Forget General Liability. Here’s the policy that actually protects your startup

Forget General Liability. Here’s the policy that actually protects your startup.

The Slip-and-Fall Policy for a Boardroom Battle

As a startup founder, I bought a General Liability (GL) policy because that’s what “businesses” do. Then, an early investor sued me and my co-founders for mismanaging funds after a product launch failed. I was shocked when my GL insurer denied the claim. They explained GL is for “bodily injury and property damage”—like a customer slipping in your office. It doesn’t cover your business decisions. For that, we needed Directors & Officers (D&O) insurance. I learned the hard way that a startup’s biggest risks are in the boardroom, not the lobby.

Stop chasing lower premiums. Chase a stronger balance sheet with captive insurance instead.

The Premium That Became a Profit Center

My construction company was tired of volatile, sky-high insurance premiums. We were just sending massive checks to an insurer every year. A consultant suggested we form our own “captive” insurance company—a subsidiary that insures our own risks. Instead of paying an outsider, we paid premiums to our own captive. It built up a huge cash reserve from underwriting profits, which we then loaned back to our construction company to buy new equipment. We turned our biggest expense into a strategic financial asset that strengthened our entire balance sheet.

The hidden truth about Business Owner’s Policies (BOPs) that brokers won’t admit.

The “All-in-One” Policy That Left Everything Out

My broker sold me a Business Owner’s Policy (BOP), calling it the perfect “all-in-one” solution for my small consulting firm. I thought I was fully covered. After a data entry error in a report cost a client thousands, I filed a claim. The hidden truth was revealed: the professional liability coverage in my BOP had a tiny $25,000 sub-limit that barely covered the loss. BOPs are built for “main street” businesses like a flower shop, not for the complex professional and cyber risks of a modern service business.

What nobody tells you about navigating a business insurance claim.

The Adjuster Is Not Your Friend

After a fire at our warehouse, I was so relieved when the friendly insurance adjuster showed up, promising to help. What nobody tells you is that the adjuster’s job is not to help you; their job is to minimize the claim for their employer, the insurance company. He was an expert in finding reasons to pay less. His first offer was a lowball number that would have bankrupted us. We had to hire our own public adjuster to fight for the money we were rightfully owed. I learned you must manage the claim, because the other side certainly is.

I spent 5 years bootstrapping my business. Here’s what I learned about risk management.

When Every Dollar Is Your Own

When you’re bootstrapping, there’s no venture capital safety net. Every dollar of revenue and every dollar of loss is personal. For five years, this reality was my business school. It taught me that risk management isn’t a corporate department; it’s a survival instinct. I couldn’t afford a single uninsured slip-up. Every decision, from contracts to safety procedures, was viewed through the lens of “can this bankrupt me?” Bootstrapping teaches you the most valuable lesson in business: risk isn’t an abstract concept, it’s the wolf that’s always at the door.

Unpopular opinion: Your LLC is not a substitute for liability insurance.

The Shield That Protected the Owner but Sacrificed the Business

I formed an LLC for my e-commerce business on day one, thinking my personal assets were now totally safe. I felt bulletproof. When my company was hit with a major product liability lawsuit, my house was indeed protected. But the lawsuit still bankrupted the business itself, wiping out its bank accounts and inventory. The unpopular truth is that an LLC protects your personal assets from the business, but only liability insurance actually protects the business itself. Your shield isn’t worth much if there’s nothing left behind it to run.

90% of entrepreneurs don’t understand this about Directors & Officers (D&O) insurance.

The Insurance for Your Decisions

Most founders think D&O insurance is a luxury for big public companies. They don’t understand that it’s the only policy that protects them from their own business decisions. An investor can sue you for mismanagement. A competitor can sue you for breach of fiduciary duty. A partner can sue you after a disagreement. Your General Liability policy will not cover any of these claims. D&O is not for when you accidentally break something; it’s for when you are accused of breaking the business itself through your choices.

This simple weekly risk assessment transformed my business’s resilience.

The Friday Firewall

Every Friday afternoon, I block 30 minutes on my calendar for a “risk huddle” with my leadership team. We don’t talk about sales or marketing. We ask three simple questions: “What is the biggest risk to our business right now? What is our single point of failure? What one thing could put us out of business next week?” This simple habit has transformed our resilience. We’ve identified data security gaps, supply chain weaknesses, and potential legal issues long before they became crises. It’s the most productive and important meeting of my week.

You’re not struggling to get funded because of your pitch. It’s because of your uninsurable risks.

The Risk No VC Will Touch

My startup had a great product and a killer pitch deck, but we kept getting turned down by venture capitalists. We couldn’t figure out why. A friendly VC finally told us the truth. “It’s not your pitch,” he said. “It’s your risk profile. Your business model depends on a new technology that has no regulatory framework, and your supply chain is based in a politically unstable region. You’re fundamentally uninsurable.” We learned that investors don’t just invest in an idea; they invest in a business that can be protected from catastrophic failure.

Stop buying off-the-shelf business insurance. Buy a manuscript policy instead.

The Policy Tailored Like a Suit

For years, my company bought a standard, off-the-shelf insurance package. It was like buying a suit off the rack—it mostly fit, but it was tight in some places and loose in others. We switched to a specialist broker who negotiated a “manuscript policy” for us. This meant our lawyers and broker worked with the insurer to draft a policy from scratch, with definitions and coverages tailored specifically to our unique business risks. It cost a bit more, but now our coverage fits us perfectly, with no dangerous gaps or unnecessary frills.

The uncomfortable truth about cyber insurance warranties.

The Promise You Made Without Knowing It

We diligently bought a cyber insurance policy. We thought we were protected. Then we had a data breach. The insurer denied our claim. Why? Buried in our application was a “warranty” clause. By signing the application, we had legally warranted that we had certain security controls in place, like multi-factor authentication on all accounts. We didn’t. The uncomfortable truth is that your cyber insurance application isn’t a questionnaire; it’s a binding legal promise. If your security practices don’t match your application, your expensive policy is worthless.

Why everything you know about Workers’ Comp is backwards.

The Experience Mod and the Race to the Top

Most business owners see Workers’ Compensation as a painful, uncontrollable tax. This is backwards. Your “experience modifier,” or e-mod, is a number that directly impacts your premium based on your company’s safety record compared to your peers. A good safety program that reduces claims can lower your e-mod below 1.0, earning you a significant discount. A bad record will raise it, costing you a fortune. Workers’ Comp isn’t a fixed cost; it’s a controllable one. It’s a race where having the best safety program actually makes you more profitable.

