Podcast
Jessica's Risky Business
Hosted by Jessica Villarreal · EN
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.
10episodes
Episodes
Newest firstAll episodes
Covered Or Denied: The Hottest Gameshow in Insurance!
Mar 700:09:32Tap to summarizeSend us Fan MailWe 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 renewal.• coinsurance explained with windstorm loss and valuation impact• sprinkler warranty as a material representation and denial risk• business income triggers and civil authority limits• auto liability following the vehicle after-hours• flood exclusion clarity and separate flood options• subrogation after tenant-caused fire and lease waivers• power outage spoilage and utility services endorsements• ordinance and law coverage for code upgrades• why renewal choices decide claim outcomesIf this episode helped you, share it with the business owner you care about, and I'll see you next week
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New Year, No Chill. Assuming Coverage is NOT a Strategy!
Jan 2400:04:58Tap to summarizeSend us Fan MailPause 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-documented accounts, casualty still tight, auto still brutal, and GL with completed ops under a heavy spotlight. You’ll hear how underwriters are viewing employee decisions that touch customer property and why even paid gray claims can harden terms, raise deductibles, and trim flexibility. More importantly, we show how a five-minute conversation could have altered coverage structure, tightened protocols, and set expectations long before adjusters parsed policy language.This is a blueprint for moving from transactions to strategy. We share the exact questions to ask your agent—what scares underwriters about our account, which claims keep you up at night for our industry, where are we exposed—and how those answers shape endorsements, training, and decision rights. If your broker only appears at renewal or when a certificate is needed, it’s time to demand more: real updates on appetite, claim perception, and the steps to future-proof your program. The payoff is simple: fewer surprises, better pricing power, and a risk posture that actually matches how your business operates.Ready to pressure test your coverage and close the gap between intention and policy language? Follow the show, share this episode with your ops and finance leads, and leave a quick review with the one question you’re asking your agent this week.
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A Christmas Eve Claim Shows Why Insurance Only Works When You Plan
Dec 2500:04:36Tap to summarizeSend us Fan MailA 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 that triggered emergency response and operational shutdowns. From property policies to business interruption, we highlight why improper electrical use can limit recovery and how sublimits, waiting periods, and endorsements can either cushion the blow or magnify it. This is a practical guide for owners, operators, and leaders who peak in Q4 and can’t afford surprises when orders pile up and staff rotate.Then we get specific about prevention. The naughty list includes last-minute certificates, unvetted pop-ups and events, temp staff added without notice, and the dangerous myth of “we’ve always done it that way.” The nice list is simple and powerful: a pre-holiday check-in, fresh property values for peak season, confirmed sublimits and endorsements, early loop-in with your broker, and a quick electrical safety walkthrough before the lights go up. We share why the best outcomes come from relationship-driven risk management—clients who ask questions early, invite transparent conversations, and make coverage decisions intentionally.If you want fewer frantic calls and more resilient operations, this one’s for you. Share it with the teammate who owns facilities, the partner who handles pop-ups, or the finance lead eyeing next year’s limits. Subscribe for more real-world claims, practical risk tactics, and candid stories from the front lines of insurance. And if this helped, leave a review and tell us what seasonal risk you’re tackling next.
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Cannabis, Caramels, And A Christmas Claim Gone Sideways
Dec 1200:05:59Tap to summarizeSend us Fan MailPeppermint-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 equipment, surging orders, and SOPs that didn’t reflect what the line was actually doing. One heat bump later, pressure met infused caramel and the facility met disaster. Two shredded tanks, hundreds of thousands of units lost, and a peppermint THC glaze over everything—plus an unlucky neighbor reporting contamination and employee exposure.The real story lives inside the policy. Property coverage narrowed under undisclosed equipment upgrades and out-of-bounds temperatures. Product loss limits lagged because production volume was under-reported to save premiums. Business interruption didn’t trigger due to employee actions outside written SOPs. Liability for airborne vapor across the wall? Not without products pollution, contamination, or neighboring premises endorsements. We break down each miss and map the structure that would have paid: accurate equipment schedules, equipment breakdown with BI, products pollution and contamination, recall, neighboring premises liability, and production records that match reality. We also get tactical about culture—training tied to the real workflow, deviation logs, safe throughput metrics, and pre-peak stress tests.If you’re scaling for holidays, launching new SKUs, or recovering from the MJ Biz whirlwind, this is your checklist to keep growth from outrunning your risk program. Subscribe, share with your ops and finance teams, and leave a review with the one coverage you refuse to ship a season without.
