Samuel Summers - Partnering in Business Protection - Sihle Insurance Group

10/12/2026

A few things I’ve noticed since the book has been out.

Business owners don’t ask me what I expected them to ask. They don’t want policy summaries or coverage comparisons. They want to know whether the conversations they’ve been having with their current agent are actually the right conversations.

The response that keeps surprising me is some version of: “I’ve been sitting on this question for years and never had anyone to ask.”

There’s a shelf of commercial insurance content aimed at insurance professionals. There’s almost nothing aimed at the people actually buying commercial insurance. The gap isn’t about complexity — business owners handle complexity in every other part of their work. The gap is that nobody wrote for them.

That’s turned out to be the most useful thing about having written this. Not the book itself — the conversations it’s starting.

A few patterns I’m noticing:

Owners who’ve been in business 15+ years are the most hungry for this material. They’ve seen enough renewals, enough claims, and enough carrier changes to know something’s been missing.

The questions I get most often aren’t about specific coverage — they’re about how to evaluate whether their agent is really representing them. That’s why I ended up writing the recent framework on questions to ask at renewal.

The hardest part of the book to write was the chapter nobody specifically asked for: how to think about a program as a system rather than a stack of policies. It turns out that’s the chapter readers mention most.

Appreciate everyone who’s been part of the conversation so far. More to come.

10/05/2026

A business owner called me last month, two weeks after we'd finished his renewal.

He said: "I just want to make sure I understand what we did."

It wasn't that he was second-guessing the decisions. He wasn't. He just wanted to walk through the structure one more time, out loud, so he could explain it to his business partner.

So we did. Thirty minutes on the phone, policy by policy. What changed from last year. Why we moved the deductible where we did. What triggers each coverage. What falls into gaps between policies and how we’d handle a claim that landed in one.

At the end, he said something that stuck with me: "This is the first time I’ve had an insurance conversation where I actually knew what questions I needed to ask."

That sentence is why I wrote the book.

Not because business owners are incapable of understanding commercial insurance. They’re capable of understanding anything. They run complex businesses, read complex contracts, and manage complex teams every day.

But commercial insurance has quietly built an industry assumption that the buyer either doesn’t need to understand the mechanics, or won’t take the time to try. Agents build proposals around that assumption. Carriers design policies around it. The result is a market where even sophisticated owners end up accepting what’s put in front of them, because the alternative requires a vocabulary nobody ever taught them.

The fix isn’t making every business owner into an insurance expert. The fix is giving them enough of the mechanics that the conversation becomes a real one.

That’s what the book is for. More on it in the comments.

09/28/2026

Something I've noticed lately.

The business owners who reach out after reading the book almost always ask the same first question: not "what should I be doing differently?" but "am I even asking the right questions to my current agent?"

That's the more useful place to start.

Most business owners don't need to fire their agent. They need to know what to ask so they can tell whether their agent is actually representing them or just processing their renewal.

A few questions worth asking your commercial insurance agent at your next renewal meeting:

What's changed about my business in the last 12 months that should change my program?

Which exposures do you think I'm underinsured for, and which am I overinsured for?

What are the top three claim scenarios you'd expect on a business like mine, and how does my current program respond to each?

If we filed a claim today for [X specific scenario], walk me through exactly how the coverage would work.

What did you flag internally about my account this year that we haven't discussed?

An agent who can answer these clearly is doing the work. An agent who can't — or who redirects to premium and coverage limits — probably isn't representing you the way you think they are.

More on evaluating your program in The Commercial Insurance Buyer's Playbook. Link in the comments.

09/21/2026

This is one of the most common claims I see. Tell me it couldn't happen to your entity.

An employee gets an email from a longtime vendor requesting an updated wire routing number for an upcoming invoice. The email is well-crafted with correct branding, matching signature, familiar language. The employee updates the payment file. The next invoice goes to the fraudster's account for $250,000.

The business had a cyber policy. The claim was denied.

The gap is called silent cyber, and if you carry a cyber policy, there's a real chance you don't have the coverage you think you do.

