Robby Berger had been a fast riser.
He’d started working overnight shifts at the front desk of the Four Seasons Beverly Hills, but in just a couple years he’d climbed the ladder, reaching the esteemed title of Guest Services Manager. Suddenly, Berger found himself with 50 reports as he quarterbacked the comings and goings of Los Angeles’ rich and famous.
But it was soon after that something funny happened.
“Someone came up to me and asked for a picture,” he remembers. “And I remember the employees seeing that and they were so confused — and I was confused as well, because it was so bizarre to me.
“And then it kept happening.”
Berger loved the Four Seasons. He was a people person, after all. Liked talking to people. Liked watching people. Liked figuring out what made them laugh. But when you work in Guest Services at the Four Seasons, there’s a certain expectation that you’ll be buttoned up, professional; mildly and pleasantly forgettable.
“It’s not really supposed to be about you,” Berger says.
And that became the moment that Berger decided to change his life forever.
“WHAT EXACTLY DO YOU TELL PEOPLE THAT YOU DO?“
That was the question I’d been eager to ask Berger. I showed up right on time to our interview but he arrived early, grinning from beneath the bill of a white rope hat with HAVE A DAY printed on the front.
When he was at the Four Seasons he was a hotel man with an Instagram account on the side. His online persona showcased one man’s musings on the world, riffing on everything from hangovers to breakfast sandwiches, sports bets and more. These days? The Four Seasons is in the rearview but the Instagram account has grown into a modern media behemoth — a network of pages, brands and income streams. Once upon a time, Robby Berger’s account handle was BrilliantlyDumb; now his brands include Bobby Fairways, Bob Does Sports and Breezy Golf. Berger’s engaging, affable presence is at the center of a massive, spinning content wheel that regularly attracts millions of viewers.
So what does he do?
“Dylan, your guess is better than mine,” he says.
Let’s get specific. In the years since the Four Seasons, Berger has become unlikely golfing royalty. The 30-year-old grew up in New Jersey, where he was a good athlete (he’d go on to pitch in college) and an avid sports fan. He reluctantly admits that golf was not at the center of those youthful interests. The extent to which he followed the sport was “just kinda knowing what was going on with Tiger.”
“Back then, golf wasn’t really the cool thing to do,” he remembers. “Once I started doing it, of course I fell in love with it. But it’s insane what’s happened to golf the last few years.”
It’s insane what’s happened to Berger’s golf, in particular. Three years ago he was a new California resident who’d barely played golf at all.
Less than a year after that more than two million people watched a YouTube video in which he promised his friend Joey Cold Cuts (a Vancouver transplant with a terrific nickname) a round at Torrey Pines and took him instead to “the worst golf course in America.”
A few months after that, two million more watched Bobby and Joey finish 18 Fireball shots in nine holes.
A few months after that two million more watched the now-expanded Bob Does Sports troupe play an 18-hole golf match against Max Homa.
And a few months after that more than a million saw them take on three NFL quarterbacks, headlined by Josh Allen. A third on-screen member of the crew had joined by then, a guy who goes by Fat Perez, completing a lovable trio.
As Berger might say: Not a bad couple of years for the young man. Not bad at all.
He hardly did it on his own; Berger enthusiastically name-checks the people who helped elevate his efforts. That includes Reid Hailey, whose creator-focused media company, Doing Things, became Berger’s next launching point. He joined a portfolio that includes brands with massive social followings (meme pages and brands like OverheadLA, Recess Therapy and Middle Class Fancy) and had the infrastructure to help with apparel and events (thus extending Berger’s empire to Breezy Golf). Plus, on the internet, having viral friends always helps.
As for how he describes what he does? He doesn’t turn his nose up at the term “influencer,” but he prefers to say he has a golf show. That invites too many confusing questions from his parents’ friends in Florida, though, so in those settings he just says he works for a media company and hopes for no follow-ups.
