Love Yourself: The Greatest Lessons From A Silicon Valley Entrepreneur

SLIDESHOW

More and more NBA players are placing bets on tech startups, but none have done so as aggressively, or with as much quiet determination, as Kevin Durant.

 

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Durant, photographed at his summer home in Los Angeles on August 29.

 

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With his business partner and manager Rich Kleiman running point, Durant has rapidly become a fixture in powerful Silicon Valley circles.

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Durant, after sinking a threepoint charity bucket in front of Rubrik employees at VMworld, with Kleiman, as always, in the foreground.

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"Data management! Data management!”

At 4:30 on a blow-dryer-hot August afternoon in Las Vegas, a three-beat chant booms from the back seat of a black SUV. Behind the tinted windows, two men named Kevin and Rich, dressed slouchily in untucked button-downs and sneakers, are getting psyched up for a tech conference at the Mandalay Bay Convention Center. Minutes ago they stepped off a private jet at McCarran International Airport after a brief but rocky flight from Los Angeles, where Kevin is living this summer. Now they’re being chauffeured to VMworld, perhaps the largest, and certainly the rowdiest, cloud infrastructure conference on the planet.

Kevin and Rich aren’t IT guys, and they admit to not knowing much about the products and services being proffered at VMworld. But they are committed angel investors, and they’ve landed in Vegas to lend support to the newest addition to their rapidly growing investment roster: Rubrik, a three-year-old company that provides cloud-based data management (hence the chant) and that claims to be one of the fastest-growing startups in Silicon Valley. Kevin is technically Rich’s boss, but they invest and operate as partners, and they have the easy, teasing rapport of brothers.

“I can’t believe we’re in Vegas right now and we’re going home in four hours,” Rich says to Kevin as the SUV rumbles north up the Strip. “That doesn’t even make sense! It’s Vegas!” He recalls how he used to fly here from New York at least once a month for DJ shows with his music industry buddies Mark Ronson and Q-Tip. This trip will not be sick like that. “We’re just here for Rubrik,” Rich stage-whispers to himself. “Just here for Rubrik. Only Rubrik. Only Rubrik.”

The SUV stops short at a green light while a bridal party drunkenly jaywalks across the Strip, pausing to take selfies in front of the city’s famous welcome sign. “Getting married in Vegas,” Kevin says, shaking his head. “We’ll see how that one ends.” Rich, still imagining how much fun this night might’ve been if he were 15 years younger and surrounded by DJs, reaches over to touch Kevin’s shoulder. “What if,” he says, “the Rubrik guys are like the guys in Hangover that, like, do a shot and then, the next thing they know, they are, like, hanging from the lion at Caesars Palace?” Kevin chuckles lightly as Rich plays out the rest of this scenario.

“It’s like, ‘Yo, you tattooed “Rubrik” on your stomach last night?’”

“Yes!” Kevin shouts.

“Yes! Data management! Data management!

The back seat roars with laughter.

As the SUV approaches the rear loading dock of the convention center, Rich, who is 12 years Kevin’s senior, gives his employer a final piece of advice. “Remember: OD on the excitement and the happiness,” he says. “Just be like, I fucking love Rubrik.” Kevin nods silently. He doesn’t really need to be told this. “Or,” says Rich, his eyes widening, “you could do the opposite and if somebody asks you why you invested in Rubrik, be like, ‘Fuckin’ Rubik’s Cube! I love that shit!’” They laugh in chorus again.

As Kevin and Rich step out of the vehicle, they’re met by John Koo, VP of corporate marketing at Rubrik, and two casino security agents muttering into earpieces. Koo, crackling with nervous energy, tells Kevin how excited the whole team is to meet him. Kevin, OD’ing on enthusiasm, says he’s excited too. The contingent opens a double door beside the loading dock and emerges into a recycled-air coliseum of brands, booths, bright logoed shirts, and several hundred attendees all craning to get a peek at the most famous cloud storage data management investor on earth.

The roar begins the moment Kevin Durant’s 6-foot-11-inch frame emerges from behind a curtained bullpen: “KD! Woooo!” Several hundred smartphones simultaneously dart into the air. Durant, followed by Rich, real name Rich Kleiman—his omnipresent agent, manager, media handler, business partner, and back-seat ball buster—hustles through the crowd to a waiting Airstream trailer parked in front of a makeshift basketball half-court.

