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

0:04So Samyr, 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?

0:40Samyr Laine: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 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 a great, great, great, great listener. And Will is a phenomenal listener as well.

1:15Samyr Laine: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, right? 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 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.

1:47Samyr Laine:They're both tremendous communicators through different mediums. uh and then i 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 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 i for me the idea of never meet your heroes is um 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 and so i was fortunate enough to not do to not do that right and i understood that i'm at rock nation jay's my boss right and same thing when i'm at westbrook and wills 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.

2:51Samyr Laine:When Jay-Z says, I'm not a businessman, I'm a businessman. He told you what it was. And then when you get with him, 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, right? 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 Roc Nation, I think literally my first or second day, was the idea was, hey, we want to launch a book publishing division.

3:36Samyr Laine: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 Hachette books and a ping of random house. You're figuring out a joint venture. And I've never published a book myself, let alone launched a JV with a big international book publisher. But 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.

4:12Samyr Laine:Are you okay with that? You want me to pivot anything else? And for anyone like that, anyone in 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. um not not there are there is such a 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 uh but yeah communicate with clarity and concision those two are are very very important and they were for me in that time no i appreciate that i i think it's like um 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.

5:04I 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've started your own thing, Freedom Trail Capital? What did you take away from all the things you did before? Wow.

5:23Samyr Laine:Yeah, 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 reproach to some extent. right? Like if there's 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 skillset 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.

6:00Samyr Laine: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 grew 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.

6:37Samyr Laine: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 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 &L or over looking at a balance sheet and all that stuff, right?

7:11Samyr Laine: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.

7:45Samyr Laine: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. 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 yeah 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 reminds me the m &m song, right?

8:26Like, yeah, that's it. You got one moment, one shot. So mom's spaghetti. Like, what was that feeling? Like, tell me the feelings, what was going in through your head in that moment?

8:40Samyr Laine: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. And I 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.

9:10Samyr Laine:Because I tried four years prior. I didn't make it. And so I was relieved. But then there was a little bit of a 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 my mind to, my mind, body, and soul too, to be honest. And it was four years plus in the making.

9:44Samyr Laine:And it was everything you'd imagine it would be, right? But it's also tough because you're balancing the idea of I don't want to wrestle 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 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 did it.

10:21Samyr Laine: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 I put it all out there, right? And I had tremendous experience. And it really was everything that you anticipated being. And for me, that's from watching way, way back in Barcelona in 92 and Atlanta in 96. and eventually I'd have watched every summer games and you get to 2012, you're like, this experience was everything I imagined it would be in men's sum. Competitively, it could have gone better, but just being there was phenomenal, to be honest. How was it in the Olympic Village?

10:59I've heard stories.

11:00Samyr Laine: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, a whole lot of debauchery. I didn't partake. My, my, my wife was also Olympian. We were both competing at the same Olympic game. So, so we had fun.

11:35Samyr Laine:We had fun ourselves. That's epic by the way. Yep. Yeah. Usman and wife competing at the same Olympic. Okay. Yeah. That's so it was phenomenal. But it's funny because when I competed in my – and I think they flip-flopped 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.

12:12Samyr Laine: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 competing 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 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.

12:47Samyr Laine: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 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 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 McDonald's and I won't gain weight.

13:17What 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?

13:40Samyr Laine: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 lifting the same thing in the weight 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, uh, we tried to not add pressure to our kids, right.

14:10Samyr Laine:Cause 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. Um, 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 at practice or it's a tough thing or something like that, especially because we both did the same event. Right. So we had our coach and, and, and again i'm not trying to jump far for 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 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.

15:03I 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, I wonder if I could do that, but I know I, I for sure can't. My knee is horrible. Um, when you, when you think about, uh, when you were 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?

15:41Samyr Laine:Yeah. Yeah. And it was funny for me, a lot of it was I'd spent time as an athlete and then was at Roc Nation in Westbrook. And so I had a front row see, 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 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 investor's look at these talent-led businesses, right?

16:23Samyr Laine: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. 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 and the 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.

17:03Samyr Laine: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?

17:42Samyr Laine: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 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.

18:18Samyr Laine:And in venture, setting the trend or being innovative is usually what gets you the returns that people are looking for. 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 skincare and makeup. There's like everyone under the sun 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.

19:01Now 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-backed brand is successful to when in the same category it fails?

19:13Samyr Laine:Yeah, it's a few things. And it's exactly what we look for as a fund, right? But in general, authenticity first and foremost. So 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 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.

19:50Samyr Laine:Your margins matter. Your supply chains matter. Your SKU assortment matter. 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. 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. But 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.

20:29Samyr Laine: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.

21:04Samyr Laine: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 they're 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 when you actually get that success as opposed to I saw four of the tequila brands and that's actually not the way to go about doing it. I've seen a lot of tequila brands. For people that don't even drink, that's the fascinating part. They're not known drinkers. I've seen them.

21:43They don't even care about the brand.

21:45Samyr Laine:I've seen their pitch decks too. 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 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. Yeah. 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, right?

22:25Samyr Laine: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. That's a communication, first and foremost, above all else, from the top down and from the bottom up, right? And so the entire organization, 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.