Episodios

  • Embracing Tech Change and AI in Insurance with Jason Cass

    Embracing Tech Change and AI in Insurance with Jason Cass
    Nov 26 2025
    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 "logic routing engine" manual and the upcoming IndieTech conference in January, focused on agent-driven innovation and learning.The hosts also candidly debate the use and risks of AI and automation in insurance, sharing real examples and compliance caution. Scott Howell entertains with behind-the-scenes stories—including a surprise live tasting of his homemade Moon Creek Farms wine. This episode delivers a unique blend of actionable tech advice, compliance insights, and genuine camaraderie, making it a must-listen for insurance professionals looking to stay ahead in a rapidly changing industry.
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    57 m
  • Today’s Crazy M&A Market

    Today’s Crazy M&A Market
    Nov 19 2025
    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 essential, whether or not you’re planning to sell. Carey Wallace explains how agency valuations are much more nuanced than simple revenue multiples, emphasizing the impact of risk factors, agency structure, and market timing. The conversation highlights why seeking professional advice is crucial before buying or selling an agency (and avoiding the ramen noodle diet that sometimes follows a badly structured deal). They also discuss the importance of culture fit in acquisitions and why emotional decision-making can be dangerous in business transactions. The episode wraps up with actionable advice for insurance agents: get clarity on your financials, seek outside guidance, and always think long-term when building value in your agency.
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    1 h y 3 m
  • Scott And Bradley Pull Their Pants Down

    Scott And Bradley Pull Their Pants Down
    Nov 12 2025
    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 processes, maximizing outbound lead potential, and the importance of focusing on sales activities. Listeners get an inside look at agency operations, hiring practices, budgeting lessons, and the power of training and progression for new staff. Key takeaways include leveraging texting to reduce inbound call volume, strategies for overcoming phone tree frustrations, and the value of process discipline. This episode also features two big announcements: a call for unique agency stories to be featured on the podcast, and a subscriber contest—a chance to win a personalized agency consultation with Scott and Bradley by subscribing to their YouTube channel. The show wraps with a reminder that rewards come from action and encourages agents to focus on driving revenue through intentional sales efforts.
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    1 h y 8 m
  • Listener Call-In Show

    Listener Call-In Show
    Nov 5 2025
    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 practical uses for AI notetakers and cold-call reluctance in today’s climate of spam calls. The team discusses inbound versus outbound lead generation, compensation structures (W2 vs. 1099), and smart ways to maintain relationships with referral partners. They also get candid about handling difficult agency fires and the importance of documenting phone calls to minimize E&O risk. The episode wraps with a reminder that growing your agency is all about taking action and staying connected in your community.
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    50 m
  • Improving Agency Communication and Automation

    Improving Agency Communication and Automation
    Oct 29 2025
    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 real-life customer voicemail, prompting a discussion on how agencies should handle service slip-ups and the importance of over-communicating with clients to build trust and retention. The hosts also discuss the challenges of automation in insurance, its impact on internal processes, and why excessive automated communication can overwhelm everyone—agents, carriers, and clients alike. Bradley and Scott wrap up with honest insights on agency growth, recruiting talent, and the evolving landscape of insurance rates, noting the current shift toward a softer market. It’s a candid, relatable conversation packed with practical advice for insurance professionals on providing better customer experiences and strengthening agency operations.
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    47 m
  • Scott and Bradley Check In

    Scott and Bradley Check In
    Oct 22 2025
    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 workflow. The conversation dives into real-world lessons from agency acquisitions, retention rates post-purchase, and the realities of managing debt service and office consolidation. Scott and Bradley also exchange insights on the changing insurance market, the resurgence of M&A activity, and creative tech tools like the M1 AI app to streamline client communications. Personal stories, like bathroom mishaps and hurricane preparedness, pepper the episode with humor and humanity—reminding listeners that agency ownership is as much about adaptability as it is about strategy.
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    43 m
  • A Tribute To My Friend Steve Fisher

    A Tribute To My Friend Steve Fisher
    Oct 15 2025
    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 & Crisis Lifeline by calling or texting 988. This free, confidential service is staffed by trained counselors and operates 24/7 to provide immediate support. For more resources, visit 988lifeline.org. Your life matters, please don't hesitate to seek help.
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    16 m
  • IRS Challenges and Captive Insurance with Van Carlson

    IRS Challenges and Captive Insurance with Van Carlson
    Oct 8 2025
    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 compelling argument for how insurance fuels commerce and helps societies recover from disasters. Van weighs in, emphasizing that without accessible, affordable insurance, prosperity and commerce grind to a halt. The conversation dives deep into alternative risk solutions for business owners, with Van explaining the 831B tax code and the role of micro-captives in managing otherwise uninsurable or retained risks. He discusses how recent IRS scrutiny has shaped the space and underscores the importance of understanding both insurance and tax incentives to preserve wealth and fuel growth.From branding and technology tips for agencies to the risks and rewards of self-insuring, this episode delivers actionable insights for insurance professionals seeking to provide more value to their business clients—and warns agents to stay informed about emerging risk management tools before their competitors do.
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    57 m