I tried to self-insure my company’s risks for a year. It was a disaster.

The Fund That Wasn’t

I thought I was being clever. Instead of paying high insurance premiums, I decided to “self-insure” by putting money aside into a rainy-day fund. It felt like I was saving a fortune. The disaster came when we were hit with two large, unrelated claims in the same quarter—a vehicle accident and a slip-and-fall. Our rainy-day fund was wiped out in a month, and we had to drain our operating cash to cover the rest. I learned that self-insuring isn’t just saving money; it’s taking on 100% of the volatility of unpredictable, catastrophic risk.

Hot take: Key Person insurance is overrated for most small businesses.

The Myth of the Irreplaceable Founder

Insurance agents love to sell “Key Person” life insurance, which pays the company if a founder dies. Here’s the hot take: for most small businesses, it’s overrated. If the business’s success is truly dependent on one single person, the business model itself is fundamentally broken. A far better investment of that money is in creating robust systems, cross-training employees, and building a business that can survive without any one individual. The goal should be to make Key Person insurance unnecessary, not to buy a policy that bets on your own indispensability.

Most business owners waste hours on insurance renewals. Do this instead.

The Broker Bake-Off

Every year, our renewal process was a nightmare of paperwork and meetings with our incumbent broker. We changed our approach. Now, 90 days before renewal, we initiate a “broker bake-off.” We send a formal Request for Proposal (RFP) to our current broker and two other, new specialist brokers. We make them compete for our business. This forces them to bring their best ideas and their most competitive pricing to the table. Instead of wasting hours in meetings, we spend a few hours reviewing professional proposals. It has saved us time, money, and improved our coverage.

The 15-minute habit that replaced my fear of employee lawsuits.

The Documented Conversation

As a manager, I used to live in fear of an employee dispute spiraling into a lawsuit. I started a 15-minute habit that has given me complete confidence. After any significant conversation with an employee—about performance, a complaint, or a schedule change—I take five minutes to write a simple, factual email to myself or our HR file summarizing the conversation, the date, and the outcome. This creates a contemporaneous, written record of my management actions. That simple paper trail is the most powerful defense against any claim of miscommunication or mistreatment.

Your business interruption isn’t caused by the disaster. It’s this.

The Real Reason You’re Still Closed

A fire destroyed our main supplier’s factory. Our business interruption insurance was supposed to cover our lost profits. But our claim was denied. The reason? Our policy covered interruption from damage to our property, not our supplier’s. The real cause of our shutdown wasn’t the fire itself, but our failure to have “contingent business interruption” coverage. This specific policy is designed to protect you when a critical supplier or customer is shut down, a nuance that can mean the difference between a paid claim and bankruptcy.

If you’re not carrying Employment Practices Liability Insurance (EPLI), you’re already losing to your competitors.

The Lawsuit and the Lost Opportunity

My company was hit with a wrongful termination lawsuit from a former employee. We didn’t have Employment Practices Liability Insurance (EPLI). The legal fees to defend ourselves were astronomical, even though we eventually won. That money—hundreds of thousands of dollars—was cash we couldn’t invest in new equipment or marketing. Meanwhile, our competitor, who had EPLI, was using their cash to grow. A lawsuit doesn’t just cost you legal fees; it costs you opportunity. By not carrying EPLI, you are letting your competitors get ahead.

Stop glorifying “hustle culture.” Start building a sustainable risk management plan.

The Hustle That Hid the Hazard

I was a disciple of “hustle culture.” I worked 80-hour weeks, cut corners to move faster, and ignored “boring” things like contracts and insurance. I thought I was being a gritty entrepreneur. In reality, I was just building a house of cards. The first time a major operational risk I had ignored—a supply chain failure—came to fruition, the business nearly collapsed. The hustle meant nothing. I learned that glorifying speed at the expense of stability is a fool’s game. A sustainable business is built on a solid foundation of risk management, not just on caffeine and ambition.

The real cost of a “free” business insurance quote that nobody calculates.

The Quote and the Hidden Cost of Your Time

Dozens of websites offer a “free” business insurance quote. The quote isn’t free. You are paying for it with your valuable time and, more importantly, with your company’s data. You spend hours filling out forms, only to be bombarded with calls from agents who don’t understand your business. The real cost is the wasted productivity and the risk of your data being sold. A better approach is to invest your time in finding one single, specialist broker who truly understands your industry. Their expertise is worth far more than a “free” quote from a generalist.

What successful founders do with their business insurance that struggling owners don’t.

The Strategic Shield

Struggling business owners see insurance as a necessary, painful expense to be minimized. Successful founders see it as a strategic tool for growth. They use robust insurance coverage as a competitive advantage. They know that having high liability limits gets them in the door with large corporate clients. They use their policies to attract and retain top talent. They understand that by transferring risk to an insurer, they can free up capital to invest in innovation. They don’t just buy insurance; they leverage it.

The myth of being “fully covered” is destroying your business’s future.

The Gaps in the “Full” Coverage

I proudly told my board we were “fully covered” by our insurance program. It was a dangerous myth. After a major claim was denied, I learned that there is no such thing as “fully covered.” Every single insurance policy has exclusions, sub-limits, and conditions. The phrase creates a false sense of security that leads to complacency. A better, more honest approach is to say, “We are covered for these specific risks, and we have consciously chosen to retain these other risks.” Acknowledging the gaps is the first step to managing them.

I quit using a captive agent and my company’s coverage improved by 200%.

The Agent and the Allegiance

For years, I used a “captive” insurance agent who only represented one single insurance company. He was a nice guy, but he could only offer me the products his one company sold. His allegiance was to his employer, not to me. I switched to an independent broker who represented dozens of different insurance carriers. The difference was stunning. The broker had access to specialized policies I had never heard of and was able to tailor a program that was vastly superior to my old one. My coverage improved dramatically because my new broker’s only allegiance was to my business.

Controversial: Your industry’s standard insurance program is holding you back.

The Standard That Stifled Innovation

My business operated in a niche industry that had a “standard” insurance program offered through a trade association. It was easy, but it was also a one-size-fits-all solution that hadn’t changed in 20 years. As my company innovated and our risks evolved, the standard program couldn’t keep up. It was holding us back. We made the controversial decision to leave the program and seek our own, manuscripted policy. It was more work, but it gave us the freedom to get coverage for our modern risks, not the risks of a bygone era.

95% of online advice about commercial insurance is wrong. Here’s why.

