Wolf of Property Casualty
The commercial property and casualty industry is desperate for a fresh voice. This podcast features a 15 year industry retail broker who grew a book of business to over $4M in commission but faced personal struggles and bad decisions, essentially the rise and fall of a 1% producer. The podcast aims to attack P&C concepts in a short format aimed at three target audiences - Brokers, Insurance Carrier Representatives, and Insurance Buyers. Authentic, real talk, from someone passionate for the business.
Episodes
Commissions to Convictions: The Mess Hall
Derek shares the "mess hall" lesson from a former mentor: the peer group you talk with — good or bad — shapes what you end up believing. He traces it from his three and a half months in county jail, where ten minutes at the wrong table can turn you against people who turn out to be nothing like the reputation, to the negativity bandwagon he sees among producers and managers in insurance
The Four Indexes That Beat Any Carrier's "6% Trend"
Carriers can't get rate in today's soft property market — so they're going after values instead. Derek walks through how to use four independent construction cost indexes to challenge inflated trend assumptions from underwriters, plus his take on why 90% (not 100%) insurance-to-value is often the right call for accounts with a spread of risk.
Don't Ignore a CRIT or pick a fight with the bureau
A workers' comp "crit" might seem like a minor administrative issue. It isn't.In this episode of Wolf of Property & Casualty, Derek breaks down what a criticism letter actually is, why workers' compensation bureaus issue them, and why brokers should take them far more seriously than the dollar amount of the potential fine might suggest.Derek walks through how workers'
PIP in 5 Minutes: The 5 Things Every Broker Needs to Know
PIP shows up on commercial auto proposals in no-fault states — and if a client asks "what's this?", you need an answer. Derek covers the 5 things to know: how PIP differs from MedPay, why it pays fast, priority of payments, and why it doesn't waive future lawsuits.
Commissions to Convictions: What Happens When They Take Your Title Away?
For years, I thought professional titles meant something.Partner. Director. Senior Account Executive. Those titles represented years of work, success, and climbing the ladder. Then I lost them—and I realized something I wish I'd understood much earlier: my clients never cared about my title nearly as much as I did.In this episode of Commissions to Convictions, I talk about professional titles,
HR Screw-Up Insurance": Employee Benefits Liability Explained
Employee Benefits Liability — the coverage Derek calls "HR screw-up insurance." One missed COBRA notice during a layoff. One forgotten dependent enrollment. One overlooked disability election. These are the mistakes that get HR teams sued — and this episode breaks down the coverage built to catch them, including a real claim from Derek's own career that settled for over $600K.
Break Down the Wall Between Your Carrier and Your Client
Loss control visits and claim reviews are necessary — but they're not where the real leverage lives. In this episode, Derek breaks down the two types of carrier engagement every broker needs to master, and shares his exact playbook for building the relationship that gets you through bumpy renewals and messy claims. No fluff, no selling — just what actually works.
Commissions To Convictions: What Jail Taught Me About Money
Derek made millions as a top insurance broker — then lost it all chasing the wrong thing. In this Commissions to Convictions episode, he breaks down the warning signs he ignored, what jail taught him about money, and why your worth was never tied to your paycheck.
Claiming The News: Meta's $1.4T Problem & Why Insurers Are Refusing to Defend Them
20 state AGs are suing Meta for $1.4 trillion — and its own insurance carriers say they don't have to defend the company. Derek unpacks the duty-to-defend fight playing out in Delaware court, why "intentional acts" exclusions are doing the heavy lifting here, and the coverage lesson every buyer should take away: it's not what happened that triggers your policy — it's what'
A Picture Is Worth 1,000 Insurance Policies
Most insurance programs are buried inside proposals, policy binders, and 20-page renewal summaries.But what if you could understand an entire commercial insurance program in less than 30 seconds?In this episode we break down one of the most valuable tools I used throughout my commercial insurance career: the Balanced Risk Management Approach (BRMA).This simple one-page visual document summarizes:I
Commissions To Convictions: Confidential But Not Anonymous
When a box of bananas goes missing and my off-the-record guess gets someone fired, I remembered a phrase from my time in sales: confidential but not anonymous. In my sales career, where "confidential" employee surveys/votes turned out to carry a lot more traceability than anyone let on. A candid, unflinching episode about information, trust, and the systems we assume are safer than they
The AOR Checklist That Would've Saved Me a Headache
Everyone's talking about how to win an Agent of Record letter — Lets talk about what happens after you win it. We break down six operational mistakes I've made (and one bonus trick) around carrier AOR rules, wholesaler transfers, commission timing, orphaned audits, fresh submissions, and getting documents signed without the awkward back-and-forth.
