In short
Consumer VC Podcast Episode Summary
Episode Title
He Worked with JAY-Z, Was an Olympian, and Now Runs a VC with Samyr Lainé, Founder of Freedom Trail Capital
Host
Mike Gelb
Guest
Samyr Lainé
Overview
In this episode, Mike Gelb interviews Samyr Lainé, an Olympian, and former operator for high-profile figures like Jay-Z, Will Smith, and Jada Pinkett Smith. Samyr discusses his unique journey, highlighting his experiences in sports, entertainment, and venture capital.
---
Key Themes and Topics Discussed
Early Life and Olympic Journey
- Samyr trained for the Olympics while being a full-time law student, exemplifying his drive and ambition.
- He reflects on balancing athletics and academics, emphasizing the importance of maximizing one's potential.
Career Path
- Monumental Sports:
- Worked with the Washington Wizards and Capitals, focusing on legal and legislative affairs.
- Major League Soccer (MLS):
- Transitioned to a full-time role in player relations and competition, where he was close to the athletes.
Working with Jay-Z
- Received a recruitment email regarding an opportunity with Jay-Z's businesses.
- Joined Roc Nation, contributing to various projects, including:
- Artist management
- Creating a book publishing division (Rock Lit 101)
- Explores the authenticity and strategic thinking behind Jay-Z's ventures, such as his approach to consumer products (e.g., Ducey, Armand de Brignac).
Transition to Westbrook
- Joined Will and Jada Pinkett Smith's company, which aimed to incubate brands alongside media and entertainment ventures.
- Discussed the importance of partnerships and operational expertise in brand creation.
Launching Freedom Trail Capital
- Founded his own venture capital firm focusing on talent-led brands, capitalizing on his operational experience.
- Emphasized the importance of authenticity and quality in consumer products, noting successful celebrity-driven brands.
---
Insights on Talent-Driven Brands
- Authenticity: Brands must resonate with their audience and be true to the talent's persona.
- Quality Product: The product must be compelling and deliver on its promise to avoid negative reviews and ensure repeat purchases.
- Operational Excellence: Brands should have a strong operational team to manage growth effectively.
- Consumer Engagement: Monitoring social media and community feedback is crucial for understanding product reception.
Key Considerations for Investment
- Market Analysis: Understanding the P&L, margins, and overall business health.
- Consumer Feedback: Evaluating sentiment through surveys, social media comments, and retailer insights.
- Unique Value Proposition: Identifying how the product or company stands out in the marketplace.
Future of Talent-Led Brands
- Samyr believes there's still room for growth in talent-led brands across various categories, including consumer tech and AI.
- Success hinges on the authenticity of the talent's involvement and the quality of the product.
---
Conclusion Samyr Lainé's journey from an Olympian to a venture capitalist exemplifies the intersection of talent, entrepreneurship, and consumer innovation. His insights into the dynamics of celebrity-driven brands provide valuable lessons for aspiring entrepreneurs and investors in the modern consumer landscape.
Thank you to our Partner – Propeller Industries, the leading strategic finance and accounting partner for venture-stage companies.
For more information and updates, visit [Consumer VC](http://www.theconsumervc.com) or follow [Mike Gelb on Twitter](https://twitter.com/MikeGelb).
---
Key Takeaways
- Authenticity and quality are crucial for talent-led brands.
- Partnerships can enhance operational efficiency and brand storytelling.
- Continuous market engagement and feedback are vital for product success.
Written by AI. May contain mistakes. Listen to the episode to check what was said.
Transcript
Automatic transcript. May contain errors.0:00a really smart recruiter who had some foresight, uh, which sent me an email and they were kind of like, what the email said essentially I think I probably still have it somewhere it was like Jay-Z is looking for someone who can do x y and z and has an interest in a b and c do you know anyone who might be interested or would you be interested right and so and I'm guessing that's a recruiter tactic right do you know anyone who's interested and I was like you know if this is a real email I might be interested right and so that that led to like me making the like the difficult decision especially like because I was happy at major league soccer but left for a lot, a lot, a lot more money.
0:39Right. So part of it is ambition, but then the other piece of it, it was like just the idea of, you know, at that point in time, like what Jay meant and does mean to the culture, the opportunity to do work, especially the sort of work that I was going to be doing there was, was, was once in life and to have an impact on the culture at large, to, to work with a black entrepreneur like that, who's created what he's created, there was an allure there. And that's what I told the folks at MLS, like, yeah, I love it here. I'm happy here. But this is an opportunity. It's tough to say no to this opportunity, and especially what it became during my time there too.
1:18Hello, I'm your host, Mike Gelb, and this is the Consumer VC Podcast brought to you by Propeller Industries, the leading strategic finance and accounting partner for venture stage companies. On this show, we discuss the intersection of venture capital and consumer innovation. If you're enjoying the show, please subscribe on YouTube or whichever platform you're viewing this content. And if you want the full experience, highly recommend checking out the newsletter at theconsumervc.com where I share weekly updates of all the fundraising news that's happening in the world of consumer and you'll be the first to know when a new episode drops.
1:53All content and episodes are for informational and entertainment purposes only and is not investment advice. Thank you, Sarah McGuire, for the intro to our guest today, Samir Lane. Samir has one of the most diverse resumes that bounces around sports and entertainment. He was an Olympian who trained and qualified while being a full-time lawsuit. He worked for the Washington Wizards, Washington Capitals, MLS, Jay-Z, Will Smith, and is now the founder and general partner of Freedom Trail Capital. There's quite a few themes in this episode. One I was particularly interested in learning from, Samir, was the intersection of talent, talent celebrity and consumer brands what makes for example an ideal partnership between brand and talent i really love this one samir thanks again for coming on without further ado here's samir samir thank you so much for joining me here today how are you doing well doing well can't complain it's a little cool and supposedly sunny southern california but i'm doing well i know uh cool and rainy right i mean i guess this is i guess this is like the first day that we've had in uh in a little bit with some sunshine um um but um but anyway yeah it's it has been it has been pretty cool um i want to i want to start out just asking where does kind of like your drive come from um because you know what when we last spoke and of course like as we've like gotten to know each other was pretty remarkable about your journey um and of course we're going to go through the entire um the the entireness of your journey and where you are now with your vc fund but you were in law school full-time i have friends that went through law school and holy shit it's like freaking hard um and it's a lot of work and it's a lot of work it's a ton of work and you were also like flying around the world competing in um in trying to qualify for the olympics and and eventually you did and become an Olympian.
3:51Where did that, where did that kind of, when you're kind of living like almost like a double life in that, you know, you're, you're, you're, you're kind of in law school and then also competing to become an Olympian. Where did that kind of drive for you kind of stem from? Yeah. Yeah. I think it's twofold, right? I think at some point for me, I was intent and I still am and always have been intent on just seeing how deep the rabbit hole goes, right? Making sure that I can get as much out of my skill level, my talent, the efforts I put in as possible. And so when I got to law school, I'd, of course, was an athlete in college.
4:25I had an extra season of eligibility because I had an injury my senior year. So I went to the University of Texas. I used my last season of collegiate eligibility there. When I finished there, I still felt as if I was improving and getting better as an athlete, in particular in the triple jump, which is my event. And so when I got to law school, it was kind of like, I haven't achieved my maximum potential. I haven't tapped out yet. So let me see if I can't go ahead and like continue competing and try and like maximize everything I can get out of this, you know? And so a part of it was just trying to make sure that as long as I was continuing to learn and grow and develop and improve, I wanted to keep doing that, right?
5:03Like I'm always down to like keep growing. And then the other part of it is I've got two, two parents who came to the States from Haiti and always understanding like, you know, family wise, I have two younger brothers. So setting example for them, but then looking at the example, my parents and my family set for me as, as most like first generation parents say that that's always a big deal. But, um, a lot of it that morphed into this concept of like, I'm still learning. I'm still growing. I've got to like learn as much as I can and grow as much as I can in whatever it is, right? It might be the trouble jump.
