Tom Rowland Podcast Episode 495 is my conversation with Captain Jonathan Moss, the Florida fishing guide and host of The Captain's Log TV on Waypoint. Jonathan built a family-friendly fishing show from scratch while guiding full-time, teaching elementary PE, and raising young kids. We talk about the Cuban work ethic he inherited from a grandfather who fled Castro, the restaurant gigs he played to buy his first skiff, and what it takes to launch a TV show without quitting everything else.
▶ Watch on YouTube · 🎧 Listen now
Jonathan Moss is a Florida fishing guide and the host and creator of The Captain's Log TV, a family-friendly fishing show that airs on Waypoint. He is a former elementary school PE teacher who left the classroom to guide full-time, and he built his television show while continuing to run charters and raise a young family. He is the grandson of Cuban immigrants and credits his work ethic to the way his family was raised.
The Captain's Log TV is the fishing show Jonathan Moss created and hosts. It is built to be family-friendly while still delivering the excitement of chasing big fish and telling a complete story on the water. The show airs on the Waypoint outdoor network, and Jonathan describes it as bringing the pages of a captain's log to life.
Jonathan worked relentlessly to save for his first flats skiff. While teaching during the week, he played guitar and sang at restaurants, bars, churches, taco shops, and grand openings around Orlando, eventually performing twelve to fifteen times a month. He even ate half his dinner and saved the rest for the week to cut costs, putting every extra dollar toward a new boat so he could start guiding.
Jonathan was an elementary school PE teacher, a job that gave him summers off and time to fish, but he says he grew tired of the politics of teaching. The pull toward guiding and the desire to build something of his own led him to leave the classroom, even though he kept teaching through his first year of guiding because a brand-new guide's phone does not ring right away.
Jonathan traces his work ethic directly to his family. His Cuban grandfather lost everything when Castro came to power, flew to America, took a job as a busboy without speaking English, and built a life on the simple rule that if you want to eat, you work. That mindset passed down through his parents to Jonathan, and he says he would not be the man he is without it.
Tom Rowland Podcast Episode 495 with Jonathan Moss is available on Apple Podcasts, Spotify, YouTube, and wherever you get your podcasts. The video version is embedded at the top of this page.
Jonathan and I got to know each other over the last year, mostly through workouts in a dirty parking lot at ICAST. He came to all of them and never complained about a deck of cards in the dirt, which told me something about him before we ever talked about his show. What got me to bring him on is that he is doing the thing most people only talk about: building a TV show from nothing while holding down a guide career, a family with young kids, and another one on the way. I wanted him to walk me through how that actually gets done.
Jonathan's whole drive traces back to a grandfather who lost a business when Castro took over, flew to America, and took a job as a busboy eating leftovers off the plates he cleared. The rule in the family was simple — if you want to eat, you work. Jonathan grew up inside that, and he connects it directly to why he can build a show and run charters at the same time. He tells the story better than I can summarize it, so listen to that part of the episode.
Before Jonathan could guide, he needed a boat, and a new guide's phone does not ring, so he played music — guitar, mandolin, a cajon drum box — at restaurants, churches, taco shops, and grand openings, sometimes fifteen times a month. He even cut his steak dinner in half to stretch it across the week and banked the difference. The discipline behind that period is the part I keep thinking about. Press play to hear how he pulled it off.
Jonathan had the setup a lot of people would envy — a PE teaching job with summers off and time to fish. He explains why he still left it, what the politics of teaching wore on him, and why he kept one foot in the classroom through his first year of guiding. The way he describes that transition is honest about the risk. Watch the YouTube player above for the full account.
▶ Watch the full conversation on YouTube · 🎧 Listen now
The Captain's Log TV did not come from a production company handing Jonathan a budget. He built it while guiding, teaching, and raising kids, with a clear vision of family-friendly content that still chases big fish. He walks through the challenges, the setbacks, and the mindset that kept it moving. If you have ever wanted to build something on the side, this is the section to hear.
Jonathan is guiding, filming, editing, and parenting, with another child on the way. I wanted to know how he keeps all of it from falling apart. His answer comes back to the same work ethic and the same belief that creating something with your hands — a fly, a fish brought to the boat, an episode — is its own reward. Listen to how he balances it.
The day after talking to Jonathan, the thing that stuck with me was not the TV show — it was the busboy story. A grandfather who arrives with nothing and decides that work is the answer sets a pattern that runs three generations deep, all the way to a guy filming a fishing show between charters.
Jonathan is a reminder that you do not have to quit your life to build the thing you want. You can teach, guide, play music, raise kids, and still bring a show to life if you are willing to do the work nobody sees. That is the real story here.
▶ Watch the full conversation on YouTube · 🎧 Listen now
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.
Jonathan Moss is a Florida fishing guide and the creator and host of The Captain's Log TV, a family-friendly fishing show that airs on the Waypoint network. A former elementary school PE teacher and the grandson of Cuban immigrants, he funded his first flats skiff by playing music around Orlando and built his television show while continuing to guide and raise a young family. He is known for an old-fashioned work ethic and for telling complete fishing stories on screen.
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