Jessica's Risky Business
Insurance doesn’t have to be dull — and Jessica Villarreal is here to prove it. Every Friday, she takes you inside the high-stakes world of business, risk, and claims with unapologetic energy and fearless insight. From behind-the-scenes war stories to real-world strategies that keep businesses alive when things go sideways, this podcast is equal parts bold, fun, and just a little dangerous. If you came for boring, you’re in the wrong place.
Jessica's Risky Business
Latest Episodes
Covered Or Denied: The Hottest Gameshow in Insurance!
We 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 coverage turns on definitions, promises, and endorsements—not guesses at renew...
New Year, No Chill. Assuming Coverage is NOT a Strategy!
Pause 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 between general liability, faulty work, negligence, and professional exposure....
A Christmas Eve Claim Shows Why Insurance Only Works When You Plan
A 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 real seasonal claim and walk through the exact points where coverage helped, ...
Cannabis, Caramels, And A Christmas Claim Gone Sideways
Peppermint-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 into an explosive manufacturing failure—and what it really takes to keep a...
How Leaders Turn Turbulent Layoffs Into Risk-Ready Strategy
The headlines say “realignment,” but we call it what it is: a new wave of layoffs reshaping tech, AI startups, logistics, and professional services. We pull back the curtain on how soft language hides hard problems—insider threats, broken SLAs,...
