it like being a husband and wife Olympian? My wife and I are very competitive as it is. I'd say we're two entrepreneurs who are competitive. But if her and I were Olympians, and I don't know, I'm not sure how the dynamic would be. I think we'd be ultra competitive. But how is it for you two?

Yeah, and it's funny. We got married after our athletic days, but we trained We've been playing together for almost a decade as well with the same coach. And clearly, we're not doing the exact same. We're not lifting the same thing in the waiting room. But still, we're competitive to a point. I'm watching her do something, and she's watching me do something, and we're cheering each other on and so on and so forth. And even now, we're playing board games. That competitiveness is still there. We tried to not add pressure to our kids because we have two kids. But yeah, I think it motivated each of us in different ways. And we weren't competitive with one another. It allowed us to be better support system for another and also just understand what each of us was going through, whether it's an injury or whether it's a bad day of practice or it's a tough day or something like that, especially because we both did the same event. We had our coach, and again, I'm not trying to jump farther further than her, but I see what she's doing, and I'm like, All right, I see you worked on this.

You did this well. I've got to go as hard or I've got to do as well as you do. Or even she'll go to a competition. I'm like, Man, that's phenomenal. All right, now I've got to do the same, and vice versa. I would do a lot of competition, and she'd use that as motivation. So we always played off one another, but to each of our bettermen, for sure, because we were trying to push one another as opposed either competing against one another or tearing each other down.

I like that. Yeah, you're working off one another. I have to say, the people that do that sport are crazy fit. I always like to see who's really that, swimming. Then I want to go do that exercise or that workout. I'm like, I wonder if I could do that. But I know I for sure can't. My knee is horrible. When you think about what you're doing right now and the problem that you needed to solve, going through your work and experience, Olympian, school, all the things that you did, at what point did you say, Okay, this is a major problem, and this is how I'm going to solve it?

Yeah, it's funny. For me, a lot of it was I'd spent time as an athlete, and then was at Roc Nation and Westbrook. And so I had a front row seat. I got to manage some artist, right? I got to manage, work with a few billboard platinum recording artists. But having a front row seat at seeing how Jay leverages his cultural cachet to build brands, how Will does the same, how they manage their own brand, how they've built consumer brands, how they've utilized their personal brands and lent them to consumer brands to add value. But what I hadn't seen was people taking a real, rigorous investor's look at these talent-led businesses. More often than not, it's, I got the biggest star in the world, let's go launch a liquor brand. That's usually how it goes. But no one had said, there is a world of investing here where you could marry the idea that the right person with the right platform and the right audience could add value to your business. But as an investor, especially as a venture investor, I've got scalable returns that I need to give back to my own investors. And on top of that, I want to invest in great businesses.

And the idea of ethos of venture was always, I want to invest in innovative businesses that solve problems, that can have a reason to exist and are differentiated from anything else out in the marketplace. And then if you can leverage a Jayzee, a Will Smith, or whoever else to grow or scale that business faster to reach a new audience, then you want to combine those two things. And more often than not, what typically happens is it's the hot space. So it's tequila, usually. I have a famous person, and I'm going to use their name to launch a tequila brand. As opposed to for us, the problem we're solving is we want great businesses, first and foremost, that do have a reason to exist that are unique and are innovative and solve a problem. And then if there's someone who can authentically tell that story and authentically lend their audience and their brand cache to this business that we have, how do we marry it to? And so for me, it was after time of being an operator, after time of being in this world of talent-led businesses, seeing success, having a ton of success on the Rock Nation side, and then also on the Westbrook side, and then understanding that as people, especially now as these talent businesses become more prevalent, Most people aren't building as thoughtfully as they could and should.

It's more about chasing the hot thing, chasing the prime drink or chasing the energy or whatever, chasing the trend, as opposed to, to some extent, setting the trend, which is, I think, what you ultimately want to do. And in venture, setting the trend or being innovative is usually what gets you the returns that people are looking at.

I've always wondered what made the biggest difference when you look at famous person-led brands. I'm just using the word famous. Could be creator, could be artist, whatever this... I don't want to say influencer, but let's say celebrity-backed brands. There are In skincare and makeup, there's everyone under the sun launched, but surprisingly, many of them failed. Then the ones that succeeded, though, this success was so big that I almost feel like then others just launched to match them, now realizing that majority of people are failing. What do you think? What did you see? And what do you feel is the difference between when a celebrity-back brand is successful to when in the same category it fails?

Yeah, it's a few things. And it's exactly what we look for as a fund. But in general, authenticity, first and foremost. You get a lot of instances where people are just launching things because they're chasing the returns that they saw someone else get or a friend get. So if it feels like you're chasing a return, it's usually because you are. And nowadays, the consumer is a lot more discerning than that. I think the other thing is people do it in reverse. At some point, you've got to have a great brand that is excellent, that is, again, differentiate from anything else out in the marketplace, that is built upon a foundation of a great business. You got your margins matter, your supply chains matter, your SKU assortment matter. I have all of those things that go into creating a good business matters. Your executive your brand, your story, all that matters before the idea of who's the famous face that we're going to slap on. And if it feels like you're just slapping a famous face on it, then that's usually where you get into trouble. But if it's, hey, I always use this example, but if it's a Jennifer Garner, her brand, Once upon a Farm just had an IPO.

