Wolf of Property Casualty

This episode breaks down the one sales skill nobody talks about — treating your job like a performance, not a con. From reading a room to holding a consistent character through three months in jail, this episode reframes "acting" as discipline, not deceit.

Your US insurance policy doesn't cover your "rented" Mexico plant — and the Mexican government made sure of it. This episode breaks down maquiladora structures, the locally admitted insurance requirement, and the one relationship every buyer needs on the ground before a claim.

Key Man Life Insurance is a simple product that arguably most organizations need to have, and yet, unless mandated by lenders it is often overlooked or not discussed. I turned this conversation with customers into frequent referral commissions while demonstrating the ability to think about risk in a broader context.

Standing in front of a judge before sentencing I was called out for something I didn't expect, talking about "choices" not "mistakes. Even if they both have consequences, there is a difference.

Work comp is the highest-touch, highest-risk relationship between buyer and carrier — and most never negotiate it. This episode breaks down the special handling instructions that should be built into every account: reserve thresholds, nurse case management, dedicated adjusters, and the "team member not employee" detail that changes the experience.

The coverage audit was the bread and butter of middle market sales — get the policies, find the gaps, unseat the incumbent. I ran my old audits through an AI tool and got back in five minutes what used to take eight hours. So what does that mean for how you sell? The audit isn't dead, but the version you've been running might be.

Work comp loss runs look like spreadsheets full of numbers — until you know what you're looking at. This episode walks through a real loss run: valuation dates, reserves vs. paid, loss ratios, and the claims that demand more than a glance. A practical, no-fluff guide based on how I mastered it in five minutes sitting in my client's parking lots.

DNA breaches. Ozempic patient records. Federal regulators with a new task force. The healthcare cyber space just got a lot more dangerous — and most policies aren't built for it.

How eroded trust means losing the benefit of the doubt, even when you're telling the truth

Most people in leadership chase power — the title, the approvals, the seat at the table. But power without authority is just leverage nobody respects. This episode breaks down why authority is more achievable, more durable, and ultimately more powerful than power alone.

Whether a client runs fifty vehicles or five, the commercial auto policy structure works the same way — and the stakes are just as high. This episode walks through the symbol framework that governs how coverage attaches to vehicles, why scheduled vs. blanket approaches matter more than most buyers realize, and which add-ons should be standard on every auto program regardless of fleet size.

It's not a sexy topic. Somebody hit your client's van, cop showed up, fault's clear. Easy, right? Not so fast — inserting yourself into a "small" not-at-fault auto claim is one of the highest-ROI moves a commercial broker can make. Subrogation black holes, claims history penalties, and how a two-week hustle can turn into long term client appreciation.

There's a difference between what people can't do and what they simply won't. The lesson isn't about being the most talented person in the room. It's about being the one willing to step into a role or do something that nobody else will. In commercial insurance, that willingness helped build my career, in jail, it built my freedom.

When you strip out the AI buzz and the VC money, what are the actual insurance fundamentals underneath Corgi's model?

Additional Insured becomes such a common term thrown around insurance agencies and with buyers, every contract, every certificate, they all have requirements for additional insured. In this episode I discuss what it means and the 7 reminders of why this common coverage is important and how to make sure you are getting it right.

The market is soft, capacity is everywhere, but the claim environment is still challenging. This episode unpacks recent news in the cyber liability market, and update on litigation trends, and some calls to action surrounding coverage encroachments and risk management recommendations.

Validation comes in all shapes and sizes and means different things to different people. While a president's club trip might validate some, others may need just your time.

Most insurance professionals know TRIA exists, but few understand how it actually works. I think TRIA gets passed off as a "tax" in many cases. This episode breaks down what TRIA is, what actually needs to happen for it to be triggered, and calls out the question if it is really worth it, especially in the middle market/national account space.

Reinsurance might not be the thing everyone is blaming as the market softens. However, it remains a critical part of the insurance ecosystem and those who have a basic understanding of what it is, how it works, are in a position to sound intelligent, and therefore educate their customers.

Construction type, Occupancy, Protection and Exposure are the pillars of property insurance underwriting. Because of that, they can be an afterthought on mature customer relationships and brand new ones. This episode unpacks the importance of each and the little things that help make sure you have the fundamentals right to ensure the best presentation to the marketplace.

Not every mentor is a role model — and that distinction matters more than most people realize. In this episode, we explore why the person guiding your career climb isn't always the one shaping who you become. Whether you're 25 or 55, role models show up in unexpected places, and recognizing them changes everything about how you grow.

The Supreme Court just unanimously ruled that freight brokers are liable for the vetting of the companies that they broker loads to. The Supreme Court rarely gets involved in P&C litigation, what does this mean, and why should I care?

This podcast has gotten away from what the title suggests, and it is because you can get comfortable...comfortable with what you know, what you are good at. It's time to be a little uncomfortable and talk about more than just insurance. Listen for an update on my personal journey and a new direction talking about all the things I've learned from "Commissions to Convictions".

I focused on the Middle Market and Upper Middle Market Space, 831b captives were either believed to be snake oil or something only reserved for the biggest of companies. Neither are true, they are incredible risk management tools that plug unfilled gaps of risk for organizations, and yea, there are some tax advantages as well.

The construction boom associated with building data centers to support AI is everywhere. It is providing a nice organic growth boom for brokers who are entering a softer insurance market. This got me thinking about the first stage, Builders Risk. This episode unpacks builder's risk basics and more importantly how to position it with some key considerations when you are not an expert.