Commissions to Convictions: The Best Ability is Availability
Sometimes in a quest to chase accolades and achievements we lose sight of the basics of what make you successful and great on and off the field.
Business Income Q&A: Extra Expense, Continuing Expenses, Monthly Limits & Extended BI
Four follow-up questions from the previous business income episodes, answered: extra expense as your "slush fund," the continuing expenses people forget (rent between related entities, corporate debt, depreciation), managing coinsurance and related time period limitations on limit, and the forever profit stop gap that comes with Extended Business Income.
The Work Comp Endorsement I Wasn't Batting 100% On
A conversation with a former customer reminded me of a mistake I made more than once in mt broking career — not consistently securing the alternate employer endorsement on staffing arrangements. We break down why a waiver of subrogation alone isn't enough, walk through a real injury scenario at "ABC Manufacturing," and explain why this endorsement matters even more outside states wit
How I Cut a $150M Distribution Client's Business Income Limit to $3M (Legally)
Most buyers — and plenty of brokers — treat business income as a mystical number pulled from a worksheet. In this episode, we explain a niche but powerful strategy specific to value-added distribution companies: valuing inventory at selling price instead of cost, and using that to right-size (and often shrink) your business income and extra expense limits. Includes real client numbers, carrier pus
Claiming the News: Taylor Farms, False Positives, and Explosive Diarrhea
Taylor Farms voluntarily recalls lettuce. The FDA confirms contamination. Then walks it back as a "false positive." Taylor Farms keeps recalling anyway. In this Claiming the News breakdown, we unpack the coverage triggers hiding inside this real, unfolding claim — voluntary vs. mandated recall language, the reimbursement-policy trap, and an "adverse media coverage" trigger most
Commissions to Convictions: Putting Your Boot In Your Mouth
This episode reflects on impulsivity — the moments where words fly out before they're thought through, and the real cost of that habit. From an unwitting insult to my father's legacy, to a comment that mortified me in front of our CEO, to words twisted in a courtroom, this episode draws the line between being bold and being reckless with your words.
Call The Baby Ugly: 5 Things To Do With Carrier Declinations
The soft market is producing more marketing activity — and more declinations, as carriers hold their underwriting line instead of chasing growth. We break down five things every broker should do with a "no," from documenting the real reason in writing to using declinations as leverage for future submissions. If you're just logging "declined" on your marketing table and movi
Pigs Get Fed, Hogs Get Slaughtered: Structuring Fee Agreements with KPIs
Soft market got you eating commission cuts on every renewal? We break down how to build KPIs and bonus structures into your fee agreements — from captive quoting to shared-savings clauses — so you get paid for the work you're actually doing.
Commissions to Convictions: Condescension Kills Culture & Confidence
Condescension doesn't announce itself — it hides in tone, in dismissiveness, in the small ways people remind you where you stand. A subtle exertion of power that doesn't just deliver a message, it delivers a reminder that you're a notch below. From a guard who wouldn't bend the rules just because he "didn't want to," to a moment I raised my hand in a room of executive
Retrospective Rating Workers Compensation Explained In Plain English
In this episode we break down retrospective rating in plain English. You'll learn the difference between guaranteed cost and loss-sensitive programs, how basic premium and loss funding work, the difference between incurred and paid-loss retros, when these programs make financial sense, and the hidden negotiation opportunities that many brokers overlook.