The Generalist Advice for a Specialist Problem

Almost all the advice you find online about business insurance is written by content marketers, not by insurance professionals. It’s generic, simplistic, and often dangerously wrong. It will tell you that you need a “BOP” without understanding your unique risks. It will talk about “general liability” without mentioning the critical professional or cyber liability you actually need. Commercial insurance is a complex, specialized field. Getting your advice from a blog post is like getting medical advice from a random stranger. You need a professional who understands your specific industry.

One small endorsement to our policy eliminated a major supply chain risk.

The Supplier and the Savior Endorsement

Our entire business relied on a single component from one specific supplier. Our biggest fear was a fire at their factory shutting us down. Our business interruption insurance only covered a fire at our own factory. Our broker suggested we add a “contingent business interruption” endorsement. It was a small additional premium, but it was a lifesaver. Six months later, our supplier’s factory had a major fire. Because of that one small endorsement, our insurance policy paid for our lost profits while they were rebuilding.

The truth about trade credit insurance that banks profit from hiding.

The Unpaid Invoice and the Unseen Protection

My business sells products to other businesses on credit. Our biggest risk was a major customer going bankrupt and not paying their invoices. Our bank told us this was just the “cost of doing business.” The truth they didn’t want us to know is that a product called “trade credit insurance” exists for this exact scenario. This insurance protects your accounts receivable. If a customer defaults, the policy pays you. It’s a powerful tool for de-risking your balance sheet that makes your business much more stable and attractive to lenders.

Stop renewing your policies on autopilot. It’s killing your bottom line.

The Autopilot Renewal and the Rip-off

For five years, I was so busy running my business that I put my insurance renewals on autopilot. My broker would send the renewal paperwork, I’d sign it without reading it, and send a check. I thought I was being efficient. I was actually being lazy and costing my company a fortune. When I finally decided to aggressively market my insurance program to other brokers, I discovered I had been overpaying by almost 30%. My complacency was a profit center for my old broker and insurer. Never renew on autopilot.

Replace your annual insurance review with a quarterly risk summit. Thank me later.

The Annual Autopsy vs. The Quarterly Checkup

The traditional annual insurance review with our broker always felt like an autopsy on the past year. It was reactive. We replaced it with a mandatory “quarterly risk summit.” Every 90 days, we meet with our broker, our attorney, and our key department heads. We don’t just review the policies; we discuss emerging risks, new contracts, and recent incidents. This proactive approach has transformed our risk management. We now solve problems in real-time, instead of just reviewing them once a year. Your future self will thank you.

The manufacturing industry secret that could save you millions in liability claims.

The Batch and the Blame

Here’s a secret from the manufacturing world that can save you from a massive lawsuit. It’s called “batch traceability.” For every single product run, we assign a unique batch number. We keep a physical sample from that batch, and we track which customers received products from it. When a customer claimed a defect in our product caused them damage, we were able to test our sample from the exact same batch. More importantly, we could prove the problem was isolated to that one batch, preventing a costly, full-scale product recall.

Why your traditional liability policy fails in the age of social media.

The Tweet and the Tort

Your General Liability (GL) policy was designed in an era before social media. It covers you for things like slips and falls. But what happens when your marketing manager posts a tweet that uses a competitor’s trademark, or an employee writes a blog post that defames another company? Your GL policy will likely not cover this. These are “personal and advertising injuries.” You need a modern policy with a broad definition of these injuries that specifically contemplates the risks of online content, or you’re facing down a modern lawsuit with an analog policy.

I ignored my lawyer’s advice on D&O insurance for years. It cost me my board seat.

The Board and the Brink of Bankruptcy

As the CEO of a private company, our lawyer always urged our board to buy Directors & Officers (D&O) insurance. We always voted against it to save money. Then, a disgruntled shareholder sued the entire board after a deal went bad. Facing the prospect of paying for our own legal defense out of pocket, the board was thrown into chaos. The conflict and financial strain were so intense that I was ultimately forced to resign. I lost my position because I was too cheap to buy the one policy designed to protect it.

Let’s be honest: Your “all-risk” policy is just a marketing term.

The Risk That Wasn’t “All”

My broker sold me an “all-risk” property insurance policy. The name made me feel incredibly secure. I thought it meant every possible risk was covered. Let’s be honest: it’s a marketing term, not a reality. When we had a flood, I discovered my “all-risk” policy had a very specific exclusion for flood damage. I learned that an “all-risk” policy doesn’t cover all risks. It covers all risks except for the long list of risks that are specifically excluded in the policy’s fine print.

87% of small businesses get business interruption insurance wrong. Don’t be one of them.

The Interruption and the Idol Hands

Our factory had a fire and had to shut down for three months. I thought our Business Interruption (BI) insurance would save us. It didn’t. The policy had a 30-day waiting period, so the first month of losses was completely uncovered. It also didn’t cover the wages for my key employees, so I lost them to competitors while we were rebuilding. I learned that BI insurance is incredibly complex. Without a detailed understanding of the waiting periods, coverage limits, and payroll provisions, the policy you buy might not be the lifeline you think it is.

This weird habit of reading the exclusions page first outperforms just checking the declarations page every time.

The First Page I Read

When my insurance policy arrives, I have a weird habit. Before I even look at the declarations page with the pretty premium numbers, I flip straight to the back and read the “Exclusions” section first. This is where the insurance company tells you what the policy doesn’t cover. It’s the most important part of the entire document. This habit has saved me countless times. It has helped me spot dangerous gaps in my coverage that I would have completely missed if I had only focused on the premium and the limits.

The real reason you can’t get affordable product liability insurance (hint: it’s not your product).

The Contract and the Uncovered Claim

My company manufactured a very safe product with a perfect claims history. Yet, we couldn’t get affordable product liability insurance. The real reason wasn’t our product; it was our contracts. We were signing sales contracts with huge retailers that contained broad indemnification clauses. We were contractually agreeing to be responsible for the retailer’s negligence. The insurance underwriters read these contracts and saw that we were taking on massive, unmanageable risks. Our bad contracts, not our good product, were making us uninsurable.

Ditch your high-deductible plan. Use a captive for your primary layer of risk instead.

The Deductible and the Disappearing Cash

My company had a liability policy with a huge, $100,000 per-claim deductible to keep our premiums low. The problem was, we had to pay that first $100,000 out of our own cash flow every time something happened. We ditched that plan and formed a captive insurer. Now, we pay premiums to our own captive, which covers that first $100,000 layer of risk. The money stays within our own corporate structure, earns interest, and can even be used for other business needs. We turned a volatile expense into a controlled, strategic asset.

