I don’t have your typical “CEO success story.” I haven’t been dreaming up businesses since birth or running startups since I was 17. My dreams were on the baseball diamond, where I learned what it takes to compete, strategize, push through setbacks and rally a team to victory — it’s shaped how I approach leadership today. Even now, coaching my sons’ baseball teams is where I find solace and solutions.
I’ve always loved an underdog story. Players defying the odds, teams rallying from a 10-run deficit in the 7th inning to pull off an impossible win. Those moments are unforgettable. Baseball, at its core, is about strategy and beating the odds. Running a business isn’t much different, and when I took over a company poised for change, those lessons became my playbook.
Moving to the big leagues: Online boom or bust
In 2004, I was an insurance broker working in the excess and surplus (E&S) lines space at a brokerage called Stratus in some of the riskiest areas of commercial casualty insurance. Sporting equipment, climbing gyms — you name it — businesses few wanted to touch because they were so risky.
Online distribution models were starting to take off, but the insurance industry just wasn’t ready for it, especially for niche, high-risk businesses. Buying coverage was already such a headache, and we realized we needed to approach things differently if we wanted to keep up. Then everything changed.
Stratus’s former owner bought back his portion of the company after a merger in 2005 and decided to move the business to Utah. He wanted someone who could take the blueprint and foundation he had and transform it into a new business before he retired. When he saw my vision, he put that trust in me. My family packed up, left Richmond, Virginia, and headed to Pleasant Grove, Utah, ready to start fresh.
We knew we needed to rethink our model to not only survive but actually thrive in this new digital age. But the odds weren’t just against us; the industry was practically shouting, “This can’t be done!” Honestly, that only pushed us harder. We had a clear vision and determination to prove naysayers wrong, and out of that, Veracity Insurance Solutions was born.
Swinging for the fences: Taking risks on overlooked markets
We were a small team that brokered insurance policies for manufacturers and mid-sized companies in high-risk industries. Soon, we started getting leads from new customers: startups, entrepreneurs and micro-businesses. They weren’t big accounts, but they were passionate small business owners who couldn’t get coverage anywhere else.
The insurance industry doesn’t usually favor small or risky businesses. It leaves entrepreneurs with two options: either give up because no one will insure you (so your options to grow are now slim to none), or gamble on your risks and operate without coverage.
We saw hundreds, if not thousands, of business owners trying to create solutions for themselves. Quitting just wasn’t an option; their business was their dream, so they got innovative to find ways to keep going. Talking to them felt like cheering for the underdogs I loved in baseball. They had grit, determination and an energy impossible to ignore. Their stories stuck with me.
“We wrote 250,000 new policies in 2024 — enough to fill nearly seven baseball stadiums — and served our all-time 1,000,000th customer last year.”
— Daryle Stafford
As more requests came in, it was clear we had an opportunity to do something different. If you could buy auto or homeowners insurance online, why not business insurance? But to reach niche markets online, we needed to simplify the complex liability policies we were used to and create something affordable and accessible for everyday people.
This was also our chance to support businesses at the start of their journeys with something they absolutely needed to grow. I felt especially connected to them because we were in the same boat — a small business building something new from the ground up. We’d worked with businesses of all sizes, so we knew the risks they faced and what they needed to succeed, and we set out to find them insurance.
But we were trying to create a product that didn’t exist yet, and we heard a lot of “no’s” from insurance carriers. Whenever I heard a “no,” I doubled down. I pitched directly to carriers, helping to develop programs that didn’t yet exist, and eventually, no’s turned into yes’s. We built relationships with carriers who saw the potential and started to trust us to craft solutions for niche markets. It took persistence, but in the end, it paid off.
Base hit: Handcrafted coverage meets quick custom quotes
We launched our first direct-to-consumer program for handcrafted beauty products in 2009. I took customer calls myself back then, often spending 15 to 20 minutes talking to someone about a policy that only cost $39. The sale was only worth a few dollars to us, but the conversations were priceless market research — a chance to hear our customers’ challenges firsthand and adapt policies to fit their needs.
Over the next few years, those calls opened my eyes to more overlooked markets. We added coverage for artists and crafters, food businesses and beauty professionals, meeting a growing demand for accessible, affordable insurance. It was incredible to see how many people just needed the right coverage to get their business off the ground.
