
In this episode of Founder’s Story, Daniel Robbins sits down with Samyr Laine, Co-Founder and Managing Partner of Freedom Trail Capital, whose journey spans Olympic competition, Harvard and Georgetown education, leadership roles at Roc Nation and Westbrook, and now venture investing. The conversation explores lessons from working alongside Jay-Z and Will Smith, the mindset of elite performers, and how Samyr built a fund focused on talent-led businesses that prioritize authenticity, real problem solving, and strong fundamentals over hype.
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Interviewer
ADP knows anything can change the world of work. Like what if a blocked shipping port caused a worldwide coffee shortage? Suddenly, businesses are scrambling to manage an increasingly drowsy workforce. Productivity slips 20% just due to the extended time it takes to conduct a job interview while yawning.
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Interviewer
From HR to payroll, ADP helps businesses take on the next anything. ADP always designing for people.
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Samir Lane
Prices and participation may vary.
Interviewer
Not Valder McDelivery.
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Interviewer
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 at Roc 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 with 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 then working with someone like Will Smith?
Samir Lane
Yeah, yeah, it's, it's a good question. It's, 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 gonna 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 is more. He's a great, great, great, great listener and Will is 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 is very poignant and very thoughtful. Whereas Will is a storyteller. Was a storyteller. If you read his book, if you hear the audio version, you know, he's a phenomenal storyteller. Right. But. 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. And so. Yeah, but. But from. 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. And then I learned a lot, but 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.
Interviewer
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?
Samir Lane
Yeah. Yeah. For me, the idea of never meet your heroes is salient if you've put people like that on a pedestal.
Interviewer
Right.
Samir Lane
Because they can never live up to the image that you have of them. And so I was fortunate enough to not do. To not do that. Right. And I understood that. I'm at Roc Nation, Jay's my boss. Right. And same thing when I'm at Westbrook and Will was the boss. But I think what 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 Jay Z says, I'm not a businessman, I'm a businessman, that that was. He told you that 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. And so on and so forth. Right. And so. 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, 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 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. Right. And it took a little time to chat with the different legacy publishers and Simon and Schuster and the Hachette Books and picking a random house, you're figuring out joint ventures. And I've never published a book myself, let alone launched a JV with a big international book publisher. But, but, but the, 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. Not. Not there. 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 when 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.
Interviewer
No, I appreciate that. I. I think it's like you. 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, oh, 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've, you know, you've started your own thing, Freedom trail, capital. What did you take away from all the things you did before?
Samir Lane
Wow. Yeah. You know, 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. But then in my career, I've always tried to make sure that I was beyond reproach to some extent. Right. Like if it was something I wanted to do, if I. 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. No one knows everything. You've got to. 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, 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, tweak your supply 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 skillset, where I could strengthen whatever weaknesses I could have, where I could learn, where I could grow. It was always about growth. I did, I do take that from my time as an athlete, right? Like as 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 kind of tinkering away at those 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 and 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 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 skill set 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 cases, maybe you can, but they're tough to eliminate. You 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.
Interviewer
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.
Samir Lane
Yeah.
Interviewer
In your life. You've been practicing most of your life. Like, it's not just, you know, four years before two. It's most likely your whole life running up to this moment. And you have one. It reminds me of the Eminem song.
Samir Lane
Right? Like, yeah, that's it.
Interviewer
You got one moment, one shot. So, mom spaghetti. Like, what was that feeling like? Tell me the feelings. What was going in through your head in that moment?
Samir Lane
Yeah. You know, it's funny because for me, and I competed professionally throughout law school, right. So. So I competed in college. I was an all American college. I went to University of Texas. I used my last season of eligibility while I got my master's degree there was. And then went to law school and competed throughout law school. Right. 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 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, tried in 08, didn't make it. I'm working for four years. And in between, you 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 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. 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 it's. You take the opening ceremony, all the fanfare, 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 didn't. So. So it was my one shot. Still have some regrets, I guess you can call it regrets, but as Jay Z says, you got to learn to live with regrets. But, but I put it all out there, right. And had tremendous experience and it really was everything that you anticipated being. And for me, that, that's from watching way, way back in Barcelona 92 and Atlanta in 96. And eventually I've watched every Summer Games and you get to 2012, you're like, this experience was everything I imagined it would be and then some competitively could have gone better, but just, just being there was, was phenomenal, to be honest.
Interviewer
How was it in the Olympic Village? I've heard stories. Yeah. But I imagine it go. 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?
Samir Lane
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, my wife was also Olympia. We were both competing at the same Olympic Games. So we had fun. We had fun ourselves.