Stop pretending your general liability covers reputational harm. Try a specialized policy.

The Rumor and the Ruined Reputation

A false, damaging rumor about my company’s product went viral on social media. Our sales plummeted, and our brand reputation was shattered. I thought our General Liability policy, which covered “advertising injury,” would help. It didn’t. That coverage is for things like libel and slander, not for the broader business impact of a damaged reputation. I learned that a specialized “reputational harm” insurance policy exists. It can cover the costs of a PR crisis firm, marketing campaigns to restore trust, and the lost profits from a damaged brand.

The 5-word phrase that changed how I think about insuring my business.

Insurance follows the contract, not logic.

I used to think that in a claim, the insurance would just logically pay for what seemed fair. I was wrong. My lawyer told me something that changed my entire approach to risk: “Insurance follows the contract, not logic.” This means the final decision on a claim isn’t based on what’s fair; it’s based on the exact, specific, and often confusing wording of the 100-page insurance policy you signed. This phrase forced me to stop assuming and start reading my policies like a lawyer.

What the logistics industry doesn’t want you to know about cargo insurance.

The Container and the Contract

When you ship goods with a freight carrier, they’ll offer to sell you “cargo insurance.” What the logistics industry doesn’t want you to know is that this is often not real insurance. It’s just a limited liability waiver where the carrier agrees to a very low, per-pound payout if they lose or damage your goods. For a shipment of high-value electronics, this would result in getting pennies on the dollar. To be truly protected, you need your own, separate transit or ocean marine insurance policy that covers the full value of your cargo.

I was today years old when I learned about contingent business interruption coverage.

The Supplier’s Fire, My Financial Freeze

A fire destroyed the factory of my company’s sole supplier for a critical component. Our own factory was fine, but without that component, we had to shut down production. I was today years old when I learned my business interruption policy wouldn’t pay a dime. It only covered interruptions caused by damage to my property. I discovered that a special coverage called “contingent business interruption” exists for this exact scenario. It protects your business when the property of a key supplier or customer is damaged, a risk I never even knew I had.

Normalize saying no to insurance audits that overstep their bounds.

The Auditor and the Overreach

Our workers’ compensation insurer sent an auditor to review our payroll records, which is a normal process. But this auditor started demanding access to documents and records that were far beyond the scope of the audit. He was on a fishing expedition. I learned to normalize saying “no.” I politely but firmly told the auditor that he was welcome to review the specific payroll documents outlined in the policy, but nothing else. You have a right to protect your company’s privacy and push back on an audit that oversteps its legal bounds.

Plot twist: Your biggest competitor isn’t the problem. Your uninsured supply chain is.

The Rival and the Real Risk

I spent years obsessed with my biggest competitor. I tracked their pricing, their marketing, everything. I was focused on the wrong threat. The plot twist came when a flood halfway around the world knocked out the factory that made a critical chip for my product. My entire supply chain was severed. My business was shut down for months. I realized my competitor was never going to put me out of business, but my fragile, uninsured supply chain could, and almost did. The real risks are often the ones you’re not watching.

The policy form everyone ignores that gives me an edge in a claim.

The Form and the Favorable Language

Most business owners just look at the price and the limits of their insurance. I look at the policy form number. Every policy is built on a standard, numbered form from an organization like the ISO. But insurers can use different versions of that form from different years. I always ask my broker to get me a policy written on the most recent, and often broadest, form available. I also ask them to identify any company-specific manuscript endorsements. Understanding the underlying form gives me a huge edge in knowing exactly what is, and isn’t, covered.

Stop optimizing for the lowest premium. Optimize for the broadest coverage.

The Premium vs. The Promise

For years, my company’s goal during insurance renewal was to get the lowest possible premium. We treated it like buying a commodity. This was a huge mistake. A low premium is often a sign of a weak policy, full of exclusions. We had a claim denied because our “cheap” policy had a narrow definition of our business operations. We changed our entire philosophy. We now optimize for the broadest possible coverage from the highest-rated carrier. A slightly higher premium is a small price to pay for a promise that will actually be kept when you need it most.

The brutal truth about why your risk management efforts aren’t lowering your premiums.

The Safety Program and the Silent Underwriter

My company invested a fortune in a new safety program. We had trainings, new equipment, everything. We were proud. Then our insurance renewal came, and the premium barely budged. We were furious. Here’s the brutal truth: the insurance underwriter doesn’t know, and doesn’t care, about your new program unless you tell them in a way they understand. We learned we had to professionally “market” our risk management efforts to the insurer, with documentation, statistics, and a formal presentation from our broker, to get the premium credit we deserved.

Throw away your standard contract’s insurance clause. It’s making you worse at risk transfer.

The Clause and the Court Case

Our company used the same standard insurance clause in our client contracts for a decade. We thought it protected us. It was actually making things worse. It was vague, it used outdated terminology, and it didn’t properly transfer risk. After a lawsuit where the clause proved to be unenforceable, our lawyer helped us draft a new one. It’s now sharp, specific, and tailored to our work. It clearly defines the other party’s insurance requirements and our rights. Our contract is now a tool that effectively transfers risk, instead of just creating confusion.

The 30-second test that reveals if your broker truly understands your industry.

The Acronym and the Answer

To find out if a potential new insurance broker really knows your industry, try this 30-second test. In your first conversation, use a common, but specific, technical acronym or term of art from your field. For a construction company, it might be “OCIP.” For a tech company, “SOC 2.” If the broker immediately understands the term and can discuss its insurance implications, they are a specialist. If they stare at you blankly or have to look it up, they are a generalist, and you should end the conversation.

Why everyone is wrong about the necessity of terrorism insurance.

The Act and the Aftermath

Most business owners outside of major cities think terrorism insurance is an unnecessary expense. They are wrong. They are thinking about a massive, headline-grabbing attack. But the definition of “terrorism” under the federal law that governs this insurance is broad. An act of politically motivated violence by a lone wolf against a specific business could be certified as an act of terrorism. If that happens, any damage to your property would be excluded from your standard policy unless you had bought the specific terrorism coverage. It’s a much broader risk than most people think.

Stop asking “what’s my premium?”. Ask “what’s my total cost of risk?” instead.

