#240 Matthew Berry – Trailblazing Fantasy Football, Standing Out and Chasing Happiness

1:18 Caring Deeply

Matthew’s non negotiable is to care.

“The biggest issues I’ve had in my career with whether it’s management, or a client or a company that I’ve worked with or somebody else, has been when I don’t feel like they’ve cared”

3:18 Matthew’s Early Career

After graduating from Syracuse, Matthew moved to Los Angeles to start his career as a sitcom writer. Matthew dives into a story about how the opportunity to make the film Crocodile Dundee 3 came about and the lesson he learned from taking a job purely for the money.

“That moment Sean, taught me a big moment to never take a money gig. Never take something that you don’t love or aren’t passionate about because life’s too short and it wasn’t worth the money”

12:50 Transitioning from Show Business to Fantasy Sports

Matthew had played fantasy sports since he was 14 years old and in 1999 he answered a blind ad from Rotoworld that was looking for writers. Once they found out that Matthew had written Married… With Children, Matthew was hired.

“I’m being paid a lot of money by these movie studios to write movies and tv shows and all I care about is this dumb little blog that I have”

Once Matthew had a big enough following from Rotoworld, he began building his own website.

“By chasing my passion, going back to the thing that I cared about, what’s amazing is I’ve made so much more money, I’ve been so much more successful, I’m so much happier than I ever was in show business”

19:53 Giving 100%

Matthew has always been someone that gave 100% to everything he got, talking about his background as a competitive tennis player. If you’re interested in how Matthew has always been someone who dove all in, Matt wrote his book Fantasy Life that goes further into his background.

23:00 Chasing Happiness

Matt’s family has a long history of clinical depression. He explains how he realized that while everything on the outside looked good, he was extremely depressed.

“I chased happiness not out of some grand master plan but I did it to, not to be hyperdramatic but I did it to save my life”

29:58 Refining His Craft

“For better or worse, I am very different than anyone else that does what I do which is give advice on how to win at fantasy sports”

Matthew purposefully has done the opposite of what people assume a sports analyst would be like and how they would run their show.

“Trying to refine that in a way that’s true and authentic to me but it also entertaining and presentable to a large audience”

37:00 The Journey is the Fun

“Fantasy is ultimately a hobby we play for fun and we should approach it as such”

38:43 The Biggest Moment for Matthew

ESPN came to Matthew and told him they wanted to do the format of Mad Money with Jim Cramer but with him and fantasy sports. This is how Matthew came up with the idea to use puppets on his show as a way to set his show apart on ESPN. The show has been airing for four years with over 250 shows done on ESPN+ and it’s one of the most popular shows on the platform.

“Instead of playing it safe and saying, give me an ex-NFL player and a female host and let’s do some cookie cutter television which would be safe and right down the middle, I said nope, I’m going to do what I think is funny”

41:30 Matthew’s Filtering System

When deciding to take on a project, Matthew considers two things:

Will I enjoy doing it?
Will I be successful at it?

“Is this something that fits my skill set or adapt my skill set to learn what needs to be done to succeed at it?”

Matthew’s advice for college students looking to join the ESPN team:

“Whatever it is your passionate about just get good because I promise you that if you’re good, we will find you or if we don’t find you we’ll be upset that we didn’t because someone else did”

53:37 Partnership with Jet It

Matthew explains the background of the company Jet It and it’s founder Glenn Gonzalez, the first Black man to start a private aviation company.

“When you talk about entrepreneurship and taking a chance and following your passion, like a lot of the themes that resonate with me in my life are very evident with Jet It”