There's a story behind the small black triangle forever imprinted on Kevin Durant's wrist. Like the rest of his tattoos -- "Maryland" (his home state) across his shoulder blades, a portrait of Tupac on his leg -- the ink is an attempt to grab hold of a moment in time and mark it as meaningful.
The triangle tattoo is a symbol of the friendship between Durant, his business partner Rich Kleiman and their friend Charlie Bell. A few years ago the three men were hanging out, talking about the incredible possibilities in front of them, and someone thought it sounded like a good idea to get tattoos commemorating the bromance.
It feels a bit quaint now, even to them. Aww, friendship tattoos. How cute!
"I wouldn't get most of the tattoos I have now," Durant says with a smile. "But that's why they're cool. I got each of them at a point in my life I was feeling something I wanted to remember."
Kleiman laughs and points to a Chinese character tattooed on his arm.
"Like, this means 'patience,' " the 41-year-old executive says. "Could you imagine if I went in somewhere now and was like, 'Yeah, what up, my man? Could you give me the Chinese symbol for patience?'
"The guy would be like, 'OK, midlife crisis. What up, Dad?' But when I was 19, in Miami, I'm like, 'Yooo, give me "patience"!' "
We're sitting at a shady table at the cafe atop the Montage Hotel in Beverly Hills. The Warriors have the day off after a win over the Lakers, and Durant and Kleiman are making the most of it. There was a morning meeting with Brat (a company that created a network for young YouTube stars), this lunch interview, house hunting in Beverly Hills in the afternoon, then a red-eye flight to Washington, D.C., to attend the opening of College Track, which prepares high school students to apply to and graduate from college, at the Durant Center in Prince George's County, Maryland.
Life as a two-time NBA Finals MVP and budding entrepreneur can be a little like taking a speedboat down the chocolate river in Charlie and the Chocolate Factory -- sensory and experiential overload around every turn.
"My platform is hoops," Durant says. "Billions of people are watching, so why not leverage it to do the cool stuff that we like to do?"
As one of the best basketball players on the planet, Durant can meet anyone he thinks is interesting, invest in any company he digs and get into any event he wants. Twitter and Square CEO Jack Dorsey? He flew in for Durant's birthday party this year. Apple VP Eddy Cue? A huge Warriors fan whose company just greenlighted a scripted show called Swagger based on Durant's experiences in AAU basketball. David Geffen, Oprah, Diane von Furstenberg? Durant hung out with them at Google's invite-only celebrity camp at the Verdura Resort in Sicily the past few summers.
His world is wide open -- and so the challenge for Durant and other superstar athletes-turned-business moguls isn't just in finding the time to take advantage of the exclusive opportunities in front of them but in searching for the right reasons to do so.
A great brand is a lot like a great jump shot: The best ones appear effortless. And yet, underneath the surface, years of sweat, grind and refinement have gone into it. Athletes used to wait until they were done playing to start building their businesses off the court. They'd let their teams or agents with dozens of other clients handle their marketing. Even back then, they knew they were leaving money and leverage on the table. But who had the bandwidth to build out a portfolio while playing?
In the business world, that's called a market gap. Customers want a product that doesn't exist yet? Somebody should go create that product.
In this case, first a superstar athlete such as Durant had to believe he was capable of building his own brand while playing. Then he had to figure out how to do it.
Earlier in his career, Durant says, he mostly just wanted to do what he saw other superstars do.
"'Gatorade, I need that. McDonald's,' " he says. "I need a trading card, Upper Deck, because I've seen other great players do that."
"You also thought your off-days had to be completely filled," Kleiman says from across the table.
Over the six years they've been working together, Kleiman's job has been to help Durant be purposeful and intentional about his projects and to take advantage of the creative freedom Durant's considerable platform has afforded him.
That filtering process can be dizzying for a curious soul like Durant, who readily admits he's still searching -- and probably always will be -- for what he wants to be. So a few years ago, in one of their daily deep dives, Kleiman laid it out: "You need to understand that this part of your life should be enjoyable."
