Founder's Story - 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

Episode Date: February 23, 2026

Samyr Laine joins Founder’s Story to share his unconventional path from Olympic athlete to operator inside some of culture’s most influential companies before launching Freedom Trail Capital. He reflects on what it was like working directly with Jay-Z and Will Smith, the discipline and communication patterns that define elite performers, and how those experiences shaped his investment philosophy around authentic talent-driven businesses. Key Discussion Points:Samyr describes how observing Jay-Z and Will Smith revealed a shared foundation of discipline, listening, communication, and clarity of objectives that drives sustained high performance. He explains how his career was intentionally designed as a series of learning environments to minimize weaknesses before entrepreneurship, mirroring the constant improvement mindset he developed as a triple jumper. The conversation highlights his realization that talent-led businesses were often built without rigorous investment thinking, which led to the creation of Freedom Trail Capital to pair authentic talent with strong companies solving real problems. He also emphasizes that celebrity alone does not create successful brands, noting that authenticity, operational excellence, and clear differentiation consistently separate winners from copycat ventures. Takeaways:This episode reinforces the power of designing your career as preparation rather than destination, intentionally stacking skills and experiences that compound over time. Samyr’s story shows that proximity to greatness offers learning opportunities only when paired with humility, curiosity, and disciplined execution. His framework for evaluating talent-driven brands highlights that fundamentals must precede influence, and that consumers quickly detect inauthenticity. Ultimately, his journey illustrates how an Olympic growth mindset can translate directly into business, investing, and leadership. Closing Thoughts:Samyr Laine’s path demonstrates that elite performance principles are transferable across arenas, from track and field to global entertainment to venture capital. His story serves as a reminder that long-term preparation, authentic storytelling, and disciplined communication remain timeless advantages in any field. Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

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

It's a good question. It's a great question. I think they're very similar in a sense, right? 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, right? And as, as you know, any high performer in almost any field, you can kind of one-to-one, there are things that they're doing to get to that place. and they're similar. So 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 more, he's a great, great, great, great, great, great listener. And Will's a phenomenal listener as well. But I think with Jay, it's, he's a man of a few words in most instances, right? And so, but when he speaks, he's very poignant and very thoughtful. Whereas Will is a storyteller. Well, is a storyteller. And if you read his book, if you hear the audio version, you know, he's a phenomenal storyteller, right? But he's also a great listener because he's listening and then he's giving it back to you through sorry and connecting with you in that way. And so, yeah, but from a performance level, what's gotten into where they are is discipline, is understanding how to connect with people, understanding how to communicate. They're both tremendous communicators through different mediums.

And 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 with tremendous learning experiences for me. So there's a saying, you know, like you never want to meet your heroes. And how was it when you, when you were able to meet these people, like one, was it what you thought it was going to be? And then two, were you nervous to then also give them feedback and were they open to it? Yeah, yeah. For me, the idea of never meet your heroes is, is salient if you've put people like that on a

pedestal, right? Because they can never live up to the image that you have of them. I was fortunate enough to not do that, right? And I understood that I'm at Rock Nation, Jay's is my boss, right? And same thing when I'm at Westbrook and Will's was the boss. But I think my anticipation of what they were like was spot on, because again, from the outside looking in, I understand that they're tremendously successful. When Jayes 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, right? 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, right? And so for me, for example, one of the first things I did at Rock Nation, I think literally in 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, right? And it took a little time to chat with the different legacy publishers and Simon & Schuster and the hashette books and a ping of a random house and you're figuring out of joint ventures. And 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, right? And you want to communicate, you want to be as, crystal clear as possible. Ask questions. There is such thing as a dumb question, not 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 is that for you now that you've, you know, you've started your own thing, freedom trail capital. What did you take away from all the things you did before? Wow. Yeah, you know, you hit the nail in 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, right? Like if there was something I wanted to do, if I hung my own shingle and I wanted to be an entrepreneur, that I checked the boxes beforehand from a pedigree standpoint, from a skill set standpoint, then I could be as bulletproof as possible, right? And you're always going to have some weaknesses, knowing. knows everything. You've got to, you make sure you align yourself with teammates and,

and partners who can be the ying to your yang. But in my career, I was always, hey, I'm going to this topic. 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, you know, I went to law school and I practiced law a little bit. And then from there pivoted and grow as an operator. And I was able to kind of understand what it meant to build a brand, build a business, build a marketing plan, chain, improve your margin. 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 skill set, 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, right? 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 jumper, that part of my job. And it was really kind of tinkering away at Bill's so-called weaknesses. Exactly like you said, it's been the same in my career, right? If I'm not a great Excel modeler, great, can I take a role where I don't have to be the best, but I can learn as I go along and improve, you know, looking at Excel spreadsheets or making models or reviewing a P&L or over looking at a balance sheet and all that stuff, right? 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 them all 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 skill set standpoint. I'm not there 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, but to minimize them to make sure that you're as prepared as possible once you go out on your own. So I've always wanted to know what is it like to be an Olympian?

