Legacy · August 2026

Exclusive interviews featuring athletes building wealth beyond sports.

There is a version of career risk-taking that Silicon Valley has made almost fashionable: the engineer who leaves a stable job to chase a startup with a ninety-nine percent chance of failure. Matt Singletary took a version of that bet. The odds were probably worse.

Matt’s father is in the Pro Football Hall of Fame. For most of his life, it felt less like an inheritance and more like an audit. Every snap, every game, every season invited comparison to one of the greatest linebackers the game has ever seen. He played through college and briefly in the NFL and CFL before football ended the way it does for most players, abruptly, and on someone else’s schedule.

Most people would enter their next chapter staying close to the game. Matt chose to leave it all behind.

He moved to Los Angeles to start over in an industry where he had no experience, no relationships, and no obvious advantage - except for a lifelong obsession with comics and anime, a side of himself he’d spent most of his childhood keeping quiet.

But what makes Matt’s story interesting isn’t the transition itself. Plenty of athletes reinvent themselves. It’s the mindset behind it. He approached acting less like a second act and more like a search for product-market fit - testing, learning, refining until something finally clicked. Mark Ruffalo’s advice, that one role might come from every hundred auditions, became a useful benchmark. Every “no” became another step toward the inevitable “yes.”

Eventually, the work began to compound. He appeared on Chicago P.D., worked with Hugh Laurie in Chance, landed a lead role in the film Hood, and wrote and starred in one of the earliest athlete-led YouTube series, years before “creator economy” became a category of its own.

I sat down with him to talk about the weight of carrying a Hall of Fame last name every time he stepped onto a football field, the unlikely path from football to Hollywood, and the mindset he developed along the way - one that now shapes far more than his acting career.

This Q&A has been lightly edited for clarity and length.

Your dad is a Hall of Famer - someone whose name carries weight with anyone who follows the NFL. How did that shape the way you approached the game?

Matt: Honestly? I was scared to play. I felt like I was growing up in a Hall of Famer and NFL coach’s shadow, and that I had to earn my last name.

My dad played twelve years. Ten trips to the Pro Bowl. All-Pro. Hall of Fame. Anything short of that would’ve been a failure.

There was a part of me that was excited too, but I knew I’d get compared to my dad no matter what I did, and that usually won out.

Early on, I wouldn’t even let myself find out if I loved football. I played hockey, baseball, basketball, soccer, water polo, anything that wasn’t football, just so I wouldn’t have to face it.

Eventually, the thinking became: if I’m going to get compared to him anyway, I might as well find out if I even like this thing.

At first, the fear was I hope people think I’m good enough. It was about external validation. Over time it turned inward, and got heavier: what if I don’t even think I’m good enough. That’s the harder version. I actually preferred when it was about other people. Because that one’s easier to live with.

At what point did you realize the real question wasn’t whether you could keep playing, but whether you wanted to?

It happened in one of those quiet moments, probably on the floor of a shower, which became a habit for me. Lights off, water running, some Hans Zimmer on repeat. That was how I’d shut everything out.

It did take me a while to ask that question. Life just kept presenting the next step, and I took it, without processing whether I actually wanted it. Some of that was a trap of my own making. Every year I played, these questions would be running in the background. If I quit, would people think I gave up? Would people respect it if I didn’t want to play anymore? I never had clean answers to these, but they were a big part of why I kept playing.

Most career transitions happen between adjacent worlds. Football to Hollywood isn’t one of them. Where did that ambition come from, and what gave you the conviction that it was a bet worth making?

I was a nerd who happened to play sports. Comics, anime, Harry Potter, Tolkien, I was excited about all of it. What I loved about those worlds was that they gave me somewhere else to go.

Growing up, I struggled to fit in. I got bullied. Back then, they offered an exit. I remember reading my first Harry Potter book in fifth grade, and it completely rearranged something in me. I was in Chicago, but I was also at Hogwarts.

So there was always this quiet thought underneath everything: I have so many stories in my head. What if I could make them?

One day, I met a guy, JT Neal, who’d been doing some acting work. We saw Straight Outta Compton together, and it hit both of us the same way, watching Ice Cube, Dr. Dre, Eazy-E just decide to build something themselves. We walked out of that theater and said, what if we just did our own thing? We didn’t know how to write at the time, so we got a few MasterClass subscriptions and started learning. Our first scripts were terrible. Then they got a little less terrible.

By the time I had to decide whether to commit to this, I already knew what the alternative looked like. I had a corporate job after football ended, doing spreadsheet work I didn’t really understand, and there was an older guy training me on Excel who told me, “One day you’ll look back on this and laugh, you’ll know this stuff like the back of your hand, just like me.” I remember thinking - I don’t want this, I don’t want to become you.

I wasn’t running the math on my odds in the industry. I just knew the bad days here beat the best days over there. Once I realized that, it stopped being a risk I had to talk myself into.

In what ways is Hollywood similar to, or different from, football?

The overlaps are obvious once you see it.

The more you can do, the more valuable you are. A long snapper who can also block and catch is more valuable than one who only snaps. A lineman who can play center and guard has a longer career than one who only knows one position. It’s the same instinct that made me want to show range as an actor instead of getting boxed into one type.

Another similarity is that you’re allowed to experiment and fail, as long as it happens somewhere safe. In football, that’s a practice rep. In acting, that’s the auditions.

But you can only take those risks responsibly if you’ve actually studied. As a defensive end, I can’t gamble on a cutback lane if I don’t know the defense. During an audition, I can’t improvise a scene if I don’t know how the director likes to operate.

Every director in Hollywood is basically a different defense you have to study. Someone like Aaron Sorkin or Quentin Tarantino wants every word delivered exactly as written, no improvising. Whereas other directors might hand you three words on a page and say go. Knowing which one you’re working with before you walk on set is its own skill.

At 6’4” with an athletic background, it would’ve been easy for Hollywood to put you in one box. How intentional were you about avoiding being typecast?

Not at the start, because you can’t afford to be. My first real role was on Chicago P.D. It was basically, “you want to play a cop?” And the answer was yes, because it got me on camera.

Part of why JT and I wanted to build our own stuff eventually was exactly this. The industry looks at a big guy and sees “cop” or “security guard.”

My personal cheat code is you show as many sides of yourself as you can, as often as you can. The audition is the one place I get to create on my own terms. Even in a role written as “no-frills cop,” it’s my shot to show range. I’m not just auditioning for the role in front of me. I’m auditioning to be remembered, because Hollywood is a small town. There are maybe sixty major casting directors in the whole business, and they scroll social media just like everyone else. If they’ve already seen a different side of you online, that’s one more reason to remember your name.

It’s a fine balance. I spend a lot of energy trying not to become the difficult actor who says no to everything, while also not becoming so agreeable I disappear into whatever box people put me in.

You landed the lead in Hood before you had years of credits behind you. Why do you think someone was willing to take that risk on you?

Most of my career, in sports and in Hollywood, has been built on potential rather than a track record. That part actually felt familiar.

Around that time, I got introduced to WME. Their read on me was pretty direct. They thought I had the potential to be something like a Dwayne Johnson type. They wanted to hip-pocket me, build me up quietly on my own projects until I had something real to show for it.

Hood was kind of a perfect storm of what production was looking for. A bigger guy. Physical. Durable enough to save them the stunt budget. And, on top of all that, someone who could actually act. I wasn’t the best at any single one of those things. But I could do all of them at the same time, and that’s rarer than being the best at one. Nobody hires the jack of all trades because he’s the best. They hire him because he’s the only one who can do four things at once, none of them perfectly, but well enough that it works.

Taking on a lead role that early came with real risk. Too much exposure, too soon, can hurt you more than it helps. I knew that. But I’d studied, practiced, worked with coaches. So by the time the cameras were rolling, I was ready.

Looking back, Roommates feels like an early creator-economy play. You wrote and starred in a scripted comedy series that lived on YouTube before creators were building businesses around their own audiences. Did you see a bigger shift happening?

I’d love to tell you we saw the whole creator economy coming and got ahead of it on purpose. Some of that was planning. A lot of it was blind faith and a good amount of naivety.

There’s a piece of advice that’s stayed with me ever since I heard it. Mark and Jay Duplass were speaking at South by Southwest, and their whole message was basically: stop waiting for someone else’s permission. Make your own stuff. It’ll be bad. The next one will be a little better. Just keep going.

Roommates came together around 2016, 2017, when YouTube wasn’t yet a place people associated with “a show.” We had a hunch there was something there, and that we’d retain more creative control building it ourselves than going through a traditional studio path. That was the mentality. The stuff we actually cared about, writing our own characters, being funny on our own terms, happened to line up with the one lane that was open to us.

Along the way, I also picked up something from Mark Ruffalo. He said that it takes roughly a hundred auditions to get a job. I’m like, okay, that’s just a volume play then. If that’s the ratio, the only lever I can control is volume. Roommates was my way of putting that into practice. I’d rather make forty bad episodes of something we built ourselves than wait around for two perfectly written auditions a year.

Today you also spend your time helping athletes navigate their careers. What’s the thesis behind that work?

If there’s a thread connecting everything in my career, football, the auditions, my roles, all of it, it’s that failure became useful to me once I stopped scoring it against what other people thought. At some point it just became more about what I actually learned from trying the thing.

For most of my life, I was performing for people who didn’t even have my phone number. What will they think was all I thought about, and half the time I couldn’t even say who “they” were. People who couldn’t reach me if something happened, good or bad, somehow lived rent-free in my head.

It took me a long time, close to thirty years, to realize that an identity built entirely on performance is a liability.

That’s the whole idea behind my work today. I help college athletes work through the same stuff I never had help with. We’re talking to a dozen schools in Texas this year, with the goal of eventually reaching all fifty states. There are a lot of people around college athletes for the wrong reasons these days, especially with NIL money in the mix. Some are there for the trips, the perks, the gifts. Very few of them are actually in your corner, helping you navigate the ups and downs.

I tell these kids the same thing I had to figure out myself. You treat failure as part of the process, and put in the reps until nobody in the room can say anything that shakes you. Get to the point where you can look at any room and say, nah, I’ve done this and failed two hundred times, nothing you say is gonna shake me. Not because you’re arrogant. Because you put in the reps, and you were harder on yourself than anyone could ever be.

It’s tempting to tell Matt’s story as one about an athlete who became an actor. After talking to him, that feels like the least interesting part. What stayed with me wasn’t the unconventional career path, but the mindset that made it possible. He approached uncertainty the way founders build companies - treating rejection as feedback, iteration as progress, and success as the byproduct of staying in the game long enough for the odds to tilt in his favor.

These days, most of that mindset goes into his work with professional and college athletes. To keep up with what he’s building, you can find him on LinkedIn, Instagram, or at his website.

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Deal brief · Week of August 17

Tracking the deals shaping the business of culture.

Investments

Derek Jeter backs ALUM, a luxury hospitality brand built for college towns

Jeter is in as investor, board advisor, and ambassador on ALUM, which is building members’ clubhouses, condo-hotel residences, and chef-driven dining within walking distance of campus. The first property — 116,000 square feet in Tuscaloosa — is underway, with sites secured or in talks at Oregon, Michigan, Ohio State, Oklahoma, Kentucky, and Notre Dame, and a target of 30–40 locations.

Arthur Fils joins performance cosmetics brand Tiva as investor and ambassador

The French tennis player closed out Tiva’s funding round as both a backer and a user — the startup’s grip gels and friction balms were already part of his match routine. Tiva is now in 130 retailers across France.

Vaca adds a group of athletes and CPG operators to the cap table as part of its $1.5M seed round

The beef-tallow tortilla chip brand closed a $1.5M seed led by BAM Ventures, pairing athlete backers (DeAndre Hopkins, Nyjah Huston, and MLB’s Shane Bieber, Mark Canha, and Shelby Miller) with operators like Sweetgreen’s Nic Jammet and Kettle & Fire’s Justin Mares. Built DTC first, it’s now moving to shelf at Whole Foods.

DeAndre Hopkins invests in Lemon Perfect

Hopkins now owns a piece of Lemon Perfect, after approaching the brand about buying in rather than taking a partnership deal. He was already drinking it. What convinced him, he says, was that it tasted like the lemonade he loved as a kid with no sugar added — so ownership was the only version of the conversation he was interested in. He frames it as where athlete deals are heading: asking for equity instead of taking the check.

Alix Earle takes an equity stake in Cymbiotika

Earle bought into the liposomal supplement brand, which hit $150M in 2025 revenue. It’s a familiar pattern for her — she already holds stakes in Poppi, SipMargs, and Gorgie, and launched her own brand, Rēale Actives, in March. She joins a cap table that includes The Weeknd, Post Malone, Kendall Jenner, and Hailey Bieber.

New ventures

Travis Kelce launches NIL venture Tekta with Publicis Sports

Kelce is building Tekta with Publicis Sports and 3 Arts Sports — a consulting and activation firm that helps brands find, structure, and measure NIL deals across a network of 45,000 Division I athletes and 68 Power Four schools. The timing tracks the market: NIL spending is projected at $4.5B for 2026–27, up from $3.6B. Tekta plans to add branding and financial-literacy education for the athletes on the other side.

Tracy McGrady revives the ABCD Camp after a 20-year hiatus

McGrady acquired an 80% stake in the storied high school showcase Sonny Vaccaro ran from 1984 to 2006, with Vaccaro keeping the rest. The first edition in 20 years ran in Phoenix, sponsored by Adidas. ABCD is where Kobe won MVP in 1995 and a 16-year-old LeBron outplayed Lenny Cooke. A documentary is now in development with Carmelo Anthony’s Creative 7.

