Kevin & Greg LIVE at the Port

Jaksot

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  Your Booking System Isn’t Enough: Why You Need a CRM Ft. Kyle Reed - Episode #221 24.09.2026 45min

  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 how CRMs and open API integrations can fill those gaps. Kyle also shares his perspective on refe...
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  "From the Archives" Bareboat Charters: What You Probably Don't Know Ft. Kenny Hilderbrandt of RentABoat.com - Episode #144 16.09.2026 43min

  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 operator...
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  From Arival to AI: The Biggest Challenges Facing Watersports Operators Ft. Bruce Rosard - Episode #220 09.09.2026 53min

  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 t...
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  Stop Selling Boat Rides: How Sandbar Joe’s Built an Experience-First Business - Episode #219 02.09.2026 51min

  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 convers...
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  From Rentals to Recurring Revenue: The Elevated Boat Club Story - Episode #218 27.08.2026 44min

  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...
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  From Dirt Floors to Building Boats for the Biggest Operators, The A&M Story - Episode #217 19.08.2026 44min

  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 sing...
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  A New Name, The Same Mission - Episode #216 23.07.2026 38min

  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 ...
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  The Future of Marine Tech: A Conversation with Buoy's CEO Ft. Shea Unti - Episode #215 16.07.2026 50min

  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 te...
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  From Party Buses to Party Boats: An Entrepreneur's Evolution Ft. Nikki DuBois - Episode #214 12.06.2026 43min

  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, prev...
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  The Future of Tours & Watersports: Smaller Teams, Smarter AI, Bigger Opportunities - Episode #213 28.05.2026 32min

  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...
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  Breaking the Cycle: Addiction, Mental Health & Growth on the Water - Episode #212 30.04.2026 32min

  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 ...
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  Smarter Boats, Fewer Headaches: The Telematics Takeover Ft. Kevin Walsh - Episode #211 23.04.2026 43min

  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 st...
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  From the Rave to the Marina: Fresh Ideas for Water Sports Growth - Episode #210 16.04.2026 44min

  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 b...
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  From OEMs to Rentals: The Fleet Model Manufacturers Missed Ft. Brian Mazanti - Episode #209 09.04.2026 54min

  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 po...
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  Peer to Peer Power: How Boatsetter Is Scaling the Global Boat Rental Marketplace Ft. Michael Farb - Epsiode #208 12.03.2026 1t

  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...
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  Fraudulent Policies, Rising Premiums & How to Stay Covered Ft. Chris Murray - Episode #207 05.03.2026 55min

  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 ...
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  Death by Regulation: The Slow Squeeze on Operators - Episode #206 19.02.2026 49min

  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...
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  AI on the Dock: Smarter Marketing & Reservations for Watersports Operators Ft. Evan Tipton and Ivy Duncan - Episode #205 05.02.2026 57min

  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 worl...
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  Stop Playing Small Ball: Mindset Shifts for Scaling Watersport Operations - Episode #204 28.01.2026 42min

  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 to scale without burning out. The episode also introduces peer coaching groups designed specific...
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  Why Charter Fishing Isn’t Just About Fish Anymore Ft. Kyle Lowe & Cliff Atwell - Episode #203 22.01.2026 1t 2min

  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 double edged sword of online booking platforms and social media marketing. Then the discussion un...