Awkward Insurance

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!

Episodes

March 10, 2025 37 mins
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...
Mark as Played

Wesley Pergament, Sola

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...

Mark as Played

Key Takeaways:

  • 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 educati...
Mark as Played

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 ...

Mark as Played
January 10, 2025 36 mins

Judy Hughes

With over a decade of experience in the insurance industry, Judy has been a licensed Property and Casualty agent since 2010 and a licensed Life and Health agent since 2011. Currently, she serves as a Personal Lines Account Manager at Anderson and Green Insurance Agency, where she has been for the past five years. In this role, Judy recently expanded her expertise to assist Medicare customers with their prescr...

Mark as Played
December 5, 2024 39 mins

Regent James M. Benham was appointed to the Texas Southern University (TSU) Board of Regents by Texas Governor Greg Abbott in October of 2020 and was reappointed for a second term in 2023. He is currently the Vice Chairman of the Texas Southern University Board of Regents and is Chairman of the Administration and Finance Committee.

Regent Benham is the CEO of JBKnowledge, a 280-employee global insurance software company he co-founde...

Mark as Played

Insurance vs History is a podcast that examines the intersection of insurance and history. Meredith Brasher is a 20-year veteran of the insurance industry, specializing in General Liability, Umbrella and Excess insurance products, wording development, and education. She also has extensive experience in the development and management of MGA programs, as well as auditing for MGA programs and Casualty books of business.

She has both a ...

Mark as Played
November 6, 2024 47 mins
In this special conference episode, the Awkward Insurance Podcast hits the road to ITC Vegas, where technology meets insurance in surprising ways. Join host Dustyne Bryant as she dives into the industry's pressing challenges around talent recruitment, uncovers inspiring career journeys, and explores the ever-evolving insurance landscape. From motivational stories to insights on how AI will reshape industry roles, this episode offe...
Mark as Played

Key Takeaways:

  • Diverse Sessions: A comprehensive agenda covering compliance, risk management, and cybersecurity awareness.
  • Leadership Vision: Arkansas Insurance Commissioner Alan McClain’s forward-looking view on industry challenges and opportunities.
  • Next-Gen Engagement: UCA student Connor Black shares perspectives on attracting young professionals to the field.
  • Reinsurance Insights: Lee Covington delves into the evolution of rein...
Mark as Played

Level up your industry language by visiting www.riskeducation.org/insurtech to learn about a brand new self-paced course developed with BrokerTech Ventures: Introduction To Insurance for Insurtech Professionals.

 

Douglas Ver Mulm is currently the Chief Executive Officer at Turris, a financial infrastructure platform for the insurance industry. Prior to this, Douglas was the Co-Founder & CEO at Stable Insurance, focusing on distribut...

Mark as Played

Mark Olson is a seasoned communications professional with extensive experience in strategic communications, spanning agency and in-house leadership roles. As the Director of Corporate Communications at Hippo, he specializes in developing corporate narratives, preparing spokespeople, and providing counsel on reputational issues. Mark has a proven track record in enhancing brand reputation and driving strategic initiatives. He holds ...

Mark as Played

Thomas Raabe has been in real estate development and sales for the last 11 years. He was a project manager for Ohio University prior to becoming a licensed salesperson in 2016. He has been helping people buy and sell homes for the last 8 years. He is the broker and co-owner of Westwood Real Estate Co. located in Columbus, OH. Westwood Real Estate prides themselves in being trusted advisors and creating lasting relationships with th...

Mark as Played

Allison Albrecht is a National Sales Director for Clearspeed - with a focus on the financial services market. Prior to joining Clearspeed, Allison spent over a decade in various roles within the insurance industry - largely on the carrier side. Allison is proud to be from and reside in Columbus, Ohio - home to an eager and innovative insurance landscape, and of course - the Buckeyes!

 

Nate Curtis is a National Sales Director for Cle...

Mark as Played

Alan McClain was appointed as Arkansas’s 24th Insurance Commissioner by former Governor Asa Hutchinson in April 2020, and continues to serve as Commissioner under Governor Sarah Huckabee Sanders.  Prior to his appointment, McClain served for five years as Commissioner of Arkansas Rehabilitation Services (ARS)—a sister agency of the Arkansas Insurance Department (AID) under the state Department of Commerce.

