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! 🎤✨

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!

Monica Adwani shares her insights on hiring, retention, and the importance of the next generation in building a thriving agency. The discussion highlights how emotional connections drive passion in the industry and why collaboration is key to attracting and developing new talent.

Dustyne Bryant and Curtis Goldsborough uncover the intricate world of property inspections and their role in the insurance industry. Curtis shares his experiences with DIY projects, insights into old versus new homes, and the unique mindset required for inspections. The discussion highlights evolving consumer trends, the rise of self-inspections, and how technology like AI is transforming the process. From understanding liability hazards to addressing challenges posed by COVID-19, this episode offers valuable perspectives for navigating the complexities of underwriting and homeownership risks.

In this episode, Dustyne and Ash are back to explore various themes related to burnout, geographic identity, and the emotional impact of insurance fraud on both clients and professionals. In this engaging conversation with Judy Hughes, they delve into the complexities of insurance fraud, discussing its impact on the reputation of insurance professionals, ethical dilemmas faced in the industry, and personal experiences with fraud. They explore the psychological aspects of fraudulent behavior and the role of technology in insurance transactions, while also sharing humorous anecdotes along the way.

In this episode of Awkward Insurance, host Dustyne Bryant talks to James Benham (host of InsurTech Geek Podcast and Vice Chair, Board of Regents at Texas So. University) about thought leadership, mentorship, and entrepreneurship in the insurance industry. They explore the legitimacy of thought leadership as a role in the insurance industry, the value of intentional mentorship programs, and the impact of effective mentor-mentee matching. The discussion highlights bootstrapping benefits, networking without agendas, challenges in claims management, and evaluating industry conferences. They emphasize the barriers to success, the need for supportive networks, and the importance of tackling tough challenges for professional growth.

“Those who fail to learn from history are doomed to repeat it” is a famous quote from Winston Churchill. The Awkward Insurance Podcast agrees. In this episode host, Dustyne Bryant, sits down with self-dubbed Insurance Historian Meredith Brasher, a 20-year industry veteran and host of the Insurance vs. History Podcast. When Meredith thinks about insurance she’s not focused on policy coverage and claim details, she believes that insurance serves a bigger purpose and contains stories and occurrences that have changed the world.

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 offers an insider’s view of the conversations driving the future of insurance.  Tune in for a lively mix of professional insights, unexpected encounters, and a few quirky detours straight from the ITC floor!  Plus, don’t miss our Man on the Street coverage from the BrokerTech Ventures Happiest Hour during ITC Vegas!

In this episode of Awkward Insurance, we take you to Arkansas Insurance Day, where industry leaders gathered to share insights on the evolving landscape of compliance, risk management, and the urgent call for mentorship across generations. Through conversations with seasoned professionals and emerging voices, the episode underscores the importance of guiding young talent and passing down knowledge to shape the future of the insurance industry.

Learning a new language is difficult. Learning the language of the insurance industry and technology industry is no different. In this episode of Awkward Insurance, Host Dustyne Bryant discusses the communication barriers between technology development and the risk and insurance industry with Garrett Droege (IMA Financial) and Doug VerMulm (Turris) at Insurtech Insights. Listen to this episode to find out where technology developers may be missing the boat in the risk & insurance industry and what can be done about it.

Ever wonder what goes on behind the scenes in insurance communication? Dustyne Bryant brings Mark Olson from Hippo Insurance onto Awkward Insurance to discuss just that. Mark shares his experience in corporate communications and provides insights into working with other departments, staying ahead of industry trends, managing communication crises, and the importance of vulnerability in social media. Tune into a chat about juggling words and wisdom in insurance!

In this episode of Awkward Insurance, hosts Dustyne Bryant and Ashley Fitzsimmons welcome Broker and Co-Owner of Westwood Real Estate Co., Thomas Raabe to the pod to discuss the intersection of real estate and insurance, starting with their podcasting schedule and transitioning into the home-buying process. They highlight the importance of trust and communication between real estate agents and clients. Thomas shares his approach to building a strong brand through online presence, video marketing, and positive reviews. The discussion also covers the value of customer service, referrals, and partnerships in real estate, the role of home inspections, and the need for effective collaboration between realtors and insurance agents to provide a seamless experience for home buyers.