Interviewer
That's epic, by the way.
Samir Lane
Yep. Yeah.
Interviewer
Husband and wife competing at the same Olympic. Okay.
Samir Lane
Yeah, that, that's so it was phenomenal. But, but it's funny because when I competed my. And I think they flip flopped for the, for the 2028 Games in, in LA, the track and field portion was at the tail end and then the men's triple jump was, was at the tail end as well. Right. So. And then also usually after the Olympic Games, there are some track and field competitions international in the circuit 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, like, very big competitions after the Olympic Games still. But. But you're exactly right. It is a big party after people compete. As long as you're not competing at the talent 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. Was a lot of fun. It 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 finished, you can also realize, like, who's done competing, who's not. You can see them, and they're in line at the McDonald's. McDonald's in the. In the cafeteria. Olympic 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. 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. Who's done.
Interviewer
That's why I want to be an Olympian, just so I could eat McDonald's and I. 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 two?
Samir Lane
Yeah, you know, and it's funny, like, and we got married after our.
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Samir Lane
But we trained together for. For almost a decade as well. Right. We had the same coach. And. And clearly, I mean, like, we're not doing the exact same thing. We're not lifting the same thing in the weight room, but still, we're. We're competitive. To. To a point, right? So I. I'm. 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. We're playing board games, that competitiveness is still there. We try to not. We try to not add pressure to our kids, right, because we have two kids. But. 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. 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. 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. But to each of our betterment, for sure, because we were trying to push one another as opposed to either competing against one another or tearing each other down.
Interviewer
I like that. Yeah, you're working off one another. I have to say, the people that do that 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, yeah, I wonder if I could do that, but I know I for sure can't. My knee is horrible. When you. When you think about when you were like, what you're doing right now and the problem that you needed to solve.
Samir Lane
Yeah.
Interviewer
Going through your work 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?
Samir Lane
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 ROC Nation and Westbrook, and so I had a front row seat. I just. Not just. I Got to manage some artists, right? I got to manage, work with a few billboard and platinum recording artists. But having a front row seat at seeing how Jay leverages culture, his cultural cachet 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. And so more often than not, it's, I got the biggest star in the world, let's go launch a liquor brand, right? And that's usually how it goes. And. 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 an investor, 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 and 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 on the marketplace. And then if you can leverage a Jay Z, a Will Smith or 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 the two? 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 Roc Nation side and also on the Westbrook side, and then understanding that as people, especially now as these talented 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? Chasing the, chasing the prime and the prime drink or chasing the energy or the tequila, 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 for.
Interviewer
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 like in, in skin care and makeup, there's like everyone under the sun launched, but surprisingly many of them failed.
Samir Lane
Yeah.
Interviewer
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. Now 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 backed brand is successful to when in the same category it fails?
Samir Lane
Yeah, it's a few things and it's exactly what we look for as a fund. Right. But, 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 it's. If it feels like you're chasing 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 differentiated from anything else out in the marketplace that is built upon a foundation of a great business. Right. You got your, your margins matter, your supply chains matter, your skew assortment of 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 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 like really healthy food for kids and so on and so forth. And I want to figure out how to start that sort of business my own, 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 you, if it feels like a name slap, if it feels like a copycat product or a copycat business, that 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 celebrity. It can be a well known account. Right. And you're launching into and they've got and an audience or their. Who, whoever, you know. But it can be someone who just has an audience and is authentically married to this business. You're, you're, 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 a tequila brand and that's actually not, not the way to go about doing.
Interviewer
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 watching.
Samir Lane
I won't name names, but I've seen them. I've seen them.
Interviewer
I don't even care about the brand.
Samir Lane
That's, I've seen their pitch decks too.
Interviewer
I, 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, the person isn't really even involved. It's just like they're like a name is being put on there and 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.
Samir Lane
Yeah.
Interviewer
If you could give a few steps on how to do so, what would you say?
Samir Lane
Yeah, I think so. For me it's probably three things. Communication, accountability and consistency. Right. 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 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. I mean, you can get a culture of, of just teamwork, but, but also it's kind of an all for one sort of thing if you're. As long as you're communicating and everyone's as open as can be. I think accountability is another piece of it.
Interviewer
Right.
Samir Lane
It's kind of dovetail 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 expectation of the role. And, and sometimes maybe you're. 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, and letting folks know that when they fall short, that it's, it's you. You don't want to be people over the head, but you want to let them know that they've fallen 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, or, or at all, if you could avoid it. And last is consistency, right. Like that idea of under, under promising and over delivering, 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 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 on and so forth. So, yeah, communication, accountability and consistency for sure.
