Before the Kansas City Chiefs-Jacksonville Jaguars playoff game on Jan. 21, Matthew Berry stood in the snow on the sideline next to Chris Simms. The two men were part of NBC’s “Football Night in America,” the most-watched pre-game show in sports.
The segment centered around prop bets, a subject Berry knows well considering his nearly 25-year career as a fantasy football writer and analyst.
On air, Berry predicted Jaguars quarterback Trevor Lawrence would go over 1.5 touchdown passes, mentioning the Chiefs had allowed the most passing touchdowns in the NFL during the regular season. And he said that Jaguars receiver Christian Kirk would have at least six catches, noting the Chiefs had yielded the most receptions to slot receivers in the league.
The projections proved correct. Lawrence threw for two touchdown passes, both to Kirk, who had nine catches for 105 yards in the team’s 27-17 loss.
That’s not to say Berry is flawless in his predictions. Like anyone, he has hits and misses. But just the fact that Berry was even in the position to give his informed opinion on a national show that millions of people watch is remarkable given his roots. He wasn’t an NFL player like Simms or an NFL coach like Tony Dungy, two of his “Football Night in America” colleagues.
No, Berry grew up dreaming of working in Hollywood as a writer. He did work in high school as a nighttime radio DJ for a classic rock station and worked for the student radio and television station at Syracuse.
Still, after graduating college in 1992, he moved to Los Angeles to pursue a career in screenwriting.
“Professionally, I never thought I would be in front of the camera,” Berry said. “I always thought I would be behind the scenes as a writer and producer.”
And he did just that, writing for movies and television shows such as “Married…with Children,” a comedy that aired on Fox
“They wrote me back the next day and they said, ‘We looked you up on IMDB. Married…with Children is our favorite show of all time. You’re hired,’” Berry said. “Because I wrote mean wife jokes for Al Bundy, I was given the opportunity to write a free column for a low-trafficked website on the internet.”
Over the next few years, Berry continued working in Hollywood and writing for Rotoworld. He became known as “Talented Mr. Roto,” a nickname his wife thought of when they were watching “The Talented Mr. Ripley” movie that came out in 1999.
“I wanted a name that made me sound like an expert, but also one that was sort of goofy enough that let people know I didn’t take myself too seriously,” Berry said. “As I’m sitting there trying to come up with nicknames, my wife goes, ‘How about the Talented Mr. Roto?,’ I was like, ‘Brilliant. Sold. This is so over the top and silly.”
By 2004, Berry had developed a devoted audience who enjoyed his work, so he decided to go off on his own and start his own website. He paid someone $10,000 to build the website and content management system and brought along some contributors to write articles.
For the first year, Berry worked on the website while also juggling his Hollywood writing duties. In early 2005, he spoke with Eric Abrams, his longtime writing partner.
“I went to him and I said, ‘Listen, man. I’ll probably make no money at all. I’ll probably fall flat on my face. But I just want to be happy. I want to chase happiness, and the thing that make me happiest is this dumb little fantasy football website I’ve got. I’m just giving you a heads up. I’m giving you a year’s notice,’” Berry said.
Berry followed through on his promise, giving up screenwriting at the end of 2005. Early on, Berry didn’t have money for advertising or marketing, so he reached out to radio and television stations across the U.S., telling them he would come on the air for free as long as they promoted his website.
“A lot of people said yes to that,” Berry said. “Necessity is the mother of invention. I became a spokesperson because I had to be. I couldn’t afford one. I couldn’t afford to hire a celebrity or an athlete to go out and do this for me. I had to do it myself.”
Berry’s most high-profile gig early on was appearing on ESPN Radio’s affiliate in Los Angeles. Soon, he began writing for ESPN’s website, appearing on ESPNews and shows such as “Cold Pizza” and meeting company employees and executives. Still, he continued operating his website until 2007 when ESPN approached Berry.
“No one was buying any yachts or anything like that, but we were in the black, we had a good reputation and we had a nice subscriber base.” Berry said. “ESPN said to me, ‘We want to buy your website, move you to Connecticut and make you the guy.”
The idea was to make Berry the face of ESPN’s fantasy sports coverage similar to what Mel Kiper Jr. was for the NFL draft. And over the next 15 years, Berry became synonymous with fantasy sports thanks to his passion, enthusiasm and high-profile job.
Along the way, Berry never lost his entrepreneurial spirit. He still owns RotoPass, a subscription bundling website that he started in 2004. He was also a co-founder of Fantasy Movie League, a game/website aimed at predicting box office sales that National CineMedia bought in 2017.
Berry co-founded a fantasy app called Fantasy Life, as well, named after the best-selling book he wrote in 2013. Betsperts acquired the Fantasy Life app in 2021, but Berry continued with Betsperts as a board member and minority shareholder.
Early last year, Berry started the Fantasy Life website and daily newsletter that covers NFL news, fantasy football and sports betting. The company has a few full-time employees, including CEO Eliot Crist, as well as a board of advisors that includes Adam Ryan, CEO of Workweek; Austin Rief, CEO of Morning Brew; and Tyler Denk, CEO of beehiv, a newsletter platform.
“If you meet Matthew, you immediately realize he’s an entrepreneur,” Ryan said. “And if you look at how he got his start, it was in the same way that most entrepreneurs got his start. He was working for free, building his reputation, writing, blogging. He understood the business of fantasy, which allowed him to have success quickly. His entrepreneurial spirit is what feeds the company.”
Since Berry arrived at ESPN, he said he had clauses in his contract that allowed him to start his own companies. But during contract negotiations last year, Berry said ESPN offered him a three-year deal with the only caveat being that he had to sell his stakes in the companies he founded.
“I didn’t want to do that because I live those businesses,” Berry said. “I think there’s a very bright future with those businesses and I also made promises to investors and employees that I would be there to support and do everything I could to help those businesses.”
As such, Berry decided to leave ESPN and pursue an opportunity where he could continue with his side businesses and also contribute to overall NFL coverage, not just be part of fantasy coverage as he had been at ESPN.
“I’ve got nothing bad to say about ESPN,” Berry said. “It was a really good run…I left ESPN with hugs and handshakes. They were very gracious to me on the way out the door, and I still have a lot of very close friends over there.”
Last summer, Berry agreed to a four-year deal with NBC that included weekly appearances on “Football Night in America” and the “Sunday Night Football Final” show after games that airs on Peacock, NBC’s streaming service. He also hosts a daily fantasy football show on Peacock, where he and others discuss the latest news with an emphasis on fantasy and betting implications. This week, he’ll be in Arizona, hosting the show from the site of the Super Bowl, another highlight in his unlikely career.
“I’m so happy at NBC because I feel like I get the best of both worlds,” Berry said. “I get the opportunity to be an entrepreneur, but more importantly I also get to work with a great company and great people on the NFL and on the premier show in the NFL. I’m truly blessed.”