S2 EP27 How This Roofing Company Hit $3 Million in 36 Months!
Discover how Alpha Pro Roofing scaled to a $3M business through values-driven leadership, family involvement, and technological innovation. Learn key...
Discover how captive insurance helps small contractors reduce rising insurance costs, gain buying power, and stabilize premiums with expert Rich Hess.
Over the past several years, contractors and small business owners have faced a relentless surge in insurance costs. Whether it’s property and casualty, general liability, or workers’ compensation, premiums are climbing, squeezing already tight margins and making it harder for businesses to stay afloat. For many, insurance has become the second largest expense after payroll, and the frustration is palpable: “Insurance has been just destroying us and rising costs. We don’t know what to do.”
But what if there were alternative strategies to manage these costs—approaches that not only stabilize premiums but also give business owners more control and even the potential for profit sharing? Enter the world of self-funding, captives, and a new era of insurance consumerism.
This article explores the insights shared by Rich Hess, a seasoned insurance executive with Plexus Group, as he demystifies the insurance landscape for contractors and small business owners. We’ll break down the key concepts, practical strategies, and future trends that can help you take back control of your insurance destiny.
Most small businesses, especially those with fewer than 50 or 100 employees, are “fully insured.” This means they purchase off-the-shelf insurance products from major carriers—often referred to as the “BUCAs” (Blue Cross, United Healthcare, Cigna, and Aetna). These plans are easy to buy but offer little flexibility or negotiating power. The insurance company sets the price, and the employer pays it, often with little understanding of how the costs are determined or how to influence them.
The fully insured model leaves small businesses at the mercy of annual rate hikes. As claims increase—often due to employees’ lack of awareness about healthcare costs—premiums rise. Employers are forced to make tough decisions: cut benefits, raise deductibles, or absorb the cost and hope for a better year.
But there’s a catch: insurance companies are not benevolent. They are in business to make a profit, and they do so not just from premiums, but also from investing those premiums and managing claims in ways that maximize their bottom line.
Self-funding is a model where the employer pays for claims out of their own funds, rather than paying premiums to an insurance company. This approach is more common among larger employers but is increasingly accessible to smaller businesses through creative plan designs and risk mitigation strategies.
One popular self-funding strategy is the “bridge plan” or “donut hole” approach. Here’s how it works:
Statistically, only a small percentage of employees will need to use this fund, so over time, the employer often comes out ahead, building a reserve that would otherwise have gone to the insurance company.
Captive insurance takes self-funding to the next level by pooling the risk of multiple employers—often across different industries and geographies—into a single entity. This collective approach offers several advantages:
The biggest pushback against captives and self-funding is a lack of understanding and fear of risk. Many small business owners are overwhelmed by the complexity and worry about taking on additional financial exposure.
But as Rich Hess points out, entrepreneurs are already accustomed to risk. The key is education and risk mitigation:
A major driver of rising healthcare costs is employee behavior. Most people don’t know how much medical services cost or how to shop for better prices. The insurance industry has, intentionally or not, created a system that discourages transparency and consumerism.
Employers can combat this by:
Most employers who join a captive end up staying—and thriving. The benefits are tangible:
One exception: if a company has a known, high-cost claimant (such as a hemophiliac requiring expensive medication), it may make sense to remain fully insured for a period. But for the vast majority, captives offer a path to long-term savings and stability.
Insurance is a numbers game. Statistically, most employers will have one “bad” claims year out of every five. The other four years, they come out ahead, building reserves that can offset the occasional spike. The key is to plan for the long term and not panic when a bad year happens.
Not every solution fits every business. A good consultant will:
This personalized approach ensures that benefits align with what employees value and what the business can sustain.
The insurance industry is on the cusp of a technological revolution. Artificial intelligence is already being used to:
As employees become more educated and empowered, they are starting to behave like consumers in other markets—shopping for value, comparing prices, and making informed decisions. This shift is essential for controlling costs and driving innovation in plan design.
With an aging workforce and evolving risk profiles, captives and self-funded plans are adapting by:
While much of the discussion focuses on health insurance, similar principles can apply to property and casualty (P&C) insurance. Rising construction and replacement costs have driven up premiums for real estate and rental property owners. While the specifics differ, the core idea remains: pooling risk, leveraging buying power, and seeking out alternative structures can help manage costs.
If you’re a property owner or investor, consult with a P&C specialist to explore whether group purchasing, captives, or other innovative solutions are available in your market.
No journey is without its missteps. Rich Hess shared a candid story about leaving the insurance industry to buy a franchise in the graphics and sign business—without seeking help or understanding the nuances of the new field. The experience was humbling but invaluable, teaching lessons about the importance of preparation, relationships, and adaptability.
The takeaway for contractors and business owners: Don’t be afraid to seek advice, learn from mistakes, and build relationships that can help you navigate complex challenges.
Insurance doesn’t have to be a black box or a runaway expense. By embracing education, consumerism, and alternative funding models like self-funding and captives, contractors and small business owners can regain control, stabilize costs, and even share in the profits of prudent risk management.
The key is to approach insurance as a strategic investment, not just a necessary evil. With the right partners, tools, and mindset, you can build a benefits program that supports your business, attracts top talent, and stands the test of time.
If you’re ready to explore your options, reach out to a knowledgeable consultant, analyze your data, and start the conversation. The future of insurance is changing—make sure your business is ready to change with it.
Discover how Alpha Pro Roofing scaled to a $3M business through values-driven leadership, family involvement, and technological innovation. Learn key...
ShipShape's AI-driven smart home tech reduces maintenance costs, boosts contractor sales, and protects homes from costly water damage.
In this episode of Beers with Contractors, hosts Will and Terry interview H.B. Marshall, VP of Sales and Business Development at Your Crawlspace....
For when we add more articles just like this one!