Today's unconventional solopreneur may be tomorrow's regional success story — that's why we need more inclusive underwriting.
Insurance is a safety net many take for granted—until they realize they've been excluded from it.
For countless small businesses across the U.S., securing coverage isn't just a bureaucratic hurdle. Instead, it's a barrier to entry. Without insurance, a budding business can't bid on contracts, rent space, or even get off the ground. Yet, many are shut out because their business models don't fit neatly into a traditional underwriting box.
As an industry, we have a duty and an opportunity to do better.
Having spent much of my career in insurance product development and underwriting, I've seen the mechanics of risk evaluation up close. I've also seen how legacy approaches can leave unconventional businesses out in the cold. From part-time side hustles to gig-driven enterprises, the insurance industry often struggles to keep pace with the changing nature of entrepreneurship. This is where innovation and inclusivity must intersect.
We're often likely to insure individuals' passions that happen to develop into businesses. For instance, we insured a young man's lawn mowing business that evolved into a thriving business. He started the business before even entering high school, and most insurance carriers would have rejected him for not having enough years of experience. If we had relied on conventional underwriting rules that required three-plus years of experience to get a policy, we would have extinguished his passion before it even began.
At Simply Business, we encounter entrepreneurs every day who have been turned away by traditional channels—not because they're high risk, but because they're misunderstood.
Microbusinesses, particularly those owned by first-time founders or individuals in non-traditional trades, often face either excessive premiums or complete exclusion, with 20-30% of small businesses struggling to obtain insurance. In fact, nearly one-third of uninsured business owners in one of our recent surveys reported relying on Google or peers for insurance recommendations because they've been unable to access professional guidance or fair pricing.
That's not a sustainable future for our industry—or our economy. Small businesses generate 44% of U.S. economic activity. If we're not willing to protect them, we're failing to protect the very foundation of American enterprise.
Meeting Customers Where They Are
Expanding access starts with rethinking how we define risk. A thoughtful underwriter doesn't immediately reject a policy because it's unfamiliar. They look deeper. Our insurance carriers have stepped up to cover everything from pet waste removal professionals to holiday light installers—trades most carriers wouldn't bother pricing. But by leveraging digital platforms and informed risk frameworks, we've been able to meet these customers where they are—and help them get to where they're going.
Technology plays a key role here. Digital buying experiences can offer clarity, transparency, and ease to entrepreneurs navigating insurance for the first time. Much like the shift from paper tax forms to TurboTax, online insurance tools demystify an opaque system. But digital tools alone aren't enough—we must also rewire our risk models to accommodate the range of business owners knocking on our doors.
I remember speaking with a sweet tea vendor—formerly an airline mechanic—who traveled from fair to fair trying to grow her new business. She couldn't find anyone willing to insure her, and this prevented her from selling at the local food festival. She wasn't asking for a handout. She just wanted a chance to build the business that was her passion. And that's what insurance is really about: giving people the opportunity to achieve their dreams.
If we want to remain relevant and responsible stewards of risk, insurers must reevaluate how we define insurability. We must develop products that flex to fit emerging business models, not the other way around. This isn't charity—it's smart, future-focused business.
Now is the time to take a hard look at our models and expectations. Are we broadening our understanding of risk? Are we designing products that reflect the real world of entrepreneurship today? If not—why not? The businesses we overlook today are the ones that will define tomorrow.
Let's build an industry that makes room for all of them.
