Somebody Has to Plan the Golf Trip. He Built a Business Out of It.

Matt Sinisgalli spent years organizing his friends’ annual golf trip. Then he built a website from scratch and turned it into a business that helps golfers find the right courses and helps courses find the right golfers.

Matt Sinisgalli is the founder of Fairways & Dreams, a golf travel and marketing business based in Austin, Texas. He is a solo founder with fourteen years in marketing, and he is building the business around one idea: there is more than one way to take your game on the road.

Hosted by Ari Ratner · November 3, 2026 · Matt Sinisgalli, founder, Fairways & Dreams

The full episode

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The write-up

Golf has been part of Matt Sinisgalli’s life for as long as he can remember. He played junior tournaments as a kid and soon realized some of the other kids were in a different stratosphere. “There were kids shooting even par at ten years old,” he says. He took lessons, made his high school team, and worked at a country club as a summer job into college.

What he loves most is how golf’s role in your life changes over time. In high school he got annoyed at the bad shots. During five years in New York City, he just relished walking in an open space away from eight million people. “I don’t think I even kept score during those years,” he says.

“I call it like taking your game on the road and seeing how it travels.”

Matt Sinisgalli

The right golfers

Sinisgalli’s pitch is simple: help golfers find the right courses, and help courses find the right golfers. It all rolls up to getting more people traveling for golf.

On the travel side, he plans custom trips, pulling together the lodging, golf and transportation. He does not sell everyone the same package. “A buddies trip to Kohler is a completely different experience than maybe a father son trip to Ireland,” he says. He asks whether a group wants shared lodging or wants to double up in hotel rooms and max out the golf, and he gauges their skill level. Some courses would cost a wild driver a box of balls by the turn. “I don’t want you buying more balls at the turn,” he says.

Just start

The idea came from his own trips. Sinisgalli organizes an annual trip with his buddies that began eight or ten years ago, and he counts down to it all year. He realized he could be a resource for other people.

He thought about it for about a year first. Convincing himself took maybe a week, and the rest, he admits, was procrastinating. “The only thing that changed was that it was a year later and I was a year older,” he says. He likes a phrase he has heard: “Just start, then learn. Don’t learn, then start.”

His first real step was building a website, which he had never done before. Then he promoted it on social media, told everyone he knew, and networked.

Fourteen years in marketing

Sinisgalli has spent his career in paid media on the agency side, and the latter half has centered on travel brands. Paid media costs money, though, and he is not ready to sink fifty grand into a campaign. So he has focused on social, SEO, and “trying to get AI to know who I am.” He even has AI send him a daily update on how AI is affecting the industry.

Inquiry to itinerary

When an inquiry comes in, he usually reaches out within a day, and he calls. He wants to know who the group is, what kind of golfers they are, and whether they want breweries, the casino, or just the resort. He has worked with higher handicaps and with scratch golfers in the business who know exactly what they want. After the call, he sends a cost range per person with a couple of options.

Some trips are booked a year out, so he stays in touch without pestering, stays on standby during the trip, and follows up afterward with a couple of questions instead of a long survey. He wants clients thinking of him the next time they plan a trip.

Hidden gems and bonus rounds

What sets him apart, he says, is the custom approach. This past summer his group played Sand Valley in Wisconsin while staying off property five minutes down the road. They played three courses there, drove about 40 minutes to Lawsonia, then moved on and played Erin Hills.

Even on a trip to Whistling Straits, his group found another course nearby for what they call a bonus round. “I want to make sure all the golf gets played and all the courses get their recognition,” he says. It clicked as a business on a similar multi-stop trip to Michigan the year before. “You don’t have to go stay at Pebble Beach,” he says, though he adds that Pebble Beach is great.

The resort side

The other half of the business is marketing for resorts, especially lesser known ones. Just as no trip fits every group, no marketing strategy fits every resort. “Some of them are four hours from the nearest airport,” he says. He wants the two sides kept separate and would never recommend a stay because a resort is paying him. That side is still in its infancy.

Kids are always watching

Being a solo founder is tough, he says, because one person has to decide where all the time goes. He wishes he had leaned on his support network sooner. One of his best friends, a partner on another golf brand, keeps him moving forward. So do his golf trip buddies, his family, and dozens of people he met networking in golf this year.

He has a seven year old son and a thirteen year old daughter, and he has learned that kids are always watching.

“You have to do hard things in life.”

Matt Sinisgalli

He wants them to see that it is okay to do things differently than ninety five percent of everybody else.

Don’t give up on a round

Golf and business are alike, he says, because just when you think you have it figured out, you hit it out of bounds on the first tee. He has had stretches of real momentum in business, and then it goes radio silent. You have to trust the process, the way you do with a swing change.

He used to let a couple of bad holes blow up a whole round. Then he realized you can make a terrible score on one hole and bury the next one.

“Play the shot in front of you and find it and hit it again.”

Matt Sinisgalli

His advice for golf entrepreneurs is to just start and find the time. He worked nights and weekends for a while and keeps his screen time trending down. Success next year means repeat clients. In five years, he wants resorts to trust him to move the needle.

In the rapid fire round, his favorite course is Ballybunion, where the view was amazing. He plays to around a six. At his home club in Texas, the breakfast tacos go fast, and brisket is his pick. His dream foursome is Tiger, Michael Jordan and Larry David. The group he most wants to plan for is “the golf sickos,” guys like him and his buddies who want as much golf as possible.

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Hear the full conversation with Matt Sinisgalli on Apple Podcasts and Spotify. Find Fairways & Dreams at fairwaysanddreamstravel.com. Follow Fairways & Dreams on Instagram, X and Facebook.

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