Latest Episode
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 …
Recent Shows
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
209
April 9, 2026
From OEMs to Rentals: The Fleet Model Manufacturers Missed Ft. Brian Mazanti - Episode #209
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 to level up. Brian breaks down how KCBK helps rental and boat club businesses source the right ponto
208
March 12, 2026
Peer to Peer Power: How Boatsetter Is Scaling the Global Boat Rental Marketplace Ft. Michael Farb - Epsiode #208
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 shares insights on the key innovations making this model work from usage based insurance and certified ca
207
March 5, 2026
Fraudulent Policies, Rising Premiums & How to Stay Covered Ft. Chris Murray - Episode #207
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, underwriting experience and how long term carrier relationships can stabilize rising costs. They also exp
206
Feb. 19, 2026
Death by Regulation: The Slow Squeeze on Operators - Episode #206
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 they talk candidly about why waiting it out isn’t a strategy. If you operate on public waterways, t
205
Feb. 5, 2026
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 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 improve bookings while still keeping a human touch where it matters most. The guests share real world e
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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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