Owning the Future of Enthusiast Insurance: A Conversation with Jeff Briglia

RADwood Rising: The Growth of 80s and 90s Enthusiast Culture with Art Cervantes

Discover why vehicles from the 80s, 90s, and early 00s represent one of the hottest segments in today's collector car market. Art Cervantes, co-founder of RADwood, explains how nostalgic passion drives purchasing decisions and why these seemingly ordinary vehicles often hide extraordinary business opportunities for smart agents who know what to look for. Art Cervantes is an automotive enthusiast, photographer, and co-founder of RADwood, the nationally recognized event series celebrating 1980s and 1990s automotive culture, fashion, music, and lifestyle. Since launching RADwood in 2017, Cervantes has helped transform the brand from a grassroots enthusiast gathering into one of the most influential movements in the modern collector car community, helping spotlight the growing popularity of RADwood-era enthusiast vehicles. Prior to co-founding RADwood, Cervantes worked in the tech industry while building a reputation within automotive and photography circles as a passionate advocate for analog driving experiences and enthusiast culture. Here’s what we’ll cover in this episode: (00:27) Introducing the collector car market opportunity (01:05) What makes RADwood events unique and immersive (06:03) Most popular vehicles: BMWs, 911s and hidden gems (09:22) Why enthusiasts treasure period-correct modifications and details (13:53) Event evolution from 150 to 450+ cars per show (16:24) Introducing Millennia: celebrating early 2000s vehicles (22:22) Demographics: 41-year-old average, $175k-220k household income (26:35) Why emotional attachment matters more than vehicle value (30:11) Growing younger demographic discovering analog driving experiences (33:31) Tips for agents to identify RADwood-era enthusiast vehicles Links mentioned in this episode: RADwood: https://www.radwood.com/ RADwood Instagram: https://www.instagram.com/radwoodofficial/ RADwood Facebook: https://www.facebook.com/RadwoodOfficial/ Send your questions and feedback to Bryant and John at theacceleratorpodcast@hagerty.com

Mindset Over Metrics: The Community-Driven Growth Model with Jeremy Benjamin

What happens when deep personal passion meets smart business strategy? In this episode of The Accelerator, Bryant Kolle and John Gessner sit down with Jeremy Benjamin, a true car enthusiast who turned his love for collector vehicles into remarkable agency growth.  Jeremy shares how connecting with clients on what they genuinely love and building trust, community, and authentic relationships became a winning formula for sustained business success. Forget cold sales tactics: discover how becoming an active participant in the car community, hosting unforgettable events, and focusing on human connection can deliver real growth. Here’s what we’ll cover in this episode: (00:27) Introducing the collector car market opportunity (01:05) Jeremy’s unconventional growth approach: passion meets plan (06:03) The Central Valley’s car culture and how local insight drives business (09:22) Shifting the agency mindset and aligning teams (13:53) Account rounding and deepening relationships with car enthusiasts (16:24) Building WIS&G Cars & Coffee +: the event as marketing superpower (24:51) How referrals and real-world presence drive revenue (29:25) Embracing AI without sacrificing the power of human connections (38:26) Get started with car clubs, curiosity, and community (42:06) Key takeaways for agents Links mentioned in this episode: WIS&G Cars & Coffee +: https://www.instagram.com/wisgcarsandcoffee/ [https://www.instagram.com/wisgcarsandcoffee/]  Send your questions and feedback to Bryant and John at theacceleratorpodcast@hagerty.com [theacceleratorpodcast@hagerty.com]

Hagerty Bull Market List Explained: What Cars Are Becoming Collectible with Larry Webster

John Gessner and Bryant Kolle unpack Hagerty’s new Bull Market List with car culture legend Larry Webster. Learn what makes a car collectible today, why ’90s and 2000s models are heating up, and how agents can spot, protect, and win with enthusiast vehicles. Plus: why agreed value coverage is a must for serious car lovers. Here’s what we’ll cover in this episode: (04:12) Introducing Larry Webster (08:40) Why authenticity matters at Hagerty (11:35) Tracking classic car trends (15:23) Why Mopar muscle cars are rare (17:02) Miata, the ultimate analog sports car (20:51) Vintage cars, interest, and maintenance (23:20) BMW M5, an unexpected collectible (27:04) Condition 2: what it really means (30:30) Vehicle valuation insights for claims (33:53) Hagerty free automotive resources (38:32) V10 engines and flywheels explained (40:40) Challenges of high-performance cars (42:11) Bull market insights and patterns (46:35) Connecting through cars (48:30) Understanding audience connections (51:57) Engaging clients with the Bull Market List Links mentioned in this episode: Connect with Larry Webster on LinkedIn: https://www.linkedin.com/in/larry-webster-53896a13/ [https://www.linkedin.com/in/larry-webster-53896a13/] 2026 Hagerty Bull Market List: https://www.hagerty.com/media/market-trends/bull-market-2026/ [https://www.hagerty.com/media/market-trends/bull-market-2026/]  5 Ways to Win More Business: https://www.hagertyagent.com/resources/hagerty-insights/collector-car-market-5-ways-to-win-more-business [https://www.hagertyagent.com/resources/hagerty-insights/collector-car-market-5-ways-to-win-more-business]  The Hagerty Claims Difference: https://www.hagertyagent.com/resources/hagerty-insights/accelerating-trust-hagerty-claims-team [https://www.hagertyagent.com/resources/hagerty-insights/accelerating-trust-hagerty-claims-team]  The Cars You Should Know: https://www.hagertyagent.com/resources/hagerty-insights/cysk-shift-into-high-gear-for-a-winning-year-ahead [https://www.hagertyagent.com/resources/hagerty-insights/cysk-shift-into-high-gear-for-a-winning-year-ahead]  Send your questions and feedback to Bryant and John at theacceleratorpodcast@hagerty.com [theacceleratorpodcast@hagerty.com]

