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PODCAST

Jessica"s Risky Business

Jessica Villarreal

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.

business management

All Episodes

4:58

New Year, No Chill. Assuming Coverage is NOT a Strategy!

Jessica"s Risky Business ·

2026/01/24

Send us a text 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. We unpack why the quiet claims, not the headline disasters, are the ones that bruise cash flow, rattle operations, and redefine renewal leverage. We pull back the curtain on the 2026 insurance market: property easing for clean, well-doc...

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4:36

A Christmas Eve Claim Shows Why Insurance Only Works...

Jessica"s Risky Business ·

2025/12/25

Send us a text 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, where exclusions bit, and how a few small decisions in November could have saved days of downtime. We break down the chain reaction: extension cords and lights strung through storage, a tree too close to heat, and an overloaded circuit t...

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5:59

Cannabis, Caramels, And A Christmas Claim Gone Sideways

Jessica"s Risky Business ·

2025/12/12

Send us a text 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 claim from dying on technicalities. We start with the high-energy collide of MJ BizCon and AWS re:Invent, where cannabis operators and tech teams are swapping notes on scale. Then we zoom into Green Globe’s “12 Days” push: upgraded equi...

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7:32

How Leaders Turn Turbulent Layoffs Into Risk-Ready...

Jessica"s Risky Business ·

2025/11/21

Send us a text 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, brittle processes, and legal exposure—and we walk through practical moves leaders can take this week to steady the ship without sacrificing the humans who keep it afloat. We start with the messaging gap—why euphemisms spook teams and cl...

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7:45

How A Government Shutdown Becomes Your Biggest...

Jessica"s Risky Business ·

2025/11/13

Send us a text The 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 timer that doesn’t care who’s on furlough. We pull back the curtain on how government stoppages trigger a predictable chain reaction across hospitality, logistics, construction, and travel—and how to turn that shock into a solvable operations and insurance strategy. We start by mapping the re...

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10:49

Inside A Festival Firestorm: How One Leaky Valve...

Jessica"s Risky Business ·

2025/11/01

Send us a text The 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 discovering in real time what their contracts forgot to say. We take you into Spectre Fest’s firestorm and pull apart the liability chain link by link, showing how a missing subcontractor agreement and absent pyrotechnic operator insurance pushed responsibility straight to the organizers. From there w...

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12:45

The Brewery Seance: The Spirits Didn’t Knock Them...

Jessica"s Risky Business ·

2025/10/24

Send us a text Candles 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 physics, forcing a crash course on oxygen, liability, and reputation in real time. We walk you through the moment the vibe tipped into hazard and the exact steps that pulled it back. We start with the setup: sealed doors, a rented CO2 fogger, and 400 guests primed for a live paranormal podcast...

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10:01

Haunted Risk, Real Liability: When a Cocktail Party...

Jessica"s Risky Business ·

2025/10/17

Send us a text The 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 Bourbon Orleans Hotel for a story that blends haunted lore with very real liability, unpacking how a six-step fall spiraled into Ghostgate and what it actually takes to protect people, balance sheets, and reputations when the internet shows up before the ambulance. We start with the setup: histori...

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10:27

The Cyber Heist: How Cyber Insurance Can Save You...

Jessica"s Risky Business ·

2025/10/10

Send us a text The 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 instructions” email and another $50K after an uncannily perfect phone call that sounded exactly like the CEO. The setup felt normal, the tone was familiar, and the urgency was believable. By the time anyone paused, the money had crossed borders and the vendors still wanted to be paid. From there, w...

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6:58

The Floating Ferrari Fiasco: When A Hurricane Hits...

Jessica"s Risky Business ·

2025/10/03

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6:53

Bubble Trouble: An LA Influencer Causes a $20 Million...

Jessica"s Risky Business ·

2025/09/25

Send us a text What 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 chaos of the insurance world as we unpack a truly spectacular claim that's so quintessentially Los Angeles it hurts. Imagine a top-tier influencer with millions of followers deciding a Beverly Hills Hotel's soaking tub is the perfect stage for a skincare tutorial involving 1200 gallons of n...

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6:37

Teeing Up Your Coverage: Who Pays When The Fairway...

Jessica"s Risky Business ·

2025/09/19

Send us a text Ever 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 latte and shirt—it's a complex liability puzzle that could cost someone millions. Golf balls are more dangerous than most people realize. These small white missiles break nearly 2,000 windows annually across neighborhoods near American golf courses and can reach speeds faster than most sports ca...

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4:57

The Silent Killer: How One Broken Sensor Destroyed...

Jessica"s Risky Business ·

2025/09/12

Send us a text Pop 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 sticky situation. When a tiny temperature sensor fails in a warehouse storing prestigious bottles of Dom Perignon and Cristal, physics takes over with explosive results. Discover the fascinating science behind why champagne bottles are essentially ticking time bombs under pressure—each containing ...

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5:40

Forklift Fiasco: Joe Destroyed Your Warehouse, But...

Jessica"s Risky Business ·

2025/09/06

Send us a text What 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 cigarette-smoking forklift operator, serves as a shocking wake-up call for warehouse operators everywhere. When Joe clips a rack after returning from his smoke break, he sets off a devastating chain reaction – racks collapse, pallets burst, and workers scatter for safety. But the physical de...

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14 results

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