Jermaine O’Neal and VICTORYROAD+ launch prep sports media brand FUTR5

The six-time All-Star formed a JV to build FUTR5, covering the country’s top high school athletes across YouTube, TikTok, and Instagram, with free short-form feeding a paid tier for live games and documentaries. O’Neal’s Dynamic Prep — a three-time recent champion — anchors it, with baseball added next school year.

Serena Williams rebrands Serena Ventures as Starfire Ventures

Williams dropped her own name from the firm she’s invested through for over a decade, reasoning that a personal name can cap what a company becomes — and she wants this one bigger than her. The track record is already substantial: 100-plus startups and 16 unicorns in the portfolio.

The Cavinder twins launch wellness brand Go Two

Haley and Hanna Cavinder — among the first athletes to build national NIL profiles — launched Go Two, a “frictionless wellness on the go” brand, debuting with two products (Debloat and Sleepy) and plans to expand into hydration, protein, and collagen. It joins a portfolio that already spans the TWOgether fitness app, Azucar tequila, and Hustle Beauty.

Deebo Samuel opens Problem Lounge in Old Town Scottsdale

Samuel opened a three-level concept with chef Cleashaun Hill in the long-vacant Barney’s Boathouse building: flame-grilled dining on the ground floor, a cocktail lounge upstairs, and a rooftop open-air hookah space.

Mo Bamba opens a card shop near the Texas campus

The former one-and-done Longhorn is opening a trading card shop by his old campus, announced through his YouTube channel and the Mo Bamba Cards and Collectibles socials.

Fundraising and acquisitions

Samsonite buys 85% of Shay Mitchell’s BÉIS at a $210M valuation

Samsonite is acquiring 85% of BÉIS for $178.5M in cash, valuing the travel brand Mitchell founded in 2018 at roughly $210M. Beach House Group, the incubator that owned 70%, is selling its entire stake, while Mitchell rolls over about half her equity to keep 15% and stays on as Founder and Head of Creative and Design.

Alex Cooper’s Unwell takes its first outside investment at a $500M valuation

Whitesell’s WTSL — the Silver Lake-backed firm he launched after exiting Endeavor — invested an undisclosed sum valuing Unwell at $500 million, the media company’s first outside capital. Cooper and husband Matt Kaplan, who self-funded the business since 2023 and say it’s been profitable from day one, keep a majority stake.

Brand endorsements

Marriott Bonvoy names Alex Eala the face of its Tennis The World campaign in APAC

The highest-ranked Filipino player in WTA history, and the first to win a WTA Tour singles title, fronts the Asia Pacific edition (excl. China).

eToro extends its Formula One position with Pierre Gasly

eToro signed the Alpine driver, building on the deal that made it Alpine’s exclusive trading and investment partner — running across live events, social, and podcast activations.

Kate Spade names Tyla global brand ambassador

The Tapestry-owned label signed Tyla to a yearlong deal fronting its fall 2026 campaign, built around “joy hiding in plain sight,” with nods to her album APOP* woven in.

Charlie Puth joins Lucky Brand as brand ambassador

Puth fronts Lucky Brand’s fall campaign as the lead name in a roster approach — the brand says it’ll keep spotlighting artists and creators through the season.

Loewe names David Jonsson brand ambassador

The Spanish house tapped the Alien: Romulus and Industry actor as it sets its course under new creative directors Jack McCollough and Lazaro Hernandez.

Under Armour signs Li Yueru, its first female Chinese basketball athlete

The Dallas Wings center — a 2022 World Cup silver medalist — will work with UA across China and globally on youth basketball, women’s sports, and community programming.

New Balance signs five-star recruit Jett Harrison to an NIL deal

New Balance signed the 16-year-old Ohio State commit — the No. 1 recruit in the 2028 Rivals300 — joining his older brother, Cardinals wide receiver Marvin Harrison Jr., on the football roster.

Media deals

Alan Ritchson signs a first-look feature film deal with Netflix

The Reacher star signed a first-look deal through his Dancing Skeleton banner to star in and produce a slate of films. First up: an untitled MotoGP heist thriller from Fast & Furious writer Chris Morgan. The deal follows War Machine, which drew 139.9M views in its first 91 days.

Vic Mensa launches The Vic Mensa Show with Chance the Rapper as first guest

Mensa launched a weekly podcast and video series through ORANJ, his new production company, in partnership with Mass Appeal. Season one runs 24 episodes, with Rapsody, Lena Waithe, and Van Lathan Jr. among the lineup.

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Deal brief · Week of August 10

Tracking the deals shaping the business of culture.

Investments

Bryce Harper and Andy Roddick invest in Jimmie Johnson's Legacy Motor Club

The two-time NL MVP and the 2003 US Open champion join a new ownership group at the Cup Series team alongside IndyCar’s Scott Dixon, Dario Franchitti and Tony Kanaan, plus Kelly Slater, Chase Utley, Darius Rucker, Guy Fieri, Away’s Jen Rubio and CrossHarbor’s Sam Byrne. Johnson stays majority owner with Knighthead Capital Management.

Jack Draper, Tom Segura, Gunna and Bethenny Frankel back watch marketplace Bezel

Authenticated luxury watch marketplace Bezel has added four new investors: comedian Tom Segura, rapper Gunna, tennis player Jack Draper, and entrepreneur Bethenny Frankel. They join a cap table that already includes Kevin Hart, John Legend, J Balvin, and Michael Rubin. Founded in 2022, Bezel has since passed $1 billion in watch listings.

Arthur Fils takes a stake in performance cosmetics brand Tiva

The French tennis player invested and signed on as ambassador, closing out the funding round the startup opened earlier this year. Tiva makes grip gels and friction balms for athletes and is stocked in 130 retailers across France.

New ventures

Stephen and Ayesha Curry open three restaurants with Michael Mina in Charlotte

The Currys are collaborating with award-winning Chef Michael Mina to roll out a trio of new concepts at The Ritz-Carlton, Charlotte. The first, Bourbon Steak, will be a steakhouse. The second, The Eighth Rule, will be a bourbon-forward cocktail lounge and social dining destination. The third, Sweet July Cafe, will be a lifestyle-forward café.

Mookie Betts launches baseball glove company LGND

Los Angeles Dodgers shortstop Mookie Betts has launched LGND, a new baseball glove company that is set to debut with two collections: the MOOK Series and MVRK Series. In addition to its premium glove offerings, LGND will feature an interactive glove customization platform that allows players to design a glove that reflects their individual style and preferences.

Kevin Love opens a Topps partner card store in Lake Oswego

Kevin Love and his brother Collin launches The Alley, a new store that sells trading cards, carrying everything from packs of Pokémon cards to a special, mint condition shiny Michael Jordan card. The Topps partner store includes a wall for individual cards, a card pack bar, and a community lounge and breaking studio.

Fundraising and acquisitions

IG Group buys Underdog for up to $1.3 billion, cashing out several early athlete-investors

The London-listed trading firm is paying $1.1 billion upfront plus a $200 million earnout, with up to $850 million more to employees if the company clears $400 million EBITDA in 2028. Kevin Durant, Jared Goff, Matthew Dellavedova and Wilson Chandler came in on a $10 million round in 2021, when Underdog was valued at $485 million.

Beyoncé buys out Moët Hennessy’s stake in SirDavis

She now owns the American whisky outright, two years after launching it with the LVMH group as its first US spirits brand built in-house rather than acquired.

Jake Paul’s Most Valuable Promotions merges with the PFL

The combined company runs under the MVP banner with close to 400 fighters across boxing, MMA, live events and distribution, led by PFL chief John Martin, previously chairman and CEO of Turner. Paul and Nakisa Bidarian stay on as co-founders and board members, with existing shareholders 885 Capital and Knighthead Capital Management coming in as founding investors.

Partnerships

Kim Kardashian’s SKIMS enters India through an exclusive deal with Reliance Brands

Reliance will operate SKIMS across physical retail and digital, opening first in Delhi and Mumbai before a phased rollout. India follows London and Dubai on the brand’s international map, with Hong Kong and Seoul next.

Sydney Sweeney launches a $22 Erewhon smoothie for her lingerie brand SYRN

Sydney Sweeney has landed an Erewhon collab, launching the Blueberry SYRN — it blends MALK organic almond milk, blueberries, açaí and almond butter with vanilla bone broth protein and Erewhon’s organic A2 whey. The name does double duty. SYRN is Sweeney’s own lingerie brand, launched in January 2026 and backed by Coatue Management, so the smoothie doubles as a media buy for a business she wholly founded rather than a one-off endorsement.

De’Aaron Fox launches a Sharpie capsule with Under Armour

The limited-edition D. Fox x Sharpie collection turns hand-drawn sketches inspired by the Spurs guard’s story into footwear and apparel built on his signature line.

Brand endorsements

Coco Gauff and Taylor Fritz sign long-term deals with Oura

Oura has signed tennis players Coco Gauff and Taylor Fritz to long-term partnerships, announced heading into the 2026 US Open. Gauff’s leans on her reading life and family legacy. Fritz’s campaign frames him as the athlete-entrepreneur, launching with a digital takeover in The Athletic and extending to LinkNYC kiosks across New York City and print in The New York Times.

Luka Modrić joins Kerma Games as brand ambassador and celebrity IP partner

The Croatia captain joins a roster of global names the studio has been assembling across sport and entertainment.

Nike signs 11 high school football players to NIL deals

The prep class was selected at The Opening Finals at Nike’s Philip H. Knight Campus and spans the 2027 and 2028 recruiting classes, the brand’s largest disclosed high school group.

Bella Hadid fronts Alo’s Pre-Fall 2026 campaign

Her second for the brand after Fall 2025, shot in Los Angeles by Mert & Marcus and running across the Airlift Rebel bra, the Trail sneaker and the Softsculpt Precision tank.

Karina joins Converse as global brand ambassador

Converse has officially announced K-pop group Aespa member Karina as its newest global brand ambassador. She models two key sneaker styles: the refined Chuck 70 X and the bold platform Run Star Crush.

Pomellato names Yang Zi global brand ambassador

Kering-owned Milanese jeweler Pomellato has appointed Chinese actress Yang Zi as its global brand ambassador. Her debut campaign for the maison spotlights the Nudo collection, shot by photographer Chen Man.

Montblanc names Wang Anyu brand ambassador

Luxury maison Montblanc has appointed Chinese actor Wang Anyu as its newest brand ambassador. Known for roles in “Dreaming Back to the Qing Dynasty,” “The Last Immortal,” and “Romance in the Alley,” Wang has nearly 9.5 million followers on Weibo.

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Horizon · August 2026

First-person stories from athletes building their next chapter.

By Kotaro Umeda. Edited by Allen Lee.

Chink.

That’s the first word I ever looked up.

I was 10 years old. Nobody explained it to me. They just kept saying it. I still remember the feeling. Not anger. Not even sadness. Just confusion.

Growing up, I was usually the only Japanese kid in the room - classrooms, locker rooms, birthday parties.

I learned English through Lil Wayne. I had Tha Carter III and Tha Carter IV on repeat after school, trying to figure out what “real G’s move in silence like lasagna” actually meant.

Then summer came, and I’d go back to Japan. Except my Japanese wasn’t Japanese enough, so they’d treat me like a foreigner there too.

In Japan, I was the American kid. In America, I was the Japanese kid.

I knew I was different before I had a word for it.

“Where are you from?” was the question I dreaded most. I never felt like I had a good answer. And for a long time I thought that meant I didn’t belong anywhere.

Back then, different felt like a wall between me and everyone else. I didn’t know it would eventually become the thing I relied on most.

For most of my life, soccer was the only world I knew. It was the first place I learned that being different didn’t always mean being the person everyone noticed. Sometimes it meant noticing what everyone else missed.

I was never the flashiest player on the field. I was more interested in seeing something before everyone else did - reading patterns, anticipating situations, and understanding where the game was about to go.

From the age of 6 until I was 27, my job was incredibly specific. Sit in pockets in front of the two center backs and connect with my 10, 7, 11, or 9, and if none of that was on, maintain possession of the ball.

To someone watching from the outside, it probably looked simple. But it required me to constantly read what was happening before it happened - the space opening up, the movement of a teammate, the smallest shift in a defender’s body.

Then in 2025, I retired from professional soccer, and suddenly, the thing that had defined my life for two decades was gone. I remember realizing I would never again need to know exactly where to stand relative to a center back. Strangely, I didn’t feel sad. I felt free.

I never planned on getting into the fashion industry. It found me.

During my second year in the league, I was walking through Porto on an off day when a scout approached me and asked if I would come to a casting. I didn’t think much of it. At the time, it was just a way to make some extra money.

At first, I thought modeling was simple. I just needed to stand there, look good, and get paid. But I was wrong. I found out quickly that it’s another way of telling a story. You have a few seconds to communicate something through your face, your posture, your movement, the way you wear something. There’s nowhere to hide the way there is on the pitch, where you can blend into a system, into ten other guys.

In front of a camera, it’s just you. And that was uncomfortable.

I went from locker rooms filled with people who had spent their entire lives chasing the same dream, to studios filled with people who had never watched me play. Nobody asked about my stats. Nobody cared which leagues I had played in or what clubs I had played for. I had to figure out what else I brought to the industry.

The answer was something I’d spent years trying to overcome.

I was different.

Except this time, that wasn’t a problem to solve. It was the reason I was there.

