49ers’ Richard Sherman on tech investing, fatherhood, and yes, football

January 19, 2020, 1:00 PM UTC

Richard Sherman’s star is high—and rising. In the last few weeks, the San Francisco 49ers cornerback was invited to the Pro Bowl (it will be his fifth time playing in the all-star game) and bestowed with the title of “best cornerback of the decade” by Pro Football Focus, the authority on evaluating players for the National Football League. He’s also taken a leadership position among players—Sherman is a vice president with the National Football League Players Association, the union that represents professional athletes in the sport, and it’s possible he’ll take on an even bigger role there in the coming months. Oh yeah, and if the 49ers beat the Green Bay Packers this coming Sunday, they’ll be going to the Super Bowl for the first time since 2012, with Sherman’s help. 

But the NFL star is making a name for himself in other arenas too: venture capital. Over the last few years, Sherman has put money in Vicis, a startup that makes helmets aimed at reducing the impact of head injuries, and Oxeia Biopharmaceuticals, a drug company that’s experimenting with a drug that mitigates the effects of concussions right after they happen.

Now, he’s expanding his profile and portfolio in the investing world even more. Sherman recently joined Decibel, a new VC firm backed by tech giant Cisco, as an investor and advisor. The fund, led by former NEA partner Jon Sakoda, aims to raise $500 million, according to an SEC filing from last year. (Sakoda won’t comment on the fund size due to “regulatory restrictions.”) While Decibel doesn’t necessarily focus on companies that promote athlete safety and health, Sherman hopes his involvement with the venture capital industry will ultimately encourage more players to pursue life after football—while they’re still in the game.  

To hear more about his approach to investing, the pros and cons of social media, and why NFL players haven’t dabbled in venture capital as much as their NBA counterparts, Fortune caught up with both Sherman and Sakoda at Levi’s Stadium, the home of the 49ers. 

This conversation has been edited and condensed for clarity.

How did you guys meet?

Jon Sakoda: It was in 2014 and early 2015 that Derek Jeter and Kobe Bryant, Richard, and a handful of other athletes got together and identified that there was a pretty big difference in the way that digital media was interfacing with athletes versus traditional media. It was a lot less about trying to get to know them, and a lot more about basically just trying to come up with the stories that could get the quick engagement they wanted. So the initial way in which we met was around the founding of The Players’ Tribune. [NEA, Sakoda’s former firm, was an investor in the new media company, which publishes articles that show players’ perspectives.]

Richard Sherman: Yeah, I think that players’ relationship with media had changed, and there wasn’t a lot of trust, and players felt like there was sensationalism going on, and headline grabbing. You could have an in-depth interview about how I’m working my charity, and a small portion of that about some conflict I had on the field, and the whole article will be about the conflict we had on the field, which ruins the story about all the hard work and all the great things that I’m doing. And it always seemed like there was a negative tone and negative connotation behind it. So The Players’ Tribune kind of stripped off that layer and exposed the genuine truth, whatever the player’s truth is. If the player is talking about a tragedy that he dealt with growing up, then the story is about that tragedy. It’s not going to grab people’s attention with some crazy headline and steal the real substance of the story. 

Sakoda: I think it’s important to talk a little bit about Richard’s emergence as a player at the same time as social media was becoming this phenomenon. He became a professional athlete right at the time when Twitter and Facebook and everything was blowing up. In some ways, he became famous because of incidents that were taken out of context, or things that went viral. [One example: Sherman’s reported “beef” with Patriots quarterback Tom Brady has made for plenty of online fodder]. But then I think he realized he had an audience and a following, and turned that and used it for good.

So Richard, would you say that social media has done more positive than negative from the players’ perspective? Or more negative than positive?

Sherman: Every situation is unique. In my situation, it’s done way more good than not. You deal with the negative, you deal with the bad—the bullying and the trolling. But then I’m able to reach a kid who’s really going through depression, who’s really been sad, and just really needs some words of encouragement. And I can give those to him directly without actually knowing him, without knowing anything else about him. Social media gives you the ability to do that.

Sakoda: In general the most positive thing that social media has brought to the world is it’s given people that didn’t have a voice a voice, right? I think in general, it’s been better for the sport because the players have not really had a voice, especially in comparison to other sports, for example, like basketball, where I think the players have more of a voice in the game. In the NFL they haven’t had as much of a voice.

Why is that? 

Sherman: We have helmets on. In the NBA, you see faces. You know what I mean? You eventually see some faces in the NFL, but you don’t see them well enough to really recognize them. You know who Tom Brady is, you know who the quarterbacks are. You know a few defensive backs. But in the NBA, it’s so much easier because it’s plastered in your mind. Like the whole game, you see faces, faces, faces. In our game, you see helmets and it’s hard for people to get the helmet off. And the league makes sure of that, you know what I mean? That’s why they push certain players, but it’s mostly quarterbacks. But they don’t push players’ faces out there as often as any other sport because they don’t want the players to ever get bigger than the game.

The NBA’s okay with it because they know the players fuel the game. But in the NFL, they want it to be logos. They want it to be a shield. They want players to be interchangeable because then you lose power. There’s never community around an individual player like there is in the NBA. In the NFL, the fan worship is the logo.