Inside, Durant receives his marching orders and a small plastic cup of beer. Koo wants him to say a few words of thanks on the mic, then sign some autographs for a while, then shoot some three-pointers for charity. Shouldn’t take more than 60 minutes, he guesses. (They’ll be out of there in 45.) Koo has talking points available for Durant, but Kleiman says that won’t be necessary—Kevin’s good on his own. “We ready?” Durant asks, eager to get this phase of his investment over with. “Let’s go!” He slugs the rest of the beer, and out of the Airstream they tumble.

 

How does Durant—newly ordained as the greatest basketball player on the world’s greatest basketball team—find himself in a Las Vegas convention hall on a Tuesday afternoon promoting a Palo Alto company whose products he can’t very well explain? (“Everybody knows about the cloud,” Durant verbally shrugs when I ask what originally attracted him to Rubrik.) The sequence of events that brought a giant of the NBA to VMworld is both well-known and not. Here’s what you likely already know: Last summer, Kevin Durant left the Oklahoma City Thunder after nine thrilling but unconsummated seasons to join the Golden State Warriors, a squad that has become known not just for its exquisite shooting, sublime ball movement, and unquenchable thirst for winning, but also for being Tech’s Team, a multibillion-dollar enterprise majority-owned by Silicon Valley majordomos. In his first year as a Warrior, Durant was everything his Oklahoma fans had long exalted. He delivered the most efficient offensive season of his career, while also posting personal highs in rebounds and blocks; he led the Warriors on a masterful 16–1 playoff run; and he contributed an MVP performance against the Cleveland Cavaliers in the Finals that was almost comically dominant, capped by an instantly iconic game-winning three-pointer over a shrunken LeBron James in the waning seconds of Game 3. He’s since called it the most clutch shot of his life.

What’s less known is that, while helping to secure the Warriors’ second NBA championship in three years, Durant, who turns 29 on September 29, was also working with Kleiman on a parallel set of goals that would generate, they hoped, a second professional pursuit and a steady stream of riches after his basketball days were over. This wasn’t an entirely new idea: Bay Area–based ex-athletes like Ronnie Lott, Joe Montana, and Harris Barton have been investing in technology companies for years. And more recently, a constellation of current and former NBA stars including James, Kobe Bryant, Michael Jordan, Baron Davis, Kyrie Irving, Carmelo Anthony, Harrison Barnes, and fellow Warriors Stephen Curry and Andre Iguodala have made a raft of investments in startups of all sizes, shapes, and sectors within the tech industry. But none of these athletes has infiltrated the highest echelon of the industry or forged as many symbiotic relationships with Valley luminaries as rapidly, or with as much quiet determination, as has Durant.

With the seemingly inexhaustible Kleiman running point, Durant has, in just over a year, become a fixture in powerful Valley circles, breaking bread with, receiving intel from, and sometimes coinvesting beside such A-listers as venture capitalists Ben Horowitz and Ron Conway, Apple’s Tim Cook and Eddy Cue, YouTube’s Neal Mohan, and a raft of partners and managers at top VC firms including Andreessen Horowitz, Greylock Partners, SV Angel, and IVP. Through the 18-month-old umbrella corporation known as the Durant Company, Durant and Kleiman have acquired equity stakes in no fewer than 30 young companies, investing between $50,000 and $250,000 in seed rounds and between $250,000 and $2 million in later-stage rounds.

A short list of the Durant Company’s commitments reads like a catalog of the Valley’s current fixations: Durant and Kleiman have gone in on automated drones (Skydio), personalized medicine (Forward), food stamps by smartphone (Propel), big-data marketing (Zenreach), microlending (Acorns), on-demand delivery (Postmates), quantified health (Q.bio), and polling bots (Polly). They’ve invested in online media brands like the Players’ Tribune and in restaurant and hospitality businesses in New York (Landmark Rooms) and Los Angeles (Ken Friedman’s forthcoming Hearth & Hound). Copycatting LeBron James’s lucrative Blaze Pizza investment, they’ve bought a piece of a customized-pizza chain, Pieology. They’ve got a cold-pressed-juice brand, Wtrmln Wtr. They’ve got a dance-workout-party gym, 305 Fitness, with locations in New York, Washington, D.C., and Boston. And they’ve purchased equity in at least 15 other companies currently in stealth mode, their products too embryonic to shoulder the weight of a celebrity investment being publicized prematurely. Two-thirds of these investments, according to Kleiman, have been made in the 15 months since Durant became a Golden State Warrior.

