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How “The Fantasy Footballers” Turned Pro

Boardroom goes behind the scenes of how three friends turned their hobby into not just a bustling business, but an authentic community

When Andy Holloway was playing fantasy football with his co-workers at a gaming company some seven years ago, he did what any committed member of a fantasy league would do: He went the extra mile.

He was known around the office for his year-round smack talk, discussing the season ahead just weeks after the Super Bowl, so he figured he’d back up his talk with even more talk, launching a podcast dedicated to the NFL.

Holloway and Mike Wright, a friend, co-worker, and league member, met up once a week during their lunch breaks to rip on other managers, talk about trades, and do comedy bits. The other managers received it so well that Jason Moore, one of Holloway’s longtime friends and a fellow member of the league, had a radical idea.

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“He was actually the one that said, hey, you should point this outward. Like, people would listen to this,” Holloway told Boardroom. “We’re like, ‘Really? That doesn’t make sense.’ And he’s like, ‘no, they would. This is gonna be huge.'”

That idea punched Moore’s ticket as host No. 3 — and set the group on a path from which they’d never look back. Doing full-time fantasy content had always been a dream for Holloway, and it was suddenly time to find ways to forge a brand that could set him and his friends apart from the competition.

The Fantasy Footballers Begin

For starters, the podcast launched in February 2014, right after the Super Bowl when fantasy content was scarce. The show made a point to offer updated player projections, contrasting with traditional fantasy draft publications whose information was often outdated by the time you actually got to your fantasy draft.

While many of those features exist widely today, “The Fantasy Footballers” were pioneers in that particular corner of the space.

For as many stories as there are about great content, though, those in the industry know that good material alone doesn’t always win the day. The word “monetization” gets tossed around in countless boardroom meetings; it’s the white whale of countless content creators. It was a goal from the moment the podcast was launched, according to Holloway, but even this group couldn’t have imagined it would start to realize itself so quickly.

In a story that pulled at the heartstrings on a “Kurt Warner bagging groceries” level, Holloway and Moore would go to school to get their real estate licenses at night while working on the podcast during the day, starting in February 2015. The goal remained clear: Feed each of their families by strictly producing fantasy football content, which required a self-sustaining model with the work ethic to match.

The growth of the podcast, even at the onset, was noticeable, and it wasn’t long before the two realized they had something in their burgeoning fantasy show.

“We’d be in real estate school refreshing our download numbers because it was taking off so quick,” Holloway said.

They wound up combining to sell three houses, and by September of ’15, real estate was out of their minds completely. At that point, the trajectory of the business felt unprecedented, and caught even Holloway by surprise. Plans changed in a hurry, and “The Fantasy Footballers” became a full-time focus.

“To be realistic, we didn’t think you could develop — at least not super-fast — a business to sustain three families in full without needing to do something else,” Holloway said.

“We hadn’t heard of that happening.”

A Full-time Fantasy Focus

The way in which the business made money at first was segmented. The three would “buy months,” as Holloway put it, getting up-front payments from advertisers on the podcast to lock in enough cash to live off of for literally months at a time. The Footballers would also drive revenue by doling out fantasy football draft grades to both owners and entire leagues.

“We knew we didn’t have the bandwidth to do a full draft kit, but we were a fledgling startup and we needed revenue,” Holloway said. “There were days we were doing that for 12 hours a day.”

Now, of course, the scale has grown significantly and the Footballers do have the bandwidth to create a full annual “Ultimate Draft Kit,” which they sell on their website. It comes with draft grades, but thankfully for the guys, they don’t have to sort through thousands and do individual evaluations.

But what makes this group of three guys in Phoenix, Arizona, who wake up every morning a block away from one another and head to a recording studio, the No. 1 fantasy football podcast? It wasn’t venture capital funding — Holloway refused to accept money that came with such strings attached. It wasn’t partnering with a network.

Rather, it was all done independently through authentic community-building.

The podcast has roughly 13,000 or so members of the “#FootClan,” who have pledged monthly sums to the show on Patreon. Through that platform, supporters can get exclusive podcast episodes and other helpful tools for their fantasy football seasons.

They can also interact with the hosts directly on Discord.

To Holloway, it’s that connection with the fans that makes the podcast so successful.

“I think for any business it’s a process of constantly returning to that space where you can relate to [the listener] and listen,” he said. “Just pretending you’re relating to them and say, this is what I think I would want , that’s not enough. You need to go listen. You need to pay attention to feedback.”

Building the #FootClan Community

As a consumer of ESPN’s Matthew Berry’s fantasy analysis and various printed publications for 10 years, Holloway knows what fantasy football managers want to consume, and he’s able to keep his approach fresh by interacting with listeners, be it on Discord or even through a Reddit AMA.

Building a community allowed the podcast to run independently; connecting with fans made it easier for them to pledge money on a weekly basis.

But because Holloway believes in the product that’s consistently put forth,building this community hasn’t actually felt difficult. Not only do the three stand by their fantasy takes, but the delivery is crucial, too. The comedic aspects of their rapport make for an easier listen, as does the PG language, making the show ripe for consumption even in a car full of kids.

Above all else, though, the bond the three share — they still watch football together every Sunday — shines right through the microphone.

“You can put three really great media people in a room, but if they don’t like each other, then you probably are going to feel that on the other end,” Holloway said. “So, fortunately, we like each other. We make fun of each other all the time, but we like each other. And I think that’s been pretty key.”

Authenticity is easy to recognize; the lack of it is even easier to pick out. And judging by the overwhelming support for this podcast, the verve of “The Fantasy Footballers” is easy to get behind. Modern-day tools for community-building like Discord and the ability to monetize through Patreon have made it easier than ever for content creators to see instant returns on their hard work, and this trio has taken full advantage to become self-sufficient quicker than they ever could have imagined when they first set off on their podcast venture.

One piece of advice you won’t have to pay for, however?

“All hail Tom Brady. Tom Brady the 44-year-old plant-eater is actually a great fantasy football pick,” Holloway said. “He’s an eighth-round pick in drafts for some strange reason. It’s impossible for him to move up because of the age, and everybody should draft this year. That’s my hot take.”

You can catch the Footballers five days a week from August through the Super Bowl, and still twice a week for the remainder of the year.

For Wright, Moore, and Holloway, there’s still quite literally no offseason. And that goes for both fantasy expertise and smack talk.