Even in a professional sports league known for well-dressed men, Andre Iguodala, the 6-foot-6 Golden State Warriors forward, stands out for his fashion sense. The 2015 NBA finals MVP, who once moonlit as the menswear style director for Twice, a secondhand fashion startup that was acquired by eBay, is known for his well-tailored suits. Tonight, he is wearing a double-breasted black suit by Ralph Lauren Purple Label with a slate button-up shirt and no tie. He stands at the base of the grand marble staircase in San Francisco’s City Hall and surveys the scene.

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Iguodala on the court. Photo: Daniel Terdiman In the past, the relationship between players and companies was fairly simple: Athletes got paid handsomely to endorse brands or products such as shoes, beverages, and cars. These days, the endorsement game is still important, but rise of entrepreneurship—especially in a place like Silicon Valley—presents new opportunities. Players who are willing to take some risk by accepting equity in exchange for endorsement or other involvement in a company can make far more than they would with the traditional cash-for-service arrangement of previous generations of athletes. “Not that there aren’t valuable dollars for [cash-for-endorsement] opportunities,” says David Abrutyn, a partner at Bruin Sports Capital, a global sports investment firm, “but you can get a multiple of those dollars if you are savvy enough and have the ability to identify companies [where] you’re willing to forego cash for equity.” And it’s not just endorsements. With today’s outsized salaries, players can also become powerful investors, provided they have the right connections. Iguodala is the standard bearer for what David Carter, the executive director of USC’s Sports Business Institute, calls the “third phase” of player-company relationships, in which highly paid athletes take an active role in their portfolios and invest directly in companies. Iguodala wants to help his fellow athletes take their own first steps in this direction—which begins with recognizing the opportunity before it’s too late. “[NBA players] are really hot right now. People know our faces now, and our names are recognizable,” he says. “But it isn’t always going to be that way.” Before that popularity and power dissipates, Iguodala wants to help his fellow players, “create these relationships, build these networks and develop them, and create marketing opportunities [for ourselves].” That means, as Iguodala puts it, that players must think of themselves as businessmen even before they retire. And he’s going to help them. The Education Of Andre Immediately after almost every Warriors’ victory, Comcast SportsNet sideline reporter Ros Gold-Onwude pulls aside one of the game’s best-performing players for a short interview. In mid-November, inside Toronto’s Air Canada Centre, where the title-favorite Warriors have just dispatched the hometown Raptors, Iguodala is the man on the spot. Though the 33-year-old is a former All-Star, his stats are declining, and this is his first Gold-Onwude interview of the season. The two have a good relationship, so after some preliminaries, she asks if he was upset it has taken her 11 games to get to him. “Naw, I just figured out you gotta make shots to get interviewed,” Iguodala says. “So I’m going to work on that.”

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Your browser does not support iframes. The interview is NBA boilerplate, until suddenly, Iguodala’s thoughts seem to veer toward retirement. While talking about the Warriors roster, he mentions rookie Patrick McCaw, who has spent most games riding the bench, saying, “He’s going to take my spot [one day]. I’m going to be out of a job.” To be clear, Iguodala’s All-Star years may be behind him, but he’s still vital to the Warriors’ championship hopes. Nevertheless, he’s looking ahead. “I got a tech thing going on, ” he tells Gold-Onwude. “Life is good.” Iguodala’s quest to craft an identity beyond sports dates back to the start of his career with the Philadelphia 76ers. While Iguodala was playing in Philadelphia, his friend Herbert Hill, a Sixers draftee who never played in a regular season NBA game, often mentioned his financial adviser, Cline-Thomas. Iguodala and Cline-Thomas became friendly, bonding over their shared interest in tech and business. It was “kind of like a mentorship where it wasn’t just somebody working for me,” Iguodala recalls. “It was working together, and holding my own, and doing homework.” Eventually, in 2007, Iguodala signed on as a client, and for a few years, he and Cline-Thomas invested mainly in publicly available tech stocks via an E-Trade account. Although Cline-Thomas had developed a connection to the world of venture capital through Philadelphia-based VC Josh Kopelman, he and Iguodala didn’t have much access to the kinds of early-stage deals where the real money is made. That began to change in 2013, when—after a year with the Denver Nuggets and eight seasons with the 76ers—Iguodala signed a free-agent contract with the Warriors and moved to the Bay Area. Soon after, Cline-Thomas decided it was time to make inroads on Sand Hill Road. He reached out to Andreessen Horowitz partner Jeff Jordan, one of the top VCs in the business—albeit in an oddly analog fashion. “I actually got a letter, and I often don’t open letters,” Jordan recalls. “I ended up replying and we met for dinner in San Francisco. [They] were really intelligent men with a passionate interest in technology, and we talked tech all night.” Jordan’s specialty is consumer technology, which fit well with Iguodala and Cline-Thomas’s interests. And since they had few relationships in the Valley, the VC has played the role of matchmaker, opening doors for the pair and making introductions.

