The Insurance Guys Podcast

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, virtual organization sourcing business nationwide. The conversation uncovers the advantages and challenges of proprietary technology, integrating APIs with carriers and mortgage partners, and the long runway of hiring and training licensed agents. The trio also gets candid about industry cycles, consumer patience, AI’s impact on agency operations, and cross-selling strategies for bundling auto and home. With honest discussions about setbacks and wins, this episode is packed with lessons for agency owners seeking to grow smart in a changing market.

Neal Foard, a master storyteller and branding expert, shares his wealth of experience in shaping global brands. He reveals how storytelling can enhance client relationships in the insurance sector, emphasizing the power of authenticity and human connection. Neal promotes small gestures like handwritten notes to create lasting impressions and illustrates how personal anecdotes forge bonds. He critiques automation's impact on service and highlights actionable storytelling techniques that professionals can adopt immediately. Finally, he introduces his Storyfire course for those eager to refine their storytelling skills.

In this engaging conversation, Jason Cass, an insurance industry podcaster and tech advocate, shares insights on embracing technology for agency growth. He introduces his free Logic Routing Engine manual, aimed at automating operations and improving efficiency. The discussion also highlights the importance of foundational tech and explains the upcoming IndieTech conference focused on agent-led innovations. Jason and the hosts delve into the risks and benefits of AI in the industry, providing real examples to consider for compliance and operational success.

Carey Wallace, a financial and M&A expert in insurance agency valuations, joins the discussion to unravel the complexities of the current M&A landscape. He emphasizes that agency valuations go beyond just revenue, highlighting risk factors and market timing. The conversation stresses the need for due diligence, the pitfalls of emotional decision-making, and the importance of culture fit in acquisitions. Carey also shares insights on growing an agency's value and why tracking EBITDA matters—even for those not planning to sell.

Scott and Bradley dive into agency growth, discussing challenges like stagnant sales and lead management. They explore the importance of refining win-back processes and maximizing outbound leads. Listeners hear insights on budgeting, hiring practices, and the significance of training new staff. They also debate the efficacy of phone trees and promote strategies like texting to reduce call volume. Exciting announcements include a call for unique agency stories and a subscriber contest for a chance to win personalized consultations. Rewards come from action, urging agents to drive revenue!

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.

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.

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.

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.

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.