This investing spree began unofficially a year ago at a now-legendary barbecue and birthday party for Durant held at the Atherton home of Ben and Felicia Horowitz. The entire Warriors team showed up in support of their new teammate, as did team owner Joe Lacob and a who’s who of fellow tech eminences who came to welcome the long-limbed kid from Prince George’s County, Maryland, into the fold. It all started with Kleiman mentioning to longtime friend Steve Stoute, the former music industry heavyweight turned ad agency CEO, that Durant would love some intros in the Valley. Stoute called his pal Horowitz, cofounder of the influential VC firm Andreessen Horowitz, to ask him to throw the soon-to-be 28-year-old a coming-out party. “I didn’t know Kevin that well,” Horowitz tells me, “but Steve’s family. And if family asks for that, we’re barbecuing.”

Not that it took much arm-twisting. The Warriors, as Kleiman notes, have become the de facto “biggest company in Silicon Valley.” They are the home team of the digerati, with a bandwagon big enough to carry the imperial ambitions and mountainous egos of the triple-comma crowd. To them, Durant was the killer app atop the unbeatable operating system. He was also a kindred spirit, capable of making what Stoute calls a “critical, CEO-level, bet-it-all” decision: sacrificing millions of dollars in short-term free-agency money (not to mention complicating his nice-guy brand and infuriating millions of NBA fans) in favor of playing the long game in Northern California. Coming to Golden State was “a businessman’s bet,” Stoute says admiringly, “not an athlete’s bet.”

On that initial day at the Horowitzes’, and over the months that followed, Durant won over his new friends in the Valley with what many saw as his introspection, affability, and hunger to learn. Ron Conway, who may be the most connected angel investor in a region lousy with them, wrote in an email that he was immediately taken with Durant’s thoughtfulness and “inquisitive mind.” So impressed was he that Conway opened up his gold-plated Rolodex to Durant and Kleiman, promising to introduce them to anyone who intrigued them in the Valley. They subsequently got together for brainstorming sessions with Conway and fellow SV Angel partner Brian “Coach” Pokorny at Tosca, the current It spot for deal-closing VCs and Durant’s new favorite restaurant in San Francisco. They also convened for a lasagna dinner with the entire Conway family at their estate in Belvedere. (Conway’s wife, Gayle, would later send Durant a get-well Tupperware of lasagna after he injured his knee during a Warriors-Wizards game in February.)

As the tech pooh-bahs got to know Durant and Kleiman, and to hear their three-step vision—first, cultivate a network of blue-chip advisers; next, meet with strong executive teams in a diversity of markets; and, last, commit to long-term investments in companies that could benefit from their ownership—they became genuinely fascinated, convinced that this was no flash-in-the-pan celebrity dipping a toe in the broiling waters of tech. They began talking about Durant in terms usually reserved for hotshot founders and other industry disrupters. “He’s a little bit of an unusual guy for a professional athlete,” Horowitz says. “He actually reminds me from a temperament standpoint of the musical artists I know.” (The Horowitzes are famously tight with Jay-Z, Nas, and Kanye West, among others.) “The thing that these guys have, the real genius ones, is they can see things that other people can’t see as easily. They look at the world from a different perspective.”

As much as the adulation might seem calculated—the tech executives’ desire to cozy up to an international superstar an obvious marker of their ambition and preening self-regard—Durant, for one, doesn’t seem to mind. In fact, the adulation goes both ways. He is clearly awed by his new acquaintances’ successes. Just thinking about Conway’s “knowledge and history and connections with different people,” Durant says, makes him want to achieve more and work harder. In conversation, the quiet, reflective Durant really does come off like an attentive student, one who’s eager “to learn and willing to mess up,” and who wants to steal lessons from the playbooks of people he considers “killers.”