5:38It might be something else. Yeah, no, I mean, I really appreciate that and just find it like so impressive that you were kind of doing both things. Yeah, I don't advise though. I never advise like, you know, when I tell people like, if you're in law school, just focus on law school. It's one of the things that I always have like, just don't worry about other stuff. Like there'll be time for that. But you know, time was of the essence. When did you know on the athlete triple jump side that you thought that you, hey, I might be one of the best in the world at this and it's actually worth kind of pursuing, you know, kind of above like the collegiate, you know, sector?
6:21Yeah, yeah. You know what? As I said, there are levels to this, right? So like in college, I was an NCAA All-American my junior year. and I had one conference and I'd done, I set the conference record and the school record. But then when I got to the university of Texas for my extra season of eligibility, I was like, Oh, this is kind of a step up. Like when I went to nationals, it's like, this is a step up for what I'm used to competing in. And then even from there, of course, like doing it internationally professionally, it's, it's several steps up at that point. Right. And so what I realized was, A, after I got my master's degree at Texas, I went and I, and I spoke to the Haitian national team because both my parents are from there again and i went down to pan-american games in rio djn there which is my first international competition and just seeing you know the level people were competing at the rate at which i was improving where i was like i was nowhere near ready to like actually stand alongside people competing internationally from you know it's the pan-american games right so it's a huge huge international competition so i wasn't necessarily ready to on my own, but being there and seeing, again, in the triple jump, how far people were jumping, how fast they were, how big they were.
7:28At some point, that exposure helped me to realize I'm not as far away as it might seem. Thankfully, in the triple jump, you measure in centimeters internationally. I could see, all right, if I can improve this much, I can qualify. I can meet the minimum qualifying standard for the 2008 Olympics because I went to 2007 Pan American Games in Rio. So, you know, it was in between my master's degree in law school when I went to the Pan Am Games and I was like, I think I can do this. And I also saw like what the international standard was to qualify for a world championship, to qualify for an Olympic Games and what that took.
8:06And at that point, I was like, you know, if I jump my best, I'm not that far off. If I can improve and consistently be at or near what is now my best and improve like my upper limit, I can actually I can actually make a go of it. And so, of course, again, doing it while balancing law school, you're probably not improving at the rate you want to improve at. But after my first year of law school, I competed that summer. I missed qualifying for the Beijing Olympics by a few inches, maybe several inches, which, again, in the grand scheme of things, especially in Trippled Up, isn't that far off. And then after my second year of law school, I'd improved enough to be top 10 in the world.
8:46I think my number seven in the world. Right. And so in that enabled me to qualify for the 2009 World Championships in Berlin. And yeah, I'd like it was really like that first experience in 07 in Rio where I was like, I think I'm close. But then just working diligently. Right. Like in spite of towards class or criminal law or anything like that, working diligently to improve and just understanding the weaknesses that I had as an athlete meant that I could actually improve my performance at a place where I could qualify for an Olympics or world championships or compete alongside the world's best.
9:21What was it like in 2012 London game? We can get some behind the scenes what it's like to actually be an Olympian there. Yeah, it was surreal for starters. Part of it is just because you've got 8 ,000 to 10 ,000 athletes from around the world all at the best of whatever sport they compete in. And so being in that environment, it is electric, like people say, but also walking through the stadium for the opening ceremonies is as surreal and dreamlike as people envision it to be. If you grow up watching the Olympics, you're like, dang, that's probably so cool. It is that and then some. But then in between, the McDonald's is a huge sponsor at the Olympic Games, believe it or not, and they have like a McDonald's inside the Olympic Village.
10:12But to be, you know, in between sessions or competitions and you're in line at the McDonald's behind a Kobe Bryant or Russell Westbrook or something like that, who here, you know what I mean? But because it's the Olympics, everyone is an Olympian. Everyone stands shoulder to shoulder. Everyone is among the best of their particular sport. That was pretty cool to see too, right? And so it's one of those things where unforgettable experience to have my family there. I trained with my now wife. So she was there. She also competed in that Olympic Games as well. So to have everyone there, to experience that with family, with friends, some of my closest friends came there.
10:53But yeah, man, especially in London. And so I've competed around the world, but to be in a place like London, for me, it helped because it was an English-speaking country, right? And so, you know, we could go out into the city and just experience it and just feel the vibe, the electric vibe that the Olympics brought to all of London and not like be like, you know, sheltered in place in the Olympic Village, which a lot of times folks are. And so to experience the entire city, just having that buzz and then in the stadium to compete in the stadium, feel like all of it, every time I think about it, you're like, man, That was once-in-a-lifetime experience is an understatement, but definitely, definitely unforgettable.
11:36And also, it made all the sacrifice worthwhile. It made – at that time, I told the law firm that I was supposed to work at that I wasn't going to be coming. It made that decision worthwhile. So it was a little bit of vindication as well too. I'd imagine they were probably the first law firm to be turned down because, hey, I'm actually going to the Olympics, right? Yeah. I imagine they are. they understood too, because I spent the summer working there in between my second and third year of law school. And so I would train before heading down to the city to work there. And then I think I went to one competition and I had a few of the associates and lawyers at the firm come to watch me compete in New York City.
12:18So in that time, and I had a year gap between law school and when I was supposed to start the firm. And so in that time, I let them know, I'm not coming. They understood and appreciated it, to be honest. So, I mean, besides, I mean, obviously you were training, you were competing on the triple jump and obviously in the Olympics and everything during that period. At the same time, like we've said, you were in law school, you were obviously gonna go work at a big firm. But what, why did you decide to go to law school? What were like, what was your thinking when it came to what you wanted your career to entail?
12:54Because there is like an interesting thread, at least in like the first part of your career, which it's like mending law and a bit of law and then also like sports but was that kind of like the intention in terms of like you're actually mending like like your passion area it seemed in in sports or i mean obviously you were you were and and and being wanted to be involved in like that side of the business but thinking what are the ways actually to do that yep yeah no it's funny that was like precisely my goal all along right and so in going to law school part of it was like, I was always attracted to the law.
13:26And also I have, again, two parents who emigrate to the US, right? So at some point it's like, you're a doctor, you're a lawyer, or maybe you're an accountant, right? And so I didn't want to be a doctor or accounting. So I was like, I'm going to law school. But then on top of that, the goal for me was always, if I'm going to law school, I also want to marry with something I actually liked or am I'm passionate about or knowledgeable about. So even to be honest, when I looked for law firms that I was going to spend my summers at, I worked only specifically and I looked for and sent my resume only to firms that had sports teams or sports divisions or did sports law.
14:02And so even though like you learn in law school, like there's no such thing as sports law. It's just it's corporate law that happens to have sports clients. But like going to law school, like I want to do sports law. And you're like, it's criminal law or it's. But, you know, going to these firms, I wanted to make sure I actually got to work with sports clients or on sports matters. And so that was always the goal. And so to your point, and going to law school is like, I'm going to go from here. I take my knowledge. I'm going to work at a league or team or at a firm that had sports clients. But the goal absolutely was, and exactly like I said, it was like, if I'm going to law school, I do want to do work that I'm passionate about or excited about, especially if I'm going to put in the hours anyways at a firm.
14:44I want to make sure I'm actually enthused about the work that I'm doing and the time I'm spending doing it. How did you wind up at Monumental Sports? um i that's like a that's like as you know um huge huge fan of of monumental sports because i've i i grew up in the dc area i'm a massive capitals fan um still i still i still need to talk to them about about why they're moving the capitals and wizards to uh alexandria virginia but i'll tell i got when we're not we're not recording i've got some insights there i might be able to say wonderful wonderful oh that's great that's great to hear um but how how'd you wind up there and working for that group?
