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Awkward Insurance - Podcast

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!

Careers Self-Improvement Interviews Comedy Business Comedy Interviews Self-Help Education
Update frequency
every 16 days
Average duration
39 minutes
Episodes
89
Years Active
2020 - 2025
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Toodles!

Toodles!

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 mo…
00:37:02  |   Mon 10 Mar 2025
Natural Disaster Insurance: Fast, Fair, and Innovative Coverage

Natural Disaster Insurance: Fast, Fair, and Innovative Coverage

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 wher…

00:12:06  |   Mon 10 Mar 2025
From Problems to Praise: Navigating Feedback and Talent Development in Insurance

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

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 co…
00:35:11  |   Fri 14 Feb 2025
Inspecting the Unexpected: Uncovering Property Risks and Insurance Challenges

Inspecting the Unexpected: Uncovering Property Risks and Insurance Challenges

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 insura…

00:38:01  |   Thu 23 Jan 2025
The Emotional Impact of Insurance Fraud

The Emotional Impact of Insurance Fraud

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 …

00:36:08  |   Fri 10 Jan 2025
The Mentor’s Playbook with James Benham

The Mentor’s Playbook with James Benham

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 curr…

00:39:39  |   Thu 05 Dec 2024
Stories That Changed the World with Meredith Brasher

Stories That Changed the World with Meredith Brasher

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…

00:30:28  |   Wed 20 Nov 2024
Awkward Insurance Takes On Vegas

Awkward Insurance Takes On Vegas

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 indu…
00:47:46  |   Wed 06 Nov 2024
Guardians of the Future: Bridging Generations in Compliance, Risk & Mentorship at Arkansas I-Day

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

Key Takeaways:

  • Diverse Sessions: A comprehensive agenda covering compliance, risk management, and cybersecurity awareness.
  • Leadership Vision: Arkansas Insurance Commissioner Alan McClain’s forward-look…
00:29:45  |   Wed 06 Nov 2024
Solving the Communication Barrier Between Tech and Insurance

Solving the Communication Barrier Between Tech and Insurance

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 Pr…

00:26:33  |   Wed 02 Oct 2024
The Awkward Role of Communicating Everything: Behind the Scenes with Hippo's Comms Master

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

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 …

00:26:06  |   Fri 20 Sep 2024
The Realtor-Insurance Partnership: Building Trust in Real Estate

The Realtor-Insurance Partnership: Building Trust in Real Estate

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 pe…

00:36:19  |   Wed 11 Sep 2024
Mission Possible: From Military Ingenuity to Insurance Innovation with Clearspeed

Mission Possible: From Military Ingenuity to Insurance Innovation with Clearspeed

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 insu…

00:37:51  |   Wed 28 Aug 2024
Policy and People: The Balance of an Insurance Commissioner’s Life

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

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.  Pr…

00:15:53  |   Wed 14 Aug 2024
Season 5 Wrap Up

Season 5 Wrap Up

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 valu…

00:25:22  |   Wed 31 Jul 2024
Awkward LIVE: Insurtech Insights, USA 2024 Session on Knowledge Gaps

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

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 pr…

00:31:09  |   Thu 20 Jun 2024
Big TECH Energy with Colleen O'Hara

Big TECH Energy with Colleen O'Hara

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.…

00:37:03  |   Wed 05 Jun 2024
2024 Spencer-RIMS Risk Management Collegiate Challenge

2024 Spencer-RIMS Risk Management Collegiate Challenge

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)
  • Ill…
00:53:15  |   Wed 29 May 2024
2024 PIA Arkansas Conference: Embrace the Process

2024 PIA Arkansas Conference: Embrace the Process

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 Me…
00:51:17  |   Wed 08 May 2024
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