The Premium and the Bigger Picture

For years, the only number I cared about was my insurance premium. I thought that was my cost. I was wrong. My new risk manager taught me to ask a better question: “What is our Total Cost of Risk (TCOR)?” TCOR includes not just the premium, but also the cost of our deductibles, the administrative costs of managing claims, the cost of our safety programs, and the financial impact of uninsured losses. Shifting my focus from the small picture (the premium) to the big picture (TCOR) has allowed me to make much smarter, more strategic decisions about managing risk.

The habit of documenting everything that I wish I’d started on day one of my business.

The Paper Trail and the Payout

In the early days of my business, I operated on handshakes and verbal agreements. It was fast, but it was foolish. After my first major dispute with a client, where it was my word against theirs, I started a new habit. I document everything. Every client conversation is followed up with a summary email. Every change in scope gets a written change order. Every decision is recorded. This habit has been the single most important factor in my company’s success. My paper trail has won me disputes, clarified confusion, and even helped me win a denied insurance claim.

Here’s why generic insurance advice is terrible for tech startups.

The Code and the Coverage Catastrophe

Generic business insurance advice will tell a startup to get a Business Owner’s Policy. For a tech startup, this is terrible advice. A BOP is designed for a pizza shop. It has no meaningful coverage for the real risks of a tech company. What happens if a bug in your code causes a massive financial loss for a client? What if your platform has a data breach? What if you are sued for patent infringement? A tech startup needs a specialized portfolio of Technology Errors & Omissions, Cyber Liability, and Intellectual Property insurance.

I’ll say what everyone’s thinking: Your insurance broker is more loyal to the carrier than to you.

The Commission and the Conflict of Interest

Let’s just say what every business owner secretly thinks. Your insurance broker, especially if they are a captive agent, often has a stronger financial incentive to be loyal to the insurance carrier than to you. The carrier is the one who pays their commissions and offers them bonuses and trips. This creates an inherent conflict of interest. To combat this, you must be an educated, demanding consumer. You must force your broker to prove their value and their loyalty to you by making them compete for your business and by questioning their recommendations.

The skill of contract negotiation that matters more than your business credit score.

The Contract and the Credit

Business owners are often obsessed with their credit score, thinking it’s the key to their financial health. A far more important skill for long-term survival is contract negotiation. Your credit score might help you get a small loan. But a well-negotiated contract can save you from a multi-million dollar liability. The ability to understand and negotiate the insurance, liability, and indemnification clauses in your contracts with clients and suppliers is a skill that will have a much greater impact on your bottom line than a few extra points on your credit report.

This counterintuitive action of increasing my EPLI limits fixed my fear of hiring.

The Fear and the Freedom to Hire

I used to be terrified of hiring new employees. Every new hire felt like a new potential lawsuit for harassment, discrimination, or wrongful termination. This fear was holding my company back. I took a counterintuitive step. I worked with my broker to double the limits on my Employment Practices Liability Insurance (EPLI) and invested in a top-tier HR consulting service. The robust protection gave me the confidence to hire the people I needed to grow. I stopped seeing employees as risks and started seeing them as assets again.

Why your good intention of being transparent with your insurer is actually making your claims worse.

The Transparency Trap

I believed that in an insurance claim, the best approach was to be completely transparent and cooperative with the adjuster. This good intention was a mistake. I would speculate on the cause of the loss or offer information I wasn’t asked for, trying to be helpful. My words were then used against me to reduce or deny my claim. I learned that a claim is a legal and financial negotiation, not a friendly chat. You should be truthful, but you should only answer the specific questions asked. Do not volunteer information. It’s a transparency trap.

Quit using your insurer’s approved vendor list. It’s not worth the risk.

The List and the Lack of Loyalty

After a property loss, our insurance company gave us a list of their “approved” restoration vendors and strongly encouraged us to use them. We did, and it was a mistake. The vendor’s first loyalty was clearly to the insurance company, who sent them a steady stream of business. They cut corners, used cheap materials, and their main goal was to keep the cost down for the insurer, not to make us whole. Quit using the approved list. Hire your own, independent contractor who works for you, not for the insurance company.

The metric everyone tracks (revenue) that means absolutely nothing without proper liability coverage.

The Revenue and the Ruin

In the startup world, everyone is obsessed with revenue growth. It’s the ultimate vanity metric. We would celebrate every milestone, thinking we were successful. Then, we were hit with a product liability lawsuit that was larger than our entire year’s revenue. We had been so focused on the top line that we had neglected to buy adequate insurance. In that moment, our impressive revenue meant absolutely nothing. It was just a bigger number to lose. A business isn’t defined by its revenue, but by its resilience.

Stop calling it a “data breach.” Call it a “critical business failure.”

The Breach and the Business

The term “data breach” sounds like a technical IT problem. It allows the rest of the company to think it’s just a “tech issue.” I forced my company to change its language. We no longer call it a “data breach.” We call it a “critical business failure.” This simple shift in language makes everyone understand the true gravity of the situation. It’s not an IT problem; it’s a failure of the entire business that affects our customers, our reputation, and our bottom line. It makes everyone take the risk more seriously.

The decision I made to litigate a denied claim that everyone said was crazy (but worked).

The Denial and the Day in Court

Our insurance company denied a major claim, citing a vague exclusion in the policy. Our broker and our lawyers told us that fighting it would be long, expensive, and that we should just accept the denial. It felt like everyone was telling us to give up. I made a decision that everyone said was crazy: we sued the insurance company. It was a brutal, two-year fight. But in the end, the court agreed that the exclusion was ambiguous and ruled in our favor. Sometimes, you have to be willing to fight for the coverage you paid for.

What I learned from my first major lawsuit that changed everything.

The Lawsuit and the Lesson

We were two years into our business when we were hit with our first major lawsuit. It was a terrifying, all-consuming, and incredibly expensive experience. It was also the most valuable business education I ever received. It forced us to scrutinize every single aspect of our operations, from our contracts to our safety procedures to our insurance coverage. We learned more about our own vulnerabilities in that one year of litigation than we had in the two years prior. We survived, and the lessons we learned made our business a hundred times stronger.

The common mistake of misclassifying employees that’s costing you a fortune in workers’ comp.

The Contractor and the Costly Reclassification

To save money, my company classified several of our workers as “independent contractors” instead of “employees.” This meant we didn’t have to pay for their workers’ compensation insurance. We thought we were being clever. Then, one of the contractors was injured on our job site. The state labor board investigated and reclassified all our contractors as employees. We were hit with massive fines for back-due premiums and penalties. That “clever” attempt to save money ended up costing us a fortune and put us on the state’s radar for years.

PSA: Business interruption insurance without a contingent clause is a scam. Here’s proof.

