The Insurance Guys Podcast

Hosted by Scott Howell & Bradley Flowers

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Episodes

429

Latest episode

Jun 2026

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About the show

The Insurance Guys podcast is dedicated to agents by agents. Scott Howell and Bradley Flowers discuss all aspects of becoming an insurance agent and give real life examples of their experiences in all aspects of hiring, sales and the day-to-day reality of running your own successful insurance agency.

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60 recent

June 10, 202629 min

The Greatest Challenges Facing High-Risk Insurance Markets and Agent Classification

In this episode of The Insurance Guys, Scott Howell and Bradley Flowers dive into the greatest challenges facing high-risk insurance markets and the complexities of agent classification. Scott kicks things off with a humorous take on insuring strip clubs under a fictional Death Machine Insurance agency built for high-hazard risks, sharing an insightful anecdote about the Las Vegas strip club business model where dancers pay a nightly door fee to work. The conversation then turns serious as Scott recounts his agency's frustrating experiences with 1099 independent contractors in the property and casualty space and why that model often falls short. Bradley breaks down the IRS guidelines for determining 1099 status through behavioral control, financial control, and the type of relationship, while Scott shares how his attempt to revise contractor terms resulted in an immediate departure. The hosts also critique a Vanderbilt University study alleging widespread insurance overcharging, voice concerns about potential federal interference in P&C insurance, and highlight the massive costs of carrier advertising. Responding to a listener question, they address the legal boundaries for using unlicensed virtual assistants in an agency and strongly recommend consulting the state's Department of Insurance or a compliance law firm to ensure full clarity and avoid regulatory pitfalls.

June 4, 202659 min

Breaking the Insurance Agent Mold: Leading with EQ to Win the Long Game

In this insightful episode of The Insurance Guys Podcast, Scott Howell and Bradley Flowers sit down with Kasey D’Amato to explore how emotional intelligence (EQ) is becoming a game-changing leadership skill in the insurance industry. Rather than focusing solely on traditional sales tactics, this conversation dives deep into building scalable businesses, leading with emotional intelligence, navigating difficult conversations, and creating high-performing, trust-based team cultures. Whether you’re a solo producer or running a growing agency, this episode offers practical strategies for playing the long game in insurance.

May 27, 202654 min

The Greatest Challenges and Opportunities in Casualty Underwriting Today

Scott Howell and Bradley Flowers welcome Ty Robben, a seasoned casualty insurance expert with roots at Great American and Palomar Specialty, for a warm and insightful conversation that mixes engaging personal stories with forward thinking industry analysis. Ty shares his memorable White House internship blunder of spilling toner across the East Wing carpet and his love for Pepperdine's stunning Pacific overlook campus before the group explores the current state of the casualty market, including the transition out of the hard market, persistent challenges in habitational and auto lines fueled by social inflation, and the growing role of AI in transforming underwriting efficiency. Ty opens up about building his own AI powered platform on nights and weekends to better handle complex risks, sparking lively talk on disrupting the MGA and wholesale space, the real value of skilled intermediaries, the drag of legacy technology and slow invoicing, and the future shaped by market cycles, potential government intervention, and the pressing need for tort reform. Thoughtful, optimistic, and thoroughly human, this episode offers a smart look at both the challenges and exciting opportunities ahead in casualty underwriting.

May 20, 202644 min

The Human-AI Partnership: Redefining Roles and Relationships in Insurance Agencies

In this episode of the Insurance Guys podcast, host Scott Howell is joined by Kabir Syed and Bradley Flowers to explore how artificial intelligence is reshaping the insurance industry. They discuss AI's impact on agency management systems, workflow automation, and evolving employee roles. Through real-world examples, the guests highlight efficiency gains while cautioning against blind reliance on automation. They advise agencies to embrace AI tools proactively, maintain data ownership, and foster a culture of experimentation. The overarching message is clear: AI won't replace the human relationships central to insurance, but agencies that fail to adapt risk being left behind. Bullet Points - Impact of artificial intelligence (AI) on the insurance industry - Transformation of agency management systems (AMS) through AI - Challenges and opportunities presented by AI integration - Importance of human relationships and trust in the insurance business - Automation of routine tasks and its effect on employee roles - Predictions for the evolution of traditional roles in insurance agencies - Embracing AI tools and fostering a culture of experimentation - Integration of AI with existing AMS platforms and the challenges faced by legacy systems - Efficiency gains and cost reductions associated with AI technology - Practical advice for insurance agencies on starting small and augmenting human judgment with AI

May 13, 202649 min

Outmarket Your Competition

In this episode of the Insurance Guys podcast, hosts Scott Howell and Bradley Flowers welcome Anshu Jain and Vishal Sankhla, co-founders of Outmarket AI. Drawing on their experience at Meta, Uber, and IBM, the duo built an AI platform helping insurance agents analyze policies, compare quotes, and appeal claim denials. Scott and Bradley share real-world success stories from using the tool in their agencies. The founders also announce a $17 million Series A funding round. The episode highlights how AI is transforming insurance, empowering agents to focus on advisory roles while improving efficiency and client outcomes. Bullet Points - Introduction to Out Market AI as a technology platform for insurance agents. - Discussion of the positive experiences of insurance agents using Outmarket AI. - Backgrounds of the co-founders and their previous work in technology and insurance. - Insights on how lessons from major tech companies apply to the insurance industry. - Explanation of how Out Market AI analyzes insurance policies, claims, and quotes. - Features of Out Market AI, including customizable workflows and accuracy in data analysis. - Real-world examples of how Out Market AI has helped agents with claims and policy comparisons. - The potential impact of AI on the future of the insurance industry. - Recent funding news and plans for scaling the company. - Information on how insurance agents can learn more about and access Outmarket AI.