Durant had spent too long trying to fit the model of what he thought a superstar athlete "should" be doing. Just do what feels right or fun or interesting, Kleiman told him. Maybe one of his investments will turn into the next Vitamin Water or Beats by Dre. Maybe it'll just be a cool experience to look back on. Maybe it'll flop. But if a startup company presents a product Durant or Kleiman would use himself, or its founder had a certain je ne sais quoi they both connect to, that's what guides them.
Take Postmates. "I'm hungry one day," Durant says. "And Rich was like, 'Yeah, [this company will] bring you food from any restaurant.' I'm like, 'They've got an app like that? Can you call somebody up there? We need to get involved, because we use this s--- on a day-to-day basis.' " Soon after, in June 2016, Durant and his team bought a stake in the company, which reportedly had grown tenfold by a valuation this January.
There's a more rigorous evaluation process after that initial spark, of course. Durant says he likes to study the industry and how a company has grown from its early stages of development before he invests. But if there's a guiding principle behind the extensive portfolio they've assembled, it is to follow and trust Durant's curiosity.
So far they've invested in some 50 companies, ranging from the cold-pressed juice company WTRMLN WTR to an autonomous drone company called Skydio. There's an equity partnership in the headphone company Master & Dynamic. And starting Feb. 11, there's The Boardroom, a six-episode series on ESPN+ and multiplatform media brand in which Durant, Kleiman and ESPN college basketball analyst Jay Williams talk with players, industry executives and insiders from the worlds of sports, business, media and technology about how the culture around sports is changing.
"Me and Rich always had these times where it was just him and I, brainstorming," Durant says.
So why not turn those conversations into a show?
"It's like Sports Business Journal but for fans," Kleiman says. By now he's got this pitch down cold.
"I was watching sports last year, and there was a headline about an investment that Kevin had made. Then a headline about a Liverpool investment that LeBron had made. Then some Yankees highlights.
"When I was 14 years old, I would have been so confused about why the investment stuff is in the middle of these highlights. But in our world now, that's way cooler than the other stuff."
There's no job description that can capture what Kleiman does for Durant. He's his business partner in Thirty Five Ventures, the umbrella corporation for their production company, Thirty Five Media; the Kevin Durant Foundation; and all of their investments, endorsements and business partnerships. He's the first or second person Durant speaks to every morning, depending on how early Durant's brother, Tony, and baby nephew FaceTime him. He's definitely the first person Durant calls if anything ever goes wrong.
It's more than your typical manager-athlete relationship: By all accounts, this is a genuine friendship. They refer to each other as "my best friend" and sometimes even "brother." When ESPN shot the photos for this story, Durant preferred to share the stage with Kleiman and Williams. Yes, some of that is because they're promoting The Boardroom together. But it's also a reflection of just how close he and Kleiman are.
At first glance, it's an unlikely pairing. Kleiman grew up in New York City, attending a private high school that was a member of the Ivy League Preparatory School League. Durant grew up in an impoverished area outside of DC, often taking public transportation for several hours a day to get to and from one of the three high schools he attended.
Kleiman is boisterous, excitable and intense. He has a ton of friends, sleeps with his phone on, spends hours every day workshopping ideas at home in what he calls his think tank. Durant is sensitive, creative and thoughtful. He has just a few close friends from his youth (he was too busy with basketball), spends his off-days exploring restaurants in San Francisco or record stores in Berkeley, and talks wistfully about driving his 1969 Volkswagen bus to Mexico for surf trips.
Durant had already worked with two other agents before he started working with Kleiman in 2013. But they quickly found a professional and personal synergy.
"We just met at, like, the perfect point," Durant says of the former music industry manager he has empowered to run his business empire. "We both hit our peaks at the same time."
The story of When Kevin Met Rich began at a Jay-Z concert back in 2008. Kleiman was representing the rapper Wale. Wale knew Durant because they both were from the DC area. Before the show, Jay-Z's manager invited Durant backstage to meet HOV himself. In a moment of 19-year-old self-doubt, Durant balked. A bad case of impostor syndrome set in.