15:25Yeah, so goal was like at the tail end of my athletic career, I was just looking for ways to kind of make my transition as seamless as possible. I think a lot of times, look, I wasn't an NBA player, I wasn't making NBA money anywhere near it, not even a fraction of it. But in general, like when your identity is so tied up in being an athlete or whatever it is, a lot of times people struggle with that transition. I think for me, it was easier because I'd gone to law school. I know, I always knew what the long-term vision was and then transition from that into, you know, into athletics and then back into my professional career.
15:57But I still wanted to make sure, like, as I was like moving away from, from sport, that I had something to go into. Right. And so I had a con, I'd spoken at a sports forum in Haiti, we had like a sports development forum in Haiti and met someone there who had crossed paths with monumental sports and in particular with Ted Leonsis before. And so spoke to Ted about my objectives of working in sport, spoke to Ted about my background. Ted also loves everything Georgetown, thankfully. And so, and I'd gone to Georgetown for law school. Yep. And then they also on the legal side had a very, very, very, very lean legal team and needed some help in a very particular area.
16:38And so it was more serendipitous than anything, right? It was someone who has a passion for helping people in TED and someone who made that introduction. But then I think the timing just worked out perfectly, right? Because they needed someone who could do legal slash legislative affairs work, right? Sit at the intersection of DC, the city council, Capitol Hill, and the monumental sports teams. And so I spend a lot of time, maybe you call it lobbying, but doing some legal work, but sitting at the intersection and helping to make sure that initiatives around city counsel that would affect or impact the team in some way or another could either go through as seamlessly as possible, or at least were heard in managing that relationship, right?
17:22But I'd say a lot of it is, some of it is luck. Some of it is making sure that people understood like I could add value in a very particular way. And then the timing, and timing was a big help too. But yeah, it just so happened that someone introduced me to Ted. Ted was willing to meet and they introduced me to his general counsel, Randy Bowe. And Randy was like, you know what? I think we got some help. We could use you. And so I started part-time. I was still traveling, training, competing. And these were in the latter days of my athletic career. And then doing double duty once again, almost as I did in law school.
17:59Wow. That's awesome. That's really cool. And also appreciate also kind of like mentioning a little bit about your role there at Monumental Sports. What made you decide and how did your next opportunity come about with working at the MLS? Yeah, yeah. So I played soccer growing up, always been a soccer slash football fan. And so that was also timing, right? They had someone in a role and it was a quasi legal role as well. That person was leaving to join one of the major league soccer teams. And I was also looking for like a more robust position, like a more of a full time role. Because what I was at when I was doing that monumental was the double duty of like training, traveling, competing and my monumental work.
18:42Right. And so I wanted to actually dive into something that allowed me to no longer compete, stick my teeth fully into this sports role. And it really was it really was just timing. Right. Like they had a role that had opened up. They had a need for someone who had a legal background because what I was doing there was tangential to the player contracts that the players have with the league. And so it ended up being that I interviewed there, Major League Baseball, the NBA. I interviewed a few places, right? Because at this point in time, I wasn't competing anymore. I wasn't training or traveling.
19:19My family was in New York. Again, as we said, when I went to law school, I was like, I'm going to be in the sports world. but I'll probably go to a league. Maybe I'll go to a team. Monumental at the time didn't have a need for me to take on like a much larger role. And so I said, great, like I'll, I'll, I'm a free agent. I'll, I'll go somewhere. And so, you know, I, I, again, I was deciding between major league soccer, major league baseball and the NBA. I had a former college, a classmate of mine who was at major league soccer. And I could also see the vision of what the league, what, what it had, the path had taken and where it was going.
19:53And so the role itself also allowed me to be close to the athletes, right? Like I was, I did player relations in competition, which meant I was close to the players. I did player contracts, player agreements. I worked with the players union. I served on a couple committees, like the medical committee there. And so I got to be close to sports. I got to be in a growing league and a growing sports in the U S I kind of got to be at the forefront of this new resurgence of soccer in the States as well. And so, yeah, a lot of it was timing, but it really was like, at that point in time, I was like, I want to really dive into the sports world.
20:30I want a bigger role. Let me go up to New York and check out all the leagues and see which one has the best role. And this one was less legal than the others I was looking at, and also allowed me to be closer to the sport than I think the NBA and MLB roles that I was looking at. Yeah, I mean, it's such an interesting time in the MLS, I'd imagine, back when you worked there. I mean, even now, it's such an interesting time in terms of how the sport has grown. Obviously, the stars that have been able to even come across and be part of it, and as well as some of the very creative kind of contracts that they've worked out through with some of the stars.
21:07I think from a legal perspective, that must have been pretty fascinating. Yeah, no, it was. It was. And so when I was there, Zlatan Ibrahimovic had come over, so I got to help with his deal. and a few others, right? So Zlatan coming over similar to Messi, not the same caliber of player, but Zlatan's coming over what was a big deal. And then also on the competition side, I got to see behind the curtains of like how the MLS made its rules, how they did deals with the players, how they brought and wooed some of these players over. And we're also expanding the league at that time too. So Nashville came in when I was there, Cincinnati, maybe one or two other teams came into the league.
21:43Atlanta, this was Atlanta's first year in the league while I was there too. So exciting times, even more exciting times ahead, of course, now with Messi here and a few other players coming. So yeah, yeah, it was really, really cool. I remember Zlatan's ad in the LA Times when he came. Yeah. When he took out like a whole page and he just said, it says, dear Los Angeles, you're welcome. Like just like unreal. Yeah, the most Zlatan moment ever, but it was big for the league. It was big for LA. And I remember like being there at his first match for the galaxy and having him score two goals and yeah i remember that and like off the bench he came off the bench against lafc i remember that yeah yeah yeah that that was yeah that was really really amazing but yeah great great times and then to your point i got to be i was working in sports so i was like all right i'm good i'm i am happy i'm here i made it like i can stay i can grow in this league which is also growing yeah i got a role that i love i had a team that was great i had like like everyone at major soccer was really really amazing um so yeah it was good times it was really good times but why did you leave so you had all this you had you had you had all this going you had a league that was growing right it was there's a lot of i mean even like even just thinking about it from you know like a brand perspective um like i remember one um one kind of beverage expert telling me how you know like the rise of celsius for example um the energy drink and like they actually lashed on themselves from mls like when like like a decade ago and like that was part of the reason why they they probably not the obvious how the only reason but like what an incredible you know league to be a part of during that kind of growth spurt that i'm sure was like a lot cheaper to do than you know the the um nfl and maybe nb and nba what have you and so just saying that like so many like lashed on and and mls has really like helped like drive um um um some brands and obviously because mls has just grown so much in the past you know couple decades why leave yeah you know it's funny i had i think uh a really smart recruiter who had some foresight uh she sent me an email and they were kind of like what what the email said essentially i think i probably still have it somewhere it was like jay-z is looking for someone who can do x y and z and has an interest in a b and c do you know anyone who might be interested or would you be interested right and so and i'm guessing that's a recruiter tactic right do you know anyone who's interested and i was like you know if this is a real email i might be interested right and so that that led to like me making the like the difficult decision especially like because i was happy at major league soccer but left for a lot a lot a lot more money right so part of it is ambition but but then the other piece of it, it was like, uh, just the idea of, you know, at that point in time, like what Jay meant and does mean to the culture, the opportunity to do work, especially the sort of work that I was going to be doing there was, was, was once in life and to have an impact on the culture at large, to, to work with a black entrepreneur like that, who's created what he's created, there was an allure there.
