
By Seth Tarboro, EHD Select Producer
Spring is in the Air! As someone who is all but allergic to the wintertime, March brings quite a lot to look forward to. Warmer weather, flowers in bloom, Leprechaun traps and less layers meaning we can do away with coats over the quarter zips. Obviously, that’s not all. March is known for many things and possibly most well-known for the college basketball tournament, March Madness! What’s not to love? Sixty-eight teams going head-to-head with the same goal in mind. Representing their school with pride and being the last team standing to cut down the nets. The drama is one of a kind. Cinderella stories of low expectations and meteoric rises. Historic buzzer beaters leading to massive upsets we discuss at the water cooler. My wife filling out her bracket entirely based on best uniforms and somehow still doing better than me.
March Madness is an exciting time that brings communities together, but basketball may not be for everyone. For that reason, March is also the month of the only slightly less well-known March Margins Madness. A tournament style bracket of fictional small businesses designed to evaluate several claim scenarios for different industries and the Most Valuable Policy needed to protect their profitability against those risks… Okay — you got me. This is technically the inaugural season of this tournament but just give it a year and you’ll be wearing the T-shirt!
East Bracket – Round 1
In this first round matchup, we’ll be pitting retail against the service industry. Our first competitor, Justine’s Jerseys. Justine owns a beloved jersey shop on main street in her hometown. This isn’t just any jersey shop, however, as these are one of a kind, hand stitched and designed (sometimes bedazzled) by Justine herself. She leases an eight hundred square foot space and on average carries up to twenty thousand dollars in inventory. Her broker recommended coverages such as general liability, business personal property, business interruption and a few others that she wasn’t sure were necessary, but after helpful education decided may be worth having.
As business has been booming for a while, Justine decided to make some necessary upgrades before the spring rush. New equipment to work quicker and more efficiently. As well as some upgrades to the fixtures, cabinets and flooring. Justine’s Jerseys is operating at peak performance, and she believes she has the right coverage to take her all the way.
She has a formidable opponent in round one. That being Party Time Planners. Party Time offers a diverse range of event planning services from weddings to graduation parties to conferences and charity fundraisers. This two-man operation has never had a need for a brick-and-mortar location. They coordinate events and schedule with vendors online. They chose to find and purchase insurance themselves and were able to obtain a package that included general liability and professional liability.
Party Time Planners decided they’d like to scale their operation by offering audio/visual services. They purchased/rented up to two hundred thousand dollars’ worth of equipment which was being stored in a storage facility when not in use. They opted against purchasing the insurance offered by the facility as they were sure to manually add business personal property coverage to their package.
Unfortunately for our competitors, both businesses suffer fire losses in 2026. Many of the upgrades Justine made are damaged beyond repair. She first contacts the property owner to see if their insurance will cover it. Their policy will cover the damage but only to return the boutique to its original condition and not indemnify Justine by replacing the upgraded fixtures, cabinets and flooring. As disappointing as an airball from the free throw line…
Nearly all of Party Time Planners A/V equipment is lost in a fire that occurs at the storage facility. They immediately move forward with filing a claim for business personal property. Unfortunately, the claim is denied stating that the BPP coverage they added on their own was only to cover property kept at the primary policy address and that to include coverage at a separate location, it would’ve needed to be endorsed with Off-Premises coverage. Suddenly the event planners must shift all their focus to paying back the equipment rental company. Meanwhile, after getting bad news from her landlord, Justine contacts her broker who provides peace of mind. When setting up her policy, they included Improvements and Betterments coverage which will cover the cost of replacing her upgrades in full. Like Lamont Butler from San Diego State in 2023, this line of coverage came through in the clutch to send Justine to the Championship game.
West Bracket – Round 1
On the other side of our bracket, we find two very different businesses. First, Cornerstone Contractors, a construction company looking to ramp up their projects this year as warmer March weather brings more opportunities. Cornerstone is primarily a drywall contractor who specializes in residential properties. Their longtime broker has seen to it that they carry a satisfactory amount of general liability, business personal property, commercial auto, workers’ compensation and a host of other coverage to protect themselves and their equipment when stored or in transit/at a jobsite. As part of their expansion, they’ve begun repairing and replacing residential roofs.
Cornerstone will be tipping off against Astonishing Web Design. A new venture website design company hoping to make a name for themselves in 2026. This one-man band wanted to be well protected and sought out a broker experienced with the insurance necessities of a tech-based business. They were encouraged by the suggestions of their new advisor and obtained general liability insurance along professional liability and an extensive cyber package.
While replacing a roof for one of their new clients one of Cornerstone’s employees falls from the roof. The company braces for a hefty claim and for their previously spotless record to take a hit. To make matters worse their broker advises them that they never updated their business operations to include a roofing exposure and is unsure as to how the carrier will handle the claim.
As for our at-large team in Astonishing Web Design they have seen immediate success with their first few clients. So much so that positive word of mouth has spread and their client base has begun outgrowing their available time. Though they thought they were keeping up with all tasks, one job slipped through and they were unable to meet an agreed upon deadline to have a client’s website completed. The client was not happy about the missed deadline, but thankfully the tech errors and omissions coverage included in the cyber policy will supplement the losses the client experienced for not being up and running on time. So, the mid-major little engine that could rolls along to our championship round, while Cornerstone faces the uncertainty of claim status, increased rates and/or non-renewal.
Championship Round
Justine’s Jerseys goes head-to-head with Astonishing Web Design in our championship round. After surviving the first round of losses and rebounding to stay in the dance, both squads are again faced with a challenge. This time by way of the internet. Justine’s unique brand of sports attire goes viral and reaches new customers all over the country. Her online sales begin to balloon and with that brings new risks. Astonishing Web Design continues an upward trajectory, collaborating with expanded clientele, and providing a valuable service. Both businesses seem to be cruising to championship glory until their systems get hacked. Their networks are infiltrated and sensitive customer data is stolen and exposed publicly. Each of their trusted insurance partners advise them that their cyber liability policies will cover the direct costs incurred by the business such as data breach notification costs, forensic investigation costs to determine how the breach occurred and even business interruption losses. Unfortunately for Justine, the coverage ends there. Astonishing Web Design’s robust cyber package extends to third party liability which will provide coverage for legal defense fees and costs incurred by their clients. Justine will have to settle for runner up, because the Web Designer is cutting down the nets as this tournament’s champion!
Conclusion
This basic exercise depicts just a fraction of how many different risks exist among small business industries and hopefully provides a few actionable tips to keep your business alive in the bracket.
- Find an insurance advisor you trust to keep your business’ success their top priority.
- In an increasingly DIY world, there is no substitute for an expert.
- Be sure to regularly communicate with your advisor and update them on operational changes.
- Stats are important, but when filling out your bracket, don’t forget to consider the uniform. A bedazzled jersey is at least enough for 2nd place.