What's the feeling like? Like I was watching the Olympics this morning and I got me thinking about just the amount of nerves. Like what does it feel like when you get up there to know that this might A be the only time you go, right? Like you might only get one shot in your life. you've been practicing most of your like it's not just you know four years before to it's most likely your whole life running up to this moment and you have one sure reminds me the m&m song right like yeah that's it got one moment one shot so 10 mom spaghetti like yeah what was that feeling like tell me the feelings what was going in through your head in that moment yeah you know it's

funny because for me and i competed professionally throughout law school, right? So I competed in college. It was an All-American in college. I went to the University of Texas. I used my last season of eligibility while I got my master's degree there. And I 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. And so I was relieved, but then there was a little bit of level of expectation, right? Because to your point,

tried in 08, didn't make it. I'm working for four years. And in between, you've got world championships and different competitions, but the Olympics is, it's the pinnacle. And so I did work 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 out, 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'd imagine it would be, right? And so, but it's also tough because you're balancing the idea of, I don't want to rest of my low rolls because I got here. I feel like I could win a medal on top 10 in the world. So it's, 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. But, and then you're absolutely right because I tried to qualify for the 2016 games and did it. So it was my one shot. Still have some regrets. I guess you can call it regrets, but as Jay-Z says, you've got to learn the level of regrets.

But I put it all out there, right? And it had tremendous experience. And it really was everything that you anticipated be. And for me, that's from watching way, way back in Barcelona, 92, and Atlanta at 96. and eventually I'd have watched every summer games and you get to 2012, you're like, this experience was everything I imagine it would be a men'some.

Competitively could have gone better, but just being there was phenomenal to be honest. How was it in the Olympic Village? I've heard stories. Yeah. But I imagine it, you probably are like 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 like eat certain things. I don't have to not sleep. You know, 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, whole lot of debauchery. I didn't partake. My wife was also Olympian. We were both competing at the same Olympic game. So we had fun. We had fun ourselves.

That's epic, by the way. Yep, yeah. Husband and wife competing at the same Olympa. Okay. Yeah. So it was phenomenal. But it's funny because when I compete in my, and I think they flip-flop for the 2028 games in L.A.,

the track and field portion was at the tail end. And then the men's triple jump was at the tail end as well, right? And then also usually after the Olympic Games, there are some track and field competitions, international assertive 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, can be 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, right? Especially in the summer, you've got phenomenal weather.

And so after that, everyone's going out into 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. and you can you know you can it's there's a lot of anxiety in that first week or so and then as people start to compete and they're they're finished you can also realize like who's done competing who's not you can see them and they're in line at the macdiscan McDonald's in the in the in the cafeteria in the village right all you can eat free McDonald's right so you can see like all right i see you've had McDonald's for like every day every day for the last couple of days so you must be

done competing or i see you kind of like stumbling back into the village from from the city so you can always get a sense of like who's done that's why i want to be an olympian just so i could eat mcdonalds and i won't gain weight what is it like being a husband and wife olympian yeah like my husband my wife and i are very competitive as it is i'd say like we're two entrepreneurs who are very competitive but if her and i were olympians and i don't know like i'm not sure how the dynamic would be i think we'd be ultra competitive but how is it for you too Yeah, you know, and it's funny. And we got married after our athletic days, but we trained together for almost a decade as well, right?

We had the same coach. And clearly, I mean, like, we're not doing the exact same thing. We're not to lift in the same thing in the way room. But still, we're competitive to a point, right? So 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, right, we're playing board games. That competitiveness is still there. We tried to not add pressure.

to our kids, right, 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 kind of be better support system for one another. And also just understand what each of us was going through, right? 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, right? So we had our coach.

And again, I'm not trying to jump farther 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 do, I've got to go as hard, or I've got to do as well as you do. Or even like, she'll go to a competition. I'm like, man, that's phenomenal. All right, now, now I've got to, I've got to do the same. And vice versa, right? Like, 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 betterment for sure, because we were trying to push one another as as opposed to either competing against one another or tearing each other down.

I like that. Yeah, you're working off one another. I've just say the people that do that as sport are like crazy fit. I always like to see like who's like really that swimming. Like then I want to go do that exercise of 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 when you are like 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. Yeah, you know, it's funny. For me, a lot of it was I'd spent time as an athlete and then was at Rock Nation and Westbrook. And so I had a front row seat and just not just, I got to manage some artists, right? I got to manage.

I work with a few Billboard and Platinum recording artists. But having a front row seat at seeing how Jay leverages his cultural cashier to build brands, how Will does the same, right, 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 investors look at these talent-led businesses, right? And so more often than not, it's, I got the biggest start in the world. Let's go launch a liquor brand, right?