Owning the Future of Enthusiast Insurance: A Conversation with Jeff Briglia

As the year comes to a close, it’s time to reflect on what truly moved the needle. Bryant Kolle and John Gessner look back on a year defined by growth, community, and meaningful industry insight. They’re joined by special guest Jeff Briglia, President of Insurance at Hagerty. Jeff shares his career journey through companies like of Plymouth Rock, and what makes Hagerty genuinely different in insurance. The conversation explores customer-first culture, shifting generations of car enthusiasts, and what it all means for agents today.  Here’s what we’ll cover in this episode: (00:35) Reflections from The Accelerator in 2025 (06:01) Career shift for work-life balance (06:38) Pivoting to Progressive (10:47) Plymouth Rock’s market mastery (16:07) Hagerty’s classic car expertise (17:14) Building connection through car restoration (21:52) Enhancing insurance for modern needs (25:09) Adapting to today’s car owners (27:26) Cross-functional growth through curiosity (31:38) Hagerty’s distribution and partnerships (35:07) Supporting independent agents (37:07) Specialized car insurance guidance (42:23) Being a force for good (44:47) Generational shifts and future solutions (46:50) End better, be good Links mentioned in this episode: Connect with Jeff Briglia on LinkedIn [https://www.linkedin.com/in/jeff-briglia] The Hagerty approach to collector car claims: https://www.hagertyagent.com/resources/hagerty-insights/accelerating-trust-hagerty-claims-team [https://www.hagertyagent.com/resources/hagerty-insights/accelerating-trust-hagerty-claims-team]  The difference between ACV, Stated Value, and Guaranteed Value®: https://www.hagertyagent.com/resources/hagerty-insights/guaranteed-value [https://www.hagertyagent.com/resources/hagerty-insights/guaranteed-value]  Hagerty’s Cars You Should Know for agents and brokers: https://www.hagertyagent.com/resources/hagerty-insights/cysk-shift-into-high-gear-for-a-winning-year-ahead [https://www.hagertyagent.com/resources/hagerty-insights/cysk-shift-into-high-gear-for-a-winning-year-ahead]  Send your questions and feedback to Bryant and John at theacceleratorpodcast@hagerty.com [theacceleratorpodcast@hagerty.com]

Tuning the Frequency: How Mindset Powers Agent Success with Toby Brazwell

Today, we welcome a true multi-hyphenate guest – Toby Brazwell, who is a district leader, musician, author, and empowerment coach. Toby joins the show to explore how emotional intelligence and mindset shape performance, why building your “personal board of advisors” is a game-changer for insurance professionals, and dig into the powerful idea that every interaction is an interview.  Here’s what we’ll cover in this episode: (00:57) Introducing Toby Brazwell: mindset, music, leadership and impact (05:16) Connecting creativity, music and business (11:13) Emotional intelligence and tuning into frequencies (14:12) Coaching mindset and cultivating EQ in sales teams (18:14) Reframing failure – you either win or learn (20:00) Learning from adversity: Everest and Tom Brady (22:24) Unlocking potential and building your Friendship Incorporated (27:05) Writing ‘The Empowerment Chords’ and finding your power (30:14) Are top insurance agents born or trained? (34:02) The power of systems in sales performance (35:38) Coaching underperformers – stick, carrot or conversation? (41:32) Habit shifts: treat every interaction like an interview (45:30) From insurance to city council: purpose-driven leadership (50:10) Top takeaways and final thoughts Links mentioned in this episode: Connect with Toby Brazwell on LinkedIn [https://www.linkedin.com/in/tbrazwell/] The Empowerment Chords – Book [https://www.amazon.com/Empowerment-Chords-Change-Perspective-Power/dp/179339086X] The E-Myth Revisted [https://www.amazon.com/Myth-Revisited-Small-Businesses-About/dp/0887307280] – Book Fortune article on Tom Brady [https://fortune.com/2025/10/30/tom-brady-problem-with-modern-parenting-success/] Send your questions and feedback to Bryant and John at theacceleratorpodcast@hagerty.com [theacceleratorpodcast@hagerty.com]