Commissions to Convictions: Learning My Lines - What Acting Taught Me About Sales (and Surviving Jail)
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.
What Is a Maquiladora? Cross-Border Manufacturing Insurance
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.
Mr. Passive Income: What I Called My Key Man Life Insurance Referral Partner
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.
Commissions to Convictions: You Made a Choice, Not a Mistake
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.
Special Handling Instructions: The Work Comp Checklist Most Buyers Never Ask For
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.
Rest in Peace, Coverage Audit
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.
AI Can Read Your Work Comp Loss Run — But Do You Know What to Ask It?
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.
Claiming The News: DNA Leaks, Who's on GLP-1's & The OCR Task Force
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.
Commissions to Convictions: The Boy Who Cried Wolf
How eroded trust means losing the benefit of the doubt, even when you're telling the truth
Commissions to Convictions: You Can Have the Title. I'll Take the Room - Power vs. Authority
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.
Fleet or No Fleet - Know Your Auto Symbols
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.
Don't File That Claim Yet: The Not-At-Fault Auto Play Every Broker Should Know
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.
Commissions to Convictions: Won't vs. Can't
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.
Corgi and the Startup Insurance Bet: Disruption or Dislocation?
When you strip out the AI buzz and the VC money, what are the actual insurance fundamentals underneath Corgi's model?
The Additional Insured Illusion
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.
Cyber Liability: The Fine Print is Changing
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.
Commissions to Convictions: The Validation Trap
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.
The Truth About TRIA
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.
Risk Behind the Risk: Facultative & Treaty Reinsurance
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.
Stop Fu*king Up Your COPE
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.
Commissions to Convictions: Not All Mentors Are Role Models
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.
Claiming The News: Road to Courtroom - The CH Robinson Decision
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?
If You Do the Crime.....
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".
831(b) Micro Captives: Big Boy Insurance Is More Accessible Than You Think
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.
Bits, Bytes & Bricks: How to Talk About Builders Risk Insurance
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.
Quick Rant: CNA's Q1 2026 Doesn't Look Like Other Carriers
For publicly traded insurance carriers, their results, albeit on a macro level, can signal what is going on with their underwriting performance, which in turn matters to buyers and brokers. The CNA results paint a different picture than their competitors, what does that mean, and what should I think about?
5 Things I Did Wrong In Building My Book
Building a book of business is hard — and I made it harder. In this episode, I'm pulling back the curtain on 5 real mistakes I made along the way, what they cost me, and what I'd do differently today.
Weird Stuff That I Did......
I worked with someone that used to say "People will forget what you said, but they will never forget how you made them feel". The same applies to sales, join me for three instances where I risked be "cheesy" in an attempt to evoke feel in the sales process.
Commercial Flood Insurance: Strike While the Market's Soft
Soft market conditions don't last forever. Well recouping some rate is paramount to everyone after year's of a hard market cycle, don't forget to review opportunities to improve terms, conditions and coverages, like Flood Insurance.
Work Comp Claim Reviews: Three Seats At the Table
It is easy to become complacent with claim reviews, they can and often times feel like transactional meetings. These meetings serve a real purpose and should not be taken for granted. This episode talks about how to negotiate to make sure you have them, how to run them, and how to make sure each party at the table gets what they need out of them.
Your Past Predicts Your Premium: Unpacking the Experience Mod
The experience modification factor is not some mystical equation, well technically it is, but more than that it is an indicator and a multiplier. This episode unpacks not only an overview of what it is but also ways that it can be used to enhance the service experience of customers and open the door with prospects.
