After winning three Super Bowls and playing with the Dallas Cowboys for thirteen years, he's become a full-time analyst for ESPN. And, notably, he's devoted much of his time and efforts to charity, as well.
Put succinctly, he's a great, inspiring, and successful person.
And throughout his career, he's been a loyal customer of Q Clothier and Rye 51. So, naturally, we've been angling to get him on the site for months. And, now, we've been fortunate enough to do just that.
We hope you enjoy.
Matt Alexander: So, where are you from originally?
Darren Woodson: I was born and raised in Phoenix, Arizona. I went to Arizona State and graduated in 1991.
Soon after, I was drafted by the Dallas Cowboys in 1992 and have been here since.
Matt Alexander: You played with the Cowboys all the way through?
Darren Woodson: I did. I was with the Cowboys for thirteen years.
In fact, in my rookie year, we won the Super Bowl. It was the first time the Cowboys had been to the Super Bowl since the 1970s.
Matt Alexander: Have you always been a football player?
Darren Woodson: I played (and loved) basketball and baseball, but always came back to football. It was simple for me.
In baseball, you’d have to master breaking balls, sliders, and so on. In basketball, you needed height.
Meanwhile, in football, they’d just tell me to tackle someone and I would. It was pretty simple.
Matt Alexander: You retired 10 years ago. Was that difficult?
Darren Woodson: I’d been playing football and sports, generally, since I was 7 years old. So, stepping away was certainly difficult, but I found a way to stay close to the industry.
I’d decided I wanted to stay close to football and was exploring my options.
On the day after I announced my retirement, I got on a plane and sat down with ESPN. That day, I signed an agreement to become an analyst for them.
I’ve now been in that role for ten years.
Matt: But that’s not all you’re up to. You’re involved in some young companies. How’d that come about?
Darren Woodson: I’ve always been passionate about young companies and that sense of entrepreneurial spirit.
So, a few years ago, I decided to go along to Tech Wildcatters’ Pitch Day. And, while there, I got to hear from a gentleman called TK Stohlman.
He was developing a concept called FanTree and was looking for investment. I loved his passion and attitude — it was infectious — and so we ended up partnering together.
Now, years later, FanTree has evolved into FanPrint and become a tremendous business. They’re growing exceptionally quickly and I’m privileged to work with them on that company.
Matt Alexander: And you’re involved in another one outside of FanPrint?
Darren Woodson: Right.
As we began to scale FanPrint, we found there was a /huge/ amount of counterfeit merchandise on the market. We were expanding in-stores and in the e-commerce world and saw the problem rampantly.
Regardless of sport — basketball, baseball, football, or otherwise — we found there wasn’t a great system for tracking those counterfeits and, in turn, mitigating their availability.
So, I began to develop my own company, CounterFind, which could live alongside FanPrint. We saw an opportunity to develop a piece of software that’d help companies like FanPrint to sell legitimate products.
And, truly, we’ve seen a phenomenal impact on FanPrint and its growth as a result.
It’s a true upstart, but we’re having a lot of fun.
Matt Alexander: Where do you work?
Darren Woodson: From home. Or WeWork alongside FanPrint.
Matt Alexander: Do you have it in you to build more companies?
Darren Woodson: Well, for now, all I’m focused on is scale.
I try to focus on what I know — and do — best. And that’s reflected by FanPrint and CounterFind.
We’re straddling the line between sports and technology, which is an ideal place for me.
So, in terms of building anything else, it’s not on my mind right now. I want to stick to growing these two and focusing on things I do well.
Matt Alexander: You live in Dallas. You’ve been here for a long time. Will you stay?
Darren Woodson: This is home.
I’ve been in Dallas since 1992, so we’ve laid down a lot of roots. I have a wife and four kids who call it home, too.
Honestly, I love my family in Phoenix (and hopefully they love me), but this is our space to grow, I think.
And, honestly, it’s that sense of community and purpose that keeps us here. I feel like I’m wrapped up in this community through a lot of different projects, people, and causes. And I expect I will be for years to come.
Matt Alexander: Do you keep yourself occupied outside of all of this work? Do you play any sports?
Darren Woodson: As I mentioned, I’ve played basketball and baseball in the past. And I love them. But my body won’t let me play them too seriously.
Right now, my son is sixteen years old and is part of a Select Baseball team. Going along with him for those games has become one of my favorite hobbies.
Actually, going along with the families related to it has become one of my favorite hobbies. We’ve all been together since the kids were about seven, so it’s been rewarding to see them all grow and to get to know each other so well.
And, outside of that, I enjoy my charitable work.
Matt Alexander: You touched on a bit of charity work. Tell me more.
Darren Woodson: I’ve been involved with the Make a Wish Foundation for about twelve years.
Whether fundraising, improving awareness, or just trying to make dreams come true for kids, it’s something I’m very passionate about.
I got involved as a young Cowboys player. I was invited to attend a fashion show for the children in Dallas.
In the audience, you’ll see these kids walk down the catwalk with a series of athletes and celebrities. What you don’t see — and what really struck me — was the two or three hours we spend backstage with the kids.
It’s an amazing thing.
So, on the board or in my day-to-day life, I’m just very invested in trying to help children in any way I possibly can.
Note: this interview was conducted in-person and recorded, so some statements have been paraphrased by the editor.