24:55Right. And then that's, that's what I told the folks at MLS, like yeah i love it here i'm happy here but this is an opportunity it's it's tough to say no to this opportunity and especially like what it became during my time there too and so you know like i said it was a smart recruiter um who who just happened to especially because my background i hadn't done anything like the work that i eventually ended up doing at rock nation um so yeah i got one of these days i got to talk to that recruiting like so how did you know like what what in my profile said said to reach out to me but yeah no i i was wooed away i was wooed away by by both a recruiter and by the rock nation label um and and by by jay-z's allure as well um and it's i mean as you say like it's it kind of seems like very very different in terms of like your previous roles at like you know working for um uh monumental sports which obviously you know with working with the wizards the capitals and and obviously georgetown with georgetown's uh some of their games going um um being played at the verizon center and then um and then of course you know with mls working for a league um this is like a transition into um you know um i mean still obviously sports is part of it right because they also have like their own sports agency but can you can you tell me a little bit about how rock nation is kind of structured i know it's a it's a jv between um rockefeller records jay-z's label right um and then also like live nation if you can like but we'd love to kind of learn more about a bit of the history how did that kind of come about and and overall like how like the decision making kind of happens yeah yeah so it's it's so what i would say it's jay-z and signing his deal with live nation as part of that was to do a joint venture that ended up becoming rock nation so i'd say i'd say it's like it's more jay-z personally than than rockefeller records because rockefeller eventually Actually, Rockefeller was a previous entity, but this was the reimagination of it, right?
26:53And so reimagining of it. So it almost tied it to, it kind of was like the evolution of Rockefeller. Exactly. It's the evolution. It's new business partners, new ambitions, and so on and so forth. And so Jay and his deal with Live Nation included, hey, let's create a joint venture. That became Roc Nation. Roc Nation is one part management, one part record label slash publishing. And then also you've got sports. And then you've got a few other things as well. Like I'd say there are events, there's a venture arm to Roc Nation, but it is, it's a conglomerate to some extent, right? Whereas, and also Jay's businesses are separate from Roc Nation itself, right?
27:33So it's not like the Kanye, Jay's Kanyak or Shan or any of those things sits under Roc Nation. Roc Nation is artist management, record label, publishing, venture arm, and then sports, of course. And then you've got some events, right? There's a music festival and so on. And then, of course, J.S. Chairman. But you had a proper executive team, right? You had your sports executives across football, baseball, basketball, and so on. when I was there there was also a TV and film division you know a growing TV and film division you had CEO who was based out here in LA you had a COO who was based in New York ran the New York office so you got two offices and then you had a whole slew of amazing artists both on the management side and on the label side and so Jay of course it's his company but he has set multiple co-founders I think three or four other co-founders.
28:35And they ended up, some of them serve in like day-to-day roles and others just serve in the board capacity. But yeah, it ended up being, for me, a great experience. But from a decision making, it's run at that board and executive level, almost like you would any other agency or management company or corporate enterprise. Got it. No, that makes a lot of sense. And I also understand too, like in terms of the cognac and being like consumer goods. So that's kind of outside Roc Nation. Is that right? Yeah, exactly. And so what happened was I worked directly for Desiree Perez, who was at that time chief operating officer who is now CEO of Roc Nation.
29:19She also works very closely with Jay and all of his businesses. And so in my working with Desiree, I got to do all the Roc Nation stuff as Senior Director of Operations and then also help when and where needed on anything Desiree and Jay were involved in, which is separately, right? So Jay's separate enterprise and business entity is where, you know, you've got Tidal, the streaming platform, you've got Doucet the Cognac, Armand de Brignante the Champagne. um while i was there i launched a book publishing division i was part of rock nation and then on the flip side you also had a cannabis business that was part of of jay's enterprise right so i kind of got the second middle uh of the the rock nation and and the jay-z businesses and and like get a not just a bird's eye view of it all but a ground floor view of it all as well this episode is brought to you by propeller industries if you run a high growth business and your focus on profitability, extending your runway, and improving your operational efficiency, you probably need a finance and accounting whiz that will grow with you.
30:25Well, instead of hiring someone full-time, what would be cost-effective is working with Propeller Industries. Propeller Industries is a leading strategic finance and accounting partner for venture stage companies and has partnered with over a thousand startups and high-growth businesses across consumer products, consumer tech, and enterprise. Some of the brands that they've worked with are Liquid Death, Olipop, Hymns, Farmer's Dog, Away, MoviePass, and Giphy. Propeller also provides specialized support for fundraising and M &A with transaction advisory services. Propeller's TA team of former investment bankers and investors can step in on more of a project basis when pursuing full-scale financing and M &A.
31:03There's a link to Propeller Industries in the show notes if you want to learn more information. Well, so what was your role and how did you spend your time? If you're kind of balancing between Jay-Z's consumer businesses, monogram, title, and everything versus the Rock Nation, which is, as you say, you started a publishing company. And then as well as you have the management, you have the label, you have, of course, the venture arm and events business. Like how was, was your, did you lean more so on like the consumer good side and the actual, on the actual like inventory based businesses? Or did you lean more towards on like the, on like the service provider kind of business, but like the agency side and like the management, that sort of thing?
31:49It's a good question. So, so my title was Senior Director of Operations, which really meant Jack of all trades, Master of Some. I wouldn't say, I wouldn't say Master of None. There's some stuff I was, I was pretty, I was decent at. and I spent my time putting out fires is what I tell people but but in terms of like division of time it's probably I say 50 50 right and so 50 percent and a lot of that is because like Desiree herself as CEO just has like some so much on her plate right like run Rock Nation run Jay-Z Empire which is its own like huge conglomerate and so I went anywhere and everywhere that I was needed at any time, it meant very, very, very, very, very little sleep.
Read the full transcript
32:32But also on the Roc Nation side, I could do anything from redo the employee handbook with legal counsel, spin up an internship program. We opened two new offices while I was there, so help oversee the office construction project. I also worked very closely with a handful of art. I got a platinum plaque out of it, which I never would have imagined, especially going to law school where I'm going for sports. I never would have imagined getting a platinum plaque working with Meek Mill. But part of it was like, at some point, Desiree, there are some artists that Desiree also counsels very closely. And so I got to a place where if Desiree wasn't available, I'm the next best thing, right?
33:09So I'm in the studio with Meek Mill. I'm at a concert with Yo Gotti. I'm in a meeting with Lil Uzi Vert or with Alicia Keys. And so at Roc Nation, I got to do everything operationally. I got to do a little bit of management. I got to help oversee the Made in America Music Festival because that's operations as well. So there were times where I'm in a meeting with the city council of Philadelphia or the mayor of Philadelphia because if Des can't be there, again, I'm the next best thing and we've got this festival that requires a ton of planning. And then on top of that, the other 50 % is everything Jay was doing that Desiree has purview over, right?
33:46So there were times where she's like, I can't be there, you gotta be there or I don't have the time to be there. So you gotta be there. So I might take a day trip to France to check out the inventory on the champagne, or I might meet with the JV business partners in Miami for a few hours and I'm all over the place. But I'd say it was probably 50-50 in terms of the consumer stuff that needed help. And again, like Des and Jay are the final arbiters, but I'm there like in the weeds helping to see what needs to happen and helping to at least advise on decisions before they make their decisions. And then the other 50 % was everything Roc Nation.
34:26Everything Roc Nation, like I said, could be ops, it could be management, it could be HR work, it could be legal work and everything in between. I appreciate that kind of like demonstrating on both sides what kind of day-to-day responsibilities are, which it seems like it's kind of all encompassing. And like, there's just, um uh it's just it's just as you say like it will it seems like 50 50 in terms of how your time was spent between um uh jay-z stuff and then also rock nation yeah and no two days were the same right like i think my first day there i got a stack of printed out emails and and the assignment it was kind of like um jay wants to start a book publishing division go figure out how to do it right so i spent several months figuring out how to spin up a jv we ended up doing a jv with penguin Random House to launch what became Rock Lit 101 and now has since published books from Rich Paul and Ceci Zabathia and a few other people.
