From Radio to $2.9 Billion in Sales: Jeff Woolson on the Business of Golf Course Real Estate

Jeff Woolson did not start his career in real estate. He started in radio broadcasting. That pivot turned out to be one of the best things that ever happened to the golf and resort property market, because since 1991 Jeff has been personally involved in the sale of over $2.9 billion in properties across 22 states and 10 foreign countries as Managing Director of CBRE's Golf and Resort Properties Group.

In Episode 52 of Tools, Talents, and Techniques, Dustin sits down with Jeff to pull back the curtain on one of the most specialized and fascinating niches in commercial real estate, selling golf courses, ski resorts, marinas, and master-planned communities to private equity firms, golf course operators, and high net worth individuals around the world.

The Career Pivot: From Radio Broadcasting to Golf Course Sales

Jeff's path into commercial real estate started with a background in radio, which might seem like an unlikely launching pad for a career selling golf resorts. But the skills translate more than you might think. Communication, storytelling, understanding your audience, and knowing how to make something compelling are just as valuable when you are marketing a $50 million golf resort as they are behind a microphone.

His transition into the golf and resort space came at the right time. The 1990s were a boom period for golf course development, and Jeff was positioned perfectly to ride that wave.

The Golf Boom, the Oversupply Problem, and the Road Back

The 1990s saw a rapid explosion in golf course construction across the United States. Developers were building courses faster than the market could absorb them, and what followed was predictable. Oversupply hit, margins compressed, and courses started closing or being repurposed at a significant rate.

But the story does not end there. Two things changed the trajectory of the golf industry in ways nobody fully anticipated. First, Topgolf arrived and introduced an entirely new generation of players to the game in a low-barrier, social format. Second, the COVID-19 pandemic drove millions of people outdoors and onto golf courses as one of the few activities that remained accessible during lockdowns.

The result is a golf industry that is healthier and more active than it has been in decades, which makes Jeff's work more relevant than ever.

What It Actually Takes to Sell a Golf Course

Most people have no idea how complex a golf course transaction actually is. Jeff breaks it down in a way that makes the process tangible.

Playing the courses he represents is non-negotiable. You cannot sell what you do not understand, and walking a course gives Jeff insights into condition, layout, and potential that no report can replicate. From there, a team of underwriters and designers gets to work gathering data and building the marketing materials that will put the property in front of the right buyers.

On the buyer side, investors are evaluating factors that go well beyond the greens. Location, water availability, labor costs, and regional golf culture all play a significant role in whether a deal makes sense. A course that works in Arizona does not necessarily work in the Pacific Northwest, and understanding those regional nuances is part of what makes Jeff's expertise so valuable.

Choosing the Right Listings

One of the most honest things Jeff shares in this conversation is that choosing which listings to take on is one of the most important decisions in his business. Not every property is worth representing, and taking on the wrong listing wastes time, resources, and reputation.

That kind of selectivity is a mark of someone operating at the top of their field. The best closers in any industry know that saying no to the wrong opportunities is just as important as saying yes to the right ones.

The Lifestyle: Travel, Beautiful Locations, and the Grind

There is an obvious appeal to a career that takes you to golf resorts, ski mountains, and marinas around the world. Jeff does not shy away from acknowledging that part of the job. But he is equally honest about the grind behind it. The travel is relentless, the deals are complex, and the clients are sophisticated. None of this happens without serious hard work underneath the surface.

His bottom line on success in commercial real estate is simple and consistent with what the best operators in any field will tell you. Hard work is the foundation. Everything else is built on top of it.

Key Takeaways

• Career pivots done with intention can lead to extraordinary specialized expertise
• The golf industry has rebounded strongly thanks to Topgolf and pandemic-driven outdoor activity
• Understanding a product deeply, including physically experiencing it, is essential to selling it well
• Regional market knowledge is a major competitive advantage in specialized real estate
• Choosing the right listings is as important as closing them
• Hard work remains the non-negotiable foundation of success in commercial real estate

Connect with Jeff Woolson

• LinkedIn: https://www.linkedin.com/in/golfandresortproperties/
• Hospitality Net: https://www.hospitalitynet.org/opinion/4123224.html

Listen to the Full Episode Catch Episode 52 of Tools, Talents, and Techniques on Apple Podcasts, Spotify, YouTube, or at toolstalentstechniques.com

About Tools, Talents, and Techniques Hosted by Dustin Sutton, Tools Talents and Techniques is a podcast for founders, operators, and professionals who want to go deeper than surface-level success stories. Every episode unpacks how high performers think, decide, and build things that last.