Awkward Insurance

Awkward Insurance

The National Alliance for Insurance Education & Research

Episodes 89
Avg. Duration 39m
Activity Dormant
Apple Rating 4.6 (21)
Since Oct 2020
Latest Episode Mar 2025

Publishing Details

Schedule
Every 2 Weeks
Format
Episodic
Hosting
feeds.simplecast.com

Contact & Outreach

About This Podcast

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!

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Recent Episodes

S6E15 Recipes for Restaurant Risk Management Success

Feb 05, 2026 31m

Featured GuestJay GatesManaging Director, Gallagher National Restaurant Practice20+ years in insurance, former Applebee’s risk leader, RIMS committee member, and Kids Chance Nebraska board…

S6E14 Toodles!

Mar 10, 2025 37m

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…

S6E13 Natural Disaster Insurance: Fast, Fair, and Innovative Coverage

Mar 10, 2025 12m

Wesley Pergament, SolaWesley 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…

S6E12 From Problems to Praise: Navigating Feedback and Talent Development in Insurance

Feb 14, 2025 35m

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…

S6E11 Inspecting the Unexpected: Uncovering Property Risks and Insurance Challenges

Jan 23, 2025 38m

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…

S6E10 The Emotional Impact of Insurance Fraud

Jan 10, 2025 36m

Judy HughesWith 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…

S6E9 The Mentor’s Playbook with James Benham

Dec 05, 2024 39m

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…

S6E8 Stories That Changed the World with Meredith Brasher

Nov 20, 2024 30m

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…

S6E7 Awkward Insurance Takes On Vegas

Nov 06, 2024 47m

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…

S6E6 Guardians of the Future: Bridging Generations in Compliance, Risk & Mentorship at Arkansas I-Day

Nov 06, 2024 29m

Key Takeaways:Diverse Sessions: A comprehensive agenda covering compliance, risk management, and cybersecurity awareness.Leadership Vision: Arkansas Insurance Commissioner Alan McClain’s…

S6E5 Solving the Communication Barrier Between Tech and Insurance

Oct 02, 2024 26m

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…

S6E4 The Awkward Role of Communicating Everything: Behind the Scenes with Hippo's Comms Master

Sep 20, 2024 26m

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…

S6E3 The Realtor-Insurance Partnership: Building Trust in Real Estate

Sep 11, 2024 36m

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…

S6E2 Mission Possible: From Military Ingenuity to Insurance Innovation with Clearspeed

Aug 28, 2024 37m

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…

S6E1 Policy and People: The Balance of an Insurance Commissioner’s Life

Aug 14, 2024 15m

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. …

S5E18 Season 5 Wrap Up

Jul 31, 2024 25m

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…

S5E17 The Awkward Intersection of Tech and Insurance: LIVE from Insurtech Insights

Jul 03, 2024 54m

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…

S5E16 Awkward LIVE: Insurtech Insights, USA 2024 Session on Knowledge Gaps

Jun 20, 2024 31m

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…

S5E15 Big TECH Energy with Colleen O'Hara

Jun 05, 2024 37m

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.…

S5E14 2024 Spencer-RIMS Risk Management Collegiate Challenge

May 29, 2024 53m

Finalist Collegiate Teams:Appalachian State University | USADurban University of Technology | South AfricaInstitute of Insurance and Risk Management (IIRM) Hyderabad | India (First Place…

Frequently Asked Questions

How many episodes does Awkward Insurance have?

Awkward Insurance has published 89 episodes since October 2020, covering topics in Business, Careers.

Is Awkward Insurance still active?

Awkward Insurance is currently dormant with new episodes every 2 weeks. Average episode length is 39m.

How do I contact Awkward Insurance for sponsorship or guest appearances?

Sign up on Grep.FM to access contact details for Awkward Insurance, including email and social media links.

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