35:24But it was like, you know, Jay wants to do it, go figure out how to make it happen. Versus like on the flip side, worked very closely with Meek Mill. And, you know, he had a docu-series come out on Amazon, right? So I'm working with Amazon around what does the deal look like? And how does it have to be structured? And what are you trying to film? And now we're following Meek on trying to film and capture all that stuff. and then the next day I could be in Miami for a quarterly board review meeting of Ducey and we're talking to Bacardi about how much liquid we have and are there shortages and how we fix the shortages how much marketing dollars should be put in um so like literally no two days were the same but on top of that it was here there and everywhere but it was like a tremendous learning experience as a result why did Jay-Z want to start a book publishing division yeah I think a lot of it was to, it's the same reason he has recognition as a whole and title and so on and so forth, was A, to give a platinum for artists, a platform for artists to tell their stories in an unfiltered, unadulterated way.
36:25And also to be artists first, right? There's a reason that title, even to this day, spins out the most royalties for artists versus any other platform. And it's not even close. And so from the book publishing standpoint, it's like, it's why like a rich paul can choose to publish his book on rocklet 101 or cc sabathia or anyone to that effect right so the the deals um i'd say are artists are artist friendly but beyond that it's not like you know when it comes to like what the what the artist or the athlete or whoever is saying it allows the the clients of rock nation to have a place where they can tell their story and do so in a way where they know like Hachette Books or Simon & Schuster, the editor at Simon & Schuster is not going to like spin their words or try to soften or make it any particular way.
37:14It's like this is a place where you can tell your story, whatever that story is. And also it's an outlet for folks in Roc Nation who like, you know, in some cases might not get book deals or might not have a platform to tell that story from a typical publisher to be able to do that. And yeah, they still have their protocols and boxes you have to check in terms of which books are published because you still got to do good business. But it really was intent on being a platform for folks to say what they have to say. And that's always been, I think, his MO, right? Is uplifting artists, athletes, entertainers, and everyone else, but allowing them to kind of own their destiny to some extent.
37:51That makes sense. Another kind of outlet for them too. Another kind of way to kind of share your story, not just, you know, obviously through song, through music. another art for them to do it, another avenue. On the consumer goods side to Jay-Z, since obviously you were very involved in that, from what you've noticed and the brands that you've worked with, what do you think is Jay-Z's criteria when it comes to buying a stake or getting involved with a brand? I think a few things. I think first is authenticity with what he he stands for and with how it's going to relate or be received by the people.
38:36It's got to look and feel and be authentic to him. But in general, whatever it is has to be authentic as a brand. And it has to connect with people in a way that isn't just about like, oh, it's got his name on it. No, it's got to be like a real meaningful connection. I do think the other piece is like, for him, it's not the idea of building a brand on his back or just because it has his name. Like that's never been a thing for him, right? Like put my face here and use my face to market X product. I think the other piece is understanding that the business is good business and the product is a great product, whether or not he's involved.
39:12And then aside from that, can he come aboard and add value from like a creative direction standpoint, right? Like is there a place for him to leave his imprint and leave a mark and add value creatively in a sense that – because his brand is like it's always been aspirational. It's always been, you know, if I can do it, you can do it too. It's always been like leaving a little bit, leaving some gems a lot of times in his music, leaving some gems and breadcrumbs for people to follow, to get to whatever, whatever their level of achievement is. And so his brands always have that like aspirational quality to it too.
39:48So for him, I know he likes leaving his imprint on whatever it is, but he also wants to make sure he's able to add value and move the needle in a meaningful way, right? So he's not going to come aboard anything unless he can actually have an impact that makes sense. But authenticity is a big piece. The quality of the product is also a tremendous piece as well. So the cognac has to be excellent. He was the one who's deciding what that taste is. The champagne has to be excellent and so on and so forth. And then the last piece, creatively, is he able to have an impact that is meaningful and have an impact that will be culturally relevant, but also just moves the needle from a business standpoint too.
40:29It's not just about attaching his name to something just for the sake of doing it. It's about what does his ethos and his involvement in a project mean? And you see it nowadays, not as much on the consumer side, like he's killed it on consumer. But even with just the work he's done with some of the shows and films he's attached his name to for Netflix, right? I think The Harder They Fall was one, they had another one come out. I think for him, he's like, you know, can this film, again, to your point, another medium, right? In this case, in one case, it was book publishing. In this case, it's film.
41:01But can this film with his name attached to it, does it have cultural cachet? Will it be authentic to the community? Does it stand for something? Does it have some sort of meaning and so on and so forth? But he takes that same process through consumer goods that he's involved in, right? Like, is it a great product? Will it be meaningful? Is it authentic to me and to the culture? And, you know, when, if my name was associated with it, are people going to like scratch their head about it? Or is it going to make sense in a meaningful way? And so, you know, I think those are some of the boxes he definitely has to check.
41:33Is there like any like wild or fun stories you have in terms of having Jay-Z maybe have to do something in terms of actually put it for any one of his consumer brands? Oh, man. No, Jay's different. I think Jay is, he's not the, I saw The Rock had like a tequila truck that they drove cross country and he showed up for Taramana. He's like serving tacos out of the truck. That ain't Jay. Right. But but like, you know, as we were putting together monogram, the cannabis brand, you know, we had a meeting. I think that this is years ago. This is pre things have since fallen apart for them. But like I think we met with the Medman team, the CEO team and Jay was in the room.
42:18Right. Like to meet the CEO and the CFO and the CMO about partnering on something, an idea that he had. Right. And so he was very present in that way where it's like, I will add heft where I need that heft. otherwise I'm here for creative input right like especially like if the CEO of Bacardi is like all right we need have a meeting of the minds that that's Jay's thing or you know it's med men or anything like that right and so he was very smart about when and where he he added that you know utilized the leverage that he had and the star power that we had that he had but but also also always true to himself which is again like I know he preaches it but I think he lives it as well so it's not like he's going to be there like this is my thing go get it i'm showing up the liquor store like a dj khaled but that's also very authentic for dj khaled it just isn't for jay so it's very different in that way yeah no no that makes sense i mean obviously it's it's it's obviously very very different for effort of people i know that when i was talking to um uh to another person that was close to um the troy aikman eight um yeah troyman has the eight company and troy was like going bar to bar in texas and like you know dishing out eight and like it was like kind of like a road show for you know a beer and stuff like that and that was you know troy obviously like um um you know love to do it and everything like that but it's all it's all about you know what's authentic to you know the personality and and and and the person that matters that matters just as much as anything else right like if it's inauthentic it's gonna like if jay had like yo i'm at the liquor store go like go come get you through people would be like what like and it also it would have hurt the mystique that he has and his brands have um and that that's part of what works for him it's part of what makes what he's done so far so successful what have you learned because obviously jay-z has also sold you know a few of his business obviously has done extremely well from it um overall what have you learned um as an observer in terms of when is the right time to sell through like that experience?
44:22Yeah. So I think what I've learned, especially like being alongside these processes is when you feel, or you know, or you see that there isn't any more value for you and your team to get out of it on your own. Right. And so a lot of times a strategic will come in and can plug your brand or company into their thing and take it to an entirely different level or stratosphere. And so it doesn't mean like you sell out entirely and you might sell a portion of it, right? But at some point, you'll get a company, and especially even with talent, even with talent, you'll get a company to a place where it's like, we can't take it any further than we have to this point.