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How Leaders Turn Turbulent Layoffs Into Risk-Ready Strategy
Nov 2100:07:32Tap to summarizeSend us Fan MailThe 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 clients—and show how to pair humane offboarding with precise process. Then we trace the operational shock: engineers and analysts exit, tacit knowledge evaporates, and AI “fixes” misfire without guardrails, sometimes causing more damage than the cuts themselves. From there, we map the three big risk zones: cybersecurity during high-emotion exits, E&O exposure as lean teams ship mistakes, and client confidence as response times slip from minutes to days.To make it concrete, we share the cautionary tale of Caliber Freight Systems: a 12% cut, an AI blunder that nuked calendars, and an ex-employee who still had access long enough to trigger alarms. The twist? A competitor won the day by being ready to receive displaced talent. We close with a focused executive checklist—revoke access immediately, review cyber policy wording for insider threat and social engineering, tighten offboarding documentation, and rethink talent strategy as a redistribution event. We also break down the insurance stack that actually matters right now: cyber liability, technology E&O, business interruption for non-physical triggers, key person coverage, and EPLI.If you’re a CEO, CFO, or founder navigating contraction, you’ll leave with clear steps to reduce cyber risk, protect client trust, and rebuild a resilient core team. Subscribe, share with a leader who needs a plan, and leave a review with the one control you’ll implement today.
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How A Government Shutdown Becomes Your Biggest Operational Risk
Nov 1300:07:45Tap to summarizeSend us Fan MailThe 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 real dominoes: FAA delays, customs slowdowns, and silent permit offices that stall projects and sales. Then we move from panic to playbook with the exact tools that keep revenue alive when systems freeze: contingent business interruption that responds when your vendors fail, civil authority coverage that helps when access is restricted, event cancellation for hospitality and venues, trade disruption insurance for clogged ports, and key person coverage when your MVP goes MIA. To make it concrete, we walk through a case from airport dining, where dependent property coverage turned empty concourses into a valid claim, protected payroll, and kept the brand intact.Protection isn’t only about policies; it’s about presence. We share a leadership checklist for high-clarity communication, contract reviews that surface hidden government dependencies, and non-damage BI triggers that matter when nothing is physically broken but everything is frozen. You’ll leave with a five-step action plan to align contracts, coverage, and culture so your team stays calm, your cash flow stays protected, and your strategy stays in motion—even when Washington doesn’t.If this conversation made you rethink your blind spots, follow the show, share it with a founder who’s stuck on the tarmac, and leave a quick review to help more builders find us.
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Inside A Festival Firestorm: How One Leaky Valve Exposed Event Insurance Gaps
Nov 100:10:49Tap to summarizeSend us Fan MailThe 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 we explore the fault lines most producers don’t see until they crack. Worker classification turned “independent creatives” into employees under California law, triggering workers’ comp obligations and labor risk. A chaotic evacuation turned into a coverage quiz: commercial auto for rolling assets, inland marine for scheduled gear, and the paperwork that decides who pays when metal meets metal. The cannabis vendor’s denied claim surfaced a harsh truth about exclusions that reach into hemp-derived products; without the right endorsements or ENS policies, even small losses stay uninsured.Reputation moved faster than fire. Crisis management coverage funded a disciplined PR response while business interruption helped shoulder refunds and downtime. An umbrella policy proved its worth as claims stacked and venue expectations loomed—follow form language, higher limits, and proof that satisfies modern permitting. The second act matters most: the team rebuilt with a risk management director, color‑coded COIs, triple‑checked contracts, stronger limits, and practical safeguards like extra extinguishers and vetted vendors. The result wasn’t luck; it was design. If you produce experiences where flame meets frequency, this is your blueprint for keeping art alive and risk contained.If this story helped you spot a gap in your own plan, subscribe, share the episode with your team, and leave a quick review. Your next great idea deserves coverage that can dance with the sparks.
