Q&A: Jaylen Brown on investing, esports, and creating your own content.

Alan Cassinelli
Sports Business Radio
7 min readJul 2, 2019

The third overall pick in the 2016 NBA draft joins Brian Berger on Sports Business Radio from the Bloomberg Players Tech Summit.

BRIAN: Here with Jaylen Brown of the Boston Celtics. So, Jaylen what brings you here to the Bloomberg Players Tech Summit? I know you were here last year as well, right?

JAYLEN: I’m either two things: a fly on the wall, or the elephant in the room. Today, I’m a fly on the wall, just trying to learn and observe as much as I can.

BRIAN: So, it’s interesting to me; you’re 23?

JAYLEN: 22.

BRIAN: 22. A lot of guys used to wait until later in their careers to get into thinking about investing and business. You’re doing this at such a young age. What got you into this at such a young age?

JAYLEN: I guess, it started when I chose to come to Cal. So, Berkeley is not a basketball, traditionally, school. So, I interned at a VC when I was out here, and I kind of hit the ground running with that and, haven’t looked back.

BRIAN: What about guys like Andre (Iguodala), he’s seems like he’s kind of the Pied Piper of bringing a lot of you guys together for an event like this. Introducing you to other companies that you might want to invest with. Is he someone that other players look up to as like, the O.G. of VC investing?

JAYLEN: You said it best! That’s exactly the word. That’s what I call him; O.G. He’s actually been in this space for a long time so, you can definitely learn from him. And, they respect him in this space, which is more important — the respect. You know, a lot of guys have tried, but not a lot of guys are respected and, I think A.I. — Andre is one of the guys who gets some respect in this space. So, we try to follow his mode.

BRIAN: So, you’re a high profile guy, you’ve got money. If somebody comes to you and says, “I want you to invest,” what are the criteria that you’re looking for in order to say, “Alright! You’ve got my attention”?

JAYLEN: It depends! It depends on a lot of different things. But, also their portfolio. It depends on like, how much money they already started (with). If it’s a big company, if they’re already in late stage, or in early stage. It’s just depending on what they’re selling — the idea, and how much I believe in the idea. How much I believe in the person running the company. It’s a lot of stuff that goes into it, but uh; ultimately, it’s not just you, but a team of people to help you make kinda make that decision.

BRIAN: Do you find a lot of these opportunities on your own? Do people come to you, or do you have your own team of people? Like, I know Rudy’s a guy that helps people? Who’s on your team helping you because, you’re obviously focusing on basketball?

JAYLEN: That’s a good question. I’m actually putting my team together, so. I’ve been learning a lot. I’ve been in this space for a few years, and I still got a long way to learn and a long way to go. But, I’ve learned a lot over these last few years; probably more than most, for my age. But I want to continue to learn. I didn’t want to just throw money at stuff. I wanted to understand this space a little bit more. So, I’ve held off on investing, and I’ve missed out on some good opportunities. It’s a part of, it’s a part of it. Like, I’m kicking myself because, some companies have came to me and I could’ve invested early, before they are what they are now, right? So, it’s about putting the right people in place and having a better understanding of it.

Photo via Fox Sports

BRIAN: In the locker room, it used to be guys talking about their cars and things like that. Are you guys talking investing in the locker room now?

JAYLEN: Not in my locker room, not yet. But it is becoming more of a cool sort of subject. I hear a lot about how the Warriors are talking about what they’re investing in. But they’re a little bit further along. I play on one of the youngest teams in the league. They don’t want to hear about that. Not yet, so I’ma stay in their ear and hopefully start the change.

BRIAN: Do you ever see a scenario like, I know from talking to Andre like, sometimes he does some business with some of his teammates. That might be kind of fun to go in on an investment with some of your teammates, or is that too close to home?

JAYLEN: Nah, I wouldn’t put it past us. It’s endless. All the possibilities are endless. It’s based on like, how you feel and your relationship with people. Because, it’s like the post-internet age. It’s a million different ways to skin a cat. Just choose one.

BRIAN: Obviously we’re here for tech today. But, what are some of the other sectors that you see that are hot sectors for investing?

JAYLEN: I think hardware. I think that’s under the portfolio of tech, though. Of course, there’s CBD products — it’s a lot that’s extremely hot. Popular is like, really killing the game.

BRIAN: Here today, Al Harrington was talking about CBD. I just talked to David Stern last month in New York and he said that three sectors; Esports, sports gambling, and cannabis.

JAYLEN: Esports is like something I have been trying. I’ve been doing like Twitch streaming and just trying to understand that space. Because, my mom used to always say like, “What are you doing? Get off that video game!” It was looked at like a negative thing, to my parents at least. But now, people are making millions of dollars playing video games all day. Who would have thought? That’s the post-internet age that I talk about. Now there’s so many different ways to be successful, you can’t rule out anything, you know.

BRIAN: And your teammate, Gordon Hayward, he’s one of the biggest gamers out there. Do you guys ever talk Esports and gaming?

JAYLEN: No, me and G have never really talked about that but, I’m just now getting into that space. So, the more and more I get into it, the more and more the conversation builds. Gaming is definitely is something I want to immerse myself into. Because, like I grew up and I love video games. I’m like a big kid. I love anime, I love cartoons; I love stuff like that. It keeps you young. So uh, I’m definitely going to be in that space heavily.

BRIAN: What are some other things that you enjoy? Like, I know (from) talking with Kevin Durant, he was a big fan of Postmates. So he just like; he and Rich Kleiman cold called them and were like, “Hey, we want to invest because, we’re a fan of your product.” Is there any company out there that you say, “I like that product and I might want to invest in them,” or no?

JAYLEN: That comes to mind? No. I’mma keep that to myself. But there is some companies there for sure, that are in the works. There is one (company) that I like, that I’ve seen in Paris. I’mma keep it to myself, but it’s some stuff that’s coming for sure.

BRIAN: What about content? Content is really big right now. Obviously there’s the mainstream media outlets but Players Tribune, Uninterrupted, guys are doing their own content channels. What do you think about where content is going?

JAYLEN: Content is king! I think that’s the phrase that everybody uses. I have my own content. Traditional television and stuff like that is phasing out. Everybody is more on their phones and laptops and stuff. So, creating your own content platforms is very easy, very simple. Just get a videographer and tell them to turn the camera on, and now you can show your fanbase what you’re doing, or create your own channel; pretty much create your own TV Network in the comfort of your own home. So, the easiness of that and the leverage that you create with that, it’s a no brainer.

BRIAN: Last question. I gotta ask you about the Celtics. So what do you do during the off season. You know, I know guys always kinda go into the lab to work on their game. What’s your off season regimen?

JAYLEN: I’m locking myself in the gym and I’m not coming out until the season starts.

BRIAN: Do you do that here (Bay Area), or do you go to Boston?

JAYLEN: I’ll be in Boston until they kick me out.

BRIAN: (laughs) Alright! Thank you Jaylen Brown.

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