In this episode of Awkward Insurance, host Dustyne Bryant speaks to Allison Albrecht and Nate Curtis, National Sales Directors at Clearspeed, about the groundbreaking use of voice analytics in the insurance industry. We also dive into the military roots of Clearspeed’s innovation, exploring how the company’s founder and their team of veterans bring unique problem-solving skills and ingenuity to the insurance world. Tune in to hear how military experience is translating into success, innovation, and excellence in insurance.

Hey, awkward listeners! Season 6 of the Awkward Insurance Podcast is here, and you're in for a treat! We're kicking things off with the incredible Arkansas Insurance Commissioner, Alan McClain. 🎉 Get ready for a deep dive with Dustyne and the Commissioner as they explore his inspiring insurance journey in Arkansas. The insurance commissioner is a state-level official found in all 50 states. Although the specific duties can differ from state to state, the primary role of the commissioner is to serve as a consumer advocate and oversee insurance regulation. Whether you're seeking industry insights or career motivation, this episode is your inside look into the insurance world's inner workings. So cozy up and join us as we discuss the impactful role of state insurance commissioners.

Awkward Insurance closes season five in the usual fashion with hosts Dustyne Bryant and Ashley Fitzsimmons and Producer Mac discussing their favorite episodes of the season! 

In the latest episode of "Awkward Insurance," host Dustyne Bryant dives back into insurtech from the ever-informative hub of Insurtech Insights, USA. This episode features insightful conversations with six industry leaders who are driving change and innovation in insurance. Tune in to this episode to hear these leaders discuss their innovative ideas and the future of the insurance industry and check out the previous LIVE stage recording to listen to an exclusive conversation about bridging the knowledge gaps and communication gaps between Insurtech and the insurance industry with Rick McCathron, CEO of HIPPO Insurance, and Jelani Fenton, President of E.G. Bowman.

This special episode of Awkward Insurance was recorded live on stage at the 2024 Insurtech Insights USA Conference! As technology advances at breakneck speed, the insurance industry struggles to trust technology and keep up. Join Dustyne Bryant, CIC, CISR, Director of Risk & Insurance Education and Research at the Risk & Insurance Education Alliance, as she moderates an insightful session on bridging the foundational knowledge gap between the tech and insurance sectors. Featuring panelists Rick McCathron, CEO of HIPPO Insurance, and Jelani Fenton, Founder of Safari and President of E.G. Bowman, this discussion explores what it takes to foster mutual understanding, build trust, and achieve better outcomes by aligning the languages of technology and risk management. Don’t miss this essential conversation on the future of insurance technology integration!

In some agencies, TECH may feel like one of those "bad four-letter words". Colleen O'Hara is here to change that. In this episode of Awkward Insurance, hosts Dustyne Bryant and Ashley Fitzsimmons are joined by Fideles Advisors, Colleen O'Hara who has found her calling helping agents understand and adopt new technologies while also educating them on why technology is so important to thrive in a hard market.  Tune in and make sure to follow Awkward Insurance on Facebook!

In this episode, Awkward Insurance hits the road to San Diego, CA to cover the 2024 Spencer-RIMS Risk Management Challenge hosted at the 2024 RIMS Risk World Conference. Host, Dustyne Bryant, followed the journey of eight domestic and international collegiate teams competing to develop and present the most comprehensive risk management program for the city of Tukwila, Washington. Following a roll call of all eight teams, Dustyne interviewed the three finalist teams following their final-round presentations and caught the emotional excitement of the winning team right after accepting their award. Special guest, Tandeka Nomvete Director of External Communications with Spencer Education Foundation, live reacts to the insightful, exciting, and sometimes emotional responses of the competitors. Spencer Education Foundation Executive Director, Megan Miller, wraps up the episode with the impact the Spencer-RIMS Challenge has on the risk and insurance industry.

In this episode, Awkward Insurance hits the road to cover the 2024 PIA Arkansas conference in Fayetteville. Host Dustyne Bryant diligently captures insights into the evolving needs of the insurance and risk management industries. Our discussions offer valuable advice for both aspiring professionals transitioning from high school or college and current insurance professionals seeking guidance on balancing work and life. Remember, we only have one shot at life, so let's not just live it, but live it together!