Capt. Greg Dini | From Minor League Baseball to Full-Time Fishing Guide | Tom Rowland Podcast 330

Captain Greg Dini is the founder of Flywater Expeditions, a full-time guide service based in New Orleans who transitioned from minor league baseball to chasing redfish in Louisiana, tarpon in the Florida Keys and Apalachicola, and sight-fishing opportunities year-round. In this conversation, Greg reveals how he made the leap from professional baseball to professional guiding, what it takes to build a guide business from scratch, and the specific techniques he uses to target Louisiana redfish and Florida tarpon. If you've ever wondered what it really takes to go full-time in the fishing industry, this episode pulls back the curtain on the reality of making a living on the water.

From the Diamond to the Flats: Making the Transition

Greg Dini's path from minor league baseball to full-time guide wasn't a straight line, and the story of how he made that transition reveals the real challenges of building a guide business. With a background that includes playing at the University of Miami and competing in minor league baseball, Greg had to figure out how to leverage his competitive nature and work ethic in an entirely different arena. The decision to leave baseball behind and commit fully to guiding required more than just a love of fishing—it demanded a business plan, a willingness to grind through slow seasons, and the ability to build a reputation from scratch. Greg's full story of the transition from baseball to guiding and how he built Flywater Expeditions starts early in the conversation.

Louisiana Redfish: Techniques and Tactics

When it comes to Louisiana redfish, Greg Dini has developed specific approaches that work in the unique marsh environments around New Orleans. The conversation digs into the techniques he uses for sight-fishing redfish in Louisiana's complex marsh systems, including how he adapts his approach based on water conditions, tides, and seasonal patterns. Greg discusses the differences between fishing Louisiana marshes versus other redfish destinations, and what makes the New Orleans area such a special fishery for both fly and conventional anglers. The detailed breakdown of Greg's Louisiana redfish tactics and what makes the marsh fishing unique begins around the middle of the episode.

Tarpon in the Keys and Apalachicola

Greg doesn't just guide in Louisiana—he follows the seasons to chase tarpon in both the Florida Keys and Apalachicola. In this part of the conversation, he reveals the differences between these two tarpon fisheries and how he approaches each one differently. From the pressured fish in the Keys to the unique opportunities in Apalachicola, Greg shares insights on what it takes to be successful in both locations. The discussion covers gear selection, fly choices, and the mental game required when you're staring down a hundred-pound tarpon. Greg's tarpon strategies for both the Keys and Apalachicola, including what separates these two fisheries, come later in the episode.

The Reality of Full-Time Guiding

What does it actually take to make a living as a full-time fishing guide? Greg pulls back the curtain on the business side of guiding, including how he structures his season, manages his time between different fisheries, and builds the relationships that keep clients coming back year after year. This isn't a glamorized version of life on the water—it's an honest look at the work, the challenges, and the rewards of building a legitimate guide business. From marketing to boat maintenance to managing client expectations, Greg covers what it really takes to succeed in this competitive industry. The complete breakdown of what full-time guiding actually looks like, including the business realities most people don't see, unfolds throughout the conversation.

Final Thoughts from Tom

I really enjoyed this conversation with Greg Dini. It's not often you get to sit down with someone who made the leap from professional sports to professional guiding and can articulate exactly what that transition looked like. Greg's honest about the challenges, the business side, and what it really takes to make a living on the water.

What stands out to me is how Greg approaches guiding with the same competitive mindset he brought to baseball. He's not just taking people fishing—he's building a business, refining his techniques, and constantly working to improve. That's the kind of approach that separates guides who make it from those who don't.

Whether you're thinking about going into guiding, you're interested in Louisiana redfish or Florida tarpon, or you just want to hear what it's like to build something from the ground up in the fishing industry, this episode is worth your time. Listen to the whole thing.