Episodes

  • Underwriting The Gig Economy

    Underwriting The Gig Economy
    Jun 24 2026
    In this episode of The Insurance Guys, hosts Scott and Bradley kick things off with some lighthearted Southern banter about accents before welcoming Ryne Ring, Director of Gig Economy and Embedded Products at The Citadel, a program administrator specializing in embedded insurance solutions. The conversation explores the evolving role of AI in insurance, from its potential to cover emerging risks to cautionary tales of agents misusing the technology and losing contracts, while diving deep into embedded insurance models. Ryne shares insights on how these products integrate seamlessly into customer journeys, from popular travel insurance in Japan and innovative jewelry programs like BriteCo’s appraisal tools to master policies covering thousands of gig economy workers on platforms connecting independent contractors for tasks like cleaning or lawn care. The discussion highlights practical opportunities for agents to participate through custom programs for rental equipment, tenant liability, and more, emphasizing benefits like consistency, customization, and stronger client relationships rather than being sidelined. Personal stories add warmth, including Ryne’s college-era diner management adventure, chaotic first days in the industry, and a memorable recruiter lunch at Taco Bell, alongside reflections on the industry’s endless learning curve and the strategic use of AI in HR and hiring. The episode wraps with ways to connect with Ryne on LinkedIn and Twitter, offering valuable takeaways for insurance professionals navigating the gig economy and embedded opportunities.
    Show More Show Less
    42 mins
  • The Al Assistant That Never Sleeps: Transforming the Agency Management System

    The Al Assistant That Never Sleeps: Transforming the Agency Management System
    Jun 17 2026
    In this episode of The Insurance Guys Podcast, Scott Howell and Bradley Flowers welcome Michael Lebor and Kayden Stephens from Momentum AMP to discuss how artificial intelligence is transforming agency management systems. The conversation traces the evolution of Momentum from its early days as NowCerts through its development into a fully integrated, conversational platform designed to be keyboard free. Guests explore the inevitability of AI in insurance, its role as a superpower for agents, and practical applications such as natural language automation workflows and the advanced AI agent known as Momentum Claw. They also cover carrier adoption of AI, the acquisition of TrustedChoice.com for enhanced digital market access and referrals, and an open agnostic approach that integrates with any tool to benefit agents. The episode includes a live demonstration of an AI voice assistant handling complex policy questions in real time, offering actionable insights for professionals ready to embrace the future of insurance technology.
    Show More Show Less
    1 hr and 6 mins
  • The Greatest Challenges Facing High-Risk Insurance Markets and Agent Classification

    The Greatest Challenges Facing High-Risk Insurance Markets and Agent Classification
    Jun 10 2026
    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.
    Show More Show Less
    30 mins
  • Breaking the Insurance Agent Mold: Leading with EQ to Win the Long Game

    Breaking the Insurance Agent Mold: Leading with EQ to Win the Long Game
    Jun 4 2026
    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.
    Show More Show Less
    59 mins
  • The Greatest Challenges and Opportunities in Casualty Underwriting Today

    The Greatest Challenges and Opportunities in Casualty Underwriting Today
    May 27 2026
    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.
    Show More Show Less
    55 mins
  • The Human-AI Partnership: Redefining Roles and Relationships in Insurance Agencies

    The Human-AI Partnership: Redefining Roles and Relationships in Insurance Agencies
    May 20 2026
    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
    Show More Show Less
    45 mins
  • Outmarket Your Competition

    Outmarket Your Competition
    May 13 2026
    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.
    Show More Show Less
    50 mins
  • How CJ Hutsenpiller Crushes AI

    How CJ Hutsenpiller Crushes AI
    May 6 2026
    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
    Show More Show Less
    50 mins