Wolf of Property Casualty

Epizodai

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  Commissions to Convictions: The Mess Hall 18.09.2026 8min

  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 sales orgs. A reflection on association, gratitude, and controlling what you let echo in your own mess hall.
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  The Four Indexes That Beat Any Carrier's "6% Trend" 11.09.2026 10min

  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.
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  Don't Ignore a CRIT or pick a fight with the bureau 07.09.2026 11min

  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' comp class codes are monitored, how payroll can be moved into a higher-rated classification, and what happens when a state bureau disagrees with the way a policy has been classified.But the bigger lesson is about relationships.What happens when a carrier receives a crit and the broker has to go back to the client and admit that something may have been done incorrectly? Why might a broker want to think twice before requesting a bureau inspection? And why can a relatively small compliance issue become a much bigger problem for the carrier relationship?Derek shares lessons from his experience in the middle-market and national-account workers' compensation space, including why he believes brokers should respond quickly, respect their underwriters, and be extremely careful when challenging a bureau's classification determination.No textbook answer. No sales pitch. Just practical workers' comp knowledge from someone who's been in the trenches.Welcome to Wolf of P&C.
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  PIP in 5 Minutes: The 5 Things Every Broker Needs to Know 31.08.2026 7min

  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.
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  Commissions to Convictions: What Happens When They Take Your Title Away? 30.08.2026 9min

  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, industry designations, status, and the danger of allowing your career to become your identity.Because your business card might say one thing, but the people who know you best know you by something else: husband, father, friend, mentor, coach.I've had a lot of titles. I've lost a lot of titles. And I've learned that what you do matters a hell of a lot more than what your title says you do.Focus on what's behind the title.
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  HR Screw-Up Insurance": Employee Benefits Liability Explained 27.08.2026 11min

  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.
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  Break Down the Wall Between Your Carrier and Your Client 26.08.2026 10min

  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.
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  Commissions To Convictions: What Jail Taught Me About Money 21.08.2026 15min

  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.
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  Claiming The News: Meta's $1.4T Problem & Why Insurers Are Refusing to Defend Them 20.08.2026 10min

  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's alleged.
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  A Picture Is Worth 1,000 Insurance Policies 19.08.2026 9min

  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:Insurance carriersPolicy limitsPremiumsDeductiblesLayered programsProgram evolution over timeWhether you're a broker, CFO, controller, risk manager, or business owner, this episode will show you how a simple visual dashboard can improve communication, simplify decision-making, and make your insurance program significantly easier to understand.No BS. Just insurance.
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  Commissions To Convictions: Confidential But Not Anonymous 14.08.2026 8min

  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 are.
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  The AOR Checklist That Would've Saved Me a Headache 13.08.2026 16min

  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.
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  Commissions to Convictions: The Best Ability is Availability 07.08.2026 8min

  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.
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  Business Income Q&A: Extra Expense, Continuing Expenses, Monthly Limits & Extended BI 05.08.2026 17min

  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.
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  The Work Comp Endorsement I Wasn't Batting 100% On 01.08.2026 9min

  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 with strong workers' comp protections like Wisconsin.
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  How I Cut a $150M Distribution Client's Business Income Limit to $3M (Legally) 28.07.2026 11min

  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 pushback you should expect, and the coinsurance/agreed value details that make it work.
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  Claiming the News: Taylor Farms, False Positives, and Explosive Diarrhea 24.07.2026 10min

  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 brokers have never actually seen paid out. If you touch food manufacturing, distribution, or product recall placements, this one's for you.
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  Commissions to Convictions: Putting Your Boot In Your Mouth 22.07.2026 9min

  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.
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  Call The Baby Ugly: 5 Things To Do With Carrier Declinations 22.07.2026 14min

  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 moving on, you're leaving value on the table — for your client and for yourself.
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  Pigs Get Fed, Hogs Get Slaughtered: Structuring Fee Agreements with KPIs 15.07.2026 9min

  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.