In this episode of, “Financial Freestyle with Ross Mac,” oftentimes individual success is seen as overall success for one’s family and loved ones. Kai Cunningham, co-founder and partner at Limited Ventures has lived this first hand. He recalls, “When I got my first check… my family was like… ‘we made it’.” Knowing the importance of creating generational wealth to maintain success, Cunningham takes his experience from humble beginnings in Baltimore to Goldman Sachs to Limited Ventures, and uses it to become a force in wealth management for athletes and entertainers.
Cunningham recognized the unique influence that athletes and entertainers have and sought to leverage this influence in venture capital and private equity deals. This innovative approach helped bridge the gap between his clients and high-level investment opportunities, making it easier and sustainable for the success story of everyone to continue.
Financial Freestyle with Ross Mac” on Yahoo Finance strives for economic prosperity for all. Through expert insights, actionable advice, and inspiring success stories, we empower you to build and accelerate wealth. Join us on a transformative journey towards financial freedom and inclusive economic growth.
Video Transcript
As a culture, we’re just at a comfortable place, I would say in the last 20 to 30 years to where we’re obtaining substantial amounts of wealth.
But we don’t have too many examples of passing that wealth for the next generation.
Sports gave me access to a space where black investors don’t have access at scale.
If you think about who we looked up to, it was athletes and entertainers.
I think now the narrative is changing to where it’s actually cool to be a venture capitalist, have a family office, be a private equity investor, sports team owner and other leagues.
When I got my first check on Wall Street, it felt great.
But I’m like, I still got a long way to go, but my family was like, alright, we made it and you know what I mean?
Hey, I’m Ross Mack and welcome to financial freestyle.
Look whether you’re a professional on Wall Street, a first time investor or someone just looking to change their overall financial situation.
There’s always the first step you gotta take and look no further.
I’m gonna be speaking with some of the most influential voices in my universe and asking them, how they got to where they are now today, I’m joined by my guy, Kai Cunningham Limited Ventures founder, Kai.
What’s up, brother?
How you doing, man, man?
Never been better.
Yeah, I uh appreciate you coming on the financial freestyle and more importantly, man, to the people that are at home.
Let’s talk about who Kyle Cunningham is, man.
Who, who are you?
I mean, first thing I always point out is and we talk about this all the time.
This is a father.
You know, I got my six year old daughter, Nova.
Um and then business owner, entrepreneur, you know, we started on Wall Street and you know, hats off to you.
We always connected on the fact that we’ve been able to be entrepreneurial in an industry that doesn’t really support, you know, black entrepreneurs and business owners in an innovative way.
So the fact that we’re able to kind of think creatively and execute on our networks while still having the Wall Street pedigree.
And I did today I think is, you know, something that’s very powerful.
So obviously you started on Wall Street, you was at Goldman.
So let’s kinda walk into, you know, how does a kid from Baltimore A K A or a guy like me from the south side of Chicago end up on Wall Street?
And let’s talk about how that upbringing kind of helped catapult you to where you are today.
Yeah, I mean, I think the lessons that we learned in those environments actually translate 1 to 1 to having a career on Wall Street.
I mean, for me, I was catching the megabus from Philly at one in the morning because it was $4 sleeping on my friend’s floor and then going into Goldman just interviewing people asking questions, taking notes following up.
And I think like that mentality of like, you know, not being afraid to lose but also the reality of what we could potentially be going back to if we didn’t make it, you know what I mean to Wall Street, you know, it was frightening.
So I think the fear of going back um and not accomplishing what I set out to do was actually a catalyst for why I was catching the mega bus at two in the morning with $20 to my name.
Um And I think when you come from those types of environments, right?
And, and I know it’s cliche but you’re really only given a few different options, you know, sports music or, you know, an illegal alternative.
And, you know, I wasn’t doing the last one and it was from me playing against guys that are now NBA NFL superstars, but I realized there was no place for me in the league.
So I started focusing on academics.