Your Attorney or Mine? - Unpacking Choice of Counsel
When a claim hits, who actually gets to pick your attorney — you or your insurer? In this episode, we break down the choice of counsel battlefield across different policy types, from CGL to D&O. We'll cover when policyholders have the right to select their own defense counsel, when insurers get to call the shots, and the critical conflict of interest triggers that can shift control. Whethe
Claiming The Headlines: Stretchy Fabric, Sticky Risk - LuLu + PFAS
Yoga pants, meet forever chemicals. Texas AG has launched an investigation into the use of PFAS in the manufacturing of Lululemon's products. While they say they have ceased use in products since 2023, it provides a good context and reminder of the changing landscape related to PFAS investigations and litigation. These types of long tail chemical related risks hit the intersection of multiple cove
Arson by a 3rd Party - Insurance Implications of the Kimberly Clark Fire
LINKE TO ARTICLE https://www.insurancejournal.com/news/west/2026/04/08/864876.htm A recent total loss fire at a KC facility in California hit the news yesterday. Thankfully, no one was hurt. But the facts of this loss raise a number of insurance questions that are good reminders of what happens when multiple parties are involved in large losses.
Agency Dynamics: Insurance Company Contingencies
Contingencies are nothing more than incentive payments based upon qualified metrics. These are not uncommon in any industry, so why are they sometimes considered taboo within the insurance agency industry? This episode discusses what they are, and how they are managed in a way to prevent moral hazard in achieving the best experience for buyers.
Off the shelf: Product Recall Insurance
Product Recall is common coverage for higher hazard industries, notably, food manufacturing, life sciences, and the auto industry, but the coverage can be useful in covering areas for companies that fall outside of those industries. Watch out, coverage is not uniform, and claims can be challenging, but applying knowledge of this product can help solve coverage gaps that other products simply do no
Claiming The Headlines: Tinder and Marsh - A Match.com made in heaven?
Details are available about litigation between Tinder's parent company (Match.com) and litigation they filed against Beazley (carrier) as well as now Marsh (broker) all regarding the handling of and reporting of a claim. This episode discusses the merits of the accusations and serves as a good reminder that handling Claims Made liability policies requires special attention, specifically surroundin
Softening Market: 5 Things To Think About
Softening market conditions is a relief for those close to the P&C Insurance marketplace. The transition or "bridge" year is always the most chaotic because the market does not move in "lock step" and neither does a cycle of renewals. This episode unpacks 5 strategies to how to stay ahead of the changing market dynamics in your interactions with your target audience.
January 1st is a Crappy Time to Buy Insurance
It's estimated that over 60% of commercial property and casualty insurance renews on January 1st. Why? It Sucks! This episode uncovers why it sucks so much, why you might think you need to, and the basic steps to move it - and ideal dates to move it to if you can.
Agency Dynamics - Service Team 101 & Professional Relationships
They say insurance is a relationship business I would argue none are more important than the ones you have within your organization. This episode focuses specifically on the importance of the service team in the agency setting. It discusses some tips on how to create a winning culture within the team and also some hard lessons I learned about how to manage all professional relationships.
Cyber Liability Tabletop Exercises
A tabletop exercise simulates a cyber security incident. I have performed over 100 of these for organizations ranging from $10M up to $10B. These are the single most important risk management item you can do to prepare yourself for an incident. This episode discusses the basics and reveals 6 key takeaways that these exercises can offer organizations.
10 Documents to Elevate Insurance Relationships
Every insurance relationship has the basic insurance stuff, statement of values, estimated payroll, drivers lists....yada yada. These 10 documents demonstrate a different level of operational intimacy that helps accounts stand out and provides a platform to elevate your risk management discussions.
Business Income Basics
Business Income insurance is not as finite as most components of a commercial property insurance policy. It is less science as it is art. However this concept can open the doors to having a deeper understanding of true business risk, and if positioned correctly can be a differentiator when it comes to insurance design and cost.
The Down & Dirty on Group P&C Captives
The market seems to be softening, that must mean group captives will go away. Not necessarily, the last ten years have showed that the group captive concept is now more of a risk management strategy rather then a refuge from harsh market cycles. This episode unpacks some basics and some strategies as to how to approach this insurance program concept.
