The Insurance Guys Podcast

In this episode of the Insurance Guys Podcast, Scott Howell and Bradley Flowers talk with Matthew Vega-Sanz, CEO and founder of Gail, about how AI is changing the insurance industry. Matthew shares his story, starting with a car-sharing app for college students, then building Lula, a top insurtech company, and now working on Gail, an AI platform focused on insurance and financial services. They ta...

On this episode of the Insurance Guys Podcast, Scott Howell and Bradley Flowers welcome the always insightful and entertaining David Carothers. The trio dives into practical strategies for insurance agents, focusing on personal and agency branding, leveraging technology for efficiency, and the importance of sticking to your lane within specialized markets. David Carothers shares the story behind h...

In this engaging episode of the Insurance Guys Podcast, Scott Howell and Bradley Flowers welcome back Becca Rubenfeld, co-founder of Anchor Watch, to discuss the evolving landscape of crypto insurance, specifically insuring Bitcoin assets. The conversation covers real-world scenarios, including a story of $160,000 in stolen Bitcoin and the challenges of recovering crypto after theft. Becca Rubenfe...

On this episode, Scott Howell and Bradley Flowers welcome Shelby Tirado and Chris Huebener from Brightway Insurance in Jacksonville, FL. The crew explores the agency’s impressive operations, including a high-volume new business model that writes about $1 million in new premium each month and has a network of over 600 referral partners. Shelby Tirado and Chris Huebener share insights from their res...

On this episode of the Insurance Guys Podcast, Scott Howell and Bradley Flowers welcome David Watson, partner at Mappus Insurance Agency and founder of Risk Advisor. The conversation starts with laughs about wild car stories, lost SD cards, and minivan mishaps. The discussion then moves to the core topic, which is bringing technology-driven efficiency to personal lines insurance. David shares the...

On this episode of the Insurance Guys Podcast, hosts Scott Howell and Bradley Flowers sit down with Jeff Wingate, President at Rate Insurance, for a deep dive into the realities of building a top 100 insurance agency through organic growth—not mergers and acquisitions. Jeff Wingate shares Rate’s journey from relying almost entirely on mortgage-generated leads to creating a scalable, tech-driven, v...

On this episode of the Insurance Guys Podcast, Scott Howell and Bradley Flowers welcome master storyteller and branding expert Neal Foard. Drawing from decades of shaping global brands like Toyota and Budweiser, Neil Ford shares practical insights on how storytelling can transform an insurance business, elevate client relationships, and create long-lasting impressions. The conversation covers why...

On this episode of the Insurance Guys Podcast, Scott Howell and Jason Cass sit down with insurance industry OG podcaster Jason Cass for a lively discussion on technology, compliance, and agency growth. The conversation dives into practical tech solutions, novel ways to automate agency operations, and the importance of routing tasks to the right team member. Jason shares details about his free "log...

In this insightful episode of the Insurance Guys Podcast, Scott Howell and Bradley Flowers welcome financial expert Carey Wallace to discuss the ever-evolving landscape of insurance agency M&A, valuations, and agency growth strategy. The hosts share some laughs and personal stories before diving into critical topics for agency owners, why understanding your agency’s financials and EBITDA is essent...

On this episode, Scott Howell and Bradley Flowers dive into the realities of agency growth, retention, and sales strategies amid shifting market conditions. The conversation covers personal anecdotes from industry events, the challenges of lead management, and the impact of agency expenses versus revenue. They candidly discuss solutions for “stuck in neutral” growth, including refining win-back pr...

In this episode, Scott Howell and Bradley Flowers are joined by CJ for an energetic round of listener Q&A. The hosts dive into branding strategies for insurance agencies, the power of automation tools, and the evolving nature of agency locations, exploring the pros and cons of multiple offices versus a central hub. The conversation covers modern marketing tactics, from creative referral ideas to p...

In this episode, Scott and Bradley dive deep into the realities of running an insurance agency, focusing on everything from branding and agency operations to the growing pains of hiring and customer service. Bradley shares candid stories about managing his Airbnb, highlighting lessons on communication and the unavoidable headaches of dealing with warranties and service companies. Scott presents a...

In this episode of the Insurance Guys Podcast, hosts Scott Howell and Bradley Flowers reconnect with candid updates on agency growth, branding, acquisitions, and operational challenges. Bradley shares his agency’s focus on refining processes, improving staff capacity, and targeting organic sales growth, including an upcoming learning trip to Billy Wagner’s office to revamp their new business workf...

This special episode of The Insurance Guy is dedicated to honoring the life and legacy of our dear friend and colleague, Steve Fisher. We reflect on his friendship, infectious enthusiasm, and the profound impact he had on our community and the insurance industry. If you or someone you know is struggling with suicidal thoughts or emotional distress, help is available. Reach out to the 988 Suicide &...

On this episode of the Insurance Guys Podcast, hosts Scott Howell and Bradley Flowers sit down with Van Carlson, founder and CEO of SRA 831B Admin, to dig into the importance of insurance in driving economic prosperity and explore innovative risk management strategies. Scott kicks things off by sharing data linking property and casualty insurance penetration to national prosperity, making a compel...

In this episode of the Keep Hustling podcast, co-hosts Scott Howell and Bradley Flowers are joined by Becca Rubenfeld, co-founder and COO of AnchorWatch. Becca shares her journey from a corporate career at Starbucks to pioneering insurance solutions for Bitcoin and crypto assets. The discussion dives into the challenges of building insurance products for digital assets, working with Lloyd’s of Lon...

In this episode, Bradley and Scott speak with Matthew Vega-Sanz, Co-founder and CEO of Gail, to discuss the latest updates on their insurance GPTs.

In this episode, Bradley and Scott sit down with Landry Fields from Nova Insurance Group. The guys talk bourbon and the way Landry uses MCPs in his agency.

In this episode, Bradley and Scott sit down with Pat Cline from 101 Weston Labs. Pat takes us through his journey of living in Iraq to his important role in insurance today. In addition to that, Scott drops a HUGE bomb with an unbelievable insurtech idea that is poised to revolutionize the insurance landscape.

In this episode Bradley and Scott sit down with Adam Boca, president of NCM Insurance based out of The National Corvette Museum. The guys discuss Adams role in insuring more corvettes than anyone in the country, how their partnership with The National Corvette Museum and the infamous sinkhole that swallowed millions of dollars of corvettes.

In this episode of the Insurance Guys podcast, hosts Scott Howell and Bradley Flowers engage in a dynamic discussion with Darren Nix, CEO of Steadily, an insurance company specializing in landlord insurance. They delve into the challenges and opportunities in the insurance industry, exploring topics such as the importance of branding for insurance agents, the impact of technology on agency operati...

In this episode, Bradley and Scott sit down with Kody Houk from Prime Risk. The guys break down the recent Alex Hormozi book Launch, dive deep into Kody's agency, and talk about the mistakes they see that other agencies make.

In this episode, Bradley and Scott do one of their favorite show formats, listener call in show.

In this episode, Bradley and Scott sit down with Paul VanderMarck, Chief Technology and Innovation Officer at Sagesure.

In this episode Bradley and Scott sit down with John Gessner, Director of Marketing Strategy at Hagerty and Bryant Kolle Vice President of National Sales and Insurance Partnerships at Hagerty. The guys dive into what makes Hagerty tick.