Jessica's Risky Business
Jessica Villarreal
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About This Podcast
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.
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Recent Episodes
S2E1 New Year, No Chill. Assuming Coverage is NOT a Strategy!
Send a textPause 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…
A Christmas Eve Claim Shows Why Insurance Only Works When You Plan
Send a textA 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…
Cannabis, Caramels, And A Christmas Claim Gone Sideways
Send a textPeppermint-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…
S1E12 How Leaders Turn Turbulent Layoffs Into Risk-Ready Strategy
Send a textThe 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…
S1E10 How A Government Shutdown Becomes Your Biggest Operational Risk
Send a textThe news says “shutdown,” but what you feel on the ground is a standstill: flights slowed to a crawl, terminals half empty, permits paused, containers waiting for clearance, and a payroll…
S1E9 Inside A Festival Firestorm: How One Leaky Valve Exposed Event Insurance Gaps
Send a textThe flames weren’t part of the show. One desert gust, one misfiring valve, and Ghost Light Canyon lit up for all the wrong reasons—phones out, tents airborne, and a festival team…
The Brewery Seance: The Spirits Didn’t Knock Them Out, the CO2 Did
Send a textCandles flickered, fog curled across the floor, and the crowd leaned into the mystery—until the room leaned back. A Halloween brewery show aimed for supernatural and bumped straight into…
S1E7 Haunted Risk, Real Liability: When a Cocktail Party at a Haunted Hotel in New Orleans Takes a Fall
Send a textThe room glowed with candlelight, the jazz was perfect, and the staircase looked like a movie set—until one selfie turned a black tie gala into a trending hashtag. We take you to the…
S1E6 The Cyber Heist: How Cyber Insurance Can Save You From AI Voice Clones and Fake Invoices — and What Insurance Actually Covers
Send a textThe heist doesn’t kick in a door—it slips into your inbox, borrows your boss’s voice, and asks you to hurry. We walk through a Texas family business that lost $150K to a “new wiring…
The Floating Ferrari Fiasco: When A Hurricane Hits Miami, Who Pays for the Bugatti in Biscayne Bay?
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S1E4 Bubble Trouble: An LA Influencer Causes a $20 Million Hotel Bath Bomb Disaster
Send a textWhat happens when influencer culture collides with luxury hospitality? A catastrophic pink flood, $20 million in damages, and a masterclass in modern risk management.Dive into the glittery…
S1E3 Teeing Up Your Coverage: Who Pays When The Fairway Becomes Unfair & Golf Balls Slice?
Send a textEver wondered what happens when a peaceful Saturday walk to brunch near a country club is interrupted by a rogue golf ball traveling at 150 mph? The aftermath isn't just about a ruined…
S1E2 The Silent Killer: How One Broken Sensor Destroyed Millions in Liquid Gold
Send a textPop the cork on luxury disasters! Jessica Villarreal dives into a spectacular champagne warehouse catastrophe that transforms from a climate control mishap into a multimillion-dollar…
S1E1 Forklift Fiasco: Joe Destroyed Your Warehouse, But Your Lack of Insurance Might Destroy Your Business
Send a textWhat happens when a single forklift accident triggers a $10 million catastrophe? More importantly, what happens when that accident occurs in a bonded warehouse? The story of Joe, our…
Frequently Asked Questions
Jessica's Risky Business has published 14 episodes since September 2025, covering topics in Business, Entrepreneurship.
Jessica's Risky Business is currently declining with new episodes every 2 weeks. Average episode length is 7m.
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