The Interruption and the Incomplete Coverage

Here’s a public service announcement: if your insurance agent sells you a business interruption (BI) policy without also offering you contingent business interruption (CBI) coverage, they are selling you an incomplete product. A standard BI policy only covers your lost income if your own property is damaged. But what if a fire at your main supplier’s factory shuts you down? Or a flood at your biggest customer’s warehouse? A standard BI policy will not pay a dime. Only CBI covers you when a key partner in your supply chain goes down.

The skill of risk identification that business schools should teach but don’t.

The MBA and the Missed Risk

Business schools are great at teaching finance, marketing, and operations. But they almost never teach the single most important skill for a business leader: risk identification. They teach you how to pursue opportunity, but not how to see the threats lurking around the corner. The ability to look at a new product, a new market, or a new contract and ask, “What could go wrong here?” is a skill that is far more valuable for long-term survival than being able to build a complex financial model. It’s the biggest gap in modern business education.

This 5-minute action of reading your policy’s definitions beats trusting your broker’s summary every time.

The Definition and the Denial

My broker provided me with a neat, one-page summary of my new insurance policy. I trusted it and filed the full policy away. That was a mistake. After a claim was denied, I discovered that the policy’s definition of “employee” was different from my own understanding. The broker’s summary had glossed over this critical detail. I now have a 5-minute habit. When a new policy arrives, I immediately read the “Definitions” section. Understanding how the policy defines its own terms is the only way to truly understand what you’ve bought.

Why that big-name commercial insurer is actually doing it wrong for small businesses.

The Behemoth and the Small Business

I thought getting insurance from a massive, big-name commercial insurer would be the best choice for my small business. I was wrong. The big insurer’s systems, processes, and underwriters are all designed for giant corporations. My small business was just an annoyance to them. My application got lost, my claims were handled by a call center, and they had no flexibility. I switched to a smaller, regional carrier that specializes in small businesses. The service was better, they understood my needs, and I was no longer just a tiny, unimportant number on a behemoth’s balance sheet.

Stop waiting for a lawsuit to happen. Start with a comprehensive liability audit.

The Audit and the Avoidance

Most businesses only think about their liability risks after they’ve been served with a lawsuit. This is like waiting for your house to be on fire before you look for a fire extinguisher. The professional approach is to be proactive. We hired a law firm to conduct a comprehensive “liability audit” of our entire operation. They reviewed our contracts, our employment practices, our website, and our safety procedures. They gave us a report card with a dozen potential lawsuits waiting to happen. We spent the next six months fixing those issues and avoiding the fight altogether.

The risk management information system (RMIS) I use daily that most entrepreneurs have never heard of.

The Dashboard That Drives Decisions

I used to manage my company’s risks with a messy collection of spreadsheets and emails. It was chaos. Then I discovered the tool that professional risk managers use: a Risk Management Information System, or RMIS. It’s a software platform that centralizes all of our risk data—our insurance policies, our claims history, our safety incidents, and our vehicle fleet information. It gives me a single dashboard to see our entire risk profile in real-time. It’s a powerful, but little-known, tool that has transformed our ability to make smart, data-driven decisions.

Your claims problem exists because you believe the adjuster’s first offer is their best offer.

The Offer and the Opening Salvo

After a major loss, the insurance adjuster came back with a settlement offer. It seemed low, but I was tempted to take it just to be done with the process. My mentor stopped me. He said, “You believe that’s their best offer. It’s not. It’s their opening offer.” He was right. A claims negotiation is like any other negotiation. The adjuster’s first number is just a starting point. Your claims problem exists because you are treating a negotiation like a final declaration. By pushing back and documenting our full loss, we were able to double their initial offer.

Delete your insurer’s “small business” app. Your data privacy will improve instantly.

The App and the Unseen Data Mining

My commercial insurer had a slick “small business” app that let me manage my policy and file claims. It was convenient. It was also a data privacy nightmare. By using the app, I was giving the insurer a constant stream of data about my business’s location, my driving habits (if I had commercial auto), and my operations. This was all data they could use against me to raise my rates or deny a claim. I deleted the app. I would rather make a phone call than give my insurance company a 24/7 window into my business.

The advice on captives I give that makes CFOs uncomfortable (but works).

The Captive and the Calculated Risk

When I suggest to a CFO that they should use their new captive insurance company to insure a really difficult, high-risk part of their business, they get uncomfortable. They want to put the “safe,” predictable risks in the captive. My advice is to do the opposite. The commercial insurance market is great at pricing predictable risks. Use your captive to solve the problems the market can’t. By taking on a calculated, well-understood risk inside your own company, you can build a massive strategic advantage that your competitors can’t replicate.

Why the common fear of high premiums is irrational and the real fear of a company-ending lawsuit is ignored.

The Fear of the Known vs. The Fear of the Unknown

Business owners have an irrational fear of their insurance premium. They see it as a definite, painful cost, and they fight to reduce it. The real, rational fear that they should have—but often ignore—is the fear of a massive, company-ending lawsuit. The premium is a known, manageable number. The potential size of a lawsuit is an unknown, catastrophic number. Fearing the small, definite cost while ignoring the massive, potential risk is a classic psychological trap that leads to chronic underinsurance and, ultimately, to ruin.

I tried to use a Professional Employer Organization (PEO) for my insurance so you don’t have to. Here’s what happened.

The PEO and the Problem

I thought I was being clever by outsourcing my HR and insurance to a Professional Employer Organization (PEO). They handled our payroll and gave us access to their “master” insurance policies. It was a disaster. When we had a major workers’ comp claim, we discovered we had no control over the process. We were just one small company among hundreds on their policy, and our unique needs were ignored. When we tried to leave the PEO, we found we had no insurance history of our own, making it incredibly difficult to get standalone coverage.

The question about reinsurance that instantly reveals if a broker knows their stuff.

The Question About the Insurer’s Insurer

When I’m interviewing a new, large commercial insurance broker, I ask them this one question: “Can you walk me through the reinsurance structure of the primary carrier you are recommending?” An amateur broker will stare at me blankly. A true professional will immediately be able to discuss the insurer’s financial strength and how they use their own insurance—reinsurance—to protect themselves from catastrophic losses. This question reveals whether your broker is just a salesperson, or a sophisticated advisor who understands the deep financial structure of the insurance market.

This old-school method of using an independent broker beats every modern insurtech platform.

