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Episode Show Notes
Captain Jonathan Moss is the host of The Captain's Log TV, a family-friendly fishing show that airs on the Waypoint channel. A fishing guide by trade who guides approximately 200 days per year in the Florida Keys, Jonathan built his TV show from the ground up while balancing a full-time guiding career and raising two young children aged seven and five. In this episode, Jonathan reveals how he financed the first season out of his own pocket while refusing to compromise his clients' experience, the unconventional choice that made his show stand out from typical fishing television, and the grinding reality of producing professional content while working sunrise to sunset on the water. If you've ever wondered what it actually takes to build something meaningful while juggling multiple businesses and a family, this conversation pulls back the curtain.
What is The Captain's Log TV?
The Captain's Log TV is a story-based fishing show that airs on Waypoint, featuring beautiful cinematography and focusing on the people, places, and culture around fishing rather than just catching fish. Jonathan Moss created it with approximately 10 episodes filmed in 2019 and 2020, bootstrapping the production with his own money and a talented crew before securing a network deal with Waypoint that aired in summer 2021.
Who is Jonathan Moss?
Jonathan Moss is a Florida Keys fishing guide who works approximately 200 days per year targeting bonefish, permit, and tarpon. He's also the host and creator of The Captain's Log TV on Waypoint. Jonathan met Tom Rowland during early morning workouts at ICAST and balances his guiding business with TV production while raising two children with his wife.
Title Sponsor
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The Decision That Separated His Show From Everyone Else
Most fishing guides would jump at the chance to film their clients and call it content. Jonathan made the opposite choice. He realized early that trying to shoot his TV show while on paid guide trips would compromise the client experience—and that wasn't acceptable. So instead, he did something that sounds financially insane: he took full weeks off from guiding, walked away from that income, and dedicated those blocks entirely to filming episodes. He'd shoot multiple episodes in a week-long production window, traveling to different locations with his crew. It meant sacrifice, but it meant his show could focus purely on storytelling without the distraction of managing paying clients. That clarity of purpose shows in every frame. Jonathan explains this philosophy and how he structured his production schedule starting around 00:04:05.
Bootstrapping a TV Show on a Guide's Income
Building professional television isn't cheap. Jonathan didn't wait for investors or network funding—he put his own money into season one, relying entirely on his guiding income to finance production. He and his production partner cobbled together resources, got creative with what they had, and pushed forward with the belief that if they could create a few episodes showcasing their vision, they could pitch it to networks later. They used professional-grade cameras, drones for aerials, GoPros and underwater cameras for unique angles, and professional audio equipment. The investment was real, but so was the commitment. Eventually Waypoint believed in what they'd built and picked up the show. The story of how he financed the first season begins at 00:03:30.
Hear Jonathan explain how he balanced production costs with guiding income
What 200 Days of Guiding Actually Looks Like
Jonathan guides roughly 200 days per year in the Florida Keys, targeting the holy trinity of flats fishing: bonefish, permit, and tarpon. These aren't easy fish—bonefish are fast and spooky, permit are incredibly smart and selective, and tarpon are big, powerful, and challenging to fight. A typical day starts at 5 or 6 a.m. when clients meet him at the dock, then it's a full day on the water with a lunch break before returning around 4 or 5 p.m. He estimates clients catch fish on 70 to 80 percent of days, but the conditions dictate everything. When someone lands their first permit or jumps a big tarpon, those moments make the job worth it. And remarkably, even after guiding all day, Jonathan still loves to fish on his own time. Jonathan describes the guide life and his success rate starting at 00:08:11.
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SubscribeManaging Family, Business, and Creative Ambition
Raising two kids—one seven, one five—while guiding 200 days a year and producing a television show is the kind of schedule that sounds unsustainable on paper. Jonathan admits it's challenging but credits intentionality with his time, a supportive wife who manages the household, and working smart instead of just hard. He tries to be home by dinner most nights, spends evenings and weekends with his family, and squeezes production work into early mornings or late evenings. His kids have even appeared in some episodes, though they don't fully grasp what a TV show is yet. When asked about burnout, Jonathan points to passion—the fishing and filmmaking drive him. His advice to anyone with a similar dream? Just start with what you have, surround yourself with believers, work hard, stay persistent, and don't give up. The conversation about balancing everything begins at 00:11:44.
Don't miss this one.
This conversation goes deep into the realities of building something meaningful while living a full life.
