From the Ballpark to the Boardroom: A CEO’s Unique Path
I’m not your typical CEO, and my path to business leadership wasn’t the conventional one. Instead of a childhood spent dreaming up business plans, my early passions lay on the baseball diamond. It was there, competing and strategizing, overcoming setbacks, and uniting a team, that I learned the fundamental skills shaping how I lead today. Even now, when I’m coaching my sons’ baseball teams, I find both a source of solace and insightful solutions to business challenges.
I’ve always been drawn to an underdog story: players beating the odds, teams making improbable comebacks. Those moments are the core of why I love the game. Baseball, at its essence, embodies strategy and fighting for victories when the odds are stacked against you. This concept became my playbook when I took the reins of a company poised for change.
Entering the Insurance Big Leagues
In 2004, I was an insurance broker specializing in excess and surplus (E&S) lines. I worked at a brokerage named Stratus, operating in the high-risk areas of commercial casualty insurance. We often found ourselves insuring businesses that others wouldn’t touch, such as sporting equipment companies and climbing gyms.
While online distribution models were gaining momentum, the insurance industry, especially for these high-risk niches, was slow to adapt. Because securing coverage was already a headache, we knew we needed a new approach to stay ahead of the curve. And then, everything changed.
In 2005, after a merger, Stratus’s owner sold his part of the business and prepared to retire. He was looking for someone to take his established foundation and evolve it into a new business. When he saw my vision, he put his trust in me. My family and I left our home in Richmond, Virginia, and moved to Pleasant Grove, Utah, ready to start anew.
We saw that we needed to rethink our whole business model if we wanted to thrive in the coming digital age. The industry practically told us: “This isn’t going to work!” That’s a challenge I was more than happy to meet. We were driven by our clear vision to prove the skeptics wrong. That determination led to the birth of Veracity Insurance Solutions.
Taking Risks, Serving Overlooked Markets
Our team at Veracity began by brokering insurance policies for manufacturers and mid-sized companies operating in high-risk fields. Soon, we started to get leads from a new type of customer: startups, entrepreneurs, and micro-businesses. Not the biggest clients, but these passionate small business owners often struggled to find any coverage at all.
The insurance industry doesn’t always focus on small or risky businesses. This leaves entrepreneurs with two choices: give up because you can’t be insured (limiting your growth), or take the risk of operating without coverage.
I witnessed hundreds, if not thousands, of business owners trying to find solutions to their challenges. Quitting was not an option; their business was their dream. Talking to them felt like cheering for the underdogs I loved in baseball. Their grit and energy were impossible to ignore.
“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 the requests grew, 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.
However, creating a product that didn’t exist led to a lot of rejections from insurance carriers. Every “no” only made me work harder. I went directly to carriers, helping develop programs that didn’t exist yet. Eventually, the “no’s” turned into “yes’s.” We cultivated relationships with carriers who believed in our vision, and they began to trust us to develop solutions for niche markets. It took persistence, but it ultimately paid off.
A Winning Strategy: Handcrafted Coverage with Quick Quotes
In 2009, we launched our first direct-to-consumer program for handcrafted beauty products. I was the one taking customer calls back then, and I often spent 15 to 20 minutes talking to a customer about a policy that cost only $39. The sale may have only been worth a few dollars, but those conversations were invaluable market research: a chance to hear our customers’ challenges firsthand and tailor policies to their needs.
Over the years, those calls opened my eyes to more overlooked markets. We added coverage for artists, crafters, food businesses, and beauty professionals, answering a growing demand for accessible, affordable insurance. It was inspiring to see so many people who just needed the right coverage to launch their business.
Around the same time, online shopping was really taking off. I’ll never forget when a client first asked for a certificate of insurance for Amazon in 2004, and I thought, “Who the hell is Amazon?!” Fast forward, and Amazon was everywhere.
With online shopping’s explosion, we realized we were falling behind. We had been targeting business owners one niche at a time, creating separate programs and websites for each group. That worked for a while, but, with a small team with limited resources, it was unsustainable 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 combine our in-house brokerage with shoppable policies and make the insurance process faster, easier, and more convenient for entrepreneurs.
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 led to the creation of Insurance Canopy in 2016.
Continuing the Journey: Tax Compliance Innovation
Selling policies online to niche industries wasn’t simple. Going online meant anyone could find us, and to be profitable, we needed to sell in as many states as possible. We had to figure out offering coverage nationwide.
For E&S lines, it’s not easy. Every state has its own rules, rates, and regulations. Add to that staying on top of tax filings and deadlines. Any mistakes meant big penalties, fines, or even losing our ability to do business.
The early days of InsCipher were tough. We often worked long hours and weekends to meet tax deadlines. But it paid off. Today, InsCipher is the leading solution in the surplus lines tax filing market.
Building the Team and Technology for Growth
While launching InsCipher, I began to realize the weight of what we had built. I realized that it was time to reassess my role if we were going to build something bigger. I was involved in almost every part of the business.
We have built some great in-house teams, launched businesses as leaders in their industries, and have more than 200 employees — a milestone I never imagined in those early days.
The Goal: Empowering People and Businesses
We wrote 250,000 new policies in 2024 and served our all-time 1,000,000th customer last year. It’s insane to think about. It’s more than we ever expected. There are still millions of entrepreneurs who need insurance, understanding, and affordability, and we want to be there for them.
We stay independent and create what the market truly needs. We have bootstrapped everything in-house. The scale we’ve reached while doing this is because of the people.
We’ve made our business about the individual solopreneur, the person chasing their dream. At Veracity, our mission is to serve underserved industries and put individuals first. I like to say that if you think insurance is boring, you’re right. That’s why it’s our mission to make it interesting.
Daryle Stafford is the founder and CEO of Veracity Insurance Solutions, InsCipher, and Insurance Canopy and has over 20 years of experience.