The Broker and the Bot

The new “insurtech” platforms are slick. They promise to find you the best business insurance with an algorithm. But an algorithm can’t understand the unique nuances of your business. It can’t negotiate with an underwriter on your behalf. It can’t give you strategic advice. I’ll take an old-school, experienced, independent insurance broker over a modern insurtech platform every single day. A bot can give you a quote. A broker can give you wisdom, advocacy, and a long-term relationship. The choice is easy.

Stop romanticizing insurtech for business. It’s actually just a lead generation tool.

The Tech and the Truth

The venture capital world is pouring money into “insurtech,” romanticizing the idea of disrupting the old-fashioned insurance industry. The truth is, for commercial insurance, most of these platforms are just sophisticated lead generation tools. They have a great user interface that collects your information, and then they sell that lead to the same old-school brokers and carriers. They aren’t disrupting the fundamental business of underwriting complex risk; they are just disrupting the way that customers are acquired. It’s a marketing innovation, not an insurance innovation.

The principle of indemnity that guides every major business claim I’ve filed.

The Promise to Make You Whole

The most fundamental principle in insurance is “indemnity.” It’s a simple promise: in the event of a loss, the insurance policy should restore you to the same financial position you were in just before the loss occurred. Not better, not worse. Understanding this principle guides my entire claims process. When I present a claim, I’m not asking for a windfall; I am providing the documentation to show the insurer exactly what it will take to make my business whole again. It frames the negotiation around a principle of fairness, not a lottery ticket.

Why your premium is vanity and your risk-adjusted return on capital is sanity.

The Premium vs. The Performance

As a CEO, I used to focus on our insurance premium as a key metric. It’s a vanity metric. The number that represents sanity is our “risk-adjusted return on capital.” I now view our risk management and insurance program as an investment. We spend a certain amount of capital on premiums, deductibles, and safety programs. In return, we get a more stable, resilient business. The real measure of success is how efficiently we are using that capital to reduce our risk and improve the overall financial performance of the company.

Forget work-life balance. Aim for risk-reward optimization for your business instead.

The Balance and the Business

The concept of “work-life balance” is a popular, but ultimately personal, goal. As a business owner, a more useful concept to strive for is “risk-reward optimization.” For every major decision, from launching a new product to entering a new market, we don’t ask about balance; we ask about the relationship between the potential reward and the inherent risk. Is the potential upside worth the potential downside? This disciplined focus on the risk-reward tradeoff is the foundation of every single sustainable, profitable business.

The realization that made me quit using a direct writer for my commercial policies forever.

The Direct Writer and the Dead End

I used to buy my business insurance from a “direct writer”—an insurance company that sells its own products directly to the public. I thought I was saving money by “cutting out the middleman.” I was wrong. When my business’s needs became more complex, the direct writer had nothing more to offer me. They only had their own, limited set of products. I had hit a dead end. The realization that I needed choice, advice, and advocacy made me switch to an independent broker. I will never use a direct writer again.

What startup founders do with insurance that seasoned CEOs never do.

The Afterthought vs. The Asset

Startup founders, in their rush to grow, almost always treat insurance as an afterthought. It’s the last, annoying thing they do only when a client or an investor forces them to. A seasoned CEO of a mature company would never do this. They see the insurance and risk management program as a strategic asset. They involve their risk advisor in major decisions before they are made. They understand that a well-designed insurance program is not a cost center; it’s a tool that enables and protects the entire enterprise.

The investment in a fractional risk manager that everyone avoids that has the highest ROI.

The Manager and the Millions Saved

My mid-sized company wasn’t big enough to hire a full-time, professional risk manager. But we were too big to manage our risks on a spreadsheet. We made an investment that everyone thought was crazy: we hired a “fractional risk manager,” a consultant who acted as our part-time expert for a few hours a week. It was the highest ROI decision we ever made. He professionalized our entire program, improved our safety, and negotiated our insurance, saving us hundreds of thousands of dollars.

Stop saying “we’re insured.” Say “we’re covered for these specific perils.”

The Peril and the Policy

I used to tell my partners, “Don’t worry, we’re insured.” It was a vague, comforting, and completely meaningless statement. I learned to be more precise. Now, I say, “We are covered for the specific perils of fire and wind, but we are not covered for flood.” This simple change in language forces a more honest and accurate conversation about risk. “Insured” is a feeling. “Covered for specific perils” is a fact. Understanding the difference is the first step to true risk management.

The truth about underwriting I couldn’t say as a commercial lines underwriter.

The Underwriter and the Unspoken Truth

I used to be a commercial insurance underwriter. Here’s the truth I couldn’t say out loud: the quality of the broker matters more than you think. When two submissions for similar businesses came across my desk, I would almost always give a better price and broader terms to the one submitted by a broker I knew and trusted. A professional, detailed submission from a top-tier broker told me the risk was well-managed. A sloppy submission from a random agent signaled problems. The broker is a reflection of the quality of the client.

This tiny detail in the “other insurance” clause separates amateur brokers from professionals.

The Clause and the Court Battle

My company had two different liability policies that both potentially covered the same claim. A legal battle erupted between the two insurance companies over which one had to pay first. It was a nightmare. A professional broker understands the “other insurance” clause in a policy. They know how to structure your coverage so it’s clear which policy is “primary” and which is “excess.” An amateur broker ignores this tiny detail, which can lead to a massive, expensive court battle between your own insurers.

Why a high self-insured retention is a trap for businesses with volatile cash flow.

The Retention and the Roller Coaster

To get a lower premium, my seasonal business took on a high “self-insured retention” (SIR), which is like a huge deductible. It seemed smart in the off-season. But when we had a major claim during our busiest, most cash-intensive season, we were suddenly forced to write a massive check for the SIR right when we needed that cash the most. A high SIR is a trap for any business with volatile cash flow. It can force you into a liquidity crisis at the worst possible time.

Replace your complicated renewal process with a simple broker RFP. You’re welcome.

The Renewal and the Revolution

Our annual insurance renewal was a painful, month-long process of endless meetings and paperwork. We replaced it with a simple, revolutionary idea: a formal Request for Proposal (RFP). Ninety days before renewal, we send a detailed RFP to three different, qualified brokers (including our current one). We make them do the work. They come back to us with their best, most competitive proposals. It minimizes our workload, maximizes competition, and ensures we see the best options the market has to offer every single year.

The skill of manuscripting endorsements that’s 10x more valuable than a good relationship with your underwriter.

