Tom Rowland Podcast Episode 415 is my conversation with two Florida Keys fishing guides, Jared Raskob and Greg Dini. Jared came down from Syracuse, New York about fifteen years ago and worked his way up from fishing for tips to hosting Silver Kings on Waypoint TV. Greg followed his grandfather, who owned a marina and charter business in the Keys, and has guided for about ten years while raising three kids. We get into the honest reality of guiding with a family, the mental stress nobody sees, and how the Keys fishery is changing.
Listen now: Megaphone · Spotify · YouTube.
Jared Raskob is a Florida Keys fishing guide originally from Syracuse, New York who came to the Keys about fifteen years ago and now hosts Silver Kings on Waypoint TV. Greg Dini is a Florida Keys guide from Deerfield Beach, South Florida who followed his grandfather into the business, came to the Keys about twelve years ago, started as a mate, and has guided for about ten years while raising three children. Both specialize in Florida Keys flats fishing for tarpon, bonefish, permit, and redfish.
The biggest challenge is managing the seasonal, unpredictable nature of guide work alongside family responsibilities. Winters mean working six or seven days a week, while summers slow down and become inconsistent. Jared and Greg both describe the mental stress of self-employment, maintaining boats, finding clients, and marketing, that follows you home and makes it hard to be present even when you are off the water.
Greg and Jared have watched significant declines, particularly in bonefish populations, along with fewer tarpon and recurring challenges from red tides and sargassum blooms. They attribute much of it to environmental factors and a changing climate, and they explain how those changes force guides to stay flexible, shift species and areas, and constantly adapt presentations to keep putting clients on fish.
Both recommend starting as a mate or apprentice to learn the business side before going out on your own. Save capital for equipment, learn fishing and customer service, and do not rush the process. They stress that understanding boat maintenance, client management, and marketing is essential before launching your own operation, and that your reputation is everything in the guide business.
Tom Rowland Podcast Episode 415 with Jared Raskob and Greg Dini is available on Megaphone, Spotify, YouTube, and the Tom Rowland Podcast feed. The video version is embedded at the top of this page.
I wanted Jared and Greg on together because they are living the life a lot of people dream about, guiding in the Florida Keys, but they are honest about what it actually costs. The seasonal stress, the financial uncertainty, the difficulty of balancing family time with client demands. These are real issues that do not get talked about enough, and I wanted listeners to hear two guys who have been through it tell the truth about it.
Press play in the player above to hear it.
Jared came down from Upstate New York with a dream and not much else, fished for tips, and slowly built up to his own boat and eventually a TV show. He walks through the rough early years and the turning point. Hear how he did it in the episode.
Both guides describe the part of the job that stays with you after the dock, the constant worry about boats, clients, and bills. They are candid about how it seeps into family life. Listen to that section of the conversation.
Greg talks about quality over quantity and being intentionally present with his kids when the schedule allows. Both explain how they juggle go-go-go winters and slow summers. Press play in the YouTube player above.
Declining bonefish, red tides, and sargassum have forced both guides to shift species, areas, and tactics to keep clients on fish. They explain what staying flexible really looks like. Worth hearing in full.
Listen to the full conversation: Megaphone · Spotify · YouTube.
What struck me most was their perspective on family. Both have realized that no matter how successful you are, if you do not have family, it is not worth it. Greg put it perfectly when he talked about being intentional with the time you do have.
Their discussion of the environmental changes in the Keys matters too. Guides are on the front lines of seeing those changes, and the fact that they keep adapting tells you what it takes to last in this business. Press play in the player above, or grab Episode 415 on Megaphone or Spotify.
Jared Raskob · Greg Dini · Silver Kings · Waypoint TV · Florida Keys · Islamorada · Tom Rowland (host)
The Tom Rowland Podcast brings you long-form conversations with the most accomplished anglers, hunters, conservationists, and outdoor professionals in the game. Listen to every full-length Tom Rowland Podcast interview.
Jared Raskob is a Florida Keys fishing guide originally from Syracuse, New York who came to the Keys about fifteen years ago to pursue guiding. After working his way up from fishing for tips to investing in his own boat, he now hosts Silver Kings on Waypoint TV. Greg Dini grew up in Deerfield Beach, South Florida and followed his grandfather, who owned a marina and charter business in the Keys. Greg came to the Keys about twelve years ago, started as a mate, and has guided for about ten years while raising three children. Both guides specialize in Florida Keys flats fishing for tarpon, bonefish, permit, and redfish.
Subscribe to get the latest episodes, show notes, and exclusive content delivered straight to your inbox.