Latest Episode
"From the Archives" Bareboat Charters: What You Probably Don't Know Ft. Kenny Hilderbrandt of RentABoat.com - Episode #144
In this FTA (From the Archives) episode, the guys sat down Kenny Hilderbrandt, founder of RentAboat.com, for an in depth conversation about the legal, operational, and insurance challenges facing the boat and watersports rental industry. Kenny shares his experience operating marinas in New York and Florida while explaining the differences between bareboat charters and livery operations, how liability laws impact rental businesses, and why insurance continues to be a major concern for operators.
Recent Shows
144
Sept. 16, 2026
"From the Archives" Bareboat Charters: What You Probably Don't Know Ft. Kenny Hilderbrandt of RentABoat.com - Episode #144
In this FTA (From the Archives) episode, the guys sat down Kenny Hilderbrandt, founder of RentAboat.com, for an in depth conversation about the legal, operational, and insurance challenges facing the boat and watersports rental industry. Kenny shares his experience operating marinas in New York and Florida while explaining the differences between bareboat charters and livery operations, how liability laws impact rental businesses, and why insurance continues to be a major concern for operators.
220
Sept. 9, 2026
From Arival to AI: The Biggest Challenges Facing Watersports Operators Ft. Bruce Rosard - Episode #220
In this episode, the guys sit down with Bruce Rosard, Co-Founder of Arival. They dive into the biggest challenges and opportunities facing water sports operators today, coming straight out of Arival 2026 in Spokane. Kevin, Greg, and their guests discuss the growing influence of OTAAs like Viator and GetYourGuide, the importance of protecting margins and owning the customer relationship, and why building a strong direct to consumer sales strategy is more critical than ever. They also explore the
219
Sept. 2, 2026
Stop Selling Boat Rides: How Sandbar Joe’s Built an Experience-First Business - Episode #219
In this episode, the guys sit down with Joe Gratz, founder of Sandbar Joe’s, to break down how he built a modern, experience-first charter business in New Jersey by putting social media, hospitality, and customer experience at the center of the brand. Joe shares how he uses TikTok, Instagram, Facebook, and YouTube to drive real bookings, why niche experiences can outperform traditional boat tours, and the challenges that come with scaling a business without losing its personality. The conversati
218
Aug. 27, 2026
From Rentals to Recurring Revenue: The Elevated Boat Club Story - Episode #218
In this episode, the guys sit down with Chris Rozzo of Elevated Boat Club to break down what it really takes to build and operate a successful boat club in a challenging market like Lake Tahoe. Chris shares his journey from jet ski rentals to launching a membership based boat club, along with the lessons he’s learned about recurring revenue, pricing, member churn, marina costs, fleet management, and competing in an increasingly consolidated industry. The conversation also explores the rise of fr
217
Aug. 19, 2026
From Dirt Floors to Building Boats for the Biggest Operators, The A&M Story - Episode #217
In this episode, the guys sit down with John Hemken, CEO and owner of A&M Manufacturing, and Angela Owen, COO, for an inside look at the business of building commercial boats for watersport and tourism operators. John shares the incredible story of taking over A&M during a period of financial and operational turmoil and turning it into a respected manufacturer of COI vessels, while Angela explains how the company has built systems and a team designed to scale without relying on a single person.
216
July 23, 2026
A New Name, The Same Mission - Episode #216
In this episode, the Awkward Watersport Guys officially becomes Kevin and Greg Live, after 5 incredible years. In this milestone episode, Kevin and Greg share why they rebranded, how a podcast that started as a fun side project evolved into a thriving media company, and what's next for the community they've built. They discuss the realities of entrepreneurship, balancing business with family, avoiding burnout, and why authenticity remains the foundation of everything they do. You'll also get a p
215
July 16, 2026
The Future of Marine Tech: A Conversation with Buoy's CEO Ft. Shea Unti - Episode #215
In this episode, the guys sit down with Shea Unti, CEO of Buoy. Insurance can be one of the most confusing and most important parts of running a watersports business. The guys discuss how the marine insurance landscape is evolving and what operators need to know to better protect their businesses. From his journey through yacht management, Boatsetter, and now leading an innovative insurance platform, Shea shares practical insights on risk management, compliance, embedded insurance, and how techn
214
June 12, 2026
From Party Buses to Party Boats: An Entrepreneur's Evolution Ft. Nikki DuBois - Episode #214
In this episode, the guys sit down with Nikki DuBois, founder of Boomerang Boat Tours in Washington, DC. She shares her remarkable journey from high school teacher to owner of a thriving multi vessel charter operation. Nikki discusses how she identified market opportunities, evolved from party buses to party boats, and built a business that now operates successfully with remote ownership. The conversation dives into critical topics for watersport operators, including cashless operations, prevent
213
May 28, 2026
The Future of Tours & Watersports: Smaller Teams, Smarter AI, Bigger Opportunities - Episode #213
In this episode, the guys share stories from Kevin’s unforgettable trip to Japan. Then they take a deep dive into how AI is rapidly transforming the travel and tour industry. The conversation focuses on what watersport operators need to do right now to stay competitive, from tracking conversion rates and maximizing phone sales to adapting for AI driven search platforms like ChatGPT and Google Gemini. The hosts explain why traditional SEO and paid ads are becoming less effective, how platforms li
212
April 30, 2026
Breaking the Cycle: Addiction, Mental Health & Growth on the Water - Episode #212
In this episode, the guys dive into the often overlooked realities of addiction and mental health in the watersports industry. They unpack how environment, personality, and daily habits can quietly limit both personal well being and business growth. The guys explore the difference between physical and psychological addiction, why industry culture can reinforce unhealthy patterns, and how many operators unknowingly hit a ceiling because of lifestyle choices rather than market conditions. They bre
211
April 23, 2026
Smarter Boats, Fewer Headaches: The Telematics Takeover Ft. Kevin Walsh - Episode #211
In this episode, the guys sit down with Kevin Walsh to break down how AI and telematics are quickly becoming must have tools for watersport operators looking to run tighter, safer, and more profitable fleets. The guys unpack how platforms like Boat Fix give you real time visibility into your boats tracking engine hours, usage patterns, battery health, and more so you can stay ahead of maintenance, reduce downtime, and make smarter operational decisions. They also dive into how this data is start
210
April 16, 2026
From the Rave to the Marina: Fresh Ideas for Water Sports Growth - Episode #210
In this episode, the guys kick it off with stories from Miami, where rave culture, luxury waterfront lifestyles, and a chaotic but unforgettable bareboat charter experience spark bigger conversations about the future of the industry. What starts as a fun recap quickly turns into a masterclass for operators, as they unpack the massive opportunity in professionally managing privately owned boats as an asset light rental model, share why early investments in events like The Port can accelerate busi
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About the Hosts
Kevin O'Neil
Owner, Destiny Water Adventures
Master Captain, CEO, and head of marketing for Destiny Water Adventures. Kevin took his passion for boating, adventure, travel, and adventure and poured it into his brand. With over 12 years of commercial boating, parasailing jet skiing, as well as a myriad of other water sports and activities. In under two and a half years, Kevin has scaled Destiny Water Adventures from a single boat operation to over a dozen boats, ten jet skis, kayaks, paddleboards as well as captained excursions.
Greg Fisher
CEO of TripShock, WaveRez
Greg is a serial entrepreneur that has worked in the travel and hospitality industry for over 15 years. He is currently the CEO of both TripShock.com, an OTA for tours and activities, and WaveRez.com, a reservation software for watersport operators. Greg is a graduate of UCF, and has earned INC 500/5000 honors from 2015-2018.
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