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Awkward Watersport Guys Podcast

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AI on the Dock: Smarter Marketing & Reservations for Watersports Operators Ft. Evan Tipton and Ivy Duncan - Episode #205

In this episode, the guys dive into how AI is quickly becoming a practical tool not a scary buzzword for water sports and tour operators looking to grow without burning out. Featuring Evan Tipton and Ivy Duncan from Thomas and Yonder, the conversation breaks down how AI powered chatbots, voice assistants, and marketing automation can handle everyday customer questions, follow...


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Stop Playing Small Ball: Mindset Shifts for Scaling Watersport Operations - Episode #204

In this episode, the guys get candid about the real growth ceilings facing watersport operators, focusing on the often overlooked “keyman constraint” and the people problems that keep businesses stuck. From personal stories that set the tone to a deep dive on leadership, hiring loyal and coachable team members, and cross training staff, the conversation delivers practical ins...


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Why Charter Fishing Isn’t Just About Fish Anymore Ft. Kyle Lowe & Cliff Atwell - Episode #203

In this episode, the guys dive deep into the modern charter fishing business through candid conversations with Destin, Florida captains Kyle Lowe and Cliff Atwell, revealing how the industry has shifted from fish first trips to experience driven, family friendly entertainment. They will talk about real world insights on rising operational costs, market oversaturation, regulat...


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Experiment, Adapt, Repeat: Turning Watersports into an Experience Brand Ft. Michael & Taylor Withrow - Episode #202

This episode, they guys sit down with Michael and Taylor Withrow, owners of Island Head in Hilton Head, South Carolina. They unpack what it really takes to build and sustain a diversified, multi location watersports and experience business. From early legal challenges that forced a rebrand, to expanding beyond parasailing into ferries, charters, and unexpected wins like a Hib...


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Scaling Smarter, Not Bigger: Hidden Profits Inside Your Existing Operation Ft. Zeb Smith - Episode #201

In this episode, the guys dive deep into what it really takes to transform a watersport business from “getting by” to intentionally profitable. Kevin and Greg sit down with Zeb Smith from Zebulon LLC to unpack the powerful results of disciplined spend management, strategic pricing, and participation in peer groups like the Eddie. They share real numbers, lessons they learned ...


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