From early in his career, Matthew Berry saw a need for fantasy content in sports media. He began to fill that gap and slowly rose to become the leading voice in the field.
Fantasy sports is a multi-billion dollar business, with 60 million fantasy players in the United States and Canada alone. That helps account for a reported $18.6 billion market in 2019 that’s expected to reach an absurd $48.6 billion by 2027.
If it wasn’t for the man calling from his Connecticut area code on one of the Northeast’s rainiest Wednesdays in recorded history, the fantasy sports industry wouldn’t be nearly the behemoth it is today. You may not have even drafted your fantasy football team over the last few weeks.
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Matthew Berry is now in his 15th year as ESPN’s senior fantasy sports analyst, a role in an industry consisting of thousands of jobs that may not exist today without his efforts. He’s a constant presence all over ESPN television networks and digital platforms during football season with his annual preseason “Love/Hate” column, his Emmy Award-winning gameday show on ESPN2, his podcast The Fantasy Show., and his Twitter feed with more than one million followers (where he gives out his phone number so fans can text him).
With the new NFL season now upon us, Boardroom caught up with Berry to take stock of his journey from restless screenwriter to the Talented Mr. Roto.
“I was making more money in Hollywood… and I was miserable”
Though the first reported fantasy football league began in the early 1960s, the first football-focused fantasy magazine wasn’t published until 1987. A dozen years later, Yahoo offered the first free online fantasy product. The 51-year-old Berry started playing the game at 14, but making a living off fantasy sports was unfathomable when he graduated from Syracuse University in 1992 with a degree in electronic media.
At the time, he had his sights on a different kind of fantasy: Hollywood.
“It’s not a career path I would recommend to anyone, but it got me to where I am,” Berry told Boardroom.
He moved to Los Angeles and spent a couple of years at the bottom of the food chain as a production assistant before latching on as scriptwriter and editor for television and movies. He spent 1996 and 1997 at the groundbreaking FOX sitcom Married…with Children.
“I constantly worked, made a decent amount of money,” he said.
It allowed Berry to refine his writing skills, his ability to pitch executives, and how to convey humor. He emphasized making his words pop while keeping them accessible.
“I was making money in Hollywood. I was doing well,” Berry said.
“And I was miserable.”
“I cared more about this free column that I was writing for a low-trafficked website at the time than I did for these movie scripts I was being paid six figures to write.”
Matthew Berry
He went to therapy, searching for why he ended up feeling this way. Berry ultimately realized that he was in an unhappy marriage and he definitely didn’t enjoy his career. The creative part was great, but the politics and bureaucracy of agents, networks, and studios drove him away from what he thought was his life’s work.
The only thing that truly made him happy was his fantasy football column that he wrote for free.
In 1999, Berry started writing for a small, nascent website called RotoWorld. He saw an advertisement looking for writers and decided to apply, noting that while he was a Hollywood writer, fantasy sports were his true passion. The RotoWorld staff wrote back the next day.
They’d looked up his IMDB page and made it clear that Married…with Children was their favorite show.
Berry was quickly hired to write an unpaid column that would eventually change his life.
“I absolutely loved it, which was sort of eye-opening to me,” he said. “I cared more about this free column that I was writing for a low-trafficked website at the time than I did for these movie scripts that I was being paid six figures to write.”
Becoming “Fantasy Martha Stewart”
Berry said he chose to chase happiness, and the only thing that made sense and made him happy at the time was fantasy sports. The problem was that nobody made money writing about fantasy sports. He’d developed a nice following by writing at RotoWorld, and in 2004, he left to start his own site, TalentedMrRoto.com.
Not knowing anything about digital entrepreneurship, web design, SEO, or advertising, Berry paid $10,000 to have someone build him a website and a content management system while asking a couple of writers to work for him on the side. Instead of building a marketing budget, he met with Stamps.com co-founder Jim McDermott, to whom his now-ex-wife had introduced him.
Since there was no money for a famous athlete or a celebrity endorser for the site, Berry was asked who the Martha Stewart of fantasy sports was — the face you thought of when you thought about fantasy sports.
“I said, ‘I don’t know. I don’t think there really is anyone,'” Berry said. “And he said ‘if this thing is growing how you think it will, eventually there will be. You should try to make that you.’”
One of the reasons Berry thought fantasy football wasn’t accessible or popular to that point was that it was considered dry and overly stat-based. It felt nerdy, like doing homework. So he looked for inspiration from people he admired in other corners of media, like Howard Stern and Bill Simmons. Those were people who spoke and wrote to their audiences like they were at a bar.