“They don’t care about what people have to say about them,” he tells me aboard the jet to Vegas, as he lounges comfortably in a spacious leather seat, munching chips and sipping orange juice. “They don’t care how you feel about the decisions they make. They are just out to kill. They are just as ruthless as we are as basketball players.”

 

One thing you may be asking yourself when you hear Durant talk about the cutthroats and killers inhabiting Silicon Valley is whether he’s in any danger of being shivved himself. Isn’t it possible that this rich, talented, but relatively inexperienced pro athlete is being used by these cunning captains of industry for something other than his thoughtful, inquisitive mind? Sure, everyone wants to be buddies with Kevin Durant—he’s a veritable celebrity unicorn: humble, gracious, approachable, and self-aware. And, undoubtedly, Durant has something to teach tech entrepreneurs about leadership, resiliency, and relentless hard work. 

But for a VC firm, letting a couple of tech neophytes into your precious “deal flow” carries its own risks. And anytime a startup sells a piece of itself to an investor—whether to an individual angel or to a deeply capitalized venture firm—it’s inherently diluting the value of all of its remaining equity. For a tech founder, letting the Durant Company invest in your company means you’re effectively placing a bet on Durant and Kleiman as much as they are on you. And if the relationship fizzles, well, everybody’s kinda screwed. “These are big decisions,” says Somesh Dash, a partner at IVP who has coinvested with several other pro athletes in Valley startups. “It’s like a divorce if it doesn’t work. You can’t be just like, ‘I wanna get my money out.’ Well, you can’t just get your money out, and that leads to a lot of pain.”

When I ask Horowitz what dangers might lurk for Durant and Kleiman in the sharky waters of Silicon Valley, he says that, more or less, there’s nothing for them to fear—they’re virtually made men. “I mean, it’s, ‘What pool are you fishing in?’” Horowitz says. “Yeah, if you just try to go invest in a random company, that’s hard. But they can piggyback off the diligence and the analysis that we do on the technology side—the backgrounds and the market sizing. They don’t have to figure that stuff out themselves.”

Such was the case with Durant and Kleiman’s “mid-six-figure” investment in Rubrik, a tiny piece of a $180 million Series D fundraising round led by VC firms IVP, Lightspeed Venture Partners, and Greylock. The deal came via ex-49er Ronnie Lott, an experienced enterprise-company investor, who tipped off Kleiman that Rubrik might be a blockbuster. (The company, according to one insider, “has performed so well”—it notched $150 million in anticipated annual revenues and is currently valued at $1.6 billion by investors—“it has the optionality to go public over the next 12 to 18 months.”) Kleiman admits that, initially, “it didn’t make much sense how we fit” with the company, which lets businesses large and small store massive amounts of data on the cloud. Cool idea, but “not like something that Kevin would ever stand in front of and promote,” Kleiman says.

But then, he continues, they met the management team, who had “the same passion and paranoia about their business that Kevin has about his sport.” Rubrik’s ownership was willing to sell them a piece of the company “at a really good value,” Kleiman says. Plus it would make Durant a special adviser to the CEO and support his charity foundation. All of this in return, Kleiman says, for “offering their clients something that nobody else in their category really can”—a direct connection to Kevin Durant.

There’s no doubt that companies like Rubrik see a celebrity investment as a savvy way to pump up media exposure (hi!) and boost recruitment efforts. But to assume that those are the only reasons behind such arrangements is to misunderstand the nature of the Valley itself. It is the ultimate insider’s arena, a place where personal friendships dictate what you learn, when you learn it, and how much you can profit from that information. “One thing about venture capital is you can’t just rely on a small set of relationships and say, ‘I’ve got my people,’” Dash says. “That’s not how it works. There’s always someone new who’s popping up. There’s always somebody with expertise in an area that’s taking off.”

To VCs like Dash, Durant and Kleiman are merely the latest experts to pop up in the Valley, and their unmatched talents—not to mention their plethora of connections within the worlds of sports, media, and entertainment—make them people whom, if you’re any good at your job, you absolutely need to know. It helps immensely that Kleiman—Durant’s right hand in every aspect of his personal and professional life—is wildly eager to be known. A tireless connector, kibitzer, and deal maker, Kleiman is someone who, Dash says, “is always working, never off, an animal.” “He’s got this amazing ability to make friends, to make people like him and trust him,” says restaurateur Ken Friedman, a longtime friend of Kleiman’s, who, not coincidentally, owns Durant’s adopted San Francisco clubhouse, Tosca. “I always tell him he should be a restaurateur.”