45:00And plugging into a larger system allows us to kind of continue this journey that we're on. That's a big piece of it. And also being transparent about where you are, where the company is, and what you're able to achieve is important as well, right? And so, you know, that meant on our end, we had to have some hard conversations on everything, like on title, Ace of Spades, Duce, like all of those things around like, we've taken it as, have we taken as far as we can on our own without adding additional dollars or adding additional strategic heft or something to that extent, right? So being transparent and being honest with yourself, sometimes taking a sober look in the mirror and appreciating the idea of like, great, like we as a small nimble team, I've gotten it here in order for us to like get true to the next level.
45:50We need a little bit of strategic help in order for us to go global. Sometimes to go global, we need some strategic help. Let's sell a chunk or a piece or all of it. Like sometimes you just fall out of love with and you're like, let someone else take it off my hands. But, but really like just being honest and being open about with yourself around like, have we gotten the most out of it? and if we can or if you've gotten close to the most out of it maybe it's time to like start finding a strategic to help get it to that next level whatever that next level might be yeah and also um i think those are great points i think also like um like what is the ambition of the company too you know is it is the ambition to just to to keep it as is which is great and it could be like a great cash flowing business right um and maybe you want and maybe you never want to sell it but is it is it to take a new heights okay like maybe this is you know a really compelling offer.
46:35And, um, and so, you know, and, and, and this company, it's not like this company's going to tie, like, obviously they're, uh, they're, they're spending a good amount on this company. And so we wanted to see, uh, uh, to actually release it to global heights. So it really kind of also depends, um, as like an operator and owner, like what your, what your ambitions are for the company. So why'd you leave? It sounded awesome. Why, why again, why again, did you leave, Jay-Z and Rock Nation to head over to Westbrook, which is Will and Jada Pinkett Smith's company. Yeah. You know what? I saw an opportunity to be a part of something that was a little bit earlier on than when I jumped on the train at Rock Nation.
47:13So Westbrook was just getting the ball rolling. They'd had ambitions of being to have a multi-pronged approach to things, both consumer, TV, film, media, marketing, and so on. and then again another opportunity that i couldn't refuse right and so i was recently married at the time came came to the west coast um and wanted to take a stab at helping be a part of building something right like rock nation was was a well-oiled machine i feel like i had a tremendous value there but not as much value as i anticipated building like this is a new thing let's help build it from the ground up and so when i got here i helped uh in an operational capacity and I worked directly with the COO again at Westbrook to kind of set the foundation and get the ball rolling on things.
48:01And then slid over to oversee Westbrook's consumer product division. Right. Which was even more. I don't know. Like what I did at Roc Nation and what Jay was very diverse apparel, cannabis, books, coniac, you know. But but at Westbrook, it might have been even more so. Right. Only because I also did like licensing and e-commerce. And then we incubated brands from scratch. We did coffee, personal care. We did apparel again. And so a long list of things that I was able to kind of help be a part of and steer the ship on a little bit. And so I think all of those things were what wooed me to come over, right, to be a part of building something from the ground up.
48:41That was a lot of the appeal. yeah because jay-z's brands too like they were all done through jvs or like or like a partnership with another company is that right um they weren't they weren't kind of like incubated like or or is that wrong there most of them most of them so paper planes is is wholly owned built from scratch the apparel brand um armand to bring the the the champagne ace of spades wholly owned by jay and built from built from scratch for the most part like the champagne existed but jay bought the entirety of it and added his special sauce to it. Duce is a joint venture with Bacardi, as everyone knows.
49:18And Monogram is a joint venture with Kaliva. So, you know what I mean? He's done it in multiple ways, exactly, multiple ways. Tidal was wholly owned, already existed. He purchased it. So it was kind of like an acquisition. And then a lot of that knowledge and experience is what I wanted to bring to Westbrook as well. So talk to me a little bit about how you thought about incubating brands. I know, I believe Westbrook started out as like the media, like a media, more like media focused company. Why move into consumer goods? What was the opportunity? And how even did you think about launching these kind of brands from the start?
49:57I think it was two places, right? Like why consumer goods is like at some point, you know, Disney is really a tremendous and very, very large consumer goods company, right? Because you have IP that you own that you want to monetize. So there was a piece of Westbrook's consumer goods ambitions that were tied to TV and film and IP in general. And also because Will owned the Fresh Prince trademark, which he licensed to the company, which the company sub-licensed. So at some point you're like, we have IP that we can monetize. Consumer goods is a great place to do that. That's one silo. The other piece of it is, and the other ambition was like, Will and Jada always viewed Westbrook as a platform for artists to express themselves through TV, through film, through podcasts, and then potentially through brand and consumer.
50:44And so the other piece was like incubating brands with talent was a big deal. But my thought of it, especially seeing like Jay's multiple structures, my preferred structure is find a great partner and a great partnership structure or a great legal agreement and figure out ways so that you have an operator who can run it. And you as talent can do what you do best, which is, as we said earlier, supercharge whatever that brand is. Right. So I'm not too fond of like I'm buying 100 percent of this company. I'm going to run it myself. It's not, it's not for me, I don't think the most efficient way for talent to add value or to build or scale a company.
51:23For me, it's kind of like, is there someone who's doing it? Either you acquire the company and you kind of let that team do it and you add your special sauce to it, or you invest in the company, or if you're incubating from scratch, it's ideally is a partnership with an operator who knows how to operate that business and can do it from there. And so that's why, like, I think there were some things from, from a structural standpoint with the Duce partnership that could have been improved, but having Bacardi steering the ship on the cognac is, is the best thing, right? Like securing cognac and like that, that's, that's all of that stuff is exactly what you want to happen versus, you know, being a hero.
52:01And I'm, I'm going to start my own cognac business from scratch. And so like, I tell talent all the time, you don't need to start anything from scratch. You don't need to be the hero, find a great partner who you can plug into you do what you do well they do what they do well and everyone can kind of ride off into the sunset you know no totally and i i understand it too just just with um with westbrook and then when it comes to consumer goods i understand like merchandise um the merchandise opportunities when it came to you know the fresh prints um logo and what have you but i think to your point the product needs to be great right and and obviously like maybe it shouldn't be like talent led for the product to be great find like a great operator um find a great operator or someone that actually um uh can build an incredible product right that's what what jay-z was attracted to with with the cognac right and the and the champagne so um how for example coffee how did you guys how did you all go about doing coffee and why did you see that there's an opportunity for example within coffee yeah at that point in time and and it's it's a project I don't even know if it'll, great, great project.
53:05And they may still release it. But at some point, I think it was authentic because people didn't realize how much of a coffee, I can't even say coffee lover, like coffee fanatic Will is. And so that was the through line there, right? And so we didn't end up releasing it in the time that I was there. And I think it's still something that they have up their sleeve potentially. But the opportunity to storytell around Will's fascination and fanaticism and love for coffee partnered with his own, as we said, authentic signature blend that was kind of like tailored to his palate. That was an ultimate goal for us.
53:45Right. And so we always went around like what is authentic? And so for him, it was coffee of all things, of all things. To understand his love, his finances, the obscene number of cups that he drinks a day, among other things, that was a big part for us and why we went with coffee. Got it. Got it. Got it. So what led – and I know you had a stint at Raptive. But what led you to founding your old VC firm, Freedom Trail Capital? What was the impetus behind it? Yeah. You know what? It's more opportunistic than anything. I had worked with and experienced success as an operator in these talent-led brands.
54:30And so what I wanted to do was, and also just seeing or at least trying to skate to where the puck is going in terms of the consumer space and the fact that talent-led brands nowadays, and it's funny because I saw a quote from Mark Andreessen recently where he's talking about talent-led brands and celebrity-led brands are probably the future of consumer. seeing like the success that we had there and wanting to at least be involved there. Right. So I had a couple of deals that someone I knew had brought, had brought to my table. I'd always had deal flow just by being in Jay's orbit and Will's orbit and being in LA, like you just always have deal flow.