For the ink spilled (and subcommittee meetings held) under the guise of growing the game, in many ways Berger has become the face of the modern golfer. He tried golf during Covid, fell for it hard and now has become a beautiful reminder of nearly everything that’s good about the game. The central themes of his videos may also be considered the central themes of the sport: that golf’s a journey, that it’s about who rather than where, that an enjoyable round is more dependent on personality than score, that frustration’s fine as long as fun’s in there, too. He’s not astonishingly good — “I was a disaster when I started and still am, really,” he says — but he sure seems like an astonishingly good hang.
From a content perspective, he’s a reminder that you don’t have to be among the best in the world to make money on your game. Golf is an easy platform to showcase competition, personality and celebrity. It’s the perfect canvas for hijinks, too. Scottie Scheffler’s superpower is his golf game. Berger’s superpower is that he’s funny in an endearing way; it’s hard to imagine someone who wouldn’t like him.
The result is that his accounts have become one of the last corners of the internet unmoored by cynicism. After he published a video with Keegan Bradley, Bradley called him in shock.
“He was like, ‘There’s no bad comments in there,'” Berger remembers. “He couldn’t believe it.”
THE BURGEONING BUSINESS OF BOB DOES SPORTS has matched the rise of its central star.
We’re chatting because he’s just launched a partnership with Five Iron Golf, a sort of indoor Topgolf. A Five Iron location in New York City now has a room dedicated to Breezy Golf promising a “sports bar and lounge experience,” combining Berger’s love of golf with his love of a chicken caesar wrap. This is just the latest venture for Berger, who I ask to tick through his revenue sources. He eagerly obliges.
It all starts with Cameo. Those requests peak during fantasy football season, he says. But they’re a significant moneymaker based on sheer volume. Berger charges $95 per video (more if it’s last minute) and cranks through 20-30 per day. Even with Cameo taking its 25 percent cut, well, you do the math.
“When we’re on a Bob Does Sports trip the guys make fun of me because they just hear me in my room the entire time just shouting people out, birthdays, whatever,” he says. “It drives them nuts, but they get it.”
He ticks through the others. There’s Breezy’s apparel brand, which includes the HAVE A DAY hat he’s wearing. They have Breezy tournaments now, too, though those are more for fun and brand-building than they are straight revenue plays. There’s the YouTube channel, which racks up views by the millions. There’s a podcast. And there are brand sponsors, like SeatGeek (a recent YouTube sponsor) and Callaway (which signed the crew to an equipment deal in January). Berger has continued to work with Doing Things Media, which he says helps support it all, and there’s increasingly more to support. Berger didn’t cite exact dollar figures, but it’s safe to say things are going well at Bob Does Sports HQ.
“You just can’t say it’s work,” he says. “We’re having so much fun with it that it’s cool that we can just do it full-time. But it’s pretty insane, man.”
THERE’S A DIFFERENT WAY this all could have gone. Back when Berger was working at the Four Seasons, a fun-loving Guest Services manager with a surging Instagram following, he got a compelling message on Instagram: it was Dave Portnoy, head honcho at Barstool Sports, coming with a job offer.
Working for Barstool had always been Berger’s dream. But now that he was faced with the reality of the offer — a salary of roughly $65,000 to relocate to New York — he balked. That would mean splitting a place with several roommates. It would mean moving across the country. It would mean deserting the friends and support he’d already built up in L.A.
He said no.
In doing so he was placing a bet on his own future. Closing that door narrowed his focus and clarified what he already knew: it was time to go all in. He’s been full throttle ever since. Sometimes he’ll be on the road for a month at a time. Sometimes two.
“But it doesn’t really ever wear on me because it’s just so much fun,” he says. There are taxing moments, of course — he cites a hot dog challenge that took him out for a couple days thanks to some hearty brioche buns. But if he ever spends more than a day away from the work he starts to feel himself getting antsy.
“Since we started Bob Does Sports, people rely on it now,” he says. “It’s part of their week, part of their day, part of their routine. I don’t take that lightly, being part of people’s day.”
The business of Bob Does Sports is Bob himself. It’s Robby Berger. It’s commoditized likability. The guy selling HAVE A DAY hats very genuinely would like you to have a day. That’s the business.
And business is good.