He also took a page from his media inspirations by injecting himself into his fantasy content as part of an effort to turn Talented Mr. Roto into a proper advertisement for his growing brand.
Berry went to every radio station, website, and TV station to commit to going on their air and writing for their platforms for free — as long as they mentioned or linked back to Talented Mr. Roto.
“I didn’t say no to anything for like three years,” he said.
Moving to the Worldwide Leader
His first big break with ESPN came with the help of popular Los Angeles radio host Steve Mason, who was a big fantasy player and a fan of Berry’s content. He first did a five-minute segment on ESPN Radio 710, which led to two segments, then an hour, a guest host appearance, and a weekly Friday night fantasy football show.
His ascent then led to TV, where he landed a weekly segment on Cold Pizza, ESPN’s precursor to First Take, followed by segments on ESPNews and a column in ESPN the Magazine.
As his rise at the network continued, Talented Mr. Roto was providing frequent content for different fantasy sites like Sporting News, CBS Sports, MLB.com, NBA.com, and RotoWorld. A 2005 pitch meeting with the NBA turned into a fantasy consulting job, one that was approved by the head of NBA Entertainment at the time, Adam Silver. Two years later, ESPN thought fantasy football was finally big enough that it needed to find its Mel Kiper — its Martha Stewart — and gave Berry a two-year contract that included fully buying out the Talented Mr. Roto business.
Suddenly, it was time Berry to ditch Southern California for suburban Connecticut.
A new two-year contract tasked Berry with becoming the face of fantasy sports not just for ESPN’s audience, but internally as well. He spent 2007 and 2008 going to every producer and executive on every ESPN platform to explain the appeal of fantasy sports, the business opportunities around it, and why it made sense for the network as an area of investment.
Berry’s experience pitching and writing scripts for Hollywood execs in his previous life served him well in his role as something of a door-to-door salesman for fantasy in Bristol. Just like tailgating, watching games at a bar with friends, or filling out a March Madness bracket, he had to help make fantasy something that sports fans could enjoy regularly as part of their weekly routines. He also had to convince SportsCenter anchors and producers that fantasy sports were worth their attention and airtime despite so many other competing topics and angles.
The Weight Of The (Roto) World
After ESPN renewed his initial contract, Berry helped fantasy sports grow in size and stature around ESPN and around the world. He built a life there, meeting his wife at the company. His 2013 book, A Fantasy Life, became a New York Times bestseller the same year the American Marketing Association named Berry their “Marketer of the Year” for his work promoting all things fantasy.
Berry said he likes to think he played a role in creating all these fantasy sports jobs around the world, helping make fantasy football a household product. But that role as ESPN’s fantasy ambassador also came with added pressures.
“I sort of felt like if I screw this up, trying to carry the flag for fantasy,” he said, “it’s gonna set the movement back many, many years. I felt a lot of pressure internally to not waste what had been an amazing opportunity given to me. And once people saw ESPN getting behind it, I think people said ‘we need our own fantasy guy or woman. We need to get this figured out.'”
Berry’s role at ESPN as the preeminent fantasy guru has helped him make some incredible connections over the years, including with Seth Meyers, Jimmy Buffett, Stern, and Simmons. He made television appearances on everything from FX sitcom The League to iconic ABC soap One Life to Live.
His friendship through fantasy with directors Joe and Anthony Russo even landed Berry, a diehard fan of the Marvel Cinematic Universe, a cameo in Avengers: Endgame.
But fortunately, he’s not so busy that he can’t still be an active fantasy player himself.
One of his many leagues is called the Guts league, and features managers like Jay-Z, Chris Paul, Steve Stoute, Irv Gotti, Rich Kleiman, Jesse Itzler, Juan Perez, and Kevin Liles. It’s currently in its 13th year.
Looking ahead, with the Professional and Amateur Sports Protection Act (PASPA) repealed and sports betting becoming legal in more states, Berry is pleased that gambling is now coming out of the shadows and taking its proper place within the sports ecosystem next to fantasy. Both give fans rooting interest in games they may not otherwise care about, though the interpersonal aspect of fantasy is much different than gambling, he said.
With sports betting becoming more mainstream, fans will see more of it trickle into Berry’s football coverage as a result. There will be more fantasy-adjacent material that will relate to both fantasy players and gamblers alike, like NFL player props. He said that things are trending towards more of this type of coverage in the future.
But whatever comes his way going forward, Berry’s going to continue practicing the style and the approach he honed back in Hollywood that helped him become the Martha Stewart of fantasy sports.
“I don’t talk down to anyone.,” he said. “I just try hard to be conversational in my tone and explain here’s what I think and here’s why I think it.”
“And that seems to have worked out.”