The casting directors weren’t looking for someone who already belonged in that world. They wanted someone shaped by different cultures who could communicate with an audience in a way nobody else in the room could.

At first, soccer and fashion couldn’t look more different. One happens under stadium lights, measured in goals and wins. The other happens in studios and showrooms, measured by something harder to define - taste, emotion, a feeling nobody can quite explain.

During those years, my life became an odd combination of match days and castings. I never thought the two worlds had much to do with each other. But the more time I spent moving between them, the more familiar they started to feel.

The best people in both worlds had the same obsession. They noticed the smallest details that everyone else overlooked.

On the pitch, that meant reading a defender’s hesitation before it turned into a gap. In a studio, it was a creative director arguing for twenty minutes over a sleeve length, whether a shirt should be tucked or untucked, or a shade of blue that was almost right but not quite. From the outside, those details can look insignificant. But I’ve learned that the smallest details are usually where the biggest differences are created.

I felt that most clearly the first time I walked a runway at New York Fashion Week in 2025. I didn’t know the designer had spent over a year planning that one hour. I didn’t know even the seating was engineered - certain people in certain seats, so photographers could catch the clothes and the celebrity in the same frame.

Fifteen minutes on a runway, built on a year nobody in the audience ever saw.

Over time, I realized they were changing the way I understood storytelling itself.

Soccer taught me to think in cause and effect. One run created the next chance. One decision changed everything that came after it. Fashion showed me a story could live in a color, a silhouette, or the way someone moved. Sometimes it was one frame, caught a half-second too early or too late, and either way changed the whole feeling of the shot.

The best storytellers weren’t always trying to explain something. They made you feel something first. The meaning came later.

Today, speaking has become the place where all of those experiences come together.

After one of my recent speaking engagements, a young Asian student waited until everyone else had left before walking over to me.

Before he said a word, I knew something was wrong. I couldn’t have told you exactly why. Maybe it was the way he avoided eye contact. Maybe it was his body language. I didn’t ask. I just waited with him.

Then he said it.

“I wanted to attempt suicide.”

He told me he was one of the only Asian students at his school. He talked about the bullying, the racial slurs, and how different he felt every day - like there was no version of himself that fit anywhere.

I didn’t have the perfect answer for him. And I couldn’t erase what he had been carrying or tell him everything would suddenly be easy. I just sat with him. I told him I knew the feeling of walking into a room and wondering why you didn’t fit. We talked for a while after that. Before he left, I made sure he had someone he could call and gave him a way to reach me too.

For years, I thought being different was the thing I had to overcome. Sitting across from him, I understood it had become the one thing only I could have brought to that conversation. I didn’t need him to explain what it felt like to be different. I knew that feeling before he ever found the words.

Maybe that’s what all those years were preparing me for. Learning to notice what people weren’t saying. Learning to understand what couldn’t always be explained with words.

The same thing that once made me feel like I didn’t belong had become the way I understood people who felt like they didn’t either.

I think about that ten-year-old kid in Cleveland sometimes. The one who spent years wondering how to answer the question, “Where are you from?”

Wrong question, it turns out.

I spent years trying to figure out where I belonged. Looking back, maybe I was never supposed to belong to just one place.

Every world I entered asked something different of me. America. Japan. Soccer. Fashion. Speaking. I spent so much of my life trying to become enough of one thing that I almost missed what all those worlds had given me.

I spent years trying to become less different. Now I realize that difference was the thing I was always meant to bring.

I’m different.

Kotaro

Kotaro is a former professional soccer player who has played in Campeonato de Brasil, Campeonato de Portugal, United Soccer League, and the Hong Kong Premier League. Today, he's a keynote speaker, author, and fashion model. To keep up with Kotaro, follow him on LinkedIn and Instagram.

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Deal brief · Week of August 3

Tracking the deals shaping the business of culture.

Investments

Chan Ho Park and BTS’s Suga buy a minority stake in the Athletics

Through investment group Team61, the former MLB pitcher and the BTS member are taking a minority position in the A’s — with actors Ken Jeong and Daniel Dae Kim also in the group. Park, the first Korean to play in the majors, becomes the first Korean to buy into an MLB club and takes on a senior adviser role to owner John Fisher.

Virat Kohli takes a 28% stake in fitness chain Vault

Kohli and his brother Vikas formalized a combined 28% equity stake in the premium fitness chain, backing its franchise-led expansion across India. Vault has passed 30,000 members across 30 clubs and is targeting more than 50 by the end of 2026.

Fundraising and acquisitions

Iskra Lawrence’s Saltair sells majority stake to TSG Consumer

PE firm TSG Consumer is acquiring a majority stake in Saltair, the body-care brand Lawrence founded in 2022. She stays on as chief community advocate.

New ventures

Jake Paul launches a family office at Dallas’s Old Parkland

Paul is opening a family office at the Old Parkland campus, tapping former Merrill Lynch director Laura Brady to run it. The firm goes past wealth management — it’s built as an investment and venture-building vehicle spanning AI, defense tech, consumer brands, sports, and real estate, and a platform to scale companies across Paul’s broader ecosystem.

Lewis Hamilton opens his first trading card store

Card Culture by Lewis Hamilton opened its flagship in Frankfurt, built with Dave & Adam’s Card World as a premium retail experience. A collector since childhood, the seven-time F1 champion is positioning it as a bet on the future of the category.

Ice Spice debuts her first fragrance, In Ha Mood

Developed with Revlon, Ice Spice’s debut scent launched on Ulta Beauty’s TikTok Shop.

Brand endorsements

Zendaya becomes the face of Prada Paradoxe

Prada Beauty named Zendaya global ambassador for its Paradoxe fragrance — a scent she says she wore long before the brand approached her, discovered through a friend and turned into her signature.

MS Dhoni becomes the new face of Malabar Gold & Diamonds

The retired India captain signed a long-term deal anchoring the retailer’s “Responsible Jeweller” campaign across its 445 showrooms in 14 countries.

Lee Hyun-joong signs a three-year deal with Nike

The South Korea national-team forward will receive footwear, apparel, and equipment from Nike over three years, and take part in the brand’s global campaigns and marketing.

Roger Vivier names Tan Jianci global ambassador

The French luxury footwear house appointed the Chinese actor and singer its new ambassador, with a role spanning campaigns and personal interpretations of the brand’s archive.

Elsa Hosk becomes the face of haircare brand Lunesi

The Swedish model signed on as global brand ambassador for the premium haircare brand.

Sanju Samson joins Al Ansari Exchange as brand ambassador

The Indian international signed a one-year deal covering advertising, digital content, appearances, and customer engagement.

Roles and appointments

Eddie Pope joins the MLS front office

The former MLS and U.S. Men’s National Team star was named SVP of sporting development for MLS and SVP of competition & operations for MLS Next Pro, overseeing development pathways and the long-term vision for MLS Next Pro.

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Deal brief · Week of July 27

Tracking the deals shaping the business of culture.

New ventures

Savannah James launches holding company Signed, backed by Jay-Z’s PE firm

James and business partner April McDaniel are consolidating their portfolio under a new company called Signed, built to house women-focused media and business ventures. It brings together three existing brands — McDaniel’s creative agency Crown+Conquer, the women’s community Let It Break, and their Everybody’s Crazy podcast — as the foundation for new brands under the umbrella. The launch comes in partnership with MarcyPen Capital Partners, the PE and venture firm co-founded by Jay-Z.

Mookie Betts launches baseball glove company LGND

The Dodgers shortstop is entering the equipment business with LGND, debuting with two lines — the MOOK Series and MVRK Series — plus a customization platform that lets players design their own gloves.

Stephen and Ayesha Curry open three restaurants with chef Michael Mina

The Currys are rolling out a trio of concepts at The Ritz-Carlton, Charlotte, with award-winning chef Michael Mina: a steakhouse (Bourbon Steak), a bourbon-forward lounge (The Eighth Rule), and a lifestyle café (Sweet July Cafe). It extends a partnership that began when Curry launched The Eighth Rule with the MINA Group in San Francisco last year.

Kevin Love opens a trading card store in his hometown

Love and his brother Collin launched The Alley in Lake Oswego, Oregon — a Topps partner store with a card pack bar, a community lounge, and a breaking studio. Inventory runs from Pokémon packs to a mint Michael Jordan card at $375.

Elvis Duran and Paul Heyman launch podcast venture Podrophenia

The broadcasting veteran and WWE Hall of Famer opened Podrophenia, a podcast and creator-development company running out of MCM Studios in Manhattan — offering creators production facilities, audience development, and monetization support.

Fundraising and acquisitions

Iron Maiden sells 50% of its catalog and NIL rights to Pophouse

The band sold a half-stake in its music catalog and its name, image, and likeness rights — including Eddie, the mascot — to Sweden’s Pophouse Entertainment, the firm behind the ABBA Voyage venture. The deal runs beyond the music: the two are filming the current “Run for Your Lives” world tour for a cinematic project.

T.I. signs his entire catalog to Reservoir Media

The global publishing deal covers every song T.I. has written, from his 2001 debut I’m Serious through this year’s Kill the King — a quarter-century of catalog in a single agreement.

Brand endorsements

Ella Bright becomes Rare Beauty’s first ambassador outside Selena Gomez

The Off Campus breakout is the face of Rare Beauty’s “Made You Blush” campaign — the first time the brand has named an ambassador other than founder Selena Gomez.

Keely Hodgkinson launches her first signature collection with Nike

The Olympic 800m champion’s debut athlete pack spans footwear and apparel — black with metallic gold accents, carrying a custom “tornado” signature logo built to signal motion, energy, and control.

Napheesa Collier joins Thorne as athlete partner

Collier signed with supplement brand Thorne, joining a roster that includes Jrue Holiday, Ben Shelton, and Madison Keys.

Jordan Chiles launches her first signature leotard collection with Nike

The two-time Olympian developed the line with GK Elite, translating athlete-driven design into competition-ready apparel — and making signature styles more accessible to young gymnasts.

De’Aaron Fox and Under Armour team up with Sharpie for new shoe launch

Under Armour and Sharpie turned hand-drawn sketches inspired by Fox’s story into the limited-edition D. Fox x Sharpie collection, spanning footwear and apparel.

Napheesa Collier launches her first Jordan Brand signature shoe

Jordan Brand unveiled the “Queen Phee” Heir Series 2, Collier’s first Player Exclusive. The five-time All-Star helped design it — a True Blue and Baltic Blue colorway nodding to Minnesota, with her daughter Mila’s name tucked inside.

Media deals

SOFI TUKKER launches publishing JV Animal Talk with Third Side Music

The Grammy-nominated duo formed a new publishing venture, Animal Talk, with Third Side Music handling global administration, rights management, and sync. TSM also extended its worldwide publishing deal with the pair, a relationship dating to 2017.

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Deal brief · Week of July 20

Tracking the deals shaping the business of culture.

Investments

Nationals prospect Ronny Cruz sells 10% of his future earnings for $1.2M

Cruz partnered with Agentiq to take up to $1.2M upfront against a maximum 10% stake in his future on-field income. Public investors buy shares in his career and receive distributions as he advances through baseball and starts earning.

Coby White joins Ballislife Drink as equity partner

The Charlotte Hornets guard signed on as brand ambassador and equity partner for Ballislife Drink, joining the brand's roster of NBA athlete partners. White grew up watching Ballislife post his own high school highlights.

New ventures

Megan Moroney launches her first fragrance, Calliope, with Scent Beauty

The country star spent a year and a half developing Calliope — heart-shaped bottle included — her entry into the fragrance category, arriving mid–Cloud 9 Tour.

Togethxr and iHeart launch Everyone Watches Women’s Sports

The media company co-founded by Alex Morgan, Chloe Kim, Simone Manuel, and Sue Bird is launching a weekly podcast with iHeart, hosted by Olympic gold medalist Jordan Chiles, journalist Ari Chambers, and comedian Sam Jay.

Brand endorsements

Bryce Harper and Under Armour launch the UA Harper 11

The 11th installment of Harper’s signature cleat makes it the longest-running active signature footwear line in MLB. The pair signed a 10-year extension in 2015 — then the largest endorsement deal for a baseball player.

Livvy Dunne and JUNKLESS launch a nationwide NIL contest

Dunne is partnering with the snack brand and The Livvy Fund to award one female college athlete a paid NIL deal. Dunne personally selects the winner, who becomes a JUNKLESS brand ambassador — $4,500 cash, a semester’s supply, and monthly content features through December.

IU becomes Jaeger-LeCoultre’s first Korean global ambassador

The singer and actress joins the Swiss watchmaker as a global ambassador, debuting through its “The Hour Before” interview series.

Guo Hanyu joins Lululemon as brand ambassador

The Chinese tennis player is the first from her country signed by Lululemon to compete across all four Grand Slams. She holds six WTA doubles titles and a career-high doubles ranking of No. 9.

Sourav Ganguly joins InsuranceDekho as brand ambassador

The former India captain fronts a campaign for the insurtech platform aimed at its network of more than 497,000 advisors.

Partnerships

Amy Poehler backs new narrative audio studio Please and Thanks

The studio, launched by former Pineapple Street Studios executives Joel Lovell and Henry Molofsky, debuts with Manifesto! for Audible Originals. Poehler’s Paper Kite Productions has partnered with the studio on an investigative documentary audio series, sold to Universal Studio Group Audio for a 2027 launch.

