Awkward Watersport Guys Podcast

In this episode, the guys sit down with financial consultant Andrew Howrigan for a conversation about what it really takes to build, protect, and grow wealth as a business owner. Andrew shares how growing up in his family’s maple syrup business shaped his relentless work ethic before diving into the financial lessons he now brings to entrepreneurs from properly structuring operating agreements and...

In this episode, the guys sit down with Dustin Miller to break down how the digital marketing landscape is changing for watersports, tours, and activity operators. They dive into the rising cost of Google Ads, declining ROAS, the growing influence of platforms like Meta and TikTok, and why relying too heavily on Google or OTAAs can put serious pressure on your margins. Dustin shares practical stra...

In this episode, the guys sit down with Kyle Reed, founder of Stannect, to dive into how automation, CRM systems, and smarter technology can help watersport and tourism operators scale their businesses without adding more manual work. The conversation explores why traditional reservation systems often fall short when it comes to customer communication, upsells, follow up, and sales automation, and...

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 liabil...

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 bu...

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,...

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, a...

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...

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 fa...

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 platfo...

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 conv...

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 Gemi...

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 oper...

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,...

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...

In this episode, the guys sit down with Brian Mazanti of KCBK Group, the podcast’s newest sponsor and a leading expert in the commercial marine space, for a deep dive into what it really takes to build a profitable rental fleet. From the explosive growth of the upcoming port event and the jet ski trailer parking competition giveaway, this episode is packed with opportunities for operators looking...

In this episode, the guys sit down with Boatsetter CEO Michael Farb to break down how the peer to peer boat rental marketplace is transforming the boating and watersports industry. The conversation explores how platforms like Boatsetter and GetMyBoat are turning underutilized private boats into revenue generating assets while expanding access to boating for millions of new customers. Michael share...

In this episode, the guys sit down with insurance expert Chris Murray to break down what water sport operators actually need to know about commercial insurance from decoding complex policy language to avoiding fraudulent or inadequate coverage that can sink your business. Next they dive into why safety documentation, maintenance logs, and operational discipline directly impact your premiums, under...

In this episode, the guys dive into how local regulations are tightening, license caps are expanding, and operators are feeling the squeeze. Then they break down the real world impact of Sarasota’s controversial medallion system and what it signals for boat rental and water sports businesses everywhere. From moratoriums and insurance requirements to political blind spots and media narratives. Next...

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 TOMIS and Yonder, the conversation breaks down how AI powered chatbots, voice assistants, and marketing automation can handle everyday customer questions, follow up with leads, and imp...

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 insight for owners trying...

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, regulatory pressure, and the...

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 Hibachi cruise, the conve...

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 through their careers,...

In this milestone 200th episode, the guys look back on the journey of building a niche show and community within the watersports industry. They share lessons they learned along the way and reflect on the power of authentic, unscripted conversations and the persistence required to push through slow early growth. Then they touch on how podcasting has fueled deeper relationships, smarter business thi...