Captain Greg Dini is the founder of Flywater Expeditions, a full-time guide service based in New Orleans, and his path there ran straight through minor league baseball. Greg played at the University of Miami, competed in the minors, and then leveraged a competitive mindset and a passion for sight fishing to build a year-round operation chasing Louisiana redfish, Florida Keys and Apalachicola tarpon, and sight-fishing opportunities across multiple fisheries. This episode pulls back the curtain on what it actually takes to make a living on the water.
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Greg Dini transitioned by building Flywater Expeditions while leveraging the competitive mindset he developed in minor league baseball. The shift required real business planning, building a reputation from scratch, and committing fully to guiding across multiple fisheries, including Louisiana redfish and Florida tarpon. He treated it as a legitimate business rather than a hobby.
Louisiana marsh fishing around New Orleans offers unique sight-fishing opportunities for redfish in complex marsh systems. Greg explains that the fishery requires specific techniques adapted to water conditions, tides, and seasonal patterns that differ from other redfish destinations, which is part of what makes the New Orleans area so special for both fly and conventional anglers.
Greg guides for tarpon in both the Florida Keys and Apalachicola, and he approaches each fishery differently based on fish behavior, pressure levels, and the environmental conditions unique to each location. He follows the seasons to chase the best opportunities in each place.
Flywater Expeditions is Greg Dini's full-time guide service based in New Orleans. The operation targets redfish in Louisiana marshes, tarpon in the Florida Keys and Apalachicola, and travels year-round for sight-fishing opportunities across the Southeast.
Building a full-time guide business takes more than fishing skill. Greg describes the need for business planning, seasonal structuring, client relationship management, marketing, and boat maintenance. Success comes from treating guiding as a real business, grinding through slow seasons, and consistently producing for clients.
Greg's competitive baseball background shaped his work ethic and his approach to guiding in ways that translate directly to the water. He brings the same drive to refine techniques, build a business, and constantly improve that he once brought to professional sports, which he credits as a major reason he was able to make the leap successfully.
It is 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. I wanted Greg on because he is honest about the challenges, the business side, and the grind, and because he approaches guiding with the same competitive mindset he brought to baseball. That is the kind of approach that separates guides who make it from those who do not, and I wanted him to lay it all out.
Greg's path from minor league baseball to full-time guide was not a straight line, and the story reveals the real challenges of building a guide business. With a background that includes playing at the University of Miami and competing in the minors, he had to figure out how to channel his competitive nature and work ethic into an entirely different arena. Leaving baseball behind demanded a business plan, a willingness to grind through slow seasons, and the patience to build a reputation from scratch. Hear how he made the transition in the episode.
When it comes to Louisiana redfish, Greg has developed specific approaches for the unique marsh environments around New Orleans. We dug into how he sight-fishes redfish in those complex marsh systems and adapts to water conditions, tides, and seasonal patterns. He explains the differences between Louisiana marshes and other redfish destinations and what makes the New Orleans area such a special fishery. Listen for the detailed breakdown of his redfish tactics.
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Greg does not just guide Louisiana. He follows the seasons to chase tarpon in both the Florida Keys and Apalachicola, and he explains how differently he approaches each one. From the pressured fish in the Keys to the unique opportunities in Apalachicola, he covers gear selection, fly choices, and the mental game of staring down a hundred-pound tarpon. Hear what separates these two fisheries in the conversation.
What does it actually take to make a living as a full-time fishing guide? Greg pulls back the curtain on the business side, including how he structures his season, manages time between fisheries, and builds the relationships that keep clients coming back. This is not a glamorized version of life on the water. It is an honest look at the marketing, the boat maintenance, and the client expectations that go into a legitimate guide business. Listen for the full picture.
The day after this one, what stood out was how Greg approaches guiding with the same competitive mindset he brought to baseball. He is not just taking people fishing. He is building a business, refining his techniques, and constantly working to improve.
Whether you are thinking about going into guiding, you are interested in Louisiana redfish or Florida tarpon, or you just want to hear what it takes to build something from the ground up in this industry, this episode is worth your time. Listen to the whole thing.
Listen to the entire conversation here.
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Captain Greg Dini is the founder of Flywater Expeditions, a full-time guide service based in New Orleans. A former minor league baseball player who attended the University of Miami and Tulane, Greg transitioned to guiding after his baseball career and now chases redfish in Louisiana, tarpon in the Florida Keys and Apalachicola, and travels for sight-fishing opportunities year-round. His competitive background in professional sports shaped his approach to building a guide business and developing techniques for some of the most challenging saltwater fisheries in the Southeast.
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