Media deals

Netflix strikes a deal with celebrity chef Nick DiGiovanni

Netflix will host DiGiovanni’s full back catalog alongside new content from his “Nick DiGiovanni” and “Nick’s Kitchen” channels, streaming day-and-date with YouTube.

Stokes Twins sign a content deal with Netflix

Alan and Alex Stokes are bringing their YouTube archive to Netflix and moving into long-form with a new series set to premiere in 2027.

Colin & Samir partner with Lexus on a four-part YouTube series

The creators are producing four sponsored videos and four ad campaigns with Lexus, developed with Google Creative Works and Portal A. The series follows them driving cross-country in a GX 550 and RZ 550e to reconnect with their creativity after both lost their homes in the 2025 LA fires.

Roles and appointments

Whoop hires former Olympian DJ van Hameren

The wearables company appointed van Hameren — a two-time Olympic track cyclist who spent three decades at Nike — as Chief Marketing Officer, leading global marketing, brand partnerships, and international expansion.

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Horizon · July 2026

First-person stories from athletes building their next chapter.

By Michal Mrazik. Edited by Allen Lee.

Originally published on mainstreet on July 2026. Updated August 2026.

Seen by Millions, Known by None

For most of my life, I thought hockey would be the reason people remembered my name.

Not because I wanted fame. But because everything I did revolved around becoming the best hockey player I could possibly become.

Then one day, the internet decided something else about me mattered more.

I still remember that evening after practice. I thought something was wrong with my phone.

It wouldn’t stop buzzing.

Tons of Instagram notifications. New followers every time I refreshed the screen. First it was a few hundred. Then thousands. Then tens of thousands.

I remember staring at my phone thinking, is Instagram broken?

It took me a few days to figure out what had happened. Someone had dug up an interview I had done after the World Junior Championship, clipped thirty seconds of it, and posted it online. And the internet did what the internet does.

I actually didn’t score the game-winning goal or do anything spectacular in that game. I was simply answering a reporter’s questions after a game, the same way I had done dozens of times before. A camera happened to catch my face at an angle millions of people liked.

That’s it… I went viral because of the way I looked.

Almost overnight, strangers from every corner of the world felt like they knew me. Thousands of people confidently explained who I was without knowing a single thing about me. Some made edits with dramatic music. Others posted reaction videos. Even memes. Suddenly, I wasn’t just a hockey player.

But the strangest part wasn’t that people found me attractive. It was that the thing I had spent almost twenty years building suddenly became invisible.

Nobody cared about the years I spent chasing the NHL dream. Or that I had represented Slovakia at the World Championships. Or the early mornings, the bus rides, the injuries, the rehab, the sacrifices my family made so I could keep playing the game I love.

Twenty years of work disappeared behind thirty seconds of video. And those thirty seconds became my introduction to the world.

In some ways, it opened doors. I met incredible people, had conversations I never would have had otherwise, and connected with people far beyond the hockey world. For that, I’m genuinely grateful.

But attention has a cost people rarely talk about.

Overnight, my identity stopped feeling like it belonged to me.

People recognized me in places I had used to go. Some filmed me before saying hello. Some took photos without asking. My parents started getting questions from complete strangers. Random numbers started calling my phone. Over time, my inbox became this strange mix of kindness, curiosity, opportunities, and people projecting an entire identity onto someone they’d only seen for a few seconds online.

Then there were the comments. Some were kind. Some were funny. Some reduced everything I had worked for to four words.

“Just a pretty face.”

It’s strange how a sentence from someone you’ll never meet can stay with you longer than a compliment from someone you love.

Not because I believed it. I didn’t. But because it reminded me how quickly people mistake what they can see for who you are. And it’s not their fault. Thirty seconds isn’t enough time to know anyone.

Dealing with all that attention made me realize something. Athletes talk about physical toughness constantly - how to take a hit, play through pain, compete on little to no sleep. But nobody trains you for the mental part of professional sports. Millions of strangers could praise you, criticize you, laugh at you before you’ve even said a word to them. There’s no coach or playbook for that kind of stuff.

On every team I played for, the guys who handled attention best weren’t the most physically talented ones. They were the ones with something steady underneath it all - a workout routine, a sleep schedule, a recovery regimen, a diet, and most importantly, a relationship with their mind that didn’t shift depending on what people said about them that day. I didn’t have a name for what that was. I just knew, watching them, that I wanted whatever they had.

Retired At Twenty Three

Monday, October 2nd, 2023. Hartford.

I flew to New York five months into the hardest training block of my life, chasing one more shot at an NHL contract with the Rangers.

This was my chance.

First day of camp, I fell into the boards. A player about my size fell right behind me, knees first, straight into my lower back.

A few hours later, I was lying in a hotel room, barely able to move.

Dislocated coccyx. Multiple herniated discs.

Just like that, my first real shot at the NHL ended during the first period of my first practice.

By the end of the week, they sent me down to the ECHL in Cincinnati. I played three games in three days, barely able to stand upright. I did what I had been taught to do my entire career - push through the pain and don’t complain about it.

Looking back, I shouldn’t have. But I didn’t know how to do it any other way. Pain was just the cost of playing. So I kept training. Kept playing. Kept telling myself I’ll get through it.

In the fall of 2024, the pain came back. This time, it wasn’t something I could skate through.

I flew to Prague, then Vienna, then Paris, then London, looking for one doctor who’d tell me something different than the last one.

Nobody did.

Finally in London, I got a definitive answer. The only option left was a surgery that carried a real risk of leaving me in a wheelchair. And even if it went perfectly, my hockey career was over.

I was twenty three years old.

I wrote my retirement announcement on the four-hour train ride home. I cried the entire way.

For almost twenty years, I had asked my body to carry my biggest dream. I trained it relentlessly. Pushed it past its limits, season after season. Expected more from it every single year, and never once asked if it had more left to give.

Somewhere in there, I stopped seeing my body as something I was responsible for, and started treating it like something that simply had to keep producing.

That’s when I realized that most support systems for elite performers, athletes or otherwise, are built to manage output, not protect the person producing it. People obsess over performance. They rarely ask what it costs you, in your body or your mind, until something breaks badly enough to notice.

My mom always told me nobody cares about your health more than you do. I used to think that was just something moms say.

After Hartford, I finally knew what she meant. And I knew exactly how expensive it is to learn that lesson at twenty three years old.

What Now?

After I retired, people kept asking me the same question: what now?

For a long time, I didn’t have an answer. But I couldn’t stop thinking about one thing: how do you sustain performance at the highest level without it costing you everything else?

At first, I thought what happened to me belonged to professional sports. Then I started meeting founders, artists, actors, investors, musicians, creators. People operating at the top of their fields.

On paper, their lives looked nothing like mine. But underneath, they felt familiar in a way.

I met a founder who hadn’t slept more than five hours a night in years because there was always another urgent problem to solve. An actor who admitted he’d stopped taking care of himself because there was “no time” between projects. A creator who tracked every little detail about his content but couldn’t remember the last time he had a full night of uninterrupted sleep.

People admired them for their output. Almost nobody asked what it was costing them.

I recognized the pattern immediately because I’d lived it too.

Everyone wants elite performance. Almost nobody builds a system to sustain it. It’s never just physical. It’s never just mental, either. It’s both. I don’t think I really understood that until I’d already lost the chance to apply it to my own career.

I can’t stop wondering what my own career might have looked like if someone had helped me understand that sooner. Whether Hartford happens the same way if I’d known then what I only know now.

What frustrates me about a lot of the wellness world today is how much of it sells fragments and calls it a solution. A cold plunge here, a supplement stack there, a morning routine borrowed from a successful businessman with no connection to how you actually sleep, train, or think.

So that’s the space I’m building in now. Not another supplement. Or another app that spits out a generic plan. Something closer to what the Greeks understood a long time before wellness became an industry - that the body and the mind were never meant to be trained separately. The kind of system I wish someone had offered me before I went pro.

I don’t have all of it figured out yet. What I do have is a question I can’t put down, and a growing list of people telling me I’m not the only one thinking about this.

I believe the next generation of elite performers won’t win because they push themselves harder. They’ll win because they learn how to last longer.

That’s what I’m trying to build.

I don’t know exactly what it’ll become yet. But for the first time since I was a little kid chasing the NHL, I’m waking up every day chasing something that feels just as important.

M.M.

Michal Mrázik is a former professional ice hockey player who represented Slovakia at the World Championships and played across the Slovak Extraliga, AHL, and ECHL. He's the author of Life Doesn't End Here, and is currently building a performance system for elite performers across sports, entertainment, and business. To keep up with Michal, follow him on LinkedIn and Instagram.

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Deal brief · Week of July 13

Tracking the deals shaping the business of culture.

Investments

Alma Mater draws a group of athlete-investors

The golf footwear startup, founded by Nike Golf and FootJoy alums, brought on a wide roster of athlete backers — including NFL players Jordan Poyer and Levi Wallace, MLB veterans Kevin Millar and Jackie Bradley Jr., NHL legends Joe Pavelski and Tyler Seguin, and professional golfers Taylor Montgomery and Natasha Oon — ahead of a new fundraising round. Its shoes use a proprietary three-piece construction platform.

APEX takes a stake in the Northern Super League

The athlete-backed investment firm — whose 100+ backers include Carlos Sainz, Lando Norris, and Giorgio Chiellini — is investing an initial $20M in Canada’s first professional women’s soccer league, with an option to reach $30M. The deal values the NSL at roughly $85M.

Fundraising and acquisitions

David Beckham’s IM8 raises $1B

Beckham’s wellness startup secured $1B in growth financing from General Catalyst’s Customer Value Fund. Under the structure, the fund covers up to 70% of IM8’s monthly marketing spend in exchange for a capped return tied to each month’s cohort of newly acquired customers.

Full Swing, the Tiger Woods–backed golf simulator, acquired for $530M

Versant — the Comcast spinoff that owns Golf Channel — is buying Full Swing from Bruin Capital for $530M. Woods has held a stake since 2015; the company powers TGL, the league he co-founded with Rory McIlroy, and is the PGA Tour’s official simulator.

New ventures

Megan Thee Stallion launches her first fragrance with Coty

The three-time, Grammy award-winning singer launches her new fragrance, Hot Girl Summer Eau de Parfum, marking the latest expansion of her growing business portfolio. Developed in partnership with Coty, the limited-edition product is designed as a unisex offering, and will debut through an exclusive launch with Ulta Beauty. This marks the latest extension of her Hot Girl Summer brand, which started as a Walmart swimwear line and has since grown into menswear and pet apparel.

Michael Strahan’s SMAC Productions launches a podcast network

The media platform Strahan co-founded with Constance Schwartz-Morini is launching a podcast network this fall, anchored by two flagship shows — one with Terrell Owens and Chris Spencer, the other with Strahan and Schwartz-Morini.

Brand endorsements

Hailey Bieber and Gap launch The Hailey Jean denim capsule

Bieber reimagines Gap’s relaxed denim icons through her own ‘90s-leaning lens, with two fits — the Extra Baggy and ‘90s Low Rise Loose — anchoring a limited-edition capsule and campaign.

Kylie Jenner teams up with Dunkin’ on the King Kylie Collection

A limited-time nod to her “King Kylie” era, the collaboration pairs a retro campaign with three pink-hued drinks: a Candy Pink Lemonade Refresher, a Vanilla Pink Cloud Latte, and a Pink Lemon Drop Suncloud Lemonade.

Graff taps BTS’s Jung Kook as its first-ever global ambassador

British luxury jeweler Graff made history in by appointing BTS member Jung Kook as its first-ever global house ambassador in its 66-year history. He fronts the House’s new Laurence Graff Signature campaign in pieces from the brand’s unisex goldwear collection.

Michael Jordan named Upper Deck’s first Legacy Partner

Jordan extended his 30-year relationship with Upper Deck, granting the company exclusive rights to keep producing his authenticated autographed collectibles — and taking a more hands-on role in product selection and creation.

Sachin Tendulkar becomes the face of Sulphur Mills

The cricket icon signed on as brand ambassador for the Indian agriculture company, lending his national reach to a push for sustainable farming technologies and soil health.

Darian Mensah signs a luxury watch NIL deal with Derby Watch Supply

The Miami quarterback inked one of the first-ever luxury watch NIL partnerships ahead of his Hurricanes debut, promoting the Rolex Datejust after leading Duke to an ACC title last season.

Media deals

Viola Davis inks a first-look deal with Universal Global Television

JuVee Productions, Davis and Julius Tennon’s company, signed a first-look TV deal with UGT — kicking off with Pawn, a romantic drama adapted from a Kennedy Ryan short story.

Roles and appointments

Landry Fields joins Project B to lead its men’s basketball division

Project B, the new global basketball league, has named former Atlanta Hawks general manager Landry Fields as its head of men’s basketball. The league will feature 6 teams with 11 players and plans to expand across Europe and Asia. Valencia, Spain, and Tokyo have already been announced as two of the host cities. It has started rolling out its women’s circuit, with participation from Dallas Wings rookie Azzi Fudd, former WNBA MVP Nneka Ogwumike, Alyssa Thomas, Jonquel Jones, Jewell Loyd and Seattle Storm rookie Awa Fam.

Jeremy Lin makes his in-game broadcasting debut

Lin called live games at NBA Summer League in Las Vegas alongside play-by-play announcer Drew Carter, providing on-air commentary and analysis in his broadcasting debut.

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Deal brief · Week of July 6

Tracking the deals shaping the business of culture.