Here's why the claim didn't pay.

The carrier's reasoning: the loss wasn't caused by a network breach. No system was hacked. No data was stolen. An employee was tricked into willingly transferring money.

That's social engineering fraud, and it's specifically excluded from most standard cyber policies unless a separate endorsement is purchased.

Here's the pattern most business owners don't realize:

Cyber policies typically cover breaches, ransomware, data restoration, and business interruption from network events
They typically do NOT cover funds transferred voluntarily by an employee...even when the transfer was induced by fraud
Coverage for this exposure requires a specific social engineering fraud endorsement, or a separate crime policy with computer fraud and funds transfer fraud coverage

Three things worth checking on your cyber and crime coverage:

Does your cyber policy include a social engineering fraud endorsement? If yes, what's the sublimit? (These are often capped well below your main cyber limit sometimes at $25,000 or $50,000, on policies with $1M+ overall limits)
Does your crime policy include computer fraud AND funds transfer fraud coverage?
What's your internal dual-authentication process for any vendor payment change request?

The cyber policy you bought three years ago was probably right for the exposure that existed then. It's rarely right for the exposure that exists now.

More in The Commercial Insurance Buyer's Playbook. Link in the comments.

09/15/2026

A $200,000 out-of-pocket cost before your insurance pays a single dollar.

That's what a 10% wind deductible looks like on a $2 million commercial property, and most Florida owners have no idea what number is actually on their policy until the hurricane makes landfall.

Wind deductibles are different from the standard property deductible you're used to. They're expressed as a percentage of the building's insured value, not a flat dollar amount. And they apply specifically to named-storm or hurricane losses — meaning the deductible you're familiar with isn't the deductible that applies when it matters most.

On a $2,000,000 building:

2% wind deductible = $40,000 out of pocket
5% wind deductible = $100,000 out of pocket
10% wind deductible = $200,000 out of pocket

Higher wind deductibles are increasingly common in Florida property programs, especially on coastal properties and older buildings. Sometimes carriers require them as a condition of coverage. Sometimes brokers accept them to keep premium down without walking the owner through what they've just agreed to.

The tradeoff is real. Higher wind deductibles do lower premium meaningfully. But if you haven't planned for the out-of-pocket exposure, the "savings" evaporate the first time you have a claim.

Three things worth checking on your property policy before the next storm:

What's your wind deductible expressed as a percentage and what does that translate to in actual dollars on your building's value?
Do you have cash or credit available to absorb that number without disrupting operations?
Has your agent walked you through the tradeoff, or was the deductible increased quietly at a renewal to hold premium flat?

The time to have this conversation is not two days before landfall. It's now, while the market is calm and you have time to build reserves!

More in The Commercial Insurance Buyer's Playbook. Link in the comments.

09/07/2026

A business owner told me something last week I haven't stopped thinking about.

We were reviewing his commercial property policy for a real estate portfolio, which includes several buildings, and in a program he'd had with the same agent for over a decade.

Halfway through, he stopped and said:

"I've never actually read one of these policies. I just assumed they all say the same thing."

I don't fault him for that. No one outside of the industry reads commercial insurance forms for fun. They're dense, they're written for lawyers and adjusters, and the summaries agents provide almost never make the actual mechanics clear.

Here is what I keep thinking about: this is a sophisticated business owner. He negotiates leases. He reviews vendor contracts. He challenges legal invoices. On any other contract in his business, he'd know exactly what he was signing.

On the policy that would decide whether a $2M claim gets paid, he assumed.

He's not the exception. He's the norm. That's not a failure on his part. It's a failure of how the industry sells and services its own product.

Which is why I wrote the book, not to make business owners into insurance experts, but to give them enough of the mechanics to stop having to assume.

More in The Commercial Insurance Buyer's Playbook. Link in the comments.

08/31/2026

Two businesses with identical payroll. One pays $85,000 in workers' comp premium. The other pays $120,000.

The difference is a single number called your Experience Modification factor — your MOD (aka "E-Mod", "Experience Mod") — and if you have employees, it's one of the most consequential numbers in your business.