Commissioner McClain began...

Mark as Played
July 31, 2024 25 mins

We want to hear from you! 

Share your favorite Season 5 episode in our Facebook Group and join the conversation with fellow listeners. Whether it’s a memorable interview, a hilarious moment, or a valuable insight, let us know what resonated with you the most! Your feedback helps us create even more content you’ll love.

Join the Discussion!

Focusing exclusively on risk management and insurance professional development, the Risk & ...

Mark as Played

Bridge Insurtech with Insurance Fundamentals! Demo our upcoming Introduction to Insurance for Insurtech Professionals course!

Our guests (in order) are:

  • Kristopher Lundberg, CEO of Insurance Tech Insights, discusses the value of independent agents engaging with tech start-ups. 
  • Jacob Galecki, Managing Principal of Galecki Search Associates, highlights the disconnect between Insurtech developers and the insurance industry. 
  • Valkyrie...
Mark as Played

Get ready for Insurtech Insights, USA 2025, by registering today!

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 for confidence and success.

 

Mark as Played
June 5, 2024 37 mins

Follow Awkward Insurance on Facebook! 

Colleen O'Hara is an accomplished executive leader whose two decades in the insurance industry have transformed the way businesses achieve growth and engagement. Beginning her journey on the front lines of the retail agency world, Colleen has carved a niche for herself by applying her unique insights to foster deep engagement, adoption, and, most importantly, advocacy within the insurance distr...

Mark as Played

Finalist Collegiate Teams:

  • Appalachian State University | USA
  • Durban University of Technology | South Africa
  • Institute of Insurance and Risk Management (IIRM) Hyderabad | India (First Place Finalist)
  • Illinois State University | USA (Second Place Finalist)
  • Milpark Education | South Africa
  • Peking University | China (Third Place Finalist)
  • St. Mary’s University | USA
  • University of Wisconsin-Madison | USA

 

Special mention, Corporate Gra...

Mark as Played

In this episode (In order):

  • Jerrie Price, H.I.R.E.D Project Coordinator at Arkansas Public School Resource Center, Inc. (Special Guest)
  • Colton Johnson, James Green & Associates (Arkansas) (YIP Board Member)
  • Victor Werley, Pinnacle Advisors (Speaker)
  • Casey Nelson, StakWise Data Automation (Speaker)
  • Matthew Gleason, UA CIC, Gleason Insurance, LLC (First Time/New Professional Attendee Insight)
  • Ben Burleson, CIC, Progressive Insurance (C...
Mark as Played

Popular Podcasts

    If you've ever wanted to know about champagne, satanism, the Stonewall Uprising, chaos theory, LSD, El Nino, true crime and Rosa Parks, then look no further. Josh and Chuck have you covered.

    The Joe Rogan Experience

    The official podcast of comedian Joe Rogan.

    On Purpose with Jay Shetty

    I’m Jay Shetty host of On Purpose the worlds #1 Mental Health podcast and I’m so grateful you found us. I started this podcast 5 years ago to invite you into conversations and workshops that are designed to help make you happier, healthier and more healed. I believe that when you (yes you) feel seen, heard and understood you’re able to deal with relationship struggles, work challenges and life’s ups and downs with more ease and grace. I interview experts, celebrities, thought leaders and athletes so that we can grow our mindset, build better habits and uncover a side of them we’ve never seen before. New episodes every Monday and Friday. Your support means the world to me and I don’t take it for granted — click the follow button and leave a review to help us spread the love with On Purpose. I can’t wait for you to listen to your first or 500th episode!

    The Bobby Bones Show

    Listen to 'The Bobby Bones Show' by downloading the daily full replay.

    Dateline NBC

    Current and classic episodes, featuring compelling true-crime mysteries, powerful documentaries and in-depth investigations. Follow now to get the latest episodes of Dateline NBC completely free, or subscribe to Dateline Premium for ad-free listening and exclusive bonus content: DatelinePremium.com

Advertise With Us
Music, radio and podcasts, all free. Listen online or download the iHeart App.

Connect

© 2025 iHeartMedia, Inc.