Interviewer
It's amazing how many people get communication wrong, whether it's at work, in their personal relationship, friends. I feel like every, 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.
Samir Lane
Yeah.
Interviewer
And I think back to. In your life, what was an unlimited possibility that you had maybe as a teenager, as a young adult, and that later in life you achieved.
Samir Lane
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 got cut from the track team in eighth grade because I was a teeny, tiny distance runner. And I Not only did test this is running, I was 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. Of Olympians and I was watching and recording every track and field competition, all that stuff. And so, and then, even then, like, I didn't see myself in college, that I'm. I'm here just to go to the Olympic Games, but. 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 eventually get there in 2012, to be in the finals, qualify finals, to finish, finish time, it was phenomenal. Right. And so, but, but it was, 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 at, 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 it paid dividends in 2012 and then even, 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 competed in 2015 at the same Olympic stadium where I failed to qualify in 08. I got to compete in 2015. Olympic. The World Championships in 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.
Interviewer
Well, Samir, I mean, if that's not an unlimited possibility, then I don't even know what one is. The fact that you, like, your senior year is where you took it really, really serious.
Samir Lane
Yeah.
Interviewer
And you became an Olympian. That's amazing. I imagine most people are doing it from like the age of one, Right. Like, they.
Samir Lane
Yeah, a lot of people start early. Yeah. Yeah.
Interviewer
Really early. Right. Yeah, it's pretty rare. I think you start. I think you. And there's like a swimmer. I forgot his name. He started, like, taught himself swimming or something like that and became. But, yeah, that's. That's pretty rare. What. I think this is a testament. It's a testament to obviously, your dedication.
Samir Lane
Yeah.
Interviewer
And desire and, 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?
Samir Lane
Yeah, LinkedIn's 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.
Interviewer
Amazing. Well, Sameer, 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 in joining us today.
Samir Lane
Yeah, thank you. I appreciate it. If you like the show, please take
Interviewer
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Podcast Summary: Founder’s Story | Ep 312 – “What Jay-Z, Will Smith, and the Olympics Taught Him About Winning in Business” with Samyr Laine
In this episode, host IBH Media sits down with Samyr Laine, Co-Founder and Managing Partner of Freedom Trail Capital—a former Olympian, Harvard Law graduate, and alumnus of Roc Nation and Westbrook, where he worked directly with icons such as Jay-Z and Will Smith. The conversation explores Samyr's unique journey from the Olympic field to elite business environments, unpacking the principles, mindset, and lessons learned from both athletics and entertainment. The episode also delves into the high-stakes world of talent-led brands, entrepreneurship, and actionable advice for building winning cultures and minimizing weaknesses.
“When you come to them, you’re very to the point. Communicate with clarity and concision. Those two are very, very important.” (Samyr, 05:26)
“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.” (Samyr, 07:00)
“When you get there, you’re like, I did it. I’ve achieved something that I’ve set my mind to… But I feel like I could win a medal. I’m top 10 in the world.” (Samyr, 10:22)
“You can see… who’s done competing... they’re in line at the McDonald’s in the cafeteria, Olympic Village, right? All you can eat free McDonald’s.” (Samyr, 13:38)
“It allowed us to be a better support system for one another and understand what each of us was going through.” (Samyr, 15:35)
“For us, the problem we’re solving is we want great businesses first and foremost… then, if there’s someone who can authentically tell that story… how do we marry the two?” (Samyr, 18:32)
“If it feels like you’re just slapping a famous face on it, that’s usually where you get into trouble.” (Samyr, 21:40)
“It was a dream I had for a long, long time… it was a seed that was planted long, long before that I hadn’t realized was still germinating… Eventually, it paid dividends.” (Samyr, 26:34)
On Not Idolizing Heroes:
“The idea of never meet your heroes is salient if you’ve put people like that on a pedestal… I was fortunate enough to not do that.” (Samyr, 03:31)
On Communication with High Performers:
“There is such thing as a dumb question—not dumb, but annoying. If there’s something you can figure out without taking their time, do it on your own.” (Samyr, 05:23)
On Founders ‘Name Slapping’:
“I’ve seen a lot of tequila brands… even from people that don’t even drink.” (Interviewer 22:58, Samyr responds 23:07)
Final Takeaway:
Samyr’s story affirms the power of intentional growth, adaptability, and taking lessons from diverse disciplines. The path from Olympian to entrepreneur is one of continuous learning, clear communication, and authentic value creation—whether you’re building a culture, a brand, or your own remarkable life.