Awkward Insurance

Welcome to Awkward Insurance, the podcast that strives to bridge the thrilling world of insurance with the real-life struggles of those of us in the trenches. For producing and servicing agents, insurance centers around relationships and personal connections but let's face it, building relationships can be awkward. In this podcast hosted by Dustyne Bryant, CIC, CISR, MBA, and Ashley Fitzsimmons, CISR, our conversations are unscripted, and unplanned, and may have you wondering what just happened. Subscribe and share with all of your fellow insurance nerds!

Awkward Insurance is a education podcast hosted by Unknown Host, with 89 episodes on record and a Required Pod Score of 80. PitchCentric scores this show on Booking Probability, Listen Score, and live audience signals refreshed every 24 hours.

Unknown Host hosts Awkward Insurance, a education show with 89 episodes published.

Our AI reads these to draft pitches. Use them as grounding for a pitch that cites a real guest and a specific topic.

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  Episode #15

  Recipes for Restaurant Risk Management Success

  Feb 5, 202632 minS6

  <h3>Featured Guest</h3><p>Jay Gates<br />Managing Director, Gallagher National Restaurant Practice<br />20+ years in insurance, former Applebee’s risk leader, RIMS committee member, and Kids Chance Nebraska board member.</p><h3>What We Cover</h3>Jay’s unexpected path into risk and insuranceLessons learned investigating EEOC claims early in his careerLeadership principles developed while managing large claims teamsBuilding a full ERM program for 165+ Applebee’s locationsThe most surprising and severe claims in restaurant operationsHow Gallagher reduces the total cost of risk for restaurant clientsInnovative approaches including captives and proprietary analyticsUnderestimated risks: cyber breaches + product recallsThe growing impact of AI...

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  Episode #14

  Toodles!

  Mar 10, 202537 minS6

  It’s the end of an era! In this heartfelt farewell, hosts Dustyne Bryant, Ashley Fitzsimmons, and Producer Mac reflect on the journey of Awkward Insurance. From awkward beginnings to unforgettable moments—including their adventures in Vegas—they share highlights, podcast stats, and a countdown of top episodes. Join them for one last laugh (and maybe a tear) as they celebrate the connections made and the impact of the show. Thanks for listening—Toodles! 🎤✨ Focusing exclusively on risk management and insurance professional development, the Risk & Insurance Education Alliance provides a practical advantage at every career stage, positioning our participants and their clients...

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  Episode #13

  Natural Disaster Insurance: Fast, Fair, and Innovative Coverage

  Mar 10, 202512 minS6

  <h2>Wesley Pergament, Sola</h2><p>Wesley is CEO and Co-Founder of Sola Insurance based in Atlanta, GA. Wesley comes from a tech background and jumped into the insurance industry at a flood insurance startup where he was tasked with working on the data side with private and FEMA flood maps. Realizing this data was telling us exactly where the damage is, Wesley and the Sola team became obsessed with how data can be used to automatically trigger an insurance claim payout. Sola is starting with supplemental tornado coverage for homeowners and small businesses but plans to expand into every...

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  Episode #12

  From Problems to Praise: Navigating Feedback and Talent Development in Insurance

  Feb 14, 202535 minS6

  <p>Key Takeaways:</p>Customer feedback is a growth tool – Handling negative reviews with a positive approach strengthens relationships.Cultural fit matters – Many employees leave due to misalignment with company culture rather than job dissatisfaction.Talent is everywhere – Hiring based on traits, not just experience, can uncover high-potential candidates.The industry must evolve – Adapting to new expectations and investing in education will attract the next generation.<p>Monica Adwani is a dynamic leader whose career has been defined by breaking barriers and championing diversity.Monicais a passionate advocate for creating opportunities and fostering inclusivity, particularly for women and Latinos in the busi...

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  Episode #11

  Inspecting the Unexpected: Uncovering Property Risks and Insurance Challenges

  Jan 23, 202538 minS6

  <p>Curtis Goldsborough is the President of National Insurance Inspection Services, an evolving technology and field service provider for P&C underwriting, based in Fresno, CA. He cut his teeth in insurance as an agency owner with Farm Bureau Insurance of Michigan, where he became acutely aware of the friction and pain points associated with underwriting inspections. In 2013, he joined National Insurance Inspection Services on a quest to forge a better path forward for personal lines underwriting.  Curtis was instrumental in the development and launch of the NIIS self-inspection app and workflow, which is now in production environments with over 18 c...

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