Awkward Insurance

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! 🎤✨ 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.  

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 trigger an insurance claim payout. Sola is starting with supplemental tornado coverage for homeowners and small businesses but plans to expand into every type of natural disaster to help people cover their deductible and immediate expenses. Sola has already been approved in 14 states as the first ever admitted personal lines parametric product, is fully reinsured through Lloyd’s of London and has partnered with dozens of agencies and aggregators.

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.

 

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 education will attract the next generation.

Monica Adwani is a dynamic leader whose career has been defined by breaking barriers and championing diversity.Monicais a passionate advocate for creating opportunities and fostering inclusivity, particularly for women and Latinos in the business world. As the CEO of Breezy Seguros, she leads a company dedicated to providing accessible and comprehensive insurance solutions tailored specifically for the Latino community in the United States.

Born in Puerto Rico,Monicaearned degrees in Information Management and Medical Coding from the InterAmerican University. Her desire for continuous learning brought her to Massachusetts, where she obtained a Business Management degree from Fisher College in Boston.

Monica's exceptional leadership has earned her multiple accolades, including Young Agent of the Year in 2019, LatinX Amplifier in 2021, one of the Top 50 Women Leaders in Massachusetts in 2022, and the Top 100 Latino Influencer award in 2023. Additionally, Breezy Seguros was recognized as one of America's Top 250 Latino Companies in 2024.

Monicais deeply committed to the Latino community and is working tirelessly to reach the goal of insuring more than 5 million Latinos across the United States through Breezy Seguros. Her dedication drives her efforts to empower and protect Latino families, entrepreneurs, and businesses, ensuring their success and security for future generations.

 

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.

 

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 to forge a better path forward for personal lines underwriting.  Curtis was instrumental in the development and launch of the NIIS self-inspection app and workflow, which is now in production environments with over 18 carriers and MGAs around the country, including three of the top ten P&C carriers in the United States. In his not-so-spare time, Curtis produces insurance video content on LinkedIn under the moniker of LO$$ RATIO, with a goal to engage, educate, entertain and inspire insurance professionals around the world. 

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.

 

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 prescription plans.

In addition to her work at Anderson and Green, Judy also holds a position as a Customer Service Representative at Cravens Insurance Agency, where she specialize in Medicare Supplements where her commitment to providing exceptional service and guidance allows Judy to help clients navigate their insurance needs effectively.

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.

 

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-founded in 2001, with offices and staff in 4 countries. He served for five years as an Adjunct Professor of Construction Science at Texas A&M University and still volunteers as a mentor and advisor for student groups. Regent Benham served the City of College Station as a Planning and Zoning Commissioner from 2011 to 2012 and was elected to two terms on the College Station City Council from 2012 to 2018 where he also served as Mayor Pro Tem. He is a member of the Young Presidents Organization (YPO). He lives in College Station and is an avid airplane pilot and musician. Regent Benham received a Bachelor of Business Administration in Accounting in 2001 and a Master of Science in Management Information Systems in 2002, both from Texas A&M University.

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.

 

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 Bachelor’s and Master’s degree in history, as well as her AU, ASLI and CPCU designations in insurance. She currently works as an insurance consultant, historian, and, sometimes, as a professional actor.
www.insurancevshistory.com
Linked in: friend/follow me at Meredith Brasher

Dive deeper into the fascinating history of insurance and discover how it has shaped the world we live in today. Explore A Tedious Brief History of Insurance—a captivating publication that uncovers pivotal moments, groundbreaking innovations, and the enduring impact of insurance through the ages. Perfect for industry professionals, history enthusiasts, or anyone curious about the roots of risk management.

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.

 

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!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.  

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 reinsurance and its impact on the industry.
• Cybersecurity Focus: FBI Agent Tanja Sablatura stresses the importance of cybersecurity in today’s risk landscape.
• Generational Shift: Over 30% of attendees have 20+ years in the field, emphasizing the need for mentorship and knowledge transfer.
• Purpose-Driven Work: Encouraging professionals to find meaning and purpose in their roles, fostering a legacy for future leaders.

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.