This was right around the same time online shopping was really taking off. In fact, I’ll never forget when a client first asked for a certificate of insurance for Amazon back in 2004, and I thought, “Who the hell is Amazon?!” Fast forward a few years, and Amazon was everywhere.
With online shopping exploding, we realized we were falling behind. Up to that point, we’d targeted business owners one niche at a time, building separate programs and websites for each group. It worked for a while, but with a small team and limited resources, it wasn’t sustainable to create a new site every time we wanted to reach a different industry.
That’s when we envisioned a single hub where business owners could shop for coverage, customize it and manage their policies. We could marry our in-house brokerage with instant shoppable policies and make the insurance process infinitely faster, easier and more convenient for entrepreneurs looking to protect their big dreams.
The concept was simple but groundbreaking (at least in our industry): cut out the middleman and put the power of insurance purchasing and management directly into the hands of business owners. That’s what led to the launch of Insurance Canopy in 2016.
Stealing second: Innovation in tax compliance
Selling policies online in niche industries wasn’t exactly a walk in the park. Going online meant anyone could find us, and we needed to be able to sell in as many states as possible to be profitable. We had to figure out how to offer coverage nationwide.
For E&S lines, this isn’t simple. Every state has its own rules, rates and regulations, which meant juggling all 50 of them. We also had to stay on top of tax filings and deadlines. Any mistakes there meant big penalties, fines — even losing the ability to do business in a state.
Sometimes, it was overwhelming. I thought, “We’ve solved bigger challenges before, and we’ve got this knack for tech. Why not build our own system?” That’s how InsCipher began: a tool to manage our own filings. But then a major insurance company asked us to handle theirs, too.
With just two people and a vision, we built a demo, pitched it and landed the deal. Their down payment helped us turn InsCipher into a full-fledged platform. It was a classic “build the plane while flying it” moment; no playbook, just persistence and a whole lot of problem-solving.
The early days of InsCipher were pretty tough. There were times when we were in over our heads, working long hours and weekends to hit tax deadlines and keep everything compliant, but it paid off. Today, InsCipher is the leading solution in the surplus lines tax filing market.
Stacking the lineup: Building the tech and team needed for growth
During the grind of launching InsCipher, the gravity of what we were building started to hit me. It wasn’t just about meeting deadlines or delivering results anymore; it was about the need for a fundamental shift in how we led the company.
I’d been involved in almost every part of the business up until then. But knowing that approach would only hold us back, I knew it was time to reassess my role if we were going to build something bigger.
We needed leaders who could help take our businesses to the next level, but finding the right talent wasn’t easy. For example, developers and programmers were in such high demand that leads seemed to vanish overnight. I also had a ton to learn; I remember being baffled by how long it took to build a website, constantly asking, “Why is this so complicated?” Looking back, I’m grateful we found people who understood it better than I did.
We’ve built some great in-house teams, launched businesses as leaders in their industries, and now have more than 200 employees — a milestone I never imagined in those early days.
Touching home plate: Empowering people and businesses
We wrote 250,000 new policies in 2024 — enough to fill nearly seven baseball stadiums — and served our all-time 1,000,000th customer last year. It’s insane to think about. It’s more than we ever expected, yet we hear that well over a million small businesses start every year. That’s still millions of entrepreneurs out there who need insurance, understanding, flexibility and affordability, and we want to be there for them when they’re ready to get their first policy.
We’re at the forefront when it comes to tech, but we’re still the underdogs of insurance, going toe-to-toe with some of the bigger names in the industry. I believe in staying independent and creating something the market truly needs instead of chasing profits or answering to a board of directors or shareholders, so we still bootstrap everything in-house. The scale we’ve reached while doing this is just incredible — and it’s because of the people.
In fact, one thing I really liked that the former owner did was make people feel like they matter and like they’re part of something bigger. That’s so easy to lose as companies grow; people can start to feel like just another name or number. Keeping that culture alive as we grow is important to me.
I still meet with every new employee we hire, and our VPs go out of their way to make themselves available to their teams. We’ve created an environment without a strict line between leadership and the rest of the company. There’s just so much we can learn from one another.
We made our business all about the individual solopreneur — the person chasing their dream every single day. At Veracity, we’re committed to serving underserved industries and putting individuals first. It’s a lonely, isolating, hard job to start a business on your own, and it can be even worse when you’re trying to buy something as complicated as business insurance. I like to say that if you think insurance is boring, you’re right. That’s why it is our mission to make it interesting.