"I was just a rookie," Durant says. "Who the f--- am I to go in there? Like, I'll probably walk in there and see Kobe or LeBron. I can't be sitting in there, talking with them yet. I ain't up there on that level."
Kleiman loves telling this story. It's still the essence of his relationship with Durant. He's always begging Durant to talk more about the business and philanthropic ventures they've built together. Durant is always humbly stepping away from the spotlight. Because while Durant can impose his will on the basketball court, he's still a bit reluctant to flex off of it.
"I know Rich wishes I'd do that more: stand up for what I've done," Durant says. "But at the same time, I'm not trying to go overboard with it. We're not looking to set the flag up and say, 'Yo. This is Thirty Five Media all around the world. Make sure you pay attention to us!' "
In this sense, Durant knows exactly who he is. He's not a hustler or a hype man. He's a hooper who needs people like Kleiman and Thirty Five Ventures marketing whiz Sarah Flynn to build his business and brand for him. The company has 10 employees at the moment, but it is moving into a new office building in New York City as it continues what Durant insists is a careful expansion. "I just feel like you can do it more of a strategic way," he says. "If you put yourself out there too much and then underdeliver ... that's not good."
Kleiman laughs. If Durant is more comfortable downplaying their accomplishments and ambitions, he's fine with it.
"If I was left to my own devices, I turn into Flava Flav sometimes," Kleiman jokes. "It doesn't affect my job, my pay, my ownership, nothing, if people in Prince George's County don't fully understand the magnitude of what Kevin is doing [in opening the Durant Center]. However, it keeps me up at night -- on behalf of him. That's how much I want [recognition] for him."
This reluctance to self-promote is part of the reason Durant was intrigued by the concept of the show. He knew he couldn't be the only athlete who took time to find his footing in the business world or questioned whether he belonged in Jay-Z's dressing room.
"I did not have the experience to be in that room," Durant says of himself as a rookie. "Once I started to get experience, I had something to give back in those conversations. I was more comfortable."
It took him almost a decade to get there, though. And even now, he finds himself asking more questions of the accomplished people he meets with than answering them.
"The cool part about KD on the show is you're watching him learn with you," Williams says. "Nobody is trying to say, 'Hey we're the leaders of the free world and we know everything there is to know.' This is like an exploratory journey."
For Durant and Kleiman, Williams was the perfect choice to host the show. They felt that his own story of venturing into the business world -- his professional playing career was ended by a motorcycle accident only a year in -- gave him a unique perspective.
As the No. 2 pick of the 2002 NBA draft, he had the same kind of golden pathway laid out as Durant did as the No. 2 pick five years later. "I'm 18, 19 years old, and I'm sitting there watching Puff [Daddy] play the piano, [Scooter Braun] is pitching me on signing with Bad Boy, and I'm like, 'How the hell is any of this happening?' " he says.
"Back then nobody really saw how inefficient the model was. Your agent has 25, 30 other people and then they hire one marketing director who was just splitting his time."
Then it all went away. His second career had to begin before his first one ever got off the ground. And he started asking the types of existential questions you can see only once your existence has been fundamentally altered.
"I just think that you have guys now that are driving the car, whereas before they would sit in the back and let ownership drive the car," Williams says. "The currency has changed. Guys still do endorsement deals, but now it's not about endorsements, it's about, how do I own equity? How do I get a 10 multiple on what my investment is?"
In the past two decades, the best athletes have fundamentally changed the business of sports in much the same way Jay-Z and Diddy changed the music industry. Why let the record label own your songs -- or your agents control your image -- when you can produce, distribute and own them yourself?
It happened organically at first. Then the Warriors took it to a new level. Players such as Andre Iguodala and Stephen Curry started getting chummy with the venture capitalists and digerati who drove up from Silicon Valley to sit courtside at Warriors games. By the time the team went to the Hamptons to pitch Durant on joining as a free agent in 2016, the opportunity to immerse in the Bay Area's vibrant business scene was a major selling point.