55:06And a couple came through that we didn't even end up pulling the trigger on, but a couple came through that were good enough where I was like, Hey, I could spin up an SPV just to do these and try to raise capital. Or I can do a fund where I can try to find multiple opportunities like this that I have access to that other people don't typically have access to, right? Whether it's talent-led deals or whether it's like deals that could be good for talent, where I can bring it to contacts that I have and then try to bring talent aboard after the fact, which is something that we do as a fund as well.
55:38And so it was really like seeing these deals where I was like, this is cool, but it seems like, you know, there are consumer funds. There are even like a couple of celebrity funds nowadays, but there aren't many that A, are founded by operators who have like operated in both these businesses. B, are taking advantage of the arbitrage opportunity around like, this is a great company that could be authentic for this talent partner. Let's bring that person in and see if we can supercharge it. And then C, I also wanted to kind of like look for brands that sat at the intersection of culture, lifestyle, and influence.
56:07and so but a lot of it was just leaning on you know these couple of deals that again we didn't end up doing with a couple of deals where i was like these are great and i think there's a market here to be served and also consumer in general not just cpg but a consumer in general um there's a value add that talent and only talent can bring to the table and ryan reynolds like at the time it also helped that ryan reynolds had won with aviation gin and then he won with mint mobile and then now he's got this fintech thing we're doing but he also has his marketing company where people are seeing like the value of talent if utilized correctly.
56:40That was kind of the sweet spot that I wanted to serve. But it was more opportunistic than anything. I have a few consulting clients now. You know, after leaving Westbrook and then spending some time at Raptive, I work with talent nowadays who are very entrepreneurial, right? And they're like, help me get some structure. Help me think through how I can build this thing. I have this idea. I have this product. How do I make it a business? And on the flip, on the investing side, we're looking for like really great run businesses that can utilize talent or are utilizing talent and can do so better.
57:14And so that little bit of arbitrage opportunity that we can leverage as a fund as well. I feel like now there are a lot of talent-led brands and there's a lot of talent associated with brands.
57:28And some of them have done well, some of them have done poorly. in your mind what actually what is that right balance um what actually needs to work how are you how are you kind of analyzing in terms of when talent and brand come together when does it actually mesh to actually make something great and as well as is there particular categories that you think are right for talent or categories that you think that actually talent is very there's like so many talent-led brands it's really saturated um does it make sense to like launch other brand in like this space for example yeah so i don't think it's saturated i don't think it can get saturated and the reason i think that is like at some point the reason it works is because it's has to be in it talk about why why it works for j right like it's got to be authentic right and so at some point not just authentic but it's got to you have to have a quality bit like if you don't have a great business the thing just isn't going to work it's not going to take off no matter what.
58:26If you have a great product, Travis Scott and Cacti, right? Like Travis Scott is top of the world. You got Budweiser. I think Budweiser was behind Cacti. They released this hard seltzer thing. It's everywhere. It's going like gangbusters and the thing doesn't taste good. It's not a good product, right? It's not going to go. And so when we as a funder, our due diligence, and in general, when I think these things actually work is when you have a great product that has a reason to exist is differentiating the marketplace in some way. When you have a quality brand, right? Like it's not just about like, I got a product and I slapped someone's name on it, but when you actually put some thought into brand, brand story, brand architecture, brand equity, those things we talked about before.
59:06When you can actually cultivate a community, when you have a founding and executive team or an operational partner that knows how to run these things and operate and be efficient. And then your last consideration is the talent and how you leverage that talent. That's where it can be successful. And then on top of that, in order for it to be successful, it's got to be authentic, right? So like if the product is great and the brand is good and the operating team or the executive team is excellent and they can run an efficient business, and then you're utilizing talent appropriately, not to like build the brand, but to tell the story of the brand in a way that's authentic, then you can actually win, right?
59:41And so at some places, if you've got consumers that are like, I'm not buying it, that sounds like BS. Or in some places, if you've got people who are like, that seems fake. Like, you know, like I'm not going to point any fingers, but you have, you have alcohol brands founded by people who, you know, don't drink, or, you know, are struggling with sobriety or, you know, things like that. I think you're going to struggle. Right. And so you still have to have a great product. It's not just about slapping a name on it. You still have to have a quality business. You still have to have great distribution.
1:00:09You still have to have great margins. You still like all those things that make good businesses are a necessity. And then you have to have talent that can authentically tell the story of why they're involved. It's not just like, oh, it's a money grab. It's like, no, I think that talent partner needs to make sense for whatever the brand or the product of the company is, where it's a believable story that you're telling. Now you can do something, right? And what you can do is connect that talent's following to the consumer for that product. The product can use the celebrity as a proxy for making their own decision.
1:00:42And we do it all. It's why endorsements have always been a thing. It's all your celebrity endorsement. It just so happens that nowadays, celebrities are more entrepreneurial, so they're taking a piece of the company. So when Beyonce says, pay me in equity, it's still, you've always had endorsers, you've always had endorsements for a long, long time. It's just a new model to it. And so now the other thing is like, us as a fund, we're category agnostic within consumers. So I tell people like, you do CPG, of course, But consumer tech, consumer AI, SaaS, all those things. And again, I don't think there's a limit on where talent can be successful as long as it's authentic and it makes sense.
1:01:24And it's a believable story, right? So if you told me, I don't know, like if Kim Kardashian had a Shopify competitor and she was like, I started this company because we were running Skims and Skims weren't working X, Y, and Z. So we started this company and I use this Shopify, whatever it is, for all of my companies, all my inventory. And that's why I started it. It's believable. Right. And so at some point you get the authenticity behind it. And so I think it's also very much about storytelling. Right. It's got to be woven into the story of the brand and the company in a way that is authentic, not just believable, not just like if you tell people believe it.
1:02:02Can you trick them into believing it? It's got to actually feel authentic. But yeah, I don't, you know what I mean? Like, again, Ryan Reynolds with Mint Mobile, right? Like people are like, oh, it's a cell phone company. But he was able to weave in his reason for being involved there, his value add for Mint Mobile, why Mint Mobile was competitive. And actually take that from where it was when he got involved to new heights. He's trying his hand again with this fintech company he's invested in. And for that reason, again, like we said, like use talent to be top of the sales funnel. when you get people in that sales funnel is it believable is it authentic do they have a reason for being like cool this makes sense let me find out more when you get them to find out more product has to be great the brand has to be great it's got to connect with people it's got to be sticky and all those things still it can't just be about like again like a cacti for example like travis that thing it blew the doors off of places when it like started right it was everywhere and everyone tried it.
1:02:58Then they drank it and they're like, this is not very good. And so then you're in trouble. Then you're in trouble, right? And so you got to run a good business. You got to have a good product. And then you got to use talent appropriately. Yeah. Well, I was just trying to think, because I think that's a really interesting kind of thesis that you have in that not just consumer goods, but also consumer tech and consumer AI companies. I'm trying to think if there has been like examples of like a consumer tech company that has a successful consumer tech company that had that that was talent led um um i'm just trying to think because title wasn't really like a success from like that capacity i'm just trying to think of like a title like title wasn't so much like a success from like that like in like that kind of way yeah not not in that way but you know judging from the edges they had it's successful it's a success to somebody right but but yeah but but but it's um but you're right title is probably a good example right at some point and i don't think it achieves the heights that even jay wanted to especially like where spotify and apple music are but for him like to tell the story of like it's artist-led it's artist-founded i created this because i wanted a platform that i could have utilized and so on and so forth um i don't again i guess mint mobile is quasi cpg yeah i was i was i was thinking about mint um if if mint would kind of qualify for that um and you'll get some i think very soon especially in the ai space you'll get some creatives who are are going to be like i use this to create whatever content blah blah and like you're gonna get to and i i've seen it from us like i've seen a few of those come through that i think i have a very good sense are going to be very successful in the not too distant future um so yeah so so those those are big ones but it's got to be believable and authentic.