Investments

Premier Lacrosse League raises $100M, adds Glen Powell and Rob McElhenney as investors

The $100M Series E was led by Ares Sports and Joe Tsai, with Powell and McElhenney joining the cap table. Proceeds go toward media distribution, sponsorship growth, the Women's Lacrosse League, and youth access — ahead of lacrosse's Olympic return at LA28.

Pau Gasol invests €55M in Liga F

Gasol16 Ventures, partnering with Fortified Partners, is putting €55M into Spain’s top women’s football league — acquiring between 35% and 49% of Liga F clubs’ future commercial revenue rights for 25 years.

Kyle Lowry joins the Toronto Tempo ownership group

The former Raptors star and his wife, Ayahna Cornish-Lowry, have taken a stake in the WNBA’s Toronto Tempo — joining an ownership group that includes Serena Williams, Masai Ujiri, and Larry Tanenbaum.

Giannis Antetokounmpo doubles down on Superpower

The NBA MVP is joining preventative health platform Superpower as its first-ever Global Brand Ambassador while increasing his existing investment. The platform gives everyday consumers access to the deep diagnostic testing typically reserved for pro athletes.

Josh Morrissey invests in Indigenous food brand Mitsoh

The Winnipeg Jets defenseman came in as a strategic investor in Mitsoh’s multimillion-dollar growth round, led by Raven Indigenous Capital Partners. The capital funds national expansion and production upgrades for the traditional meat snack brand.

New ventures

Ashton Kutcher leaves Sound Ventures to launch a new VC firm

Kutcher is departing Sound Ventures to start a new fund with Morgan Beller — formerly a GP at NFX, a partner at Andreessen Horowitz, and co-lead of Meta’s Libra project. The firm targets early-stage companies building the physical layer beneath AI: infrastructure, energy, and deep tech.

Georgina Rodríguez launches activewear brand Mimoa

The Dubai-based, direct-to-consumer line debuts with 27 lifestyle basics — leggings, crop tops, hoodies — all priced under €100, positioning premium athleisure at an accessible tier.

Brand endorsements

Erling Haaland becomes the face of WALOVI

The Manchester City striker signed as global ambassador for WALOVI, the international arm of Wang Lao Ji — a Chinese herbal tea brand whose recipe dates to 1828. Another line on one of football’s deepest commercial portfolios.

Jeremy Lin signs his first beverage collaboration with Passion 24

Lin has partnered with Passion 24 to build GuoLiShui, a Taiwanese hydration drink made with fruit juice, coconut water, electrolytes, and green tea extract.

BTS’s V becomes JINRO’s first-ever global ambassador

The world’s best-selling soju has named V its inaugural global ambassador, part of a strategy to grow Jinro’s brand recognition and appeal across international markets.

Shane Lowry partners with Stryker as global brand ambassador

The major champion signed a multiyear deal with the medical technology company’s Joint Replacement division, fronting a campaign focused on the role caregivers play in recovery.

Lori Harvey named Chief Creative Advisor at Gran Coramino

Kevin Hart’s tequila brand has appointed Harvey to lead its “Coramino Woman” initiative, steering creative direction, campaigns, and cultural activations following the brand’s milestone of over $200 million in retail sales.

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Deal brief · Week of June 29

Tracking the deals shaping the business of culture.

Investments

Jalen Brunson takes equity in Just Salad

The Knicks star and 2026 Finals MVP has become a partner and equity owner in the New York–born fast-casual chain — its first-ever athlete partnership and his first restaurant investment. Brunson will be embedded in operations, working with the leadership and culinary teams.

Pat McAfee joins PB&J brand Jams as co-owner

The host's first food and beverage investment is a leadership position with Jams, a PB&J brand that launched in July 2025 and has nationwide distribution at Walmart and Target.

Baker Mayfield, Jalen Williams, and Sydney McLaughlin-Levrone invest in OKC's new soccer club

The Heisman winner, Thunder forward, and Olympic gold medalist are backing Oklahoma City's new professional soccer club and its surrounding stadium district, developed by Echo Investment Capital.

New ventures

Grace Beverley becomes co-owner of Water2

The serial founder behind TALA and SHREDDY has taken a co-ownership stake in Water2 and launched Water2skin, a shower-filter range for skin and hair. She was a customer first — her fiancé installed the filters at home before she signed on.

Matty Matheson and Ricky Staffieri launch film studio Super Athletic Film Co.

The Bear’s Fak brothers have teamed with producer Hannah Welever to launch a production company focused on original film and TV. Its first feature, Grind, won the 2026 Frontières Platform at Cannes’ Marché du Film.

NBA players union launches commercial arm PLYRS UNTD

The NBPA has launched PLYRS UNTD, a consumer-facing brand built to commercialize the collective name, image, and likeness rights of NBA players — created in collaboration with Kendrick Lamar’s creative agency, Project 3. It will pursue licensing, merchandise, content, and player-brand collaborations.

Fundraising and acquisitions

L Catterton invests in Mara Roszak’s haircare brand Rōz

The consumer-focused PE firm has taken a significant minority stake in Rōz, the clean haircare line from celebrity stylist Mara Roszak — whose red-carpet clients include Emma Stone and Zoe Saldaña. Existing backers Silas Capital and G9 Ventures joined the round.

Brand endorsements

Darryn Peterson signs one of the richest rookie shoe deals in NBA history

The No. 2 pick re-upped long-term with Adidas — the brand that first signed him at 16 — in one of the richest rookie sneaker contracts the league has seen.

Jude Bellingham joins men’s grooming brand Onside

The Real Madrid and England midfielder has signed as partner and global ambassador for Onside, the premium men’s personal care brand co-founded by NBA star Jayson Tatum.

Kaia Gerber named Uni’s first Creative Partner in Residence

The luxury body care brand tapped Gerber for a long-term role spanning content, product innovation, and creative direction — launching with a Theo Wenner–shot campaign for its 24-Hour Body Serum.

Kim You Jung joins Charles & Keith as global brand ambassador

The Singapore-based footwear and accessories brand named the South Korean actress its newest global ambassador.

Kilian Jornet joins AI running app Kotcha as athlete founder

The trail-running legend has come on as an athlete founder at Kotcha, alongside marathon great Eliud Kipchoge. The AI platform turns elite training philosophies into adaptive plans that flex around a runner’s life.

Media deals

Mercedes Ron signs first-look deal with Amazon MGM Studios

The My Fault author has signed a first-look deal to executive-produce every future adaptation of her books, and can bring other authors’ IP to the studio for adaptation.

Alex Cooper partners with Google Pixel on microdrama

Cooper is entering the microdrama space with Moving On, a 14-episode branded vertical series produced by her media company Unwell in partnership with Google Pixel.

Roles and appointments

Novak Djokovic joins General Atlantic as Global Strategic Advisor

The 24-time Grand Slam champion is joining the growth-equity firm as a Global Strategic Advisor, working directly with leadership, portfolio companies, and investors across healthcare, life sciences, consumer, and tech.

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Deal brief · Week of June 22

Tracking the deals shaping the business of culture.

Investments

Jake Paul closes oversubscribed $100M growth fund

Anti Fund — the venture firm Paul co-leads with Geoffrey Woo — closed its oversubscribed $100M Growth Fund I, bringing total AUM north of $180M. The portfolio already includes OpenAI, SpaceX, Anduril, Cognition, and Helion, backed by a global LP base spanning institutional investors and family offices.

Gareth Bale launches $500M+ sports private equity fund

The retired Wales and Real Madrid star has formed a sports-focused fund with American PE firm Juggernaut Capital, targeting north of $500M. The vehicle plans to invest across teams and leagues in both men’s and women’s sports.

Kat Stickler joins potato chip brand Snackish as part-owner

The creator has taken a stake in Snackish — a chip brand founded by SmartSweets’ Tara Bosch — which just made its nationwide retail debut at Target.

New ventures

Justin Bieber expands SKYLRK into audio equipment

Justin Bieber is taking his lifestyle brand SKYLRK into consumer tech with an audio line — headphones and speakers merging streetwear aesthetics with personal electronics.

Hailey Bieber’s Rhode drops its first bronzer under e.l.f.

Rhode released Pocket Bronze — its first cream bronzer — as part of its Summer 2026 collection. It’s the first new product since e.l.f. closed its acquisition of the brand last August for up to $1B.

Peyton Manning’s Omaha Productions brings World Series of Poker back to ESPN

Omaha Productions will produce the 2026 WSOP Main Event and Final Table for ESPN, marking the tournament’s return to the network.

Ice Cube takes BIG3 public at $290M valuation

The league co-founded by Ice Cube has struck a deal with SPAC Graf Global Corp. to go public later this year at a $290M valuation — giving fans a chance to buy stock in the league. Investors include former Baltimore Orioles owner John Angelos and Fortress Investment Group’s Peter Briger and Drew McKnight.

Brand endorsements

Priyanka Chopra joins Rolex as global brand ambassador

Priyanka Chopra Jonas has officially joined Rolex’s roster of Testimonees — alongside Leonardo DiCaprio, Zendaya, and Martin Scorsese — representing the brand from the world of cinema.

Madonna becomes KIKO Milano’s global brand ambassador

The Italian cosmetics brand named Madonna its global ambassador as it makes its first push into the American market — anchoring a U.S. retail rollout starting with three Macy’s doors, with 27 more planned in the coming months.

Harry Kane and Declan Rice sign with Ōura ahead of the World Cup

England’s captain and vice-captain have both signed as global ambassadors for Ōura, using the Ring 5 to monitor sleep, recovery, and daily readiness as the tournament gets underway.

Antoine Semenyo named Ahmad Tea’s global brand ambassador

The Bournemouth and Ghana winger is the lead face of Ahmad Tea’s new “Preparation is Everything” campaign, spanning TV, digital, retail, and on-pack activations globally.

Tyler “TD” Davis named Guardian Sports’ first-ever Loop signature athlete

The former NFL player and flag-football competitor is now the face of Guardian Sports’ Loop headband — a bet that safety gear becomes the next category as flag football heads to the Olympics.

Neymar licenses his AI likeness to microdrama platform FlareFlow

Neymar has licensed his AI likeness for a 16-title vertical microdrama franchise with FlareFlow, spanning sports redemption drama to science fiction — produced using AI-powered live-action workflows.

OG Anunoby is getting a Skechers signature shoe

After his Knicks title run, Skechers confirmed Anunoby is getting his own signature shoe — only the brand’s second basketball signature athlete after Joel Embiid, and the first to win an NBA Finals in a Skechers.

Kelsey Plum joins Adidas

The WNBA star has signed with Adidas, joining a women’s basketball roster that includes Candace Parker, Aliyah Boston, and Satou Sabally. Plum was previously with Under Armour, whose partnership ended in April.

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Deal brief · Week of June 15

Tracking the deals shaping the business of culture.

Investments

Paolo Banchero takes equity in Triad Training Systems

Banchero has become an investor and lead ambassador in Triad Training Systems — makers of the R3BAR he’s used since he was 14, from Seattle youth prospect to No. 1 overall pick. Instead of pursuing a traditional endorsement deal, he acquired an equity stake in his origin story.

20+ NFL and MLB athletes back modular housing company Kinexx

Jameis Winston, Mark Ingram, Cam Jordan, Jaylon Johnson, and a roster of pro athletes are backing Kinexx Modular Construction, which just launched a crowdfunding campaign targeting 25,000 homes. The raise is also being opened up to non accredited investors.

New ventures

Tom Brady launches organic coconut water brand Good Nut with Gopuff

Brady’s second venture with Gopuff — after GOAT gummies — is a certified-organic coconut water called Good Nut. Three flavors, $3.29 a can, Vietnamese coconuts, no added sugar. The chocolate variety is the first certified-organic chocolate coconut water on the market. Coconut water is an $11B market by 2030; Gopuff says its own category sales are up 115% YoY.

Pierre Gasly enters the functional beverage market with Minded

The Alpine F1 driver spent two years building Minded, a premium electrolyte brand bridging high-performance hydration and everyday wellness, unveiled during Monaco Grand Prix weekend.

Coco Rocha launches OFF/DUTY by Coco Rocha on QVC

The supermodel is turning her on-the-go lifestyle into a fashion and accessories label in partnership with Xcel Brands, debuting on QVC in Fall 2026.

Drake drops Cloudar, his second fragrance

Better World Fragrance House is back with Cloudar — a woody-aromatic EDP made with perfumer Michael Carby and Givaudan. $152 for 3.4 oz, exclusively at Ulta June 7.

Brand endorsements

Julián Álvarez becomes the face of AI camera startup XbotGo

The Argentine World Cup winner signed as global ambassador for XbotGo ahead of 2026, fronting a “Dare To Dream” campaign built around AI auto-tracking cameras for grassroots football. La Araña goes Silicon Valley.

Suni Lee becomes Phlur’s first-ever celebrity ambassador

The Olympic gold medalist is fronting Phlur’s “Icons with an Icon” campaign across its three best-sellers: Missing Person, Father Figure, and Vanilla Skin. The brand went viral on TikTok, and was acquired by TSG. This marks Lee's official entry into the fragrance category.

Ilia Topuria partners with neurotech brand Vielight

The UFC champion has partnered with Vielight, whose light-therapy technology targets brain performance and recovery.

Brie Bella partners with HONE Health on longevity and hormone optimization

The WWE Hall of Famer signed as official ambassador with HONE Health, using the platform for hormone optimization and post-workout recovery — as both an active competitor and a mom.

