A podcast about business, risk & the fine print
Every Friday, commercial insurance producer Jessica Villarreal, CLCS takes you inside the high-stakes world of business, risk, and claims. Real disasters, real coverage questions, and the strategies that keep businesses alive when things go sideways.
New claims every FridayNow on the docket
August 18, 2026 · 76 min
Read the full episode notes →The case files
Jessica takes the show on the road to Resorts World Las Vegas for her first on-location interview. Mark Habersack, Executive Director of Risk Management, and Shannon McCu…
Case S2 · E3 · 07/26We’re digging into the thing we all rely on but rarely understand: the modern data center, the hidden backbone of cloud computing, streaming, medical records, and the AI …
Case S2 · E2 · 03/26We play “Covered or Denied” with real claims and translate the jargon into plain English. From coinsurance penalties to flood exclusions and subrogation, we show how cove…
Case S2 · E1 · 01/26Pause the multitasking. This story starts with a routine choice, a trusted employee, and a well-run company, and ends with a six-figure bill sitting in the gray space bet…
Case file · 12/25A quiet Christmas Eve, a building full of smoke, and a hard lesson about what insurance pays for when holiday décor meets hot-running equipment. We open the door on a rea…
Case file · 12/25Peppermint-scented chaos, a late-night shortcut, and a claims maze no one wants for Christmas. We unpack how a boutique cannabis brand turned a blockbuster holiday promo …
Your host
Jessica Villarreal is a commercial insurance producer with the CLCS designation and a resume that reads like a small economy: technology consulting partner, nonprofit campaign leader, boutique owner, restaurant partner. She's been the business owner reading the policy at midnight, which is exactly why she can explain yours like a human being.
Frequently asked
A weekly podcast hosted by Jessica Villarreal, CLCS, a commercial insurance producer who turns real business disasters into entertaining, plain-English lessons about risk, coverage, and claims. New episodes every Friday.
Jessica Villarreal is a Commercial Lines Producer at a leading global insurance brokerage and holds the CLCS (Commercial Lines Coverage Specialist) designation. Before insurance she spent over a decade as a partner in a technology consulting firm, led fundraising campaigns for the Leukemia & Lymphoma Society, and built businesses of her own. She has lived the risks her clients face.
Business owners, operators, founders, and anyone who signs an insurance renewal without being totally sure what's inside it. If you've ever wondered whether you'd actually be covered when things go sideways, this show is for you.
Everywhere you get podcasts: Apple Podcasts, Spotify, and Amazon Music, or straight from the RSS feed. Every episode also has its own page on this site with a built-in player.
No. It's education and entertainment. Every business and every policy is different. For advice about your specific situation, talk to a licensed insurance professional.
The Case File
A short read on what actually happened, what the policy did, and the one question worth asking before your next renewal. No spam, unsubscribe anytime.
Education and entertainment only. Nothing here is insurance, legal, or financial advice.Follow the show and never miss a fiasco. From forklift disasters to deepfake heists, there's a lesson and a laugh in every claim.
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