Email Etiquette In the Insurance Industry
Email is the communication lifeblood of the insurance industry, whether its clients, carriers, or colleagues its how we talk. The disadvantage to email is that it is two-dimensional, which results in tone being misinterpreted. Your inbox is your first impression - and can often times be your biggest liability, this episode unpacks some strategies to enhance this communication and experience with y
Top 5 Risk Management Services From Insurance Carriers
In a competitive carrier and broker landscape, bang for your buck means everything. Maximizing the value that the insurance carrier can provide to the relationship often times will free up brokers to be more creative. These five services are low hanging fruit for most insurance carriers and can offer measurable impact to the overall insurance relationship.
Quick Rant - Combined Ratios
Combined ratio's are a leading indicator when it comes to insurance carrier and industry performance. Combined ratio's through 2025 continue to drift down perhaps signaling the start of a softer market cycle. This quick episode discusses what these ratio's are, what they aren't, and how to use them to negotiate and sound like an industry veteran.
Quick Rant - Handling the Audit Process
Many commercial insurance policies require estimates of exposures over a year ahead of time, specifically General Liability and Workers Compensation. With that level of uncertainty and so much premium on the line, this episode discusses best practices to preserve cashflow and ensure final accuracy.
There's Nothing General About General Liability
General Liability insurance is a foundational coverage in all insurance programs. It's is critical to any organization to even operate. This episode unpacks the basics of General Liability coverage, what specific types are out there, how it is triggered in the event of a claim, and things to look for when designing it.
A.I. In the Insurance Industry: Predator or Partner?
You cannot go anywhere these days without hearing about artificial intelligence. There is no doubt that industries will be disrupted and processes will be changed. This episode unpacks some areas that AI might impact the insurance industry, specifically the brokerage space, and why it presents more of an opportunity than you think.
Quick Rant - Agency Bill vs. Direct Bill
Sometimes what seem like inconsequential choices can have material impacts on customer relationships. When it comes to selling insurance the last problem anyone wants is a billing problem, this episode provides six considerations related to setting up customer billing and how ensure the best customer experience.
Agency Dynamics - Mentorship
The first episode in a series dedicated to discussing dynamics within the insurance brokerage/agency. Peer to Peer mentorship is critical to success for any insurance professional at any stage of their career. This business is too complicated and too complex to try and figure it out on your own. This episode drills down on how to find the best mentor, and ways to make the relationship mutually ben
Cyber Liability - Gotta Start Somewhere...
Relative to the history of insurance product development, Cyber Liability over the last 15 years is a phenomenon. The Wolf of P&C catapulted his career specializing in this space. This episode is an introduction to the coverage with some trending thoughts and considerations for where we are today and what's to come.
RFP's - Ready for Pain?
Request for Proposal's are an accepted part of the insurance broker and carrier review process. Today's episode discusses where these exercises fall short and five recommendations whether you are a broker or a buyer to ensure they are a good use of time.
Quick Rant - How to chose the right Wholesale Partner!
Wholesale Brokers are not dirty, they provide necessary access to the insurance marketplace. For retail brokers, they are an extension of you and your work product, and not something that should be frequently changed. This quick rant discusses the role of a wholesale broker, how to decide the best one to work with, and turning their work product into a value add.
Commercial Auto Insurance - What the hell?
The commercial auto insurance marketplace continues to be under duress, even as other segments show softening. The results are not only driving losses for this line of coverage, but also putting extreme pressure on commercial umbrella pricing and capacity. This episode unpacks different ways to think about structuring the insurance and tips and tricks to increase insurability and reduce exposure a
Quick Rant - Admitted Carriers vs. Non Admitted Carriers - Who Cares?
An insurance policy is an insurance policy...right? Well products are separated into two regulatory baskets, admitted and non admitted. This quick rant debunks some of the misconceptions that come with the difference between the two and why they are both useful tools in program design.
Top 5 Ways to Take Control of your Loss Control
Loss control meetings are a necessary part of the insurance relationship between insurance buyers and insurance carriers. They provide crucial information needed in the underwriting process. It is easy to brush these mundane meetings off as "check the box items" but failure to prepare and take control of these meetings can result in inaccurate information and embarrassment that is detrim