But my drive to get to Goldman was, was really, you know, probably um the catalyst was really not having a father figure because that, well, I’m not trying to say I have father figures, not having a father, but it, it enabled me to seek out father figures in the business in the business realm, which ultimately helped guide me and you know, help shape my path.
I love it.
So let’s talk about your path today, right?
What, what’s limited ventures?
So limited ventures is a multifamily office.
It started as a venture fund, right?
Because, and I, I heard you ask this question and we had these conversations before about just bridging the wealth gap.
And we see across Wall Street now, obviously, I’m gonna dance around a few topics, but across Wall Street now we see that sports investing is top of mind.
We see that alternative investing is top of mind.
But when we talk about how that applies to solving the wealth gap.
If we look at our communities, the people that we look up to growing up typically are athletes and entertainers.
So the thesis of my business has always been bridging that gap by helping change the narrative associated with the athletes and entertainers that the little kid from Baltimore or South side of Chicago or Compton look up to, right?
So we’ve had guys kind of blaze that pathway.
If we look at lebron Steph KD, we see that they’re philanthropists that they’re venture capital investors, they’re real estate investors.
So our entire model is about bridging the gap for guys that are like lebron Steph and KD, as well as guys who may only be in the league for 2 to 3 years.
But they’re the first person in their family to make six or seven figures as a culture.
We’re just at a comfortable place.
I would say in the last 20 to 30 years to where we’re obtaining substantial amounts of wealth.
But we don’t have too many examples of passing that wealth to the next generation.
That conversation needs to sit within a family office structure.
So we aim to create that structure for athletes and entertainers as early as possible in the process.
So, you know, obviously I know your your story because you know, we grew up in this industry but like, you know, this is the first time I’m saying it, but you kinda like Rich Paul but on the venture side, you know what I’m saying?
So let’s actually talk about how we got to, you know, doing venture capital but from from a family office.
But for athletes standpoint, yeah.
So I think over the past, so when we’re in 2024 in 2016, 2015 is when a lot of athletes kind of adopted really being proactive and venture capital investing.
And you know, it’s a sexy asset class.
You hear about how many billionaires are made, but we tend to not focus on how much capital was actually lost because of how risky the asset class is.
Um You mentioned Rich Paul actually study a lot of what he does.
I mean, in my opinion, right now, probably the most powerful agent in sports.
And I think it’s because he was careful and meticulous and strategic.
When you think about the leverage and power you have, when you can harness a collective of athletes and entertainers.
One thing that I noticed early when I was developing my thesis for my business is that there’s nothing really in modern portfolio theory that accounts for the influence of an athlete or an entertainer, let alone 50 or 100 of them.
Think about it.
How many times can you as a regular person get equity in a private company just because of your influence on who you are now multiply that times 10 and if you think about it, you know, athletes and entertainers, especially within black culture, set the trends are the influencers, but we’re, again, we’re just turning the corner on that conversation of ownership.
So if I can get an athlete or an entertainer or a group of them equity and exposure in exchange for marketing that still solves a piece of the problem.
Um And I think that that’s where things are trending.
I love that, right?
Because when you look at athletes that come from, you know, similar upbringings, you’re saying roughly what over 70 between 70 80% of NBA NFL players within the 1st 3 to 5 years of when they retire, they’re experiencing some type of financial hardship Right.
And obviously that could be overspending, you know, not being able to maintain their bills when they no longer have income coming in.
But a lot of it is sometimes bad investment.
So let’s kinda talk about how you are actually ensuring that that’s not the case for a lot of the athletes you work with.
Yeah, I think that answer wants a little bit of context because when I started out mainly and purely doing venture investing, my biggest challenge was not having complete visibility into an athlete or an entertainer’s portfolio because from the venture perspective, right?
And if you think about it 9.9 times out of 10, the athlete is the first person in their family to really even be able to earn seven figures of wealth to the family.
They think that they made it and trust me when I got my first check on Wall Street, it felt great.
But I’m like, I still got a long way to go, but my family was like, alright, we made it, you know what I mean?
So imagine I wasn’t making NBA money, but at the same time, we got to be thoughtful about the structure.