Stoute, who has known Kleiman since the early 2000s, remembers a period several years ago when the agent was managing Solange, an artist with a reputation for being “extremely talented and extremely difficult to move around.” Stoute watched up close as Kleiman defused crises while giving Solange the space she needed to maximize her creative output. “I said, if he can do that with her, this guy’s gonna go all the way. Because she is tough.”

Kleiman, 40, is tall, bald, brawny, and in constant motion. He grew up comfortably on Manhattan’s Upper West Side and became infatuated at a young age with both hip-hop (early loves: Run-DMC, A Tribe Called Quest) and sports (Mets, Knicks, Giants). After dropping out of Boston University, he started managing DJs, most notably his high school friend Mark Ronson and later Ronson’s sister Samantha. He became a music supervisor for ESPN’s hit docu-series The Life and eventually caught the attention of Jay-Z, who hired him to produce the theatrically released concert film Fade to Black. Kleiman was in awe of the rapper mogul. “He was just like this bigger-than-life character who could walk on air, and yet who was the most down-to-earth and funny person,” Kleiman says. “Like, he got every joke. He was ahead of the timing on everything. It was magical. And I was like, ‘Oh my God, I want to be around this.’”

When Jay-Z launched a talent agency out of his sprawling entertainment company, Roc Nation, he brought on Kleiman as an artists’ rep. Kleiman managed the careers of hip-hop acts Meek Mill and Wale, the latter of whom had a big fan in a certain 19-year-old NBA Rookie of the Year named Kevin Durant. The manager and the player would chat occasionally at Wale shows, and eventually Kleiman offered Durant the chance to meet Jay-Z backstage at a concert. “In classic KD fashion,” Kleiman says, Durant turned down the opportunity. “He just felt like he wasn’t ready yet. It was like, ‘Who am I? I want to accomplish more before I meet with one of my idols.’”

Several years later, in 2013, Durant signed on as the marquee client of Jay-Z’s new Roc Nation Sports agency and made Kleiman, by then exclusively repping athletes, his agent. As Durant’s star rose (he won the league MVP award in 2014 and subsequently renewed his Nike sponsorship, a whopping 10-year deal worth $250 million to $300 million), it became apparent that he wanted something more out of his career.

From the time he entered the league, Durant tells me softly, his baritone barely audible over the hum of the jet engines, “I felt like I had to be the typical basketball player. I had to do the Gatorade stuff, I had to do McDonald’s, I had to do so much stuff that I didn’t want to do.” Eventually, the demands of too many endorsement deals—a high of 13 at one point, now whittled down to 3 or 4—took their toll. “It turned me off from the love of the game. I hated talking to the media, I hated photo shoots for stuff that I didn’t even use. And then Rich came in and simplified my whole life, and now the only stuff I’m doing is because I want to do it. If I’m sitting here talking to you, it’s because I’m passionate about it.”

In 2015, Kleiman sought out Jay-Z’s approval to drop the rest of his Roc Nation client list and focus all of his attentions on a single player: Durant. The two have been working in lockstep ever since. Kleiman is now bicoastal, living full-time with his wife and two young daughters in Manhattan while spending a few weekends every month in a granny unit attached to Durant’s house in the Oakland Hills. He still represents Durant as a player agent under the umbrella of Roc Nation Sports, but the Durant Company—and a content-development arm called 35 Media, which produces videos for Durant’s new YouTube channel—is an independent entity. When they aren’t living next door to each other, the two men talk by phone four or five times a day, “and probably only one of those times is about business,” Durant says. “All our conversations are about life stuff.”

So close-knit are they that people in Silicon Valley have taken to referring to them as a single entity—up and down Sand Hill Road, KD & Rich is practically the new Jobs & Woz. “The magic of their relationship,” Horowitz says, “is that Rich believes in Kevin to the ultimate degree. For Rich to bet his career by dropping everything and putting 100 percent of his time into Kevin, just as Kevin is betting his whole career on coming to the Warriors—that is like a level of trust that you almost never see.”