But if it's like, Hey, I grew up on a farm in West Virginia, and I grow some of my kids' food in my backyard, and there aren't really healthy food for kids, and so on and so forth, and I want to to figure out how to start that business on my own, there's an authenticity there. And there's a bunch of people who have done it tremendously well. And then the list of folks who haven't done it well is a good bit longer. But I think if you're chasing trends, if it feels like a nameslap, if it feels like a copycat product or a copycat business, that's where you get in trouble. And versus, hey, I'm creating something because there's a problem I'm trying to solve. I'm creating something because there's a real business that can be profitable down the line, and we're not just pouring good money after bad money. And then I am leveraging someone with an audience, and it doesn't have to be a celebrity. It can be a well-known account, right? And you're launching, and they've got an audience or whoever But it can be someone who just has an audience and is authentically married to this business you're launching.

And that's where you actually get that success, as opposed to, I saw four of the tequila brands, I just saw me in the tequila brand, and that's actually not the way to go about doing it.

I've seen a lot of tequila brands, a lot of alcohol brands. I still see- For people that don't even drink, that's the fascinating part. They're not known drinkers, but they're launching a brand.

I own their names, but I've seen them. I've seen them.

I don't even care about the brand.

I've seen their pitch decks, too.

I imagine. It must be interesting, I have to say. But I've also seen where, like you're saying, the person isn't really even evolved. It's just like their name is being put on They have very little involvement, which I hope then that the company that's backing it is going to obviously put their name in a good light. If you could think about how to build a high performance culture with zero budget, if you could give a few steps on how to do so, what would you say?

Yeah, I think... So for me, it's probably three things: communication, accountability, and consistency. Communication is first and foremost. Communicating why people are doing things, communicating the goals and objectives of your organization, communicating people's different roles, and that communication and being clear with objectives and results and all that. So communication, first and foremost, above all of us, from the top down and from the bottom up. So the entire organization. And that's how you get a culture where everyone's bought in, everyone's rolling in the same direction at the same pace. People understand their role and other people's roles and how their role fits into the organization. You can get a culture of just teamwork, but also it's an all for one thing. As long as you're communicating and everyone's as open as can be, I think accountability is another piece of it. It's dovetail off of communication, but holding people accountable. There are deadlines or expectations, or you want people to be high performers, so you've got to hold them accountable to their role and the expectations of the role. And sometimes maybe you're giving them goals. And so you're trying to push people along to get as much performance out of your team as possible.

But holding people accountable is a big part of that. And letting folks know that when they fall short, that you don't want to be people over the head, but you want to let them know that they fall short and you're disappointed, but we'll be able to pivot and pick up the slack, but not letting people off the hook too often or at all if you could avoid it. And last is consistency, right? Like that idea of under-promising and over-delivering, doing doing so time and time and time and time again, being consistent in how you communicate, not saying I'm going to be super transparent today, and then in a couple of weeks, I'm going to be less transparent, but being consistent throughout how you approach your team, how you approach what you're building, how you approach goals, just as a whole, being consistent in your level of expectation and so on and so forth. So yeah, communication, accountability, consistency, for sure.

It's amazing how many people get communication wrong, whether it's at work, in their personal relationship, friends. I feel like every breakdown of a relationship could fall back to the communication. My final question is this. I wrote this book behind me here, Unlimited Possibilities: How to Live Without Limits. I think back to in your life, what was an unlimited possibility that you had, maybe as a teenager, as a young adult, that later in life you achieved?

Man, it was going to the Olympic Games. It's funny. I won't even go through my the entire story. But I started running track in seventh grade. I got cut from the track team in eighth grade because I was a teeny tiny distance runner, and not only did I detest distance running, I wasn't very good at it. And I didn't go back to track and field until almost my senior year of high school. But it was the Sydney Olympics in 2000, where my parents all had newspaper clippings of Olympians, and I was watching and recording every track and field competition, all that stuff. And then even then, I didn't see myself in college. I'm here just to the Olympic Games, but it was a dream I had for a long, long time. And then to get there, to not qualify in '08, to eventually get there in 2012, to be in the finals, to qualify for the finals, to finish time, it was phenomenal. But it was a seed that was planted long, long before that I hadn't realized was still germinating even as I went. So I'm in college. I'm not thinking about the Olympic Games.

I'm just thinking about improving and having this growth mindset and getting better one inch, one centimeter at a time. But eventually, I paid dividends in 2012, and then even before then. I competed at a few world championships beginning 2009 and several world championships. But I got to see the world because of track and field. I got to compete everywhere from the Berlin stadium, where Jesse Owens won four Olympic medals to Moscow, Russia, to Beijing. And so I competed in 2015 at the same Olympic stadium where I failed to qualify in '08. I got to compete in 2015, the World Championship researches of 2015. So, yeah, it was a lot of hard work, a lot of discipline. But all of that, all of those lessons do factor into my entrepreneurial journey now. So it all fits in together nicely.

Well, Samir, if that is not an unlimited possibility, then I don't even know what one is. The fact that your senior year is where you took it really, really serious and you became an Olympian, that's amazing. I imagine most people are doing it from the age of one, right?

A lot of people start early.

Early, early, right? Yeah, it's pretty rare. I think you and there's like a swimmer. I forgot his name. He started taught himself swimming or something like that. But yeah, that's pretty rare. What do you think it's a testament. It's a testament to, obviously, your dedication and desire and competitive nature. But this has been great. If people want to get in touch with you, maybe they have a business that they need funding. Maybe they want to learn more about your story. How can they do so?

Yeah, LinkedIn is usually the best bet. It's just Samir Lane. I'm on LinkedIn. Our fund is there, Freedom Trail Capital. I'm on Instagram as well, of course, but those two are probably the best bet.

Amazing. Well, Samir, thank you so much for all that you do. I'm excited to hear all the investments that you're making and what happens to those companies. I love that people can promote entrepreneurship, and obviously, funding can be a major barrier for people to continue to progress, which then brings more wealth. We were talking about generational wealth and other things. But thank you for all that you do in joining us today.

Yeah, thank you. I appreciate it.