1:04:49And nowadays with this creator economy, you'll get folks who are like, yeah, it's a tech thing, but I use it to do X, Y, and Z. And I think from a consumer standpoint, people are going to actually welcome that and actually listen. Like if Mr. Beast was like, I edit all of my YouTube videos with this AI thing, the thing's going to go crazy. Let's be honest. And so at some point it's got to be right person, right story, right product, right company, and it'll go. And then that's why for us, we're not just like, it's just CPG. It's yeah. Those, the talent that can like, uh, lift and consumer tech brand might be few and far between, but they're out there.
1:05:29It just has to be right brand, right company, right talent, right? All of those things, but you can, you can get it to go. Yeah, no, that's a great, it's a great, um, it is a great point. It is like, just like thinking back through um totally totally understand like the use case um certainly when it comes to um creators you know um uh and that i mean that that mr beast example that that you said i use like this this um uh this program to like edit like all my videos like 100 could see that you know um maybe doing quite well if obviously like the technology is that good um and people actually want to you know purchase again and again and again um you gotta you gotta have a great product right that's that's really like that that's that's what matters in that case maybe you might like maybe the software the ai serves on a per edit you can do like a monthly subscription or you can do like a per edited video i don't know something to that effect but to your point it has to be that good or if uh steve aoki or dj jesse jeff had like a djing software right like those are those are like eventually you'll get like a software thing where someone like that Calvin Harris, like I use, you know, like back in the days when Fruity Loops came out, if Fruity Loops, like the actual like editing software was a thing, you know what I mean?
1:06:47Like a producer, like nowadays you have like star producers could be like, I edit on this software and you know what I mean? So, so I do think, and that's why we're category agnostic. I think celebrity tequila is overdone, but someone could prove, because you asked about like categories that I think are too saturated. I'm over tequila, but that's just me. And then who knows? Like if there's an innovation in the tequila space that someone can come out with, then more power to them. I think it's just tequila, like Reposado on Yeho from a celebrity. I think that is overdone for sure. Okay. So ladies and gentlemen, Samir is not investing in tequila anytime soon.
1:07:33but there are agave agave based spirits that i've heard of and seen like a mezcal and a few others you know i i do think like going back i love this idea of like the consumer tech question too like it is quite interesting how in the music space you had jay-z and title you had neil young creating like his own music player i remember that um i think it was called like lalo or something like that i remember him going on um on i think it was david letterman and like am i talking about it back in the day but it is interesting how like the winner turned out not to be you know some um a company that you know had that kind of like talent led which is just quite interesting because you would have thought that you know these like big you know musical figures obviously um uh that it would be maybe come from um that the the technology would be um they'd be kind of part of that technology moving forward so that is that it is quite interesting um how how do you diligence like the actual company itself because i mean obviously you understand like the talent side and of course you have like the operations experience um uh from yourself but like in your mind how do you truly find like okay this is truly a great product and i now want to supercharge it with trying to maybe bring talent involved or talents involved like i want to be part of that but how do you how do you actually diligence like like the product itself whether it's a brand whether it's a piece of technology.
1:08:54Yeah. Yeah. I think twofold. I think, A, I look at it from an operational standpoint. Like when you unpack the business, it's like, what's the P &L look like? What's the balance sheet look like? What are the margins? How are you operating? So on and so forth. That's like your typical, it's got to be a good business. But then it's also anecdotally, right? Like at some point, how do retailers feel about it? Are you growing in distribution? Are you growing in door count if it is a product? What's the community feel about it? Like what are people saying about it? Are you growing? Is there some sort of velocity in terms of how people are adopting it or growing it?
1:09:26And then, you know, it's also subjective too, right? At some point, it's like, not only have I tried it, but have other people in the orbit tried it? What do surveys say? What's the NPR? What's the net promoter score? What are those things that I think people use to kind of get a sense when you're doing like community listening, right? Like, what are people saying? What's what's this? And it's also the same reason I know, like, talk to people and they look at like they look at cacti and like it didn't taste good. That's an issue. So at some point you want to know what's the community saying on social?
1:09:59What is what's the net promoter score? What are the retailers saying? What are buyers? Because at some point when you look at like Nielsen ratings, you know, is it moving off the shelves? How is it moving off the shelves? What does Walmart say about it? What does Whole Foods say about it? And all those things. Right. So a lot of it is like indeligence. It is the objective piece of is this a quality business? How are the margins? Can we improve margins? Can we help? It's a subjective piece of like, what are people saying about it? And then when I ask what people are saying about it, I'm curious about like retailers and distributors and also the consumer as well.
1:10:31Right. So you've got to do a lot of consumer and community listening to understand, do people like it? And also that means I might not like it. It might not be for me, but do people like it as a whole and both objectively and broadly? Because there's no one thing that's for everybody, but as broadly as possible, are people liking whatever it is? And then again, like talking to retailers and looking at Nielsen numbers and looking at all of those, all of those things that can let you know, like this thing is growing and it's bubbling and people like it and they want more of it. Or if it's like, it stays on shelves and you know, your store velocity is super low and it's shrinking and blah, blah, blah.
1:11:11All of that makes a big difference. Yeah, that makes sense. Like do people, once they buy it, is there like repeat rates? Are people, are people coming back for more and what have you? So that it makes total sense. And then you asked, and only because you asked on the tech side, it's not as simple as like looking at Nielsen and like store data and all that stuff. But the other piece of it is like, you know, what's the email list look like? What do socials look like? And then I'm going through comments in socials, right? Do people like it? Do they use it? What do they talk about? What do they complain about?
1:11:41Are they subscribing to it? What do the blogs look like? What's Reddit saying? What are the communities saying? What's Discord saying? All of those things kind of add up to make a big difference if you're actually like paying attention. And then as an investor, you got to pay attention, but also as an operator to pay attention to. Right. At some point, if there are enough people on a Reddit board saying like this part of this app stinks and I hate it, you got to listen. You got to listen. It's how you improve. It's how you get better. It doesn't mean you listen to everything. It doesn't mean that everybody has a point.
1:12:10but um if if it's loud enough you have to understand like people hate this product they like this product they like it except for this one thing or whatever it is um this solves a real problem for them from a tech standpoint like does this app solve a problem for them had they been waiting for it and so on and so forth all that makes a huge difference samir i feel like i could i i feel like this interview could have lasted honestly another hour it was so much fun talking with you. Thank you. Thank you so much for your time. I really, really appreciate it. Yeah, no, no. Thanks. Thanks for having me.
1:12:42It's been a pleasure. There you have it. It was a pleasure to have Samir. Samir, thanks again so much for coming on the podcast. If you're enjoying the show, highly recommend checking out consumerbc.com and subscribing to the newsletter. You'll receive all new fundraising updates that's happening in the world of consumer. And as well as you'll be the first to know when a new episode drops. Thank you again to Propeller Industries for being our sponsor. Thanks for listening.
From the publisher
Our guest today is Samyr Lainé, an Olympian, an amazing operator who worked with Jay-Z's, Will Smith and Jada Pickett Smith who is now the founder of Freedom Trail Capital.
We discuss:
• How he trained for the Olympics while being a full time law student
• Working at Monumental Sports (owners of the Washington Capitals and Wizards)
• Shifting towards the MLS
• Getting the email that Jay-Z was looking for someone to help run his businesses
• All of Jay-Z's businesses
• His view on how brands can collaborate with talent
• Why he left to work for Will Smith and Jada Pinkett Smith's Westbrook
• His thesis behind launching Freedom Trail Capital
Thank you to our Partner –– Propeller Industries
Propeller Industries is the leading strategic finance and accounting partner for venture-stage companies.