Roles and appointments

Queen Latifah and LL Cool J join BET Media Group’s Board of Advisors

BET’s inaugural advisory board brings together six figures across entertainment, sports, and finance — Queen Latifah, LL Cool J, BET founder Bob Johnson, NFL EVP Troy Vincent, Lazard President Raymond J. McGuire, and Paramount Skydance’s George Cheeks.

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Deal brief · Week of June 8

Tracking the deals shaping the business of culture.

Investments

Luka Dončić takes a stake in Italian club Vanoli Cremona

The Lakers star has joined an investor group, led by former Mavericks executive Donnie Nelson, that bought Lega Basket Serie A club Vanoli Cremona. The group plans to relocate the club to Rome for the 2026–27 season and has bid for it to represent the city in the NBA’s planned European league, which could launch as soon as 2027.

Anthony Edwards, Kyler Murray, Tracy McGrady and others take equity in EV maker Karma

Luxury EV manufacturer Karma Automotive launched Karma Nexus, an invitation-only ownership program. Athletes including Anthony Edwards, Kyler Murray, Bryce Young, Dylan Harper, Ron Harper Jr., and Tracy McGrady joined as investors in the company, in addition to becoming customers.

Elina Svitolina joins French startup Tiva as ambassador and investor

The tennis star has taken an equity stake in Tiva alongside a brand-ambassador role, combining the partnership with a direct investment in the company.

Fundraising and acquisitions

Khloé Kardashian’s Khloud raises $15M

The protein-popcorn brand raised $15M, bringing total funding to $27M since its 2025 launch. The brand says the round will fund distribution at Walmart, Target, and Starbucks and an expansion into chips.

Eli Manning's investment firm buys RCX Sports, the company behind NFL Flag

Brand Velocity Group — the PE firm where the two-time Super Bowl MVP is a partner — has acquired RCX Sports from Raine Partners. RCX runs the official youth programs for the NFL, NBA, WNBA, MLS, NHL, and MLB, including NFL Flag, which has more than 830,000 players.

HarbourView acquires Stefflon Don’s music catalog

The investment firm has bought the British rapper’s music catalog, adding it to its roster of artist rights.

New ventures

Grupo Frontera launches its own label, BorderTown Records

The música Mexicana group has launched a record label, BorderTown Records, taking control of its output and release strategy.

Sydney Sweeney launches production company Honey Trap

After the finale of Euphoria, Sweeney formed Honey Trap with collaborator Kaylee McGregor, who will serve as president of production and development. The company has a first-look deal with Sony Pictures, where Sweeney starred in and executive-produced Anyone But You.

Brand endorsements

Stephen Curry signs a 10-year, $400M-plus deal with Li-Ning

After ending his Under Armour partnership, Curry signed with Chinese sportswear brand Li-Ning to expand Curry Brand globally. The deal covers basketball products, athleisure, a golf line, and the ability for Curry to sign other athletes, and Li-Ning plans Curry Brand stores in the U.S. and China.

BLACKPINK's Jennie becomes Vaseline's first global ambassador

Unilever-owned Vaseline named Jennie its first global ambassador for body care — the first such appointment in the brand's roughly 150-year history — fronting its Gluta-Hya and Pro Derma lines.

Kendall Jenner becomes K-beauty brand Anua's first global ambassador

Anua named Jenner its first-ever global ambassador in a multi-year deal. The brand surpassed $500M in global revenue in 2025 across 160 countries and was TikTok Shop U.S.'s top beauty brand in 2024.

WNBA's Sophie Cunningham and Monique Billings sign with European Wax Center

The two WNBA players have signed an endorsement deal with European Wax Center.

Partnerships

Rafa Nadal Academy's Padel Tour expands across Europe with Holafly as global partner

The academy's amateur padel circuit is adding stops in Poland, the UK, and Germany — having already launched in the U.S. — with travel-eSIM company Holafly as its global partner.

Media deals

Jay Shetty’s podcast lands a joint Netflix–Spotify deal worth up to $100M

The On Purpose host signed a multi-year deal to bring his video episodes exclusively to Netflix and Spotify starting July 13, moving them off YouTube. It is the first time the two companies have jointly signed a creator, and the deal follows the end of Shetty’s run with iHeartMedia.

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Horizon · Jun 2026

First-person stories from athletes building their next chapter.

By Chisom Okpara. Edited by Allen Lee.

Originally published on mainstreet on June 2026. Updated August 2026.

I drove the lane at UVA and at the last second pulled it back to kick it out.

I don’t even remember the pass. But I remember the landing.

I felt a pain so loud it drowned everything else out. I couldn’t bend my knee. I couldn’t think. Then came the fear and panic - the kind that hits before your brain catches up.

Three days later, I was back at practice, moving slowly, with no idea what the MRI would say. Then Dr. Safran called and pulled me in.

“Patellar tendon, more than 50% torn. You’re done for the season.”

Just like that, my senior season was over. I walked into practice thinking I was managing an injury. I walked out knowing my year was gone.

What I didn’t know yet was that those few seconds at UVA were about to give me something I never really had before…

Time.

I’m four months out from surgery now - rehab twice a day, every day. But the space in between is where this whole other life has been quietly taking shape.

I’ve always known I wanted to invest in early-stage startups. Turns out, my injury moved up the timeline.

To date, I’ve met with more than 30 VC investors. I wrote my first check into an early-stage sportstech startup. And I’m building a network that’s growing faster than I can keep up with.

I’m still new at this. I’m still learning. But I’ve been getting reps in.

And for any athlete sitting on the same itch I had, wondering whether there’s actually a path into the VC world, here’s what I’ve learned so far.

Pattern Recognition Comes From Getting Your Reps In

Judgment in early-stage investing is a muscle. And like any muscle, it gets built through volume.

One piece of advice I keep hearing from veterans in the space is this: if you want to develop an eye for great startups, you need to see a massive number of deals. Take multiple founder meetings a day. Study the original pitch decks of companies that ended up becoming huge.

This feels like familiar territory, because it’s the same thing I’ve been doing my whole life. You take hundreds of shots until the motion becomes automatic. You practice alone in an empty gym so that when the buzzer’s about to go off and the lights are on you, your body already knows what to do.

Early-stage investing works the same way. You sit in enough founder meetings and eventually your brain starts picking things up - which founders have what it takes, which problems are real, and which market opportunities feel inevitable.

There’s no shortcut to pattern recognition.

VC is a Relationship Business

The best investors operate as nodes in a highly trusted network.

From the outside, this industry can look cold, cutthroat, and closed off. But once I started getting inside the rooms, it felt surprisingly relational.

I’ve had countless meetings where the next steps rarely involve anything transactional. Sometimes, one conversation turns into another introduction, then another. Over time, those relationships started opening doors I never would’ve found on my own.

One of those introductions led me to Eric Chen at OVO Fund, which eventually led to me writing my first check into a startup called The Intelligent Search Company.

VC is a relationship business. Being welcomed into the industry requires proving you can built trust. Once you have it, the industry becomes far more collaborative than people realize.

Skate to Where the Puck Will Be

After studying the history of VC, I realized that a lot of alpha comes from looking past the current hype cycle.

It’s important to become an expert in something that’ll be hot in five years. Hardware. Engineered biology. Whatever the next thing is. Build expertise in that space before it goes mainstream.

This is challenging but also exciting. It forces a different kind of patience. It demands a shift from reacting to what everyone is currently talking about to figuring out what they will be talking about.

Puneet Agarwal at True Ventures talked about a similar idea through the lens of contrarian thinking: some of the best founders can see something the market hasn’t fully priced in yet. Because by the time everyone agrees a sector is hot, most of the alpha is already gone.

This is probably the lesson that’s hardest for me to put into practice right now. I’m still figuring out which sectors are worth going deep on. But I know that’s the right question to be sitting with.

At the Earliest Stages, You’re Investing in the Founder

This has been the single biggest mindset shift for me.

At the pre-seed and seed stage, you’re not investing in a product. You’re investing in a founder’s character and their sheer force of will. The product is probably going to pivot 25 times before it finds product-market fit, and the only thing that survives all those pivots is the person at the top.

Charles Hudson from Precursor Ventures shared one of the clearest frameworks I’ve heard for evaluating founders. He focuses on three things:

1. Market knowledge: do they actually understand the space they’re in?

2. Their “why”: is there a real, personal reason they’re building this?

3. Unfair insight: do they know something the market doesn’t yet?

Steve Bowsher also introduced me to the idea of the “personality thermometer”. When he evaluates founders, he’s not just listening to the pitch - he’s reading the room. The presence. The composure. The way they handle pushback.

And separately, he looks for evidence of excellence in any domain. It could be previous jobs, athletics, music, anything. Because winners tend to keep winning. The arena changes, but the underlying traits often transfer.

A lot of these conversations ended up shaping the lens I used when I eventually wrote my first check.

Conviction Comes From Stacking Signals

Here’s the thing nobody tells you about writing your first check: you’re not waiting for one big “yes” moment. You’re stacking smaller moments of conviction until the answer starts to feel obvious.

I learned this writing my first check into Pick and Roll AI, the first product developed by The Intelligent Search Company. The platform uses AI to help basketball programs evaluate players, organize scouting information, and make smarter recruiting and transfer portal decisions.

Looking back, I can map exactly what stacked up.

First, the opportunity came through a warm introduction from, Eric Chen, someone I trust and continue to learn from. And when I saw other investors I respected getting involved too, it created another layer of validation. Their conviction didn’t replace my own thinking, but it gave me confidence the opportunity was worth taking seriously.

Second, I realized I had a form of unfair insight that a lot of people on the cap table probably didn’t. The transfer portal is chaotic. Coaches are overwhelmed with film and scouting reports. I’ve lived inside that world. I know what coaches are looking for. I know what players care about. I know how fragmented the process feels from both sides. Pick and Roll AI was solving a very specific and real problem.

Third, the founders, Arpan and Moe clearly knew the space. But what stood out even more was how they responded to pushback. The second I challenged something, they leaned in instead of shutting down. They had a combination of knowledge and humility, which left a real impression on me.

None of those things alone would’ve been enough signals.

And even after all that, it still feels scary having put capital behind an idea that’s still early. But I think that’s part of the game. Conviction doesn’t mean certainty. It just means you’ve done enough work to believe.

I’m four months in and one check deep. A lot of what I’m operating on is still instinct. And the more reps I get, the more I realize instinct is just a starting point.

I’m still building my own thesis, and that’s going to take time.

But I’ve realized that the same things that made me a basketball player - discipline, coachability, obsession with reps, comfort with being uncomfortable - are the exact same things the VC world rewards.

Lately, people keep asking me how I balance chasing the NBA while building something off the court.

Truth is, there are 24 hours in a day, and basketball is non-negotiable. But there are still hours left in the day. And I wanted to spend them building something that could grow alongside basketball, not after it.

Investing hasn’t taken anything away from basketball. If anything, it raises the stakes in a way that makes me want it more. The better I perform on the court, the more access I have, the more doors stay open, the more opportunities I get to learn from incredible people.

The two worlds feed each other.

Rehab has a way of slowing everything down.

Every morning, I wake up and rebuild the knee a little more.

And somewhere between the film sessions, founder calls, weight room, and rehab table, I realized I’ve been building something else too.

Chisom

Chisom Okpara is a NCAA Division I basketball player at Stanford. Alongside his pursuit of professional basketball, he spends his time investing in early-stage startups. To keep up with Chisom, follow him on LinkedIn and Instagram.

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Deal brief · Week of June 1

Tracking the deals shaping the business of culture.

Investments

Sydney Sweeney, Khloé Kardashian, Jessica Alba and Priyanka Chopra Jonas revealed among Phia's backers

Phoebe Gates and Sophia Kianni's AI "shopping agent" Phia revealed the roster behind its $35.5M Series A — more than 30 cultural figures, from Sweeney and Kardashian to Paris Hilton and Karlie Kloss. The raise values the company near $185M; it now reports 1.5M users and 9,600+ brand partners.

Tony Hawk backs Scott Coker's new $60M global MMA league

Former Bellator CEO and Strikeforce founder Scott Coker is launching a new global MMA league with $60M led by Creator Sports Capital, targeting a 2027 debut. Skateboarding icon Tony Hawk is among the investors, alongside backers across sport, media, and finance.

New ventures

Olivia Jade launches makeup brand o.piccola after a five-year build

The creator has gone from influencer to founder with o.piccola, a self-funded line debuting with a single hero product: a $44 Bronze & Glow Balm formulated in South Korea. The name nods to the Italian piccola — little — and her less-is-more philosophy.

Jonas Brothers launch weekly podcast ‘Hey Jonas!’

Kevin, Joe, and Nick have launched a weekly show, “Hey Jonas!”, under an exclusive deal with iHeartPodcasts — complete with a fan call-in line and an unfiltered look at life on and off tour.

Former NHL enforcer Aaron Volpatti releases his first country single

The ex-Canucks and Capitals winger — and author of a memoir about his road back from severe burns — has released his debut single, “A Beer A Day,” a country-rock track.

Fundraising and acquisitions

Martha Stewart’s AI startup Hint raises $10M seed, led by Slow Ventures

At 84, the lifestyle icon has co-founded Hint, an AI home-management platform that flags maintenance, insurance, and repair needs before they become problems. The seed round was led by Slow Ventures, with Montauk Capital and others participating.

Brand endorsements

Cardi B named Fashionphile's 2026 global ambassador

The Grammy winner is fronting luxury-resale platform Fashionphile's "Get Your Bag" campaign, with a curated edit of Hermès, Chanel, and Goyard pieces. She's the brand's fourth ambassador, after Martha Stewart, Nicole Richie, and Emma Roberts.