So for me, when I was first looking at venture, it would be completely irresponsible of me to take 30% of someone’s net liquid net worth and then put it into an extremely risky asset class no matter who’s in the deal, no matter how much diligence I did, right?
So that was always a challenge.
So, but I did know that because I had very powerful access on the venture side that eventually we would be able to come back after building relationships and having some exits with guys to look at this in a more holistic way.
And I think when you look at, you know, you mentioned Rich Paul and Mad, right?
Like in my opinion, you know, in its simplest form, we can make the argument that they actually run lebron’s family office in a sense because rich is controlling the wealth that he’s earning on the court, the primary money maker.
And then mav is handling all of the business stuff and I know there’s, you know, a lot of other people in the mix that deserve credit, but just for illustrative purposes, you have those two people that serve as checks and balances that are equipped and sophisticated enough to go out and represent you, you know, at a scale that you deserve to be represented on often times athletes and entertainers are so focused on on the stage, on the court, on the field.
They don’t have a process in place to interview select and position people to be in their ecosystem in in a formal way, representing them to the rest of the world.
So we even help interview, right?
So think about this athletes specifically have typically have business manager, financial advisor, agent, marketing agent, maybe a day to day guy or best friend or mom or parent is in the picture.
All of those people, right, have different incentives in terms of how they create wealth for themselves, relative to how they service the athlete, right?
We all know how predatory the space is, right?
There’s a reason that those statistics that you listed earlier are reality and it’s because at some point this is not every athlete and it’s changing, but those statistics exist because there’s someone who is not looking out for the athlete’s best interest, someone is incentivized in this direction and it may not go with what the advisor or the agent or the other person in the ecosystem is aiming to complete.
So we come in from a complimentary uh perspective because I don’t wanna see adversarial to anybody in the ecosystem that may be a decision maker.
So our platform is about filling in the gaps, right?
If you have a great business manager, that’s terrific, we’ll come in and add an additional layer of resources and infrastructure behind him so that he can accelerate, he or she can accelerate what she’s already doing.
You have a financial advisor?
Great.
We could be a second set of eyes.
We have someone that’s helping you and your foundation learn from the multigenerational billionaire families that often times actually speak a different language.
And that’s where I kind of step in and translate.
If you will learn from the families who have created and passed down wealth for generations.
How do we take those pieces and apply it to the athletes and entertainers who are earning 60 million a year on the court in 20 to $30 million off the court.
That’s powerful, that’s powerful people.
Listen, make sure you stick with us for more financial freestyle after this.
Welcome back to Financial Freestyle and I’m still here with my guy Kai Cunningham Lemon Adventures founder Kai.
So let’s actually talk about, you know, kinda what motivates you, especially when it comes to helping these athletes maintain that longevity when it comes to being on and off the court because obviously the stats can be staggering.
So what would you say like your why is say my, why is kids like us when we were growing up?
Right?
If you think about who we looked up to it was athletes and entertainers and now the narrative is changing to where it’s actually cool to be a venture capitalist, have a family office, be a private equity investor, sports team owner and other leagues.
Um So when we think about the ultimate goal, which is legacy and passing wealth down, it starts with the kids in our communities, seeing their favorite athletes and entertainers as more than an athlete or an entertainer.
OK, I love that.
So let’s actually talk about some of the things you’re doing, right?
It’s one thing to say you’re in venture capital, but I could attest that is real, right?
Uh My guy Kyle put me in my first ever venture capital investment that was in Air BNB, probably back in like 2014, 2015.
No, I’m lying 2016 or 2017.
And the reason I say it is because, you know, with the emergence of, you know, the, the Robin hoods of the world, like everybody now, for the most part has access to buying a stock, right?
You know, it’s been democratized because when I first bought my stock, it cost 1299 literally on e trade and oh, wait in order to buy it and another 1299 to sell it, right?
Just that actual fee.
Now with the, you know, the likes of Robin Hood, they made that free.
But I also look at that and say, ok, now that I’m able to buy the top stocks, what’s, you know, when it comes to buying a actual private company, there’s still another barrier to entry.