Key Takeaways
- Jonathan Moss guides 200 days per year in the Florida Keys while producing a television show and raising two young children—and the way he structures his time reveals a philosophy about serving one master at a time
- The Captain's Log TV focuses on story, people, and culture rather than just catching fish, shot with professional-grade cameras, drones, and underwater equipment to create something families can watch together
- He made the unconventional choice to take full weeks off from guiding to shoot episodes rather than filming on client trips—sacrificing immediate income to preserve both client experience and creative vision
- Jonathan bootstrapped season one with his own money from guiding before pitching to Waypoint, which picked up the show after seeing what he and his production partner had created
- His success rate as a guide is 70 to 80 percent of days where clients catch fish, targeting the challenging trio of bonefish, permit, and tarpon on the flats
- The timeline from first shooting episodes in 2019-2020 to airing on Waypoint in summer 2021 took roughly two years of grinding nights and weekends while maintaining his full guiding schedule
- Jonathan's advice for anyone with a big dream: start with what you have, don't wait for everything to be perfect, surround yourself with believers, and let your passion sustain you through the hard times
Final Thoughts from Tom
I really enjoyed this conversation with Jonathan. We met in a parking lot at ICAST doing early morning workouts, and I could tell right away he was someone who got it—someone who understood that you build things through consistent effort and sacrifice. What struck me most about his story is the integrity in how he approached both his guiding business and his TV show. He refused to compromise his clients' experience just to get content. That's professionalism.
The reality of what Jonathan's doing is intense. Guiding 200 days a year is a full-time job by itself. Add in producing professional television and raising two young kids, and you've got a schedule that would break most people. But he's doing it because he loves it, and because he's built a system that works. His wife is clearly a huge part of that success, and he acknowledges that openly. That's important.
If you're thinking about building something on the side—whether it's a TV show, a business, or any creative project—this episode is worth your time. Jonathan's path from bootstrapping season one to getting picked up by Waypoint is a blueprint for how to make things happen without waiting for permission. Listen to the whole thing.
Frequently Asked Questions
Where can I watch The Captain's Log TV?
The Captain's Log TV airs on Waypoint, a fishing channel available through cable and streaming platforms. The show features approximately 10 episodes focused on story-based fishing content with professional cinematography. You can access Waypoint through various cable providers and streaming services that carry outdoor and fishing content.
How did Jonathan Moss get into TV production?
Jonathan Moss had a long-standing passion for filmmaking and storytelling that he combined with his love of fishing and guiding. He partnered with a talented filmmaker he met in college and together they bootstrapped the first season of The Captain's Log TV in 2019-2020 using his own money from his guiding business before successfully pitching it to Waypoint.
What fish does Jonathan Moss target as a Florida Keys fishing guide?
As a Florida Keys guide, Jonathan primarily targets bonefish, permit, and tarpon—known as the holy trinity of flats fishing. He describes bonefish as fast and spooky, permit as incredibly smart and selective, and tarpon as big, powerful, and challenging to fight. He guides approximately 200 days per year with a success rate of 70 to 80 percent of days where clients catch fish.
How does Jonathan Moss balance guiding, TV production, and family?
Jonathan manages his schedule by being intentional with his time, working in early mornings and late evenings on production tasks, and having a supportive wife who manages the household. He tries to be home by dinner most nights and takes dedicated weeks off from guiding to film episodes rather than trying to do both simultaneously. He credits working smart, delegating where possible, and having a good production team.
What advice does Jonathan Moss have for aspiring content creators?
Jonathan's advice is to just get started with what you have rather than waiting for perfect conditions, funding, or the right people. He emphasizes surrounding yourself with people who believe in your vision, working hard, staying persistent, and not giving up. He believes that real passion for your project will sustain you through the inevitable hard times and challenges.
Related Episodes
Another conversation about balancing content creation with a fishing business
Deep dive into targeting bonefish, permit, and tarpon in the Keys
How outdoor professionals balance career ambitions with parenting responsibilities
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Shop GORUCKPeople Mentioned
Jonathan Moss - Host of The Captain's Log TV, Florida Keys fishing guide
Tom Rowland - Host of the Tom Rowland Podcast
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About this Guest
Captain Jonathan Moss
Captain Jonathan Moss is a Florida Keys fishing guide who works approximately 200 days per year targeting bonefish, permit, and tarpon. He's the host and creator of The Captain's Log TV, a family-friendly fishing show that airs on Waypoint featuring beautiful cinematography and story-driven content. Jonathan built the show from the ground up starting in 2019-2020, bootstrapping production with his own money from his guiding business before securing a network deal. He balances his guiding career and TV production while raising two children aged seven and five with his wife. Jonathan met Tom Rowland during early morning workouts at ICAST. He emphasizes working smart, being intentional with time, and surrounding yourself with supportive people to manage multiple ventures simultaneously.
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