Awkward Insurance

About 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!

Publisher

The National Alliance for Insurance Education & Research

Category

business · comedy · education

Language

en

Explicit

No

First episode

22 Oct 2020

Latest episode

5 Feb 2026

Latest episodes

23 of 90 episodes have a transcript.

1. 

   5 Feb 2026TRANSCRIPT

   Recipes for Restaurant Risk Management Success

   In this episode of Alliance Insights, hosts Mitch Dunford and Dr. Lisa Gardner talk with Jay Gates, Managing Director of Gallagher’s National Restaurant Practice, to explore the unique world of restaurant risk management. Jay shares his journey from EEOC investigator to claims leader to building an enterprise risk management program for more than 165 Applebee’s locations. He breaks down the most pressing challenges facing restaurants today—including labor shortages, cyber exposures, liquor liability, and product recalls—and explains how Gallagher helps clients reduce their total cost of risk through proactive service, innovative insurance solutions, and data-driven strategies. Jay also highlights the rising role of artificial intelligence in restaurant operations, from table‑turn tracking to drive‑through optimization, and the new risks that come with rapid adoption. Packed with real-world stories, leadership insights, and future-focused perspective, this episode is a must‑listen for anyone serving clients in the foodservice and hospitality sectors.

2. 

   10 Mar 2025TRANSCRIPT

   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 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! 🎤✨

3. 

   10 Mar 2025TRANSCRIPT

   Natural Disaster Insurance: Fast, Fair, and Innovative Coverage

   In this episode of Awkward Insurance, we sit down with Wesley Pergament, founder of Sola Insurance, to explore how his company is transforming natural disaster coverage—especially for wind and hail. Wesley shares insights into Sola’s streamlined claims process, emphasizing rapid payouts and the overwhelmingly positive response from policyholders. He also reflects on key lessons learned since the company’s launch, the critical role of agent relationships, and the personal journey that led him to create a more efficient and customer-centric insurance solution. Tune in to discover how innovation is reshaping the way we protect against nature’s unpredictability!

Inside a recent episode

Recipes for Restaurant Risk Management Success

Published 5 Feb 2026 · Transcript excerpt

[…] But those are two that sometimes some folks feel like they don't need an effort to save some money, but you know, I've seen it, I've seen it cost a lot of money quickly. So Jay, with over 20 years in the industry, where do you see the biggest opportunities for innovation and restaurant risk management over, let's say maybe the next 10 years. The next 10 years, I would say just like you hear on the news every night when you go home, it's artificial intelligence. AI is big and it's big across the world, but it's also huge in the restaurant space, you see it, people utilizing it now, whether it be enhancing their menus, whether it be in the drive through, whether it be, you know, the artificial intelligence of tracking turnover times, table times, when you walk into a restaurant and they tell you it's a 45 minute wait, some of that, AIs behind that, tracking the tables, knowing how long exactly it will be. […]

Reach and audience

Public platform figures. Ratings count people who left a rating, not total listeners.

Apple Podcasts (US)

4.6 / 5

21 ratings

Spotify

5.0 / 5

4 ratings

Podcast Authority Score: 44 / 100

A composite of feed quality, social presence, YouTube performance and engagement. Read the methodology.

Quality

54

Social presence

0

YouTube

0

Engagement

85