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When he first began working with Iguodala, Cline-Thomas had told his client that he’d have to treat investing almost as a second career if he wanted to be successful. And so Iguodala does. He makes a point of reading everything from the Wall Street Journal to TechCrunch every day; his Twitter feed features a mix of style and tech companies; news publications; and Silicon Valley investors and executives. And he doesn’t just show up for business meetings; he’s an equal partner in discussion and determinations about where to put his—and Cline-Thomas’s—money. “[For him] the normal locker room talk is about positive things in the world of tech,” says Curry, who has witnessed his teammate’s focus over the past four years. “You can pretty much ask him any question, and he’ll have a pretty educated answer.” That attention to detail doesn’t go unnoticed. Dick Costolo, the former CEO of Twitter, first met Iguodala in 2014 when the two of them were paired for the AOL video series Win/Win. In the video, Costolo mentioned that NBA great Chris Bosh had once told him that he knew he had to think about his life after basketball, and that while a tech executive could always move from one company to the next, Bosh had “to be the CEO of Chris Bosh,” taking responsibility for figuring out what comes after his basketball career. “Andre thinks very, very similarly,” Costolo says. Former Twitter CEO Dick Costolo and Andre Iguodala. When Costolo was recently raising money for his new social fitness startup, Chorus, he approached Iguodala and Cline-Thomas. It wasn’t just Iguodala’s celebrity or money that he wanted to leverage. Costolo, who had seen that Iguodala “understands the importance of a holistic approach to wellness,” wanted the player’s perspective on the venture. Over dinner, the three discussed a potential investment. “They probably asked me more questions—more pointed questions and more detailed questions—than anybody else I pitched,” recalls Costolo. Iguodala and Cline-Thomas became some of Chorus’s earliest investors. “They’re approaching it sort of as students of the game,” says Richard Smith, a former business development executive at First Round Capital who’s now at LinkedIn, and who’s helped Iguodala and Cline-Thomas with various initiatives. “They’re putting in the time to learn the industry that they’re passionate about, and picking the places that it makes sense for them to dive deeper into.” Other investments they’ve made include TruMid, a George Soros-backed electronic trading platform that recently surpassed $1 billion in total trades; the sleep-tech companies Hello and Thrive Global; Walker & Company, which makes health and beauty products aimed at people of color; and The Players Tribune, Derek Jeter’s athlete-focused media company. Iguodala likely has a few years left in the NBA. Once his playing days are over, though, he plans to ramp up his investing and advising of portfolio companies, even as he increases the amount of energy he puts into educating athletes and bridging the gap between sports and technology. All of that is why, on his LinkedIn profile, Iguodala identifies himself first as an entrepreneur and venture capitalist, and only then as an NBA player. From Student To Teacher Last summer, about 20 current and former NBA players descended on San Francisco’s St. Regis hotel for the National Basketball Players Association’s (NBPA) first Technology Summit. Iguodala, an NBPA vice president, and Cline-Thomas had worked closely with the association’s then executive director, Roger Mason, to create the event, a three-day series of educational discussions and meetings with venture capitalists, tech executives, and entrepreneurs.

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Some of the players who came already had their own businesses; others had tried and failed—and wanted to know why. Over the three days, they sat through discussions on topics like “working with founders and early-stage companies” and “understanding the technology and VC landscape.” Speakers included representatives from top-tier VCs like Andreessen Horowitz and Khosla Ventures, as well as tech companies like Twitter, Under Armour, Halo Neuroscience, and others. NBPA Tech Summit. Iguodala’s and Cline-Thomas’s interest in helping players get the kind of tech-investing education that might help them prosper began about a year and a half ago. Iguodala realized that while lots of athletes were asking him for advice, most had little investing savvy. With tech investing becoming one of the sexiest pastimes, Iguodala knew he could help athletes participate who were flush with eight- and even nine-figure contracts. But he also wanted to prepare them. Players “only read the success stories,” says Cline-Thomas. “Nobody’s writing about somebody that lost a shitload of money, which is 99% of the whole game.” Iguodala’s vision for the summit, Cline-Thomas explains, was to offer “safeguards before more players became casualties.” For Iguodala, the event was a chance to give his fellow players access to what he and his Warriors teammates have at hand every day—easy access to Silicon Valley, something that gives them a clear advantage when it comes to understanding tech investing. “[The summit is] kind of a crash course on the tech world,” Iguodala says in a video recap of the event. “You want to know everything from the ground up, and you just don’t want to dive into something because it’s kind of the cool thing to do at the moment.” According to Iguodala, the players showed up prepared—ready to take full advantage of their meetings with high-level VCs. And many, he reports, have since maintained contact with the investors. One such player is Lou Amundson, a 10-year NBA veteran who played last season for the New York Knicks. He has recently been working with a virtual reality company to start a sports division, and came to the summit for a better understanding of the startup ecosystem. But he was just as impressed by the event’s emphasis that athletes, rich as they are, need to take responsibility for their own financial well-being. “That message still needs to be delivered to some players,” Amundson says, “It’s not a secret anymore that there’s an opportunity [in tech], but there’s really a lot of bad opportunities out there, too.” To Amundson, the summit was a reminder of the kind of knowledge that athletes need to internalize—as well as a demonstration that they have someone in the Valley who’s got their back. “It’s important to really educate yourself, talk to people, and network,” he says, “and [Iguodala and Cline-Thomas] have always been open to sharing that information and talking with players and building relationships.” The Tech Summit will return this summer, and Cline-Thomas expects it to be substantially bigger. He says there’s also an interest in expanding the attendee list to players in other sports, and even from other countries. The Warriors dinners, too, are continuing, and paying dividends; Warriors newcomer McGee is investing in a portfolio company of one of the VCs he met at the City Hall event. Iguodala and Cline-Thomas hosted a second dinner, with six Warriors players and a group of VCs, in December at San Francisco’s trendy Hakkasan restaurant. They plan on having at least a couple more before the end of the current NBA season.

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“I’m trying to get the athlete to reinvent himself,” says Iguodala. “There’s a lot of hard work that goes into this, but it’s possible.” And for him, the idea of collaborating with fellow players off the court and in the tech world comes naturally. “I always tell my teammates, we’re teammates for life,” he says. “We’re going to be doing things together when we get older . . . Don’t take that for granted.”