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NFL stars Trent Williams, Fred Warner seek to score big by investing in Silicon Valley tech startups - USA TODAY

This wasn’t your typical meet and greet with these two NFL Pro Bowl players. 

The setting last month wasn’t on the gridiron or at a sporting goods store but in a large meeting space right in the heart of Silicon Valley. 

The occasion: An opportunity for San Francisco 49ers’ players Trent Williams and Fred Warner and about 30 of their teammates to tap into the minds of some of the tech industry’s savviest and emerging leaders for potential business partnerships.  

Williams and Warner each signed mega-deals during this past offseason that likely set them up financially for life. But as the franchise players are seeking to get the 49ers to the Super Bowl, they both want to get into another game: the tech space.

“Look, everybody wants to be successful, and we have a chance to help bring others to the party,” Williams, told USA TODAY. He signed a six-year, $138 million contract  in March, making him the highest-paid offensive lineman in NFL history.

As the 49ers prepare for their 2021 preseason opener against the Kansas City Chiefs on Saturday, Williams and Warner will spend part of their downtime looking to expand their investment portfolios.

Williams and Warner are both interested in financial tech, consumer tech and health care. They are being guided in their tech initiatives by venture capitalist Rudy Cline-Thomas, , who works closely with NBA star Andre Iguodala (an investor in Apple, Twitter, Facebook and Tesla to name a few), who recently rejoined the Golden State Warriors. Iguodala's success in tech rubbed off on his teammate, superstar sharpshooter Stephen Curry, who has invested in an online coaching service, and a social media platform.  

And, their former Warriors teammate and current Brooklyn Nets superstar Kevin Durant,  and his manager Rich Kleiman launched Thirty Five Ventures and invested in Postmates; fitness-tracking company Whoop; financial tech firm Brigit; and Therabody, makers of the popular Theragun personal massager. 

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After Williams signed his deal in March, he began talking extensively with Cline-Thomas about investment possibilities with tech startups. 

Soon, Williams asked Warner, a feared All-Pro linebacker who signed a five-year, $95 million contract extension with the 49ers in July, if he would be interested in similar opportunities.

“(Willams) approached me a couple of times about building my brand, my investment portfolio and really, life after football,” Warner told USA TODAY. "Now I need to also start thinking about diversifying.” 

Cline-Thomas athletes sometimes invest their money in more traditional ventures such as real estate, and an auto dealership. But athletes investing in tech is becoming more commonplace, ranging from early- to mid-stage startups and a pre-initial public offering. 

“There’s no way to avoid it, tech in some capacity is an integral part of our lives,” Cline-Thomas said. “It’s not just about using the products but also taking advantage of the financial upsides that come with it.”

And Cline-Thomas believes having “access to the club” is key, and that includes networking.

That kind of navigation can be helpful to athletes who are unfamiliar with the nuances and art of dealmaking and investing in Silicon Valley, said e-commerce entrepreneur Julie Wainwright, the founder and CEO of The RealReal, a luxury consignment startup worth an estimated $1.2 billion, who attended the event. 

Wainwright, the former CEO of Pets.com, said most athletes have a small window, about three to five years, where they make a lot of money and should consider diversifying their income as their careers could be cut short. “One hit, a devastating injury, and it could be all over,” she noted.

For athletes, especially those in Silicon Valley like the 49ers, who play their home games at Levi's Stadium in Santa Clara, California, it makes sense that they would consider investing “in their own backyard.”

“The bottom line is that not everybody is going to have this access,” Cline-Thomas said. “You might be lucky to know somebody in (Silicon) Valley, if your boy wasn’t a (venture capitalist or entrepreneur), you might be able to get in, and that’s just the reality of it.”

Williams said Cline-Thomas reiterated a similar message during their conversations. 

“I’m a team-oriented guy. I want to get the door open and bring in as many guys like me as possible,” Williams said. 

Williams said he and Warner are ready to learn and grow in tech as they have on the football field. 

“I think I speak for myself and Fred, that like playing pro football, you don’t know everything in your rookie year,” Williams said. “But as you get older and gain more experience, there are fewer things that you haven’t seen yet.”

Warner agrees, saying he is evolving more into his “grown-man decision-making.”

During the July 22 gathering, Warner said he was really impressed with Joey Grassia, the co-founder of Shef, a San Francisco-based startup that provides cooks who are mostly immigrants and stay-at-home parents the opportunity to sell affordable homemade meals directly from their kitchens. 

“He was asking if I was an investor, and I told him that I am new to all of this,” Warner of their conversation. “We really didn’t talk that much about football, and that was kind of refreshing. We really made an organic connection.”  

Grassia, whose startup received $20 million in Series A funding earlier this year, and has the likes of Iguodala as an investor, shared a similar sentiment. 

“They have an honest and genuine curiosity,” Grassia said. “I know little to nothing about sports, and I was telling them about the nuances of tech and business, and they had all sorts of questions. We’ll see where this all leads.”

That inquisitiveness can be invaluable, said CJ MacDonald, CEO of Step, a mobile banking app catering to teens, which has Iguodala and Curry as investors well as NFL great and Arizona Cardinals wide receiver Larry Fitzgerald and his teammate, offensive lineman Kelvin Beachum as investors.

MacDonald remembers before they invested, Fitzgerald and Beachum did their due diligence in researching Step and even did background checks on him and his team.

“Some athletes who invest put in the work, and some write checks,” MacDonald said. “But the athletes I work with, I know their thought process when they are making an investment. They are doing some thorough research and doing their homework.”