Conor McGregor signs as global brand partner for nicotine pouch brand ALP

The former UFC champion will front a campaign for ALP, a nicotine pouch brand tied to Turning Point Brands and the Tucker Carlson Network, as it expands into the EU and South America.

Enzo Fernández becomes BingX's first individual athlete ambassador

The World Cup–winning midfielder is the crypto exchange's first individual athlete global ambassador, extending a sports push that already includes Chelsea FC and Scuderia Ferrari. The deal is timed to the 2026 World Cup.

Banchero, Holmgren, Pritchard and Loyd headline Foot Locker's 'Hoops Lives Here' platform

Foot Locker's new year-round basketball platform, "Hoops Lives Here," features NBA stars Paolo Banchero, Chet Holmgren, and Payton Pritchard alongside the WNBA's Jewell Loyd, spanning Nike, Jordan, and Converse.

On signs Louisville distance star Elsingi Kipruto to an NIL deal

The Swiss brand has added Kipruto, a Kenyan-born Louisville freshman and record-setting distance runner, to its NIL roster — his first major brand deal and On's first Louisville distance signing.

Partnerships

Jay-Z's Roc Nation partners with Chelsea FC to grow the club in the U.S.

Chelsea has signed a cultural-marketing partnership with Roc Nation Sports International to build the club's following in the U.S. through music, influencers, and storytelling.

Stephen Curry's Unanimous Media forms a sports-content venture with Hard Carry Media

Curry and Erick Peyton's Unanimous Media has launched a joint venture with Bryan Smiley's Hard Carry Media, starting with content built around NIL college basketball players for YouTube and TikTok.

Bussin' With the Boys launches NASCAR show 'Racin' With The Boys' with Omaha Productions

The football-born podcast (hosts Will Compton and Taylor Lewan) is moving into motorsports with a 14-episode weekly NASCAR series produced by Peyton Manning's Omaha Productions, on the Bussin' YouTube channel.

Bridgerton creator Chris Van Dusen teams with Kim Kardashian and Emma Roberts on Netflix’s ‘Calabasas’

Netflix has ordered Calabasas, a YA romance drama from Bridgerton creator Chris Van Dusen, with Kim Kardashian and Emma Roberts among the executive producers. It’s the first series under Van Dusen’s new Netflix deal.

Media deals

Alex Cooper locks four exclusive shows on YouTube

The Call Her Daddy host announced four original series coming exclusively to YouTube, all produced by her Unwell Productions — a push past podcasting toward a full programming slate.

Trevor Noah signs a YouTube-exclusive travel series, ‘World Tour’

The former Daily Show host is launching Trevor Noah’s World Tour, a YouTube-exclusive travel series blending comedy, food, and culture city to city — announced alongside Cooper’s slate at YouTube’s Brandcast.

Julian Shapiro-Barnum gets YouTube’s late-night swing with ‘Outside Tonight’

The Recess Therapy creator will host Outside Tonight, a live weekly late-night show shot in New York parks and on street corners — billed as the internet’s first true late-night talk show, launching June 17.

Nick Cannon gets a Netflix docuseries on raising 12 kids with 6 mothers

Netflix has greenlit an untitled docuseries following Cannon as he balances a busy career with raising 12 children across six mothers, due winter 2026.

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Legacy · May 2026

Exclusive interviews featuring athletes building wealth beyond sports.

Originally published on mainstreet on May 2026. Updated August 2026.

Venture capital has a branding problem.

From the outside, it looks like a game of big checks, fast wins, and headline investments.

From the inside, it’s something else entirely: a grind built on repetition, pattern recognition, and a kind of invisible work that rarely gets talked about.

That gap between perception and reality is where most new investors struggle, especially athletes.

Keaton Nankivil didn’t come into the industry with a finance background, a business degree, or a traditional network. He started as an intern at Alumni Ventures after a professional basketball career in Europe.

Nine years later, he’s a Senior Principal leading the firm’s Sportstech thesis.

In this conversation, he breaks down what venture capital actually looks like, where athletes can experience challenges, and the lesser known skills from sports that can make athletes exceptionally valuable.

This Q&A has been lightly edited for clarity and length.

Venture capital is often described as a game. What do people, especially athletes, misunderstand about how it’s actually played?

Keaton: The first thing is understanding what venture capital is.

It’s a part of the financial stack that’s historically been hard to access, but it’s also where a lot of value creation is happening now, in private markets. If you’re looking for asymmetric upside, this is one of the best places to find it.

But it’s not for everyone.

The biggest mistake I see is people entering the space without understanding their role in it.

You don’t need a formal degree. But you do need to understand how returns are generated and be honest about your risk tolerance. It’s high risk and high reward. You should have a genuine capacity to take some risk with your money knowing that there is potential upside.

Because the reality is: a small number of investments actually create returns.

Before you entered VC, what did you think the job was? And what does it actually look like day to day?

Honestly, I had zero context going in.

My perception was mostly from what I heard - aggressive, sharp-elbowed, the “vulture capital” stereotype... And to be fair, parts of that exist. Luckily, most of the people I’ve met in this field are genuinely motivated by helping founders build extraordinary companies.

But the bigger disconnect is the work itself.

It’s a lot like professional basketball. From the outside, it looks like a glamorous job.

In basketball, you see the three-pointers, the dunks, the game-winners. What you don’t see is the warmups before practice, the repetitive drills during practice, and the post-game rehabs.

VC is the same. You hear about the headline investment. But the day-to-day grind before and after the investment is the actual job.

I still cold email founders every week. I take hundreds of calls a year to find a small number of opportunities that fit our fund strategy. And a lot of the job is tracking companies, supporting founders in moments no one hears about, and maintaining LP relationships over long periods of time.

It’s repetitive. And that’s the point. Because every now and then, that repetition compounds into something meaningful.

Very few people are willing to start from the bottom when they transition careers. You chose to start as an intern at Alumni Ventures and worked your way up to Senior Principal. What gave you the conviction early on to commit to this path before you had any real proof it would work out?

Honestly, I think “chose” is such a generous word. I didn’t have a clear path after basketball and kind of just stumbled into it.

The internship opportunity at Alumni Ventures came through people I trusted, and that mattered more than anything else. I believed in the people before I understood the asset class.

Looking back, that was enough to get started.

There’s this idea that you need conviction upfront. I don’t think that’s true, especially for athletes transitioning into something completely new.

A lot of this was just showing up, doing the work, and stacking reps until things started to make sense.

The hardest part actually wasn’t the lack of conviction early on. It was accepting that while I was a high-level operator on the court, I was a beginner here. I had to earn the right to compete and win in this space.

How did your experience as a professional basketball player shape the way you think as an investor today? What skills transferred over well to the investing world? Was there anything you had to unlearn?

The biggest thing that transfers is an appreciation for the dirty work that doesn’t show up on the stat sheets.

I remember a game in Spain where I wasn’t playing well, and a coach pointed out that a screen I set created a key three-point shot for a teammate. That really stuck with me.

VC works the same way.

A successful investment might trace back to a cold email, a relationship built months earlier, or internal work that helped the team move faster. It’s the result of invisible, dirty work that happens long before a check is written.

On the flip side, what doesn’t translate as well is structure.

In sports, there’s a clear chain of command. The coach calls the play. I would execute the play. And for a long time, that’s exactly what makes me valuable to a team.

In VC, the most successful investors tend to be the independent thinkers - the ones that can look beyond the status quo and push boundaries.

They generate alpha from challenging the general consensus, forming original ideas, and trusting their own instincts.

That’s something I’ve had to learn over time.

You now lead the Sportstech thesis at Alumni Ventures. Where has your background as an athlete given you a real, non-obvious edge when evaluating companies?

Context.

As an athlete, I’ve been fortunate to experience almost every part of the sports value chain.

I’ve played in youth sports. I’ve gone through the recruiting process as a college recruit. I’ve been part of teams at different levels. I’ve used performance technology as a pro. I’ve been a fan consuming sports from the outside.

So when I look at a company in this space, I’m not imagining the user. I’ve been the user.

That helps me quickly understand who a product is really for, where it fits, and whether it solves a real problem.

But there’s a trap in that too.

My experience might feel universal, but it usually isn’t.

What worked for me, or what I would have wanted as an athlete, isn’t always representative of the broader market.

So I try to treat my experience as an input. It gives me a starting point, but it doesn’t replace doing the work. If anything, it just helps me ask better questions and build conviction faster.

Athlete-investors tend to gravitate toward Sportstech and CPG due to familiarity. What’s the most common mistake they make?

I love this quote from Mark Cuban on Shark Tank: “I’ll be a consumer, but I’m not going to be an investor.”

As an athlete-investor, the most common mistake is investing in products I would have personally wanted - a youth training app, a performance supplement, a fan experience product - and mistaking that for real diligence.

Just because I like something doesn’t necessarily mean it’s a good investment.

Take CPG as an example. You can build a great business there. But the structure of these companies can make it hard to achieve venture-level returns.

Margins are tighter. Growth is more linear. Capital requirements are higher.

That doesn’t make them bad businesses. It just means they may not fit the venture model.

The second mistake is ignoring portfolio construction.

The reality is, most investments won’t work. That’s just how the asset class works.

Venture is a portfolio of opportunities. You need to see enough deals to understand what “great” actually looks like, and then let the great investments balance out the ones that never reach escape velocity.

You’re building an apprenticeship model for athletes at Alumni Ventures. Why is that the right model for venture, and what does it unlock that traditional education doesn’t?

First, the trust factor. You meet a fellow athlete and the bond is almost immediate - there’s shared values, shared communication, shared experience. That’s multiple layers of affinity. It matters when you’re learning something hard and unfamiliar.

Second, and I say this with real conviction, is that athletes are among the smartest people I’ve ever worked with. A lot of my former teammates didn’t attend top business or finance programs. They are just as sharp as many of the people I work with today. The issue has never been intelligence. It’s been access and exposure.

Third, venture is a craft. Kobe Bryant used to talk about basketball as a craft - you are a craftsman, and you hone your craft over time. Investing is the same. You need feedback loops. You need a space to make mistakes safely. You need someone who has been through it to guide you.

Ultimately, my goal is to help athletes become a formidable part of the venture ecosystem. Venture capital shapes the future economy, and athletes deserve a seat at that table.

The capability is already there. I’ve seen it up close. What’s been missing isn’t the talent. It’s access, exposure, and the opportunity to prove it.

This dynamic shows up more often than people think. Athletes bring real context, especially in areas like sportstech. The challenge is turning that context into sound judgment over time. That’s what Keaton is focused on, helping athletes build reps through apprenticeship. With the right guidance, the next generation of athletes won’t just participate in venture. They’ll play a active role in shaping it.

To learn more about VC and sportstech investing, connect with Keaton on LinkedIn.

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Horizon · Apr 2026

First-person stories from athletes building their next chapter.

By Noah Adnan. Edited by Allen Lee.

Originally published on mainstreet on April 2026. Updated August 2026.

How do I prepare for what’s next while I’m still fully committed to soccer?

That question has been sitting with me for a while now.

I’m 24. I’m in year two of my pro career. And I’m already thinking about what comes after it.

I know how that sounds.

I’m still all in on the game I love. That hasn’t changed. But I’d be lying if I said I haven’t thought about what happens if it’s taken away from me.

Not when I’m ready. Not on my terms. Just gone…

When you’re a pro athlete, your life is pretty structured.

Training. Recovery. Games. Travel. Repeat.

Outside of that, everyone fills their time differently. Some guys play Fortnite. Some golf. Some just unplug and spend time with family.

I do all of that too. But part of me can’t fully switch off.

Because I keep coming back to the same thought:

What else could I be building right now?

I think that’s why I’ve always been drawn to athletes who don’t wait until the end. The ones who are already exploring something else while they’re still in it.

Some invest. Some advise. Some write. Some just start figuring it out in public.

At first, I found myself asking a lot of questions.

How did they get started? How did they get into those rooms? Why that particular path?

But the more I paid attention, the more it stopped feeling separate from what I was doing. Because my own path into pro soccer didn’t look that different.

I went from MLS Combine invitee, to being undrafted, to going on trial, to finally signing my first professional contract, to starting the first game of my first season.

There’s nothing linear about my career. I had to roll up my sleeves and figure it out as I went. So I’m doing the same thing off the pitch.

For a long time, I thought building something off the pitch meant writing checks.

Growing up, I watched guys like Kevin Durant, Stephen Curry, and Andre Iguodala operating in the Valley, and I thought that was the model.

You make it, you earn, then you invest. That’s when you’re allowed in the room.

I believed that for a while. Most athletes my age still do.

Then I started paying closer attention to the athletes around me who are doing it without the spotlight. They aren’t necessarily the ones with the biggest bank accounts. They’re the ones who figured out their unique edge and went to work with it.

The legend Mr. Johan Cruyff said it best: every disadvantage has its advantage.

I don’t have a ton of capital to deploy yet. What I do have is a front-row seat to locker room conversations and access to people building things around a global sport in real time.

That’s a different kind of currency.

Three guys, in particular, are shaping how I approach my work off the pitch.

Jeremy Ebobisse, who played at my boyhood club, Bethesda SC. He uses capital as a learning tool. Every investment is a rep. Win or lose, he walks away sharper. I might not be writing the same checks yet, but I can still get the reps. Every room I enter, every conversation I have is a rep.

