Fly Fairways and Tuff Crowd Are Changing What a Golf Event Can Be
By Jason Bolton April 07, 2026 09:50
Rob Ultra and Jordan Southerland started Fly Fairways as a golf clothing company. That's still part of it, but calling it a clothing company now is like calling a restaurant a kitchen. The brand has grown into something harder to define and more interesting because of it events, relationships, culture, and a genuine argument that golf has been kept from the wrong people for too long. The clearest proof of where they're headed is the Tuff Crowd x Fly Fairways tournament, which brought together Dwyane Wade, Gilbert Arenas, Paul Pierce, Brandon Jennings, Snappy Gilmore, and a roster of athletes and creators for a day on the course that nobody who was there is going to forget anytime soon.
The name is a double entendre on purpose. Hit a ball flying down the fairway. Show up to the course looking fly. Both things at once. That tension between the traditional game and the culture they're bringing to it is basically the whole point.
Golf has a reputation problem they're not pretending doesn't exist. The sport was built by and for wealthy white men, and that hasn't fully changed. It's expensive to play, expensive to learn, and for a lot of people there's a psychological barrier that goes beyond the cost. Jeremy put it plainly: most everyday people don't feel like they can just walk onto a golf course and book a tee time. Compare that to basketball, where you can walk into any gym and find a run. Golf has never had that. The courts aren't public, the equipment isn't cheap, and the culture around it for a long time actively made certain people feel like they didn't belong. That feeling is real and it's been there for generations.
Fly Fairways isn't solving it with a charity campaign or a press release. They're solving it by showing up, throwing great events, building genuine community, and making the thing feel like it belongs to everyone who wants it. The momentum around golf in culture right now is real, and Rob and Jordan recognized it early. They didn't wait for the sport to come to them. They went and grabbed it.
What makes golf worth fighting for is what happens between the holes. You're locked in with three or four people for four hours. There's no escape, no phone call that saves you, no halftime. You have to actually talk. Bad shots get laughed at. Good shots get celebrated. By the time you finish eighteen holes with someone you barely knew on the first tee, you know them. Rob and Jordan figured out early that throwing a golf event is one of the best relationship-building tools on earth, and they built their entire business model around that idea. Deals get made on golf courses. They're not just acknowledging that — they're the ones setting up the course, curating who's on it, and making sure the environment produces the kind of connections that actually last.
The events are the center of everything. Ten a year, spread across different locations around the world. London, Portugal, Minnesota, Thailand, Mexico. Each one is different. Each one is deliberate. The crown jewel is their three-day August tournament in Minnesota, which is the fullest expression of everything they believe about what a golf event should be. One day is a round of golf. Three days is a relationship. That's the math they're working with, and it's the reason the format hasn't changed.
Minnesota is worth talking about because it makes no obvious sense, which is exactly why they do it there. Most people don't think of Minnesota when they think of elite golf or cultural moments. That's the appeal. The courses are legitimate and the people are genuine, and walking into something unexpected tends to bring people together faster than walking into something polished and predictable. The event pulls around 70 people, fills a coach bus, includes dinners at the family house, appearances from names like Victor Cruz and Snappy Gilmore, and a trip to the biggest state fair in the country. CashApp sponsors it. The whole thing has an energy that's hard to manufacture because it genuinely isn't manufactured. It's a group of people doing fun things together in a place nobody expected, and that combination turns out to be exactly what builds community.
Now back to Tuff Crowd, because it's the moment that shows exactly what Fly Fairways is capable of when the right collaboration comes together.
Tuff Crowd is Brandon Jennings' clothing brand. If you know Brandon, it makes complete sense — the brand carries the same energy he brought to every locker room he walked into during his NBA career. Bold, LA-rooted, unapologetically street. When Rob Ultra and Brandon started talking, the overlap was obvious. Two clothing brands, both built on culture, both with deep roots in the same city, both with audiences that hadn't really crossed paths yet. Rob and Jordan saw Fly Fairways as a golf brand pulling street culture onto the course. Tuff Crowd was bringing that same energy from the other direction. The conversation wasn't complicated: what happens if we put both of these worlds in the same place on the same day and let it breathe?
What they assembled was something the golf world doesn't see often. Dwyane Wade, Gilbert Arenas, Paul Pierce, Snappy Gilmore, and a full roster of athletes and creators who showed up ready to compete and ready to connect. Two clothing brands with real credibility in their respective lanes, using a golf tournament to introduce their audiences to each other in a way that felt organic because it was. That's the part that's hard to replicate. You can buy a headline. You can't buy the room they built that day.
The beauty of golf is that none of the names or the brands matter once you're on the first tee. Everybody's bad until they're not, and the vulnerability of four hours on a course is what opens people up in a way that a dinner or a party never quite does. Brandon Jennings spent years as a fixture in the celebrity basketball game circuit. He produced them, played in them, watched them evolve. He'll tell you himself that era has run its course. Golf is where the culture is moving, and the Tuff Crowd x Fly Fairways event made that case more clearly than anything else happening in the space right now. NBA champions, All-Stars, and some of the biggest names in basketball content, all subject to the same humbling sport, all starting from the same place. Play it as it lies.
Rob used to produce celebrity basketball games before any of this. He knows what it looks like when culture and sport collide correctly and he knows what it looks like when it's forced. Athletes and creators who came through the Tuff Crowd event have since asked to be managed through the brand. Partners are brought in deliberately and given real exposure, not a logo on a banner. The activations work because the relationships behind them are real.
The vision for Fly Fairways has always been fluid and Rob and Jordan are fine admitting that. It started as apparel. Became a lifestyle brand. Grew into a community that happens to sell great golf clothing and throws some of the most talked-about events in the sport. They're not chasing numbers. They're finding people who want to build — creators, athletes, people who understand that the best things that happen in business and in life tend to happen on a golf course with the right people around you.
"Stay fly on the fairways," as Rob puts it. That's not just a motto. It's a blueprint.
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