Here's how it works.

Your MOD can be thought of as a scorecard for you business. It compares your workers' comp loss history over a rolling three-year window against similar businesses in your industry. A neutral MOD is 1.00. Below 1.00 you're a credit and pay less than standard. Above 1.00 you're a debit and pay more.

On a business with $100,000 in standard workers' comp premium:

• A 0.85 MOD pays $85,000
• A 1.20 MOD pays $120,000

That's a $35,000 gap every year on the same payroll. Compound it over a few years and you've either funded a hire, a piece of equipment, or a distribution to yourself...or lost it.

Here's the part most owners don't realize: your MOD isn't something that happens to you. It's something you build. Return-to-work programs, claims management, safety culture, and documentation all flow into it. A proactive carrier claims team can shave points off your MOD year over year. A passive one lets losses drag it up for reasons that have nothing to do with new injuries.

Three things worth checking:

1. Your current MOD in writing — and what it was three years ago
2. Which specific claims are driving it up (and whether any are still open that shouldn't be)
3. When your agent last walked you through the calculation itself, not just the premium

A MOD is the closest thing in commercial insurance to a business metric you can actually manage.

More on this in The Commercial Insurance Buyer's Playbook. Link in the comments.

08/24/2026

A friend made this. And honestly... manifesting. Why not, right?

Until the call comes, here's where things actually stand.

The Commercial Insurance Buyer's Playbook has been out for a few weeks and the response has been better than I had any right to anticipate. Thank you all for that.

Business owners are buying it. Business owners are reading it. Business owners are reaching out with the exact kinds of questions I wrote the book to answer — which either means it's working, or means I need to write a longer book.

A few things I've learned along the way:

People care about specificity. Concrete numbers and dollar figures land. Abstract concepts don't.

Commercial insurance is something people have wanted to understand for a long time. Nobody had made it accessible in a way that respected their time. That's what this book tries to do.

The book is on Amazon in paperback, hardcover, and Kindle. Link in the comments.

And Oprah — my calendar's open.

08/17/2026

A $400,000 claim. A valid policy. And zero dollars paid.

It happens more often than you'd think, and it usually comes down to two words most business owners have never had explained: claims-made.

Here's the scenario.

A consulting firm makes a professional error in year three of their coverage. The affected client doesn't discover the problem until year seven — four years later. By then, the consulting firm has switched carriers twice, let their old policy lapse, and never purchased tail coverage.

The client sues for $400,000. The current policy denies the claim (the error happened before the retroactive date). The prior policies are inactive. The tail was never bought.

Covered on paper. Paid nothing in practice.

Here's the distinction that determines the outcome.

An occurrence policy covers losses that happen during the policy period, regardless of when the claim is reported. Year-three error, year-seven claim, year-three policy responds.

A claims-made policy only covers claims that are both made and reported during an active policy period. If coverage lapses, if the retroactive date doesn't go back far enough, if tail coverage was never purchased, the claim doesn't get paid.

Professional liability is almost always claims-made. Cyber liability typically is too. Some general liability policies are quietly sold claims-made to save premium — which is one of the worst tradeoffs a buyer can make without realizing they're making it.

Three things to check on any claims-made policy you carry:

1. The retroactive date — ideally it goes back to when you first purchased that line of coverage
2. Prior acts coverage — confirm there are no gaps if you've switched carriers
3. Tail coverage availability and cost — critical if you ever exit, retire, or sell the business

These aren't optional details. They're the difference between coverage that works and coverage that exists on paper.

I cover this and the other quiet policy mechanics that cost businesses the most in The Commercial Insurance Buyer's Playbook. Link in comments.

04/16/2026

As connectivity rises and AI matures, the threat of cyber attacks becomes increasingly threatening to businesses and consumers. Identity theft, phishing scams and AI-powered deepfake audio and video attacks are examples of rising threats occurring as technology and AI advance.
Consumer education is the first line of defense, but business and personal cyber insurance offer a valuable safety net against costly claims.

The personal cyber insurance market is expected to grow and mature in 2026.