Awkward Watersport Guys Podcast

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...

In this episode, the guys sit down with WaveRez head of sales Zach Eischen for a candid, humorous, and insight packed deep dive into the realities of selling in the watersports industry. From navigating customer acquisition challenges to understanding key metrics like CAC and lifetime value, the guys break down what actually drives growth for operators today. Along the way, they share stories abou...

In this episode, the guys mix a recap of The Port 2025 with business insights from a recent industry event. They reflect on key takeaways around community, networking, and the growing importance of Standard Operating Procedures (SOPs) for operators looking to scale beyond self employment. You will hear candid thoughts on the difference between running a business versus just working in one, the rol...

In this episode, the guys sit down with Derek Michaloski to explore the intersection of technology, and photo marketing in today’s digital age. The conversation dives into broader cultural shifts and what that means for how operators market real world experiences. Derek shares his journey from traditional film photography to digital systems, emphasizing the enduring power of tangible photos in cre...

In this episode, the guys dive deep into the realities of running a modern water sports business blending humor, honesty, and hard won experience with sharp insights on technology, operations, and customer service. Then they preview upcoming industry events like The Port conference and unveiling Greg's book Boat Boss, the conversation balances entertainment with key takeaways. Then they explo...

In this episode, the guys dive into a candid live session at Arival, joined by a live audience. The guys deliver sharp insights on hot topics for watersport operators, including dynamic pricing, conversion rate optimization, upselling strategies, and customer acquisition costs. They share real world examples of how small changes in booking funnels, social proof, and early bird promotions can signi...

In this episode, the guys sit down with Kyle Reed, founder of Stannect, a CRM and automation platform designed for industries like home services and watersports. Kyle shares his journey from launching Stannect as a side hustle during COVID to building a full scale CRM solution that helps operators move beyond being “order takers.” The conversation dives into the challenges watersport businesses fa...

In this episode, the guys sit down with Zeb Smith of Zebulon Consulting to unpack the financial and operational challenges unique to watersport and outdoor operators. Zeb shares his journey from CPA to niche consultant, explaining how he helps outfitters move beyond gut instincts and passion to build data driven, profitable businesses. The conversation dives into the “Four Ps” of the industry: Pas...

In this episode, the guys sit down with Andres Avello, Co-Founder of PADL, to explore how his company is transforming the paddleboard and kayak rental industry through a self service, app driven model. Andres shares his journey from growing up on the water in Miami to building one of the fastest growing rental networks in Florida, now operating at more than 40 locations. The conversation dives int...

In this episode, the guys sit down with Eric Pinzon, founder of Electrified Marina, to dive into the realities and opportunities of the electric boat market. Eric shares his first hand experience navigating this emerging sector, from educating customers on safety misconceptions to tackling infrastructure and challenges. The conversation explores how location, marketing, and personal branding play...

In this episode, the guys sit down with Bruce Rosard from Arival to talk about how the tours, activities, and experiences industry is evolving and what it means for water sport operators in 2025 and beyond. Bruce shares his journey from ski tour operator to Co-Founder of Arival and explains how Arival is helping operators stay ahead with research driven information, powerful networking opportuniti...