Advertise on podcast: Awkward Insurance

Featured GuestJay Gates Managing Director, Gallagher National Restaurant Practice 20+ years in insurance, former Applebee’s risk leader, RIMS committee member, and Kids Chance Nebraska board member. What We CoverJay’s unexpected path into risk and insuranceLessons learned investigating EEOC claims early in his careerLeadership principles developed while managing large claims teamsBuilding a full ERM program for 165+ Applebee’s locationsThe most surprising and severe claims in restaurant operationsHow Gallagher reduces the total cost of risk for restaurant clientsInnovative approaches including captives and proprietary analyticsUnderestimated risks: cyber breaches + product recallsThe growing impact of AI on restaurant ops and riskPrivacy + liability concerns tied to AI adoptionThe future of restaurant risk management over the next decadeKey TakeawaysRestaurant risks are broader than most expect. From contaminated produce to liquor liability fatalities, claims can escalate fast.Cyber and product recall coverages are essential, despite being commonly undervalued.AI will reshape restaurant risk—from customer service to operations tracking—creating both efficiencies and new exposures.Gallagher’s differentiator is proactive service, deep data analysis, and tailoring insurance strategy to each client's risk tolerance.Risk leaders benefit from diverse career experiences, which Jay draws on daily.Resources & LinksLearn more about the Restaurant Risk Professional (RRP) certification: riskeducation.org/restaurant-RiskProExplore additional Alliance Insights episodes at riskeducation.org 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.  

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, 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 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.  

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 Professionals.   Douglas Ver Mulm is currently the Chief Executive Officer at Turris, a financial infrastructure platform for the insurance industry. Prior to this, Douglas was the Co-Founder & CEO at Stable Insurance, focusing on distribution and analytics for insurance in the shared/on-demand economy. With a background in law and economics/finance, Douglas has also served as a Volunteer Executive Director at InsurTech Association and as a Lead Mentor at Founders Network.   Garrett Droege, CIC, CPCU, CLCS, CBIA, CWCA, CRIS serves as Senior Vice President and Director of Innovation and Digital Risk Practice Leader at IMA Financial. His role oversees IMA’s national focus in the technology, and digital risk verticals (collectively called the Advanced Industries Specialty). He also co-manages IMA Labs, IMA’s insurtech innovation, investment, and strategy with BrokerTech Ventures. Additionally, he is part of the founding team of IMA’s web3Labs initiative and helped IMA become the first broker to build an insurance and risk management facility in the metaverse and issue the industry’s first “proof of coverage” via blockchain/NFT. He serves on the Crypto.Chicks NFT Advisory Board and consults with several other NFT projects. Prior to his current role, he served as CEO/Executive Director of TechAssure Association, Inc., an international consortium of insurance agents/brokers specializing in technology-related risks.  Garrett’s expertise includes Errors & Omissions, Cyber, and Technology Risk Management. Additionally, he is a brokerage technology specialist – focused on InsurTech, AMS/BMS/CRM platforms, data mining, and client journey tech stack development.  Garrett has designed complex insurance and risk management programs for some of the most sophisticated and diverse tech businesses in the country.  These include firms in info tech, medical technology, telecommunications, new media and all types of digital risk and blockchain.  Garrett is an alumnus of University of North Carolina at Wilmington and The Hartford School of Insurance.  He was named to the Charlotte Business Journal’s 40 Under Forty list and Insurance Business America’s Young Guns of Insurance list. Garrett is routinely featured in national publications and media productions, including NPR’s All Things Considered.    He holds the esteemed Chartered Property Casualty Underwriter (CPCU) and Certified Insurance Counselor (CIC) industry designations, among others. He has been a featured keynote speaker for numerous organizations, including: Federal Bureau of Investigation, National Public Radio, CIO Magazine, Society of CPCU, Insurance Innovators, FinTech Association of Hong Kong, Net Diligence, Healthcare Information & Management Systems Society (HIMSS), Information Systems Audit and Control Association (ISACA), North Carolina Technology Association, Texas Blockchain Council and many more.   Droege has been named three times to the Hot 100 List – a group of the top 100 insurance professionals that have “moved the industry forward” over the past 12 months. Garrett also serves as an advisor and mentor to several technology startup companies and has extensive relationships with global accelerator programs and investors. He is a frequent guest on business podcasts including: “The Insurance Guys”, Lowenstein Sandler’s “Don’t Take No For An Answer,” “InsurTech Geek Podcast,” “Beyond Insurance,” “A.I. Wisdom,” “The Insurance Coffeehouse,”  has context menu 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.  

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 at Hippo, he specializes in developing corporate narratives, preparing spokespeople, and providing counsel on reputational issues. Mark has a proven track record in enhancing brand reputation and driving strategic initiatives. He holds an MBA from the McCombs School of Business at the University of Texas at Austin. 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.  

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 people buy and sell homes for the last 8 years. He is the broker and co-owner of Westwood Real Estate Co. located in Columbus, OH. Westwood Real Estate prides themselves in being trusted advisors and creating lasting relationships with the people they work with. 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.  

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 insurance industry - largely on the carrier side. Allison is proud to be from and reside in Columbus, Ohio - home to an eager and innovative insurance landscape, and of course - the Buckeyes!   Nate Curtis is a National Sales Director for Clearspeed, a technology company that enables risk assessment through voice analytics. Prior to Clearspeed, he spent a decade working in various product development and innovation roles at Liberty Mutual Insurance. Nate began his professional career as an officer in the U.S. Navy after graduating from the U.S. Naval Academy in Annapolis, Maryland.   Clearspeed focuses on risk assessment and clearance through innovation in AI-driven voice-based technology. 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.  

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.  Prior to his appointment, McClain served for five years as Commissioner of Arkansas Rehabilitation Services (ARS)—a sister agency of the Arkansas Insurance Department (AID) under the state Department of Commerce. Commissioner McClain began his career in state government in 1992 at AID, spending eight years in its Public Employee Claims Division. Prior to joining AID, he served as a Claims Manager for self-insured workers’ compensation plans at the Little Rock offices of Sedgwick James Insurance. McClain served thirteen years with the Arkansas Workers’ Compensation Commission (AWCC), where he spent almost nine years as its Chief Executive Officer.  While at the AWCC, he also served as the regulator for companies and groups seeking to self-insure workers’ compensation risks. In 2013 McClain left the AWCC to join the Workers’ Compensation Research Institute (WCRI) based in Cambridge, Massachusetts, where he worked alongside numerous state workers’ compensation agencies as they utilized the work of WCRI in making data-driven policy decisions. McClain served as President of the Council of State Administrators of Vocational Rehabilitation between 2019-20, as well as President of the International Association of Industrial Accident Boards & Commissions (IAIABC) in 2011, where he was named Co-Chair of the National Association of Insurance Commissioners (NAIC)/IAIABC Joint Working Group. During his time as Commissioner of Arkansas Rehabilitation Services, Governor Hutchinson also appointed McClain to serve on the Arkansas Workforce Development Board, and the Governor’s Council on Developmental Disabilities. In addition to membership on a number of other NAIC task forces and working groups, McClain currently serves as Chair of the NAIC Property and Casualty (C) Committee, as well as Chair of the Workers’ Compensation Task Force, a subgroup of the Property and Casualty (C) Committee. He also serves on the Financial Standards and Accreditation (F) Committee, which reviews insurance department ability to analyze company solvency. McClain is a native Arkansan. He holds an undergraduate degree from Hendrix College in Conway, as well as a Master of Public Administration from the University of Arkansas at Little Rock. 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.