The Manuscript and the Masterstroke

Having a good relationship with your insurance underwriter is nice. But the skill of “manuscripting endorsements” is ten times more valuable. A standard policy is just a collection of pre-written forms. A true insurance professional can work with the underwriter to draft custom endorsements—manuscripted language—that alters the policy to fit your specific needs. They can change definitions and delete exclusions. This skill, the ability to actually re-write the contract in your favor, is the ultimate masterstroke in commercial insurance.

Stop treating your commercial policy like a utility bill. Treat it like a capital asset instead.

The Bill vs. The Balance Sheet

Most business owners treat their insurance policy like a utility bill—a boring, recurring expense that you just have to pay. This is the wrong mindset. You should treat your insurance program like a capital asset. It’s a strategic tool on your balance sheet that protects all your other assets. It enables you to take on bigger projects, it gives you the confidence to invest and grow, and it provides resilience in a crisis. It’s not an expense; it’s a high-performing, protective asset.

The experiment I ran with a rolling claims review that proved our safety program wrong.

The Review and the Revelation

We thought we had a great safety program. We were wrong. I ran an experiment. Instead of waiting for the annual insurance review, I started a “rolling claims review” with my broker every month. We looked at every single small incident, even the ones that didn’t result in a claim. The data was shocking. It revealed a pattern of injuries in one specific department that our safety program had completely missed. That regular, data-driven review proved our assumptions wrong and allowed us to fix a problem we didn’t even know we had.

Why your old general liability policy worked before but doesn’t in the gig economy.

The Gig and the General Liability Gap

Your old General Liability policy was designed to cover the actions of your full-time, W-2 employees. But what about the dozen independent contractors, freelancers, and gig workers you now use to run your business? Your old policy likely has a maze of exclusions related to the work of subcontractors. In the modern gig economy, you need a policy that is specifically built to handle the liability of a blended workforce, or you are operating with a massive, uninsured gap.

The choice to use a non-admitted carrier that everyone judges that actually makes sense for emerging risks.

The Admitted and the Advantage of the Alternative

My business was in a new, emerging industry, and no standard, “admitted” insurance carrier would cover us. My broker suggested we use a “non-admitted” or “surplus lines” carrier. My board was nervous; these carriers aren’t backed by the state’s guarantee fund. But it was the only way to get the specific, manuscripted coverage we needed for our unique risk. The choice to use a non-admitted carrier, while seeming risky, was the only choice that allowed us to transfer our most critical business risk and grow with confidence.

I stopped automatically renewing my D&O policy and a bidding war happened.

The Renewal and the Remarketing

For years, I automatically renewed my company’s Directors & Officers (D&O) policy with the same carrier. I thought I was getting a fair deal. This year, I decided to stop. I told my broker to aggressively “remarket” our policy to every qualified carrier in the space. A bidding war erupted. We received multiple, competitive quotes, and the final premium was 25% lower than my automatic renewal offer, for broader coverage. I learned that loyalty in the insurance world is a one-way street. Make them fight for your business every single year.

The concept of “moral hazard” that nobody in Silicon Valley understands but changes everything.

The Hazard of the Hustle

“Moral hazard” is the idea that if you are protected from risk, you are more likely to behave recklessly. This concept is completely lost on the “move fast and break things” culture of Silicon Valley. Startups raise huge sums of money, which insulates them from the immediate consequences of their bad decisions. This creates a massive moral hazard. They take on huge, uninsurable risks, believing the VC money is a permanent safety net. Understanding this one insurance concept changes how you view the entire startup ecosystem.

This unpopular opinion on premium audits will trigger accountants but it’s true.

The Audit and the Argument

Here’s an unpopular opinion that triggers my accountant: you should treat your insurance premium audit as an adversarial process. The auditor sent by the insurance company is not there to help you. They are trained to look for every possible way to classify your payroll and sales into higher-rated categories to increase your final premium. You should have your own representative—your broker or an outside consultant—present during the audit to argue for the most favorable interpretations and to ensure the auditor is not overstepping their bounds.

Stop copying your competitor’s insurance limits. Do your own risk assessment instead.

The Competitor and the Catastrophe

When my CFO asked how much liability insurance we should carry, I told him to just find out what our biggest competitor carried and copy that. This was a lazy and dangerous mistake. Our competitor had a different risk profile, a different tolerance for risk, and a different financial structure. We were copying an answer without understanding the question. You should never base your insurance limits on what someone else is doing. You must do your own, unique risk assessment to determine the right limits for your own, unique business.

The mistake of ignoring defense costs outside the limit that I see everywhere that’s so easy to fix.

The Defense and the Depleting Limit

We were hit with a major lawsuit. Our liability policy had a $1 million limit. What I didn’t realize was that the cost of hiring lawyers to defend us was being deducted from that $1 million limit. By the time we got to a settlement, our legal fees had already eaten up $300,000 of our coverage. It’s an easy mistake to fix. For a small additional premium, you can often get a policy where “defense costs are outside the limit,” meaning the legal bills don’t erode your protection. It’s one of the most important upgrades you can make.

Why this new “on-demand” business insurance isn’t innovative. It’s just a reporting policy repackaged.

The “Innovation” That’s a Century Old

A new insurtech app offered my business “on-demand” insurance that I could turn on and off by the day or by the project. It was marketed as a revolutionary innovation. It’s not. It’s just a clever new interface for a type of policy that has existed for a hundred years: a “reporting policy.” You are still buying an annual policy, but you are reporting your activity (and paying your premium) on a more frequent basis. It doesn’t change the underlying coverage or the risk transfer; it just changes the payment plan.

The rule of “utmost good faith” I break with underwriters consistently (and why you should too).

The Good Faith and the Better Result

The legal principle of “utmost good faith” says I must be completely honest in my insurance application. I am. But I break the spirit of the rule consistently. I don’t just passively answer the questions. I treat my submission as a professional marketing document. I don’t just state our revenue; I provide a detailed narrative about our company’s strengths, our safety programs, and our management team. I go far beyond what is asked to proactively “sell” my company as a good risk to the underwriter. This aggressive, but honest, approach gets me better results every time.

Stop believing your BOP covers everything. Believe in the power of standalone policies instead.

The BOP and the Big Omission

A Business Owner’s Policy (BOP) is a convenient bundle of property and liability insurance for a small business. It’s also a trap. To keep the price low, a BOP is full of omissions and low sub-limits for critical coverages like cyber liability, professional liability, and employment practices liability. As my business grew, I learned to stop believing in the BOP. I “unbundled” my insurance program and bought separate, standalone policies for each of my major risks. The standalone policies provide much broader and more robust coverage than any BOP ever could.