And 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 a 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 Jay-Z at Wilson,

method to whoever else to grow or scale that business faster to reach a new audience, then you want to kind of combine those two things. And more often than not, what typically happens is, you know, 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 cachet 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 kind of being in this world of talent-led businesses, seeing success, having a ton of success on the Rock Nation side and also on the Westbrook side. And then understanding that as people, especially now as these talent-led businesses become more prevalent, most people aren't building as thoughtfully as they could. and should, it's more about chasing the hot thing, right? It's chasing the prime, the prime drink or chasing the energy or the to kill, whatever, chasing the trend as opposed 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.

I've always wondered what made the biggest difference when you look at a 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 like in skin

care and makeup. There's like everyone under the sign launched, but surprisingly many of them failed. And then the ones that succeeded though, this success was so big that I almost feel like then others just launched to kind of match them. And I

realizing that majority of people are failing. What do you think, what did you see and what, 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 fun, right? 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, right?

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, right? 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, right? You got your margins matter, your supply chains matter, your skew assortment. I have all of those things that go into creating a good business matters.

your executive team, your brand, your story, all that matters before the idea of who's the famous face that we're going to slap on it. And if it feels like you're just slapping a famous face on it, then that's usually where you get into trouble, right? But if it's, hey, I always use this example. What if it's a Jennifer Garner, right? Her brand, once upon 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 like really healthy food for kids. It's and so forth and I want to figure out how to start that sort of business on my own, there's an authenticity there, right? 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 name slap, if it feels like a copycat product or a copycat business, that's where you get into 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 here 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, you know, 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 I'm going to do with tequila brand.

And that's actually not the way to go about doing. I've seen a lot of tequila brands. A lot of, I still see brands for people that don't even drink. That's the fascinating part. Like they're not like known drinkers, but they're launching. I won't name names, but I've seen them. I've seen them. They don't even care about the brand.

I've seen their pitch decks too. I imagine. I imagine. It must be interesting. I have to say. But I've also. seen like where like you're saying like the person isn't really even evolved it's just like the like name is being put on there and they have very little involvement um 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 yeah if you could give a few steps on how to do so what would you say yeah i think um so for me it's probably three things communication accountability and consistency, right? Communication is, is first of 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 or foremost above, above all else, from the top down and from the bottom up, right? And 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 kind of an all for one sort of thing. As long as you're communicating, everyone's as open as can be. I think accountability is another piece of it, right? It's kind of dubs off of communication, but holding people accountable, right? 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 stretch goals right 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 it's it's you don't want to be people of the head but you want to let to know that they fall in short and you're disappointed but we'll be able to pivot and pick up the slack but um not letting people off the hook too often or or at all if you're you could avoid it. And last is consistency, right? Like that idea of underpromising and over delivering, doing so time and time and time and time again, being consistent in how you communicate and not saying I'm going to be super transparent, transparent today. And then in a couple of weeks, I'm going to

kind of 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 and so forth. So, yeah, communication. communication, accountability, and consistency for sure. It's amazing how many people get communication wrong, whether it's at work, in a personal relationship, friends. I feel like every breakdown of a relationship

that 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. Yeah. And 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. You know, it's funny. And I won't even, like, go through my entire story, but I started running track in seventh grade. I cut from the track team in eighth grade because I was a teeny tiny distance runner, and not only that 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, right? But it was the Sydney Olympics in 2000, where my parents' wall had newspaper clippings of Olympians, and I was watching and recording every track of, and field competition, all that stuff. And so, and then even then, like, I didn't see myself in college.

Like, I'm here just to go to the Olympic Games. But it was a dream I had for a long, long time. And so, and then to get there, to not qualify in 08, to advance to get there in 2012, to be in the finals, the qualified for every finals and finish time. It was phenomenal, right? And so, but it was a seed that was played in 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 game. I'm just thinking about improving and having this growth mindset and getting better one inch, one centimeter at a time. But eventually, they paid dividends in 2012. And then even before then, right, 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. right and so I compete in 2015 at the same Olympic stadium where I failed to qualify in 08 I got to compete in 2015 Olympic that the world championships 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 it all fits in together nicely well Samir I mean if that is not an unlimited possibility that I don't even know what one is the fact that you like your senior year is where you took it really, really serious. Yeah. And you became an Olympian. That's amazing. I imagine most people are doing it from like the age of one.

Yeah. A lot of people start early. Yeah. Really early, right? Normally. Yeah, it's pretty rare. I think you start. I think you and it was like a swimmer.

I forgot his name. He started like taught himself swimming or something like that. And it became, but yeah, that's, that's pretty rare. What I think it's a testament. It's a testament to obviously your dedication. Yeah. desire and competitive nature. But this has been great. If people want to get in touch with you, maybe they want to, 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 obviously hires more people, brings more wealth. We were talking about generational wealth and other things. But thank you for all that you do and joining us today. Yeah, thank you.

I appreciate it.