Spencer Jones I knew from Stanford. Before he became a rockstar on LinkedIn, he’d been thinking out loud about investing and sharing lessons he’s learned from his work off the court. Watching him confidently yet humbly build in public has been a good reminder that I can turn my platform into a magnet for opportunities.

Casey Toohill takes a different approach. He writes opinionated blog posts about opportunities in sportstech and emerging market trends. What I’ve taken from him is that a sharp point of view can open doors. He made me realize that proximity alone isn’t enough. You also need a perspective.

Off the pitch, I’m building. I’m building relationships, building experience, building judgment.

I now sit on the board of Spekt, a protective performance sock brand built for athletes. I help validate demand with other pros, give product feedback, share future product ideas. I’m also supporting the business development team at Game1 AI as a brand ambassador and raised money for a non-profit supporting young students to learn STEM.

My early stage work isn’t the shiny or scalable kind that makes headlines. But it’s work that I deeply care about and invested in.

Most of it is me in rooms I wasn’t in a few years ago - asking questions, listening, trying to add value however I can.

Some days I wonder if I’m doing the right things. Whether a 24-year-old in year two has any business even writing a piece like this.

I don’t know yet.

What I do know is that Jeremy, Spencer, Casey, the guys a few steps ahead of me, probably didn’t know either when they started. But they didn’t wait to feel ready. They used what they had and figured out the rest along the way.

So I’m doing the same, understanding that many failures and breakthroughs lie ahead of me. But that is the point, to learn those lessons now and use it as a trampoline for later.

I’m still all in on soccer. That part hasn’t changed.

But I’m not waiting for the final whistle to start the next chapter.

When the time comes, I want to already know the rooms. And I want to have earned the right to be in them.

Noah

Noah Adnan is a professional soccer player currently playing for Loudoun United in the USL. To keep up with Noah, follow him on LinkedIn and Instagram.

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Legacy · Apr 2026

Exclusive interviews featuring athletes building wealth beyond sports.

Originally published on mainstreet on April 2026. Updated August 2026.

I knew I was in for a ride the moment Dijon Thompson leaned back in his chair, grinned, and said:

“My first startup experience felt like my first Suns practice.”

That’s when it clicked.

The 2005–2006 Phoenix Suns weren’t just a typical basketball team.

They played like a scrappy garage band crashing Carnegie Hall - breaking rules, ignoring the sheet music, and somehow leaving everyone cheering anyway.

And here I was, sitting across from a member of that legendary team, hearing he’d found that same adrenaline again.

After leaving basketball, he made a bold pivot to the tech world, and quickly found himself immersed in something that felt eerily familiar.

The same energy, pace, and rule-breaking philosophy that made the Suns a religion…

Turns out, he’s back in it - only this time, it’s startups.

Pace Over Perfection

As I was talking to Dijon, it hit me: the 2005-2006 Phoenix Suns were basically the OG YC batch before YC was cool.

Most NBA teams in the mid-2000s lived and died by structure. The triangle demanded patience. Horns sets required precise spacing. Everything was about controlling pace.

The Suns rewrote the rules. Push the pace. Shoot early. Score in seven seconds or less. (Yes, you read that right.)

It was organized anarchy - the kind of basketball that looked like Mario Kart on hardwood.

Fresh out of college, Dijon was dropped into this system. He’d been drafted by the Knicks, traded to the Suns, and there he was - practicing with Nash, Marion, and Stoudemire in a system that saw D’Antoni turn speed into a weapon.

They won 54 games that year, and Dijon was caught up in that frenetic energy.

“I just had a feeling we were going to win the championship,” he told me.

Then came the gut punch. Not a slump. Not a bad stretch. A full stop.

His knee gave out mid-season. Microfracture surgery. The same procedure that nearly ended Stoudemire’s career. Except Stoudemire had already secured a multi-million dollar contract. Dijon hadn’t.

He was 22 years old. No guaranteed money. No fallback plan. Just a surgically repaired knee and a slim hope he’d ever play professional basketball again.

Highest high. Lowest low. Just months apart.

Fast-forward to 2020. Dijon’s retired after a career that took him across France, Germany, Russia, Ukraine, Vietnam, and Japan.

Then, out of nowhere, Dijon ran into an old friend at cryotherapy. She kept recruiting him to join her startup.

The pitch was wild. Pre-revenue. Small team. Competing against billion-dollar tech giants.

“Don’t worry, you don’t have to know tech. We’ll teach you.”

With zero tech experience and no clue what he was getting into, he said yes.

And boom. Déjà vu.

Sales hyped features that were still three sprints away. Founders tweaked the pitch deck 15 minutes before a meeting. Product shipped with bugs everyone knew about. (Sound familiar, founders?)

At YC, they call this “building the plane while flying it.”

“I realized fast that if you wait for the perfect plan, you’ll always be a step behind,” Dijon told me. “On the Suns, we moved before the play fully formed. In startups, it’s the same.”

Once you’ve played at that speed, everything else feels slow, and slow starts to feel wrong.

Speed isn’t just a style - it’s a strategy. The faster team forces everyone else to react.

This was Phoenix all over again, just in a different arena.

Positionless

In Phoenix, your listed position was basically a formality for the stat sheets.

Marion guarded 1-5. Diaw played center, point forward, and part-time magician. Dijon played the 2, the 3, and even stretch 4 when the system demanded.

You didn’t fit the system. The system stretched around you.

So when Dijon joined his first startup, he already knew the playbook. Partnerships, biz dev, fundraising, product… whatever the team needed, he jumped in.

The Suns taught him to be positionless. Startups don’t just reward that - they demand it. If you need a job description to be useful, you’re already behind.

He laughed when I asked how many hats he’s wearing these days.

“Sometimes I wear more hats than Boris Diaw in a playoff series.” (Trust me, that’s a lot of hats.)

The Suns exploited something most teams overlooked at the time: athletes thrive in ambiguity. New teams. New coaches. New roles. And sometimes even new countries.

“You know, we spend our entire careers moving around and learning to adapt,” he told me. “It’s the same muscle startups need.”

That line stuck with me. Dijon figured this out earlier than most athletes, and turned adaptability into his superpower.

The Nash Effect

There’s one person who made that Suns system click: Steve Nash.

Nash didn’t just bring the ball up the court. He saw angles two steps ahead, turned chaos into choreography, and most importantly, amplified everyone around him.

Every startup needs a floor general. Or, as Dijon puts it:

“Every startup needs a Nash.”

Dijon has learned to spot that same floor-general energy in the founders he works with.

Take Paige at Powered by Point. She saw something in him before he saw it himself and put him in a position to contribute. She also teamed up with her cofounder to level him up. Pitch deck breakdowns, UX debates, post-mortems on growth experiments, even a deep dive into consumer psychology using the GameStop fiasco as the syllabus… Dijon absorbed it all. It was like watching game film.

Now he’s seeing it again at Cache AI. Kobi, the founder, has the rare ability to read the market, pivot on the fly, and keep the team moving in perfect sync. She has a knack for putting people in the right spots - looping Dijon into key conversations, trusting him to run with opportunities, and turning small openings into real partnerships. Under her guidance, he’s gone from learning the ropes to helping land a growing slate of partnerships.

Great founders, like great floor generals, make everyone else better. Dijon learned that lesson from Nash. Now he watches for it in every founder he works with.

Seven Seconds Or Less, Cont.

When I first sat down with Dijon, I thought I was talking to a retired hooper.

By the end, it was clear he hadn’t left seven-seconds-or-less behind. He’d taken that philosophy off the court and into startups.

Move fast. Take risks. Break rules.

The Suns planted the seeds. Startups made them grow.

Dijon didn’t just find a second act. He found the same adrenaline, rhythm, and joyful chaos. Only now, it runs 24/7.

As we wrapped up, he leaned forward with that same grin from the beginning of our conversation:

“Most athletes don’t realize they’re already trained for this. I didn’t either, until Ryan Nece at Next Legacy Partners, told me: the most dangerous thing is an athlete knowing he can compete in another arena.”

He’s right. One pivot is all it takes for an athlete to become a killer startup operator. Once that pivot happens? Watch out, world.

Follow Dijon’s journey on LinkedIn and check out how he brings that same Suns-style pace to Cache AI, where he helps athletes and teams make sense of NIL valuations using AI.

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Horizon · Mar 2026

First-person stories from athletes building their next chapter.

By Miller Kopp. Edited by Allen Lee.

Originally published on mainstreet on March 2026. Updated August 2026.

What if basketball ended tomorrow?

I would stay up super late at night thinking about this. I’m talking 2, 3, 4 in the morning. You know that time of night when it feels like the whole world has gone quiet and you’re the only one still up? I like those hours. Because it’s so quiet I can actually think. Or maybe I’m just so tired by that point I can’t overthink. And honestly, that might be better.

I like to write. I would write about the options, the fears, the worries, the hopes and dreams, the past, present, future. It would be me, my pen, and some paper trying to figure out what the hell Miller Kopp is gonna do next. Then whenever my low back had enough of that chair, I would take a shower in the pitch black, brush my teeth, say a prayer, and go to bed, hoping the answer would come to me in my dreams so I could wake up and attack it in the morning.

I’ve been thinking about this question a lot lately. Not because I’m planning to retire anytime soon. I’m not. But because I think there’s something wrong with waiting. Waiting until basketball is over to start figuring out what comes after.

I used to say I don’t regret anything. That was my line. But I think that’s a cope.

I wish I hadn’t worried so much about what people think. Social media is woven so deep into the sports world that I made decisions on what to say, what to post, what to build, what to pursue based on what some nameless gray face on the internet might think of me. It pisses me off just thinking about it. We’re on this floating rock for 80 years if we’re lucky and I’m out here making decisions because some anonymous account might have an opinion?

I wish I would’ve leaned into what I wanted. I did in some areas, but I did so with one hand tied behind my back. Making that shift earlier in my career would’ve allowed me to be further ahead in whatever I build when basketball is over.

I have nobody to blame but myself.

And honestly? It fires me up.

The next chapter’s gonna get played with both hands.

So what would that actually look like?

I’d write more. Build up my Substack. I’ve always had thoughts I wanted to put somewhere - things I think about at 4am that I never said out loud because I was too busy being a basketball player.

I’d make an electrolyte product. Something I’ve used every single day for the last five years. I even got my girlfriend taking it now. Clean ingredients, high quality, dosed right. I like to nerd out on health stuff. Sleep, recovery, hydration, the details most people ignore. If I’m going to build something, I’m going to build something I believe in and would use myself.

I’d also make some calls. Not for a job. For information. I want to understand different industries and see where my skills and passion could help me build something that would disrupt some shit. My first move would probably be to contact Pat McAfee’s assistant and ask to shadow him for 30 days. Then I’d hunt down Todd Graves and do the same thing. It sounds crazy but what better way to learn than to watch. Just sit there and observe. I want to be around people who built something real, on their own terms. People who did it their way and didn’t ask permission.

I’d probably get some calls about coaching, which I’d take and talk through. I love basketball. The leadership, the interpersonal dynamics, the chess of it all. But I’m a builder, and I’m not sure if coaching is the right path for me.

There’s a Mike Tomlin line tattooed somewhere in my soul - “it’s a reasonable expectation to be continually on the rise.” I’ve failed a lot and had some successes, but I’ve always been the kid who wasn’t afraid to look like the “try hard”. The dude who made others uncomfortable with his work ethic. When I set my goals, I never negotiated with myself. One decision took care of every other one after it. Because it’s not easy. Growth is not linear. But over time, I improved… which I know now is just a “reasonable expectation”.

So I think I’d be ready. Because I’ve spent my career building toward something, even when I didn’t always know exactly what.

One of the biggest lessons the game of basketball has taught me is that there’s beauty in pursuit.

Whether I knew it or not, my younger brothers were always watching. My work ethic, my mistakes, my bad decisions, how I treated people, how I carried myself - all of it. The footsteps along the journey can leave behind a roadmap for the people behind you, if they’re hungry enough to follow it.

My days are my life in miniature. Every step I take, every decision I make, leads to the life I create. And more importantly, the life I leave behind.

As cliche as it is to say, I look back and don’t see a string of successes and failures. I see a ton of different experiences. Some days pure bliss. Some just absolute chaos.

Honestly, nobody will remember what Miller Kopp did 100 years from now. The only people I care about remembering me are my younger brothers, future kids, grandkids, great grandkids... I’d want them to feel an urge to live large, to dream big, to read a book then write their own, to ask a question and listen, to be afraid and do it anyways.

Life is greatest when you’re the Man In The Arena. When you’re the kid climbing the tree, running the race, jumping the fence and scarring your face.

There’s a story about Mozart I love.

A 21-year-old kid walks up to Mozart and asks, “How do I write a symphony?” Mozart says, “You’re too young.” The kid goes, “You were writing symphonies younger than I am now.” And Mozart says, “Yeah, but I wasn’t going around asking people how to do it.”

I think that’s pretty funny. And pretty powerful.

It’s all self discovery. That’s how it’s supposed to be.

I’m a poet, philosopher, entrepreneur, coach, teacher, speaker, writer, and psycho trapped in a professional basketball player body. Makes sense why I get confused sometimes. But I’ll take it.

What if basketball ended tomorrow?

I don’t know for sure…. and that’s okay.

What I do know is I’m a builder and builders build.

Touch the fire. Get burned. Build something.

That’s not just the plan. That’s always been the plan. I just needed to say it out loud.

Miller

Miller Kopp is a professional basketball player currently playing in the NBA G League. To keep up with Miller, follow him on LinkedIn, Instagram, or TikTok.

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