And that’s because maybe you gotta be an accredited investor, et cetera.
So, you know, right now let’s talk about what you’re working on because like I say, you got me in the air BNB and you opened up my eyes to say, yo, I want the opportunity to own the next Facebook, the next, you know, Amazon and hopefully get a 2050 100 X on my money.
Yeah.
So I think you alluded to it, but the name of the game in alternative investing is access.
And our entire platform is built in partnership with multigenerational family officers who have been investing in alternatives at a very high level for a very long time.
Right?
So if you don’t have access to skill, and I actually spoke about this uh at the Forbes summit in Africa, I had a quote when I basically said sports gave me access to a space where black investors don’t have access at scale.
And what I mean by that is leveraging the collective of a large group of athletes and entertainers with the sophistication and expertise of multigenerational families who are already vetting diligence and investing into these deals.
Combining those two networks who don’t typically speak the same language is the gray area in which we specialize in because it creates a powerful outcome because we can go into some of the top venture capital or private equity deals after the close or at advantageous pricing because of the collective.
Like we’ve gotten into deals because I’ve introduced the founder to his favorite player and he signed his son’s jersey, right?
Like that type of access in those relationships is what we try to monetize, which is why I made the point earlier.
There’s I don’t think there are examples in traditional modern portfolio theory that account for the power of an athlete or an entertainer’s influence and the impact that it can actually have on his portfolio or even the structuring of his family office or his business manager advisor.
So the fact that we have that shared Wall Street experience on what’s deemed as a sophisticated investor, the ability to speak the language of the athlete and an entertainer to go sit in his grandma’s house in the hood and explain and break these concepts down in its simplest form using things that they understand.
That’s what I’m most passionate about.
That’s what I focus on.
And that’s why I think legacy is, is super important when we’re having these conversations.
You, I actually like the way that sounds because I think we all understand like the actual stardom of certain people that are whether you’re an athlete or entertainer, he can truly move a stock’s valuation, right?
I think we heard when Beyonce was saying, pay me an equity with, you know, I think that was over and then she just put out a song early this year a few months ago called like Levi Jeans or something that stock popped like 20%.
So I like that like you, you like kinda how are you seeing that, that type of influence in your work?
I mean, if you look at any consumer face and brand and this is probably the biggest variable in pride and markets when we talk about athletes and entertainers, athletes because of their collective following and just their overall influence, it would lend to the majority of their impact being on consumer facing products or products that need eyes or that are based on popularity and venture.
Most of the upside is actually in the boring businesses, the things that we don’t see.
So we try to change the narrative on using their relationship capital to get that same exposure as well as their physical capital when it makes sense that some of those businesses where their likeness may not apply.
But to your point, someone like Beyonce can really move the needle but everyone’s not Beyonce.
So if you’re not Beyonce, why not have 20 or 30 guys coves with you or use your likeness together?
Um It’s actually funny, I know we were talking about this.
I did a program at Harvard Business School, shout out to Professor Anita.
Um and one of the core themes was how certain influencers and artists and athletes like uh lebron or Beyonce or Jay Z or Becca or Messi actually have the power to stand up to and challenge some of these larger brands.
But again, I wanna go back to this core theme actually having the infrastructure for that to even be the case.
If there’s one message I would have to the younger athletes and entertainers who are walking into wealth sooner is to really spend time focusing on infrastructure or finding someone who can help you create that infrastructure so that you’re not getting crushed on taxes so that you’re not, you know, blowing money on things that you honestly probably have the influence to get access and exposure to um from an investment standpoint or for free, right?
Like we, there are a number of lifestyle fashion gaming companies that we’ve invested in that are also backed by some of the biggest players in the game, right?
One example is Status Pro, probably one of my favorite portfolio companies founder Troy Jones and um Andrew Hopkins, uh exactly from the, you know, choice from the crib, you know what I mean?
So to have a founder like that basically create what I kind of consider like it’s our version of Madden or two K or MLB the show, right?
Like those same rights, you know, from an A RVR perspective that made Madden a monopoly in the console gaming uh arena with football, right?