May 6, 202650 min

How CJ Hutsenpiller Crushes AI

In this episode of the Insurance Guys Podcast, Scott Howell and Bradley Flowers dive into the rapid evolution of artificial intelligence in the insurance industry, joined by recurring guest CJ Hutsenpiller. The trio discuss how AI, specifically tools like Claude and ChatGPT, are transforming agency operations, from streamlining workflows to integrating with agency management systems. They highlight tangible use cases such as automating prospecting, remarketing analysis, and calculating true costs of service. The hosts also address the challenges legacy management systems face in keeping up with new AI capabilities and urge agencies to embrace these advances to stay competitive. They touch on market trends, including advertising in the insuretech space and current agency buying and selling climates, noting the impact of rate cycles. The episode wraps up with practical advice on how insurance professionals can start leveraging AI by simply asking the tools for implementation instructions, and emphasizes that taking action is key to staying relevant in a rapidly changing landscape. Show Overview 00:00 Gaining advertisers during COVID 05:55 Encouraging product trial for listeners 09:23 Mastermind event in Phoenix 11:08 Preparing an AI presentation 16:29 Explaining efficient policy updates 18:51 Using CLAUDE for daily prospecting 21:18 Legacy insuretechs evolving with APIs 26:00 Challenges in buying home insurance 27:05 AI enhancing online insurance buying 33:01 AI-driven premium adjustment tool 34:32 Tracking service costs with Claude 38:15 Using AI tools for learning 41:18 AI fear affecting agency owners 45:23 Timing insurance sales in hard market 47:55 Podcast closing and contact info

April 29, 202651 min

Invest In Your Community, Your Community Will Invest In You

In this episode of the Insurance Guys podcast, host Scott Howell and co-host Bradley Flowers sit down with Kevin Panter, a 37-year insurance industry veteran and president of Kevin Panter Insurance. Kevin shares insights on transitioning from captive to independent agencies, emphasizing ethics and proper preparation. He discusses building community involvement as a volunteer firefighter and EMT, growing his agency network SNA, and mentoring his children entering the business. Kevin offers advice for agents feeling stuck, stressing self-investment, continuous education, and community engagement as keys to long-term success. Bullet Points - Transitioning from captive to independent insurance agencies - The importance of community involvement and personal branding - Experiences and stories from the insurance industry - Advice for new agents and those considering a career in insurance - The role of ethics in the insurance profession - The significance of networking and collaboration among agencies - Family dynamics and legacy in the insurance business - Strategies for agency growth and overcoming stagnation - The impact of personal investment in community relationships - Insights on industry challenges and opportunities for agents

April 22, 202655 min

The Untold Stories of Wholesalers and Brokers

In this episode of The Insurance Guys Podcast, hosts Scott Howell and Bradley Flowers welcome Max from Novella to discuss trends and challenges in the insurance industry. The conversation covers wholesaler processes, the evolving role of brokers, and the impact of technology and surplus lines on the market. Max shares insights from his time at Lemonade and his journey founding Novella. The episode features industry anecdotes, including a humorous story about Bradley dropping his visitor badge in a toilet at Progressive HQ, and highlights the importance of relationships and adaptability in insurance. Bullet Points - Personal anecdotes and humorous stories related to the insurance industry. - Introduction and background of a new participant, Max, and his company, Novella. - Examination of the relationship between retail brokers and wholesalers. - Challenges faced by new entrants in the wholesaler market. - The evolving landscape of insurance technology and its implications. - Trends in property and casualty insurance, particularly regarding surplus lines. - The importance of independent brokers in providing tailored insurance solutions.

April 15, 202648 min

Run Your Agency Like A Football Team

In this episode of the Insurance Guys Podcast, host Scott Howell is joined by Kelly and Bradley Flowers for a lively discussion on the shifting insurance market and effective account manager compensation. The group explores strategies for navigating a soft market, emphasizes the importance of client retention, and shares insights on agency leadership, training, and culture.. The episode blends practical advice with humor and candid reflections on the realities of running a successful insurance agency. Bullet Points - Current state of the insurance market, focusing on the transition from a hard market to a soft market. - Implications of market changes for insurance agents and agencies. - Importance of client retention and effective communication in a competitive market. - Challenges faced by agencies in managing client relationships and remarketing strategies. - The significance of product knowledge among agents and its impact on client interactions. - Leadership dynamics within insurance agencies and the need for clear hierarchy and accountability. - Strategies for optimizing existing business and improving retention rates. - The importance of proactive prospecting and maintaining a growth mindset in agency operations.

April 8, 202652 min

Starting An Agency At 18 Years Old

In this episode of The Insurance Guys Podcast, host Scott Howell and Bradley Flowers interview Hunter Nelson, who started his own insurance agency at just 18. He shares his unconventional journey, from door-knocking for leads in high school to specializing in trucking insurance. The discussion covers challenges of being a young agent, fraud prevention, strategic hiring, and the importance of grit and continual learning. Bradley and Scott swap stories about client service, underwriting, and managing risk, offering practical advice for agency growth. The episode is both insightful and inspiring, highlighting innovation and determination in the insurance industry. Bullet Points - The journey of a young insurance agency owner who started at 18 years old. - The importance of customer experience and exceptional service in the insurance industry. - Strategies for recruiting and hiring experienced agents from other agencies. - Challenges faced by young agents in a traditionally older industry. - The significance of networking and involvement in industry organizations for securing carrier appointments. - The impact of fraud in the trucking insurance sector and the importance of secure certificate issuance. - Underwriting practices and client selection criteria for trucking insurance. - Financial risk management related to commission chargebacks in insurance policies. - The role of talent and team culture in accelerating business growth. - The importance of persistence and grit in overcoming challenges in the insurance business.