"It was like, 'Listen, man, we're a family. We're gonna embrace your interests,'" Iguodala says of how the team talked to Durant. "'I mean, you're gonna turn it into business anyway. So we can help out in any way possible, and we got an ownership who feels the same way.'"
Joe Lacob, Warriors owner and venture capitalist, says he does whatever he can to create a culture that encourages personal growth and exploration.
"I was really good as an investor for 30 years. But I always knew that in my second life -- I wanted to have a whole other business life, because it reinvigorates you," Lacob explains. "And to me that was about sports. So I left completely from the VC industry and went to do this full time.
"While you're in your primary career, I think you're trying to prepare for your second career. And hopefully by the time your first career has reached a normal logical end point, then you're ready to dive in and do it in a big way. That's what happened for me. That's what these guys should do too. They're not gonna be experts in investing while they're players, but they can be learning. And learning from meeting top people, learning from a few investments. So that by the time they're done, hopefully they're ready to take the next step, make that into a second life."
Ask Durant what he wants to be doing in his second life, after his playing career ends, and he sounds a bit like Phil Jackson. "I could be off in Montana on a ranch over by the water. Or living on the slopes. I don't know what I could be doing. I just like what I'm setting up for myself now -- something sustainable."
At 30 years old, he has a lot more basketball to play, and huge decisions about where he'll spend the rest of his career still to make. For now, he's focused on building a legacy on and off the court, starting with a $10 million investment in the learning center that bears his name.
But before he gets to that center's opening ceremony, he needs to make a stop. It's nearly 4 p.m., and he hasn't had time for lunch. So as Durant and his team head from the Warriors' swanky team hotel in Georgetown to Prince George's County, his caravan of SUVs pulls over at a convenience store for a croissant and some candy. No matter how far Durant travels in life, the sweet tooth comes with him. As a kid growing up on these streets, Durant would often stop at the McDonald's where his brother worked and fill up his water cup with Sprite.
On this day, he's telling that story to the first group of children who will be supported by the Durant Center.
"I told them that this building has my name on it, but it's yours," Durant says. "You're going to spend more time here than I will. Make it your home."
Durant had been wanting to expand his charitable giving in the same way he'd expanded his business portfolio. Real money -- in this case, a full third of his current yearly salary of $30 million -- that would actually make a difference to kids who were walking the same path he once walked. In 2018 alone, he donated a total of $3 million to the basketball and sports leadership programs at the University of Texas and committed this $10 million (over 10 years) to the Durant Center.
"That's doing something," he says. "We make a lot of money, so we should be able to give it back."
Just a handful of media entities were invited to the opening of the learning center, and he sent all of them away when he met privately with a small group of the 59 students in the inaugural class, who will participate in after-school tutoring, summer programs and personal development workshops throughout high school and even college.
"I can remember being a high schooler here, living next door," Durant says. "I was the No. 2 player in the country, and me and my mom were living in a two-bedroom right next door to here. You're waking up in the struggle still."
He looks around the gym at Suitland High, where he attended ninth grade. It is packed with people who knew him then, or like to claim they did. A group of high schoolers follows him everywhere, hoping for advice -- or maybe just a selfie.
Durant seems genuinely moved.
"That's what life is about," he says.
He seems to be making an effort to connect with each person reaching out, even if it's just a quick interaction. It wasn't so long ago that he was too afraid to approach Jay-Z in his dressing room, too shy to ask for advice -- or maybe just a selfie. Sometimes the barriers to entry are self-made. If he can help others find their confidence, that feels important.
It is both dizzying and inspiring -- the culmination of 30 years of work and self-discovery but also a first attempt at shaping a legacy.
"We all like different things," he says. "We're all going to do different things. But something's going to bring us together. Maybe it's here."
This story appears in ESPN The Magazine's March issue. Subscribe today!
Production and Location: Crew You/Buzz Off/Buck Off; Location: Courtesy San Francisco Art Institute; Wardrobe Stylist (Kevin and Rich): Nchimunya Wulf; Wardrobe Stylist (Jay): Raven Roberts; Barber: Eric Adams; Grooming: Tricia Turner; Prop and Set Styling: Mikhael Romain