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The Brewery Seance: The Spirits Didn’t Knock Them Out, the CO2 Did
Oct 2400:12:45Tap to summarizeSend us Fan MailCandles 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. When people began to sway, then faint, the fix wasn’t a chant—it was airflow and fast triage. From there we unpack the insurance spine that keeps creative businesses upright: commercial general liability for bodily injury on premises, liquor liability when over-service complicates claims, and the special event endorsements that separate everyday taproom service from ticketed performances with third-party vendors.Then we tackle the clause most owners overlook: pollution and indoor air quality. Many GL policies exclude gases and vapors, and CO2 qualifies, which is why an indoor air quality or pollution endorsement matters more than mood lighting. We cover workers’ comp for staff symptoms, crisis management coverage for social media blowback, and why an umbrella policy turns a $1 million conversation starter into real protection when multiple guests are involved. Finally, we map the fixes: ventilation plans, CO2 monitors, clear stop rules, vendor COIs with additional insured language, and incident logs that make renewals smooth and defenses credible.It’s a story about turning a near miss into a playbook: fewer stunts, stronger airflow, smarter contracts, and a brand that owns the lesson instead of the headline. If you care about hospitality risk, event planning, or the business side of craft beer, you’ll leave with practical tactics you can implement tonight. Enjoy the tale, take the checklist, and help us spread the word—subscribe, share with a friend who runs events, and leave a review with your must-have safety move.
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Haunted Risk, Real Liability: When a Cocktail Party at a Haunted Hotel in New Orleans Takes a Fall
Oct 1700:10:01Tap to summarizeSend us Fan MailThe 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: historic architecture, dim lighting, high heels, and high-proof cocktails. Then we map the chain of failure that risk pros recognize immediately—noncompliant lux levels, a single misplaced handrail, uneven treads, and bar logs that hint at overservice. From there, we break down the coverage stack in plain English: commercial general liability for the injury, liquor liability when pouring goes too far, special event endorsements to clarify who owns what, and the overlooked linchpin of modern risk programs—crisis management coverage that funds PR counsel, media monitoring, and message control when the story outruns the facts.You’ll hear how documentation shifts outcomes: maintenance logs that prove vigilance, training records that show bartenders know the line, and contracts that add the client as additional insured to stop morning-after finger pointing. We share the practical fixes that pay off immediately—brighter bulbs, a second handrail, anti-slip nosing, clear signage, water stations, and designated photo zones—plus the renewal changes that stick, from higher umbrella limits to annual safety audits and a tested crisis response plan. Along the way, we keep the spirit of New Orleans intact: ghost stories sell rooms, but safe design keeps margins.If you manage events, venues, hospitality, or just love a sharp risk breakdown wrapped in a good story, this one’s for you. Subscribe, share with your ops team, and leave a quick review—what’s the one safety upgrade you’d mandate for every historic staircase?
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The Cyber Heist: How Cyber Insurance Can Save You From AI Voice Clones and Fake Invoices — and What Insurance Actually Covers
Oct 1000:10:27Tap to summarizeSend us Fan MailThe 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, we zoom out to the bigger picture: deepfake-enabled fraud is accelerating, with losses climbing into the hundreds of millions and average hits per company reaching painful territory. We share how criminals scrape podcasts, social posts, and voicemails to build voice clones, then layer old-school social engineering on top for a brutal one-two punch. The takeaway isn’t panic—it’s precision. Awareness still beats any firewall when you pair it with simple, enforceable rules: verify payment changes via a known number, train often in short bursts, add out-of-band callbacks, and slow down urgent money movement with dual approvals.We also break down the insurance that actually helps when things go sideways. Most standard business policies won’t touch cyber losses; you need cyber liability with both first-party and third-party protection. And for 2025, social engineering fraud and fund transfer fraud coverage aren’t optional—they’re the core. We explain limits, exclusions, and conditions like MFA, training, and offline backups that can decide whether a claim gets paid. Along the way we cover premium drivers, sector risks, and the practical steps to take minutes after a hit. Subscribe, share this with your finance lead, and leave a review with one safeguard your team commits to this week—what’s your out-of-band verification rule?
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