Sakoda: That’s part of the structure. But I think that there’s a view in the next generation of this game that the players should be bigger partners, and that’s something that you feel passionate about. It’s much more similar to how start-ups in Silicon Valley and this whole ecosystem works, right? Everyone participates in the success and I think that’s a big part of what Richard is trying to push—for players to be better partners in the game.

It’s not a new story to see athletes investing in tech, especially here in the Bay Area. But why is it that we’ve seen more of it from NBA players, like some of the Warriors players, and not so much from the NFL side?

Sherman: There are definitely more players getting involved [in tech investing]. It’s just not as prevalent in our game as it is in the NBA mostly because of their [the NBA players’] guaranteed contracts. They can invest bigger amounts of money into things than we can. They get a $150 million deal, and you can be an average player in the NBA to get that. You probably have to be the best player to ever play in our game to get $150 million. And so the dynamic with that is just totally different. Their long-term security is much better, and the way their seasons are set up is different. We’re light years ahead of where we’ve been. But I think we’re still behind the NBA in that way.

Sakoda: This is interesting, and another way that we got together. In the summer, in the off-season, Richard brought me in to talk at an elite camp for defensive backs. They came together to study footage from games and see which wide receivers they’re matching up against and how to best prepare for that. They were doing drills together, but he invited me to come in and talk about how to work in the technology and finance industry while in the game—in preparation for after the game. 

How was it received? [No pun intended.]

Sherman: A lot of the guys are excited to be a part of it because they haven’t been exposed to it. You know, the stigma of the dumb jock football player is still strong in this day and age. So for us to even bring those guys in the room and have Jon and his team and the investors that came in to speak, they were just impressed that they were allowed to be a part of it. A lot of times, these guys are aren’t presented with the investment opportunities that the NBA guys are because of the stigma.

When it comes to your own investing, is there an overall strategy? 

Sherman: I have a strategy to it, but it’s all about interest. I’m interested obviously in technology and player safety. I sit on the board of Vicis, a helmet company that’s revolutionized the industry. And I invested in Oxeia—they’re still going through clinical trials, but it’s going to be a pill that guys can take within 24 hours of getting a concussion that will mitigate the effects of the concussion. I’m interested in making this game safer for my kids. And my kids’ kids. 

What do you see as the responsibility of the league versus the role of innovators in finding solutions for the health risks in football?

Sherman: I think it has to be on the league. The world always comes up with solutions for problems as the problems present themselves. But I think it’s on the league to find those people, to find those solutions. It’s still a violent game, regardless. There’s only so much you can do to mitigate and limit the impact of it because the human body is doing things the human body wasn’t designed to do. You run at full speed and guys are running into each other. That’s not how we were designed. 

I’m sure you get this question a lot, but given all of the health risks that come playing football, do you want your kids to play? [Sherman has two young children.]

Sherman: I let my kids play. I think the lessons that I got from football, especially at an early age, and the friendships and camaraderie and the accountability and the discipline, there are so many lessons that I don’t know how to teach or learn otherwise; that I got from just, “Hey, man, this kid’s bigger than you and stronger than you. So I’ve got to be more courageous.

You’ve taken a stand on player health and player rights. Was there a certain point when you realized that you wanted to take more of a leadership position here? 

Sherman: Yes, when I was really young. In my second year playing I was named an All Pro, which is pretty much one of the best players in our league, and I knew that if I ever was in a position of power, I would want to help more people. And that’s just how I am in general. When I was young, I always wanted to help people who were homeless. But I didn’t have any money, so I’d bring food. I’d bring blankets, or I’d do whatever I could to help with what I had.

Sakoda: I think Richard shares a lot of traits with a lot of entrepreneurs that I work with. He also shares a lot of traits with the leaders of companies who are trying to bring about change. If you think about it, the world is actually filled with people who are just trying to move the world forward as opposed to holding onto what the world has been.

So in this advisory role with Decibel, what do you think you’re contributing to the startups? What’s the change you’re helping with?

Sherman: I think my most powerful asset is being able to bring people together and allow people to be more successful as a unit, because I think people forget that it’s the sum of the parts that makes most things great. People think, man, a car is only great as its engine. But a great engine in a chunk of metal really doesn’t do anything without wheels or steering wheel, a radiator, etc.

Sakoda: Just to make this come to life, we had an investment in a very young company called Blameless. They help engineering teams basically learn from their mistakes. And obviously engineers think of this as a very technical problem. But when they met Richard, they started talking about the concept of “blameless postmortems” in sports, too. The reality is that just because the play didn’t work out, doesn’t mean that we should blame the person that was on TV for that moment.

You’ve been forward-thinking about life after football. How much of what you’re doing with Decibel and tech investing figures into what you think the next chapter of your life will be about? 

Sherman: Oh, a lot of that goes into it. But I think me being a father is the biggest thing I do. That’s my biggest goal. What I want to be known for best is, man, he was a heck of a dad. He was a good football player, he was a cool entrepreneur, he’s a good philanthropist, but man, him as a dad? And I think if I keep that in perspective and keep striving to do that, everything else will fall into place. I’ll set the example that I want to set. I’ll accomplish the goals that I want to accomplish. But those kiddos, that’s what it is about for me.

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