 

The bond between Durant and Kleiman is, on its surface, unlikely. Durant is a prodigiously athletic millennial raised by a single mother in the impoverished D.C. suburb of Seat Pleasant. Kleiman is a Jewish Gen X son of a Manhattan interior designer and a housewife. Durant is soft-spoken, reserved, and sensitive. Kleiman is loud, extroverted, and gregarious. And yet these men obviously get each other. They finish each other’s sentences, make each other laugh, and pull each other up when they are down (at least as down as two extraordinarily wealthy, successful guys can get).

Take this story about the days after Durant decided to sign with the Warriors, a time when he was feeling the full brunt of the Internet’s fury about his perceived betrayal of Oklahoma. He and Kleiman were in China for a weeklong tour of the country sponsored by Nike Basketball, and the flak he was taking from people in Oklahoma City who had once professed deep affection for him was overwhelming. “To have so many people just say, ‘Fuck you,’ that really does it to you,” Durant tells me, still clearly anguished. “Because I truly had invested everything I had into the people I played for…. And for those people that I know and love and trust to turn their back on me after I was fully invested in them, it was just…more than I could take. I was upset.”

“You were fucked up in China,” Kleiman, looking up from his phone, offers from his plane seat across the aisle from Durant and me.

“That was before I met anybody from the Warriors and dove into the culture. I was basically on my own,” Durant says.

“It was like you were in between two teams.”

“I’m telling you, I was fucked up for a while!”

“We were all messed up on jet lag,” Kleiman says, turning to me, “and I was up at 6 a.m. and he calls me and says, ‘Yo, are you up?’ And I’m like, ‘Yeah, what’s up?’ And he’s like [yelling], ‘Why the fuck did you let me do this to my life?’ And I’m like, ‘Ohh shit, I’m coming over to your room.’”

“That hotel was rock bottom,” says Durant.

Together they got through it. And by the time Durant joined Team USA Basketball for the 2016 Summer Olympics in Rio de Janeiro, he’d begun to put things back in perspective. “I was worried about how my peers were going to feel about me,” he says. “In my profession, that’s the only thing I care about. So when I was talking to Kyle Lowry and DeMar DeRozan, and they were like, ‘Congrats, man, do your thing,’ and Paul George was like, ‘Congrats, man, I am happy for you,’ and Kevin Love was like, ‘Shoot, do what you gotta do,’ that eased my mind a little bit, because I want that from my peers.”

Since then, Durant’s life has been a prolonged exercise in wish fulfillment. He played marvelously in the Olympics and brought home the gold. He jibed immediately with his new teammates in Golden State. He won an NBA title. He won a Finals MVP award. He paraded a championship trophy through the streets of Seat Pleasant for Kevin Durant Day. He continued to build basketball courts through his Kevin Durant Charity Foundation, now up to 14 courts in four countries. He visited the Taj Mahal. He publicly dissed Donald Trump and felt damn good doing it. He attended, with Kleiman, Google’s ultra-secretive celebrity “camp” in Sicily alongside Prince Harry, Elton John, and Oprah. And he laid the groundwork for a second career that could define the next 50 years of his life.

And what if those bets Durant is placing on promising young tech companies don’t pan out? Well, at least he’ll come away with some stories. A few hours after leaving the VMworld show, Kevin and Rich are making their way to a dinner with Rubrik’s management team and several venture investors at a steakhouse in the Cosmopolitan Hotel. They are riding up an escalator when two women standing behind them peer up at them and ask if they are famous. Rich answers that, yes, as a matter of fact, he’s Matthew Perry from Friends. The women scream in recognition and ask Kevin to take their picture with “Matthew.” Kevin, who has apparently been mistaken for Rich’s bodyguard, receives the women’s cell phones and, suppressing his laughter, takes photos with both cameras simultaneously. The women, grinning wildly, thank him and hug Rich. Then, at the top of the escalator, they all happily part ways.

Kevin and Rich recount this story to the Rubrik guys as they shake hands before dinner, and the Rubrik guys laugh uproariously, and Kevin and Rich laugh hysterically, and then they all sit down together and toast to their future success.

 

Originally published in the October issue of San Francisco

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Source : https://www.modernluxury.com/san-francisco/story/kd-and-the-vcs-how-kevin-durant-became-made-man-silicon-valley

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