Think about that, like for a company to have those rights be backed by Google, you know, Verizon, the NFL and the NBA are huge supporters of this.
Think about what that means.
If we grew up on gaming now, we have an opportunity as an athlete or an entertainer to actually have equity in a company that’s leading the forefront in the A RVR space.
There’s definitely a way for the young athletes, entertainers and entrepreneurs to access things that they’re actually interested in in a, in a structured way and make a lot of money doing it.
That’s fascinating man.
Uh that, that is something that young kids in barbershops need to start thinking about as opposed to just who’s the best athlete, right?
I love the concept of what is my favorite athlete investing in.
Right.
And I think that’s something that, that, that’s a lane that you were, you know, finding your purpose in.
And so now when we talk about that lane, like, what would you tell a younger Kai Cunningham?
You know, if you had the ability to go back in time, you probably tell him looking trash at basketball.
And aside from that, we know that you already know you would be Ross lo deserve because you don’t weigh enough, you need in the weight room enough.
So there is no point in even trying.
Like no, I would say um I think it’s the core thing you were talking about, right?
Like I look back at my life and said, what could I have done from an educational standpoint, do all of that time that I spent trying to go to the league when you know, it was just never in the cards.
But I don’t discount that experience because a lot of my friends who I grew up with or went to school with actually in reality helped me start my business because I understood them at their core and they trust me at their core with their capital.
So if there was one thing, it would definitely probably be to just, you know, reallocate my time from being in the gym as if I were going to the league to you know, being an investor, I lo I love it.
So look, we got this amazing segment called Dear Mac.
And you know, I always get this question, but one of the questions you know is how do you actually determine if this company is good for you to actually invest in?
And I think that could apply to either public or private companies.
Yeah, I would say um on the private side where we spend the majority of our time.
Um If I always draw this comparison, if you look at, you know, really any asset class.
But because I like to break things down for the culture and athletes and entertainers, right?
We look at the top 20 college football programs, the Alabama Clemson, Georgia or if we look at on the basketball.
So I always got a shout out Villanova Wildcats, we got the Villanova Knicks now, right?
If we look at the top, uh you know, universities, they have a pipeline and a process of developing pro level talent, the same thing on the investment side.
And that’s why I made that example earlier when you said, like, you know, think about a kid coming from the hood that comes into a situation where they’ve seen certain things, they have a certain risk profile, but they also know how to manage risk and take risk, right?
But that environment, those variables that you learn there actually help you stay out of trouble managing the ultimate risk you know, saving your life in certain situations, knowing when to leave, knowing where to be, knowing where to look.
Some of those variables actually apply in sports and some of those variables actually apply in investing, you know what I’m saying?
So when we look at the infrastructure that exists, right, a lot of that pipeline is concentrated, right?
Look at the A AU programs, right?
Like uh team mellow.
Um Russell Westbrook’s team, why not?
Like even at the high school level, Montverde Academy, like there are institutions and structures in place that develop talent and develop uh you know, companies going public.
So that’s why I mentioned before, it’s about getting access in a structured way.
But then when it comes to the athletes and entertainers, making sure that it’s a company that’s organic if they wanna be proactive, but then also building a portfolio around some of the things that may not be as organic to them, but they also need to be allocated to.
I love it.
So to the people at home, right, obviously, you can look at it from a pipeline standpoint on the public, you know, side when it comes to investing in particular stocks, I’m always giving you the game where start off buying what you know, by the companies that you believe have a competitive advantage and they’re going to continue to take things to the next level over the next 5 to 10 years.
Is it a technology that’s life changing or is it a company that has a competitive advantage and a moat that you can’t get anywhere else?
Right?
And so always start with what you know, I like his idea of, you know, looking at the pipeline, but that’s it for today, man.
I just wanna thank my guy Kai Conahan for sharing his story with us and I wanna thank everybody out there for joining us on financial freestyle and we really hope that you got some insight, some inspiration when it comes to your overall journey to wealth creation, Shabo Ross Mack.
Make sure you tune in again.
Next week we got you covered and remember, let’s always build wealth together.
