InsurePodcast

From a workers' compensation adjuster internship in college to building a commercial insurance book at one of the largest brokerages in the world, Eli Diamond has taken a somewhat unconventional path into insurance. Raised in Syracuse, New York, Eli began his career at The Hartford before moving to the agency side, where he discovered he preferred representing business owners rather than carriers....

Brian Mahon spent a decade inside startups and top-100 firms before launching Igloo Insurance in June 2025. One year in, he joins Ben to talk about what it actually takes to build an independent agency from scratch — and where the work still feels broken. We get into his multi-line book (roughly 60% commercial, 39% personal, the rest life), his cyber-liability niche, and the omnichannel hustle beh...

Kristyn Ruth runs Think Pink Insurance out of Texas. She started in insurance the way few people do: she'd been selling cars for eighteen years, opened a dealership in 2018, and didn't want to keep referring her finance customers out to other agents — so she got licensed and started writing the policies herself. Eight years later she runs a multi-line operation with seventy-seven agents across for...

Doug Wenz is Vice President at Associated Insurance Services in Plainville, Connecticut. He's been licensed since 2017 and has spent fifteen years in sales — the kind of producer whose LinkedIn tagline reads "Challenging Insurance Industry Norms" and who means it. He got into insurance the way few people do: lightning struck his car overnight, GEICO fought him on the claim, and after he won the fi...

Note: this episode recording got interrupted, so there's a sharp cut halfway through. Brandy Henriquez and W. Tom Polowy run Insure Connecticut, an independent brokerage based in West Hartford and licensed in seventeen Eastern states. Brandy came to insurance from twenty years in radio and entertainment production. After looking at real estate and insurance as his next chapter, he landed at a Stat...

Sydney Troski has been licensed in life and health insurance since 2023. Based in Boiling Springs, South Carolina, she works as an independent life insurance agent under an IMO, focusing on whole life, term life, and mortgage protection for families and individuals. She is one of the younger agents on the show and one of the few who came in without a long runway of capital — which means everything...

Jason Ferraro has spent sixteen years in life insurance and thirty-five years in sales. Based in Orlando, Florida, he manages new hires for a life and annuity IMO and runs Gator Mouth Sales — an AI sales assistant for agents transitioning from final expense and mortgage protection into the annuity arena. He's the only guest on the show so far who works the life side rather than P&C, and that c...

Steven Wiatrek is a sixteen-year veteran of the insurance industry who spent most of his career building a $4.5 million book at a captive carrier in South Texas before being let go on Christmas Eve, 2024. He started over from zero in January 2025 as a branch owner with City Centre Insurance Agency — a distribution firm with sixty-five branches that operates as a single licensed entity, giving its...

Robert Balan-Martin built Gnome Insurance Services as a scratch agency that did $300,000 in new premium almost entirely through Facebook, Instagram, Reddit, and Snapchat messages — sometimes binding policies at one in the morning, after a contractor finished work for the day. He started out cold-calling agencies in 2019, tried trucking insurance, bounced through some insurtechs, took a detour into...

Jeremy Stepp runs the property and casualty side of Synergy Wealth, Insurance and Planning, an independent agency in Coolidge, Arizona — a rural town of about 20,000 people in Pinal County, halfway between Phoenix and Tucson. The agency began with his wife Tonya's life and health practice during the COVID shutdown of 2020. Jeremy added P&C in September 2024, partly as a "low-hanging fruit" ent...

Kelly Bishop runs Montana Legacy Insurance from Livingston, Montana. She started in insurance at 18, spent 20+ years with Farmers, kept an independent book for another decade, then took a detour through real estate and a stint as a Shelter agent in Las Vegas. When Shelter pulled out of Nevada, she came back to Montana and decided that if she was going to do insurance again, she'd do it independent...