The Accidental Entrepreneur
Sean Hicks will be the first to tell you he never planned to start a company.
He spent years climbing through corporate service organizations. Sears. Montgomery Ward. Warrantech. Big operations with established systems, structured hierarchies, and steady paychecks. He was good at it. He built a career out of running service departments and managing teams at scale. The corporate world was what he knew, and leaving it was never part of the plan.
Then he left.
“I’m an accidental entrepreneur. I spent all of my time in corporates… and jumping out and becoming an entrepreneur was a very, very, very scary thing for me.”
— Sean Hicks, One Sharp Sword Podcast
In a candid appearance on the One Sharp Sword podcast, Sean described those early days of co-founding New Leaf Service Contracts with a kind of honesty that most CEOs avoid. No romanticized startup origin story. No “I always knew I’d build something.” Just the reality of a corporate veteran walking away from everything familiar and launching a company out of a Verizon internet box.
That humility isn’t an act. It’s the lens through which Sean has built every part of New Leaf—from how they grow revenue to how they treat employees to how he’s planning for the day he’s no longer running the company.
Four Singles and You’ve Scored a Run
The service contract industry is a $48 billion business in the United States. By 2030, it’s projected to reach $83 billion. Those are big numbers. And when you’re building a company inside a market that size, the temptation is to swing for the fences—chase the massive accounts, pursue the deals that could transform the business overnight.
Sean doesn’t swing for the fences. He hits singles.
“We liken it to hitting singles. Think about it—four singles and I’ve hit a run.”
— Sean Hicks
New Leaf’s growth model is built on signing independent retailers one at a time. Not landing a single national chain that accounts for half the revenue. Not betting the company on one massive partnership. Instead, they add retailers steadily, build those relationships over time, and let the cumulative effect of hundreds of consistent partnerships create the kind of revenue base that doesn’t disappear when one client leaves.
It’s a deliberately unsexy strategy. There’s no press release when you sign your 400th independent appliance retailer. Nobody writes a headline about incremental growth. But the math works. Four singles score a run. And runs add up when you keep getting on base.
This approach also creates a different kind of resilience. When no single client represents an outsized share of revenue, the business doesn’t live or die on any one relationship. That’s a structural advantage that most high-growth companies talk about wanting but rarely have the patience to actually build.
Take Care of Your People and They’ll Take Care of Everything Else
“We have the belief that if we take care of our employees, they’re going to take care of our clients and our clients’ customers.”
— Sean Hicks
That’s a statement a lot of CEOs make. What separates Sean from most of them is the receipts.
New Leaf’s 30% Employee Stock Ownership Plan isn’t a talking point—it’s a wealth-building program that is actively changing the financial trajectories of the people who work there. The average ESOP account balance for New Leaf employees currently sits at $35,000. For a company where a significant portion of the workforce are young call center professionals, many of them early in their careers, that number is transformative. These are people who might not have had a retirement account at all before joining New Leaf, and now they’re building real equity just by showing up and doing their jobs well.
But ownership is only one piece of the investment. New Leaf also pays employees to learn. The company offers up to $1,000 per year for employees to take training classes through their payroll provider. It’s not restricted to job-specific certifications or narrow skill sets. It’s an investment in the person, not just the position.
The logic behind both programs is the same: people who feel invested in are more likely to invest themselves. An employee who owns equity in the company doesn’t just clock in—they think like a stakeholder. An employee who’s being paid to grow doesn’t just do the minimum—they bring new capabilities to the team. Both programs create a compounding effect where individual development feeds directly into organizational performance.
In an industry where call center turnover often exceeds 30% annually, New Leaf’s approach to employee investment isn’t just philosophically sound. It’s a competitive advantage that gets stronger every year.
One Percent Better Every Day
“I try to make New Leaf 1% better every day.”
— Sean Hicks
This might be the most Sean Hicks statement in the entire podcast. Not a moonshot vision. Not a disruptive manifesto. Just steady, daily improvement.
On the One Sharp Sword episode, Sean talked openly about how New Leaf approaches mistakes. In a lot of organizations, especially ones built by first-time entrepreneurs, mistakes become crises. They trigger blame cycles, policy overreactions, or worse—a culture where people stop taking initiative because the cost of failure is too high.
At New Leaf, mistakes are treated as data. Something went wrong in a process? Figure out why, fix the system, move forward. A new approach didn’t land the way the team expected? Extract the lesson, adjust, and try again. The goal isn’t to avoid mistakes. The goal is to make sure the same mistake doesn’t happen twice.
The 1% philosophy also applies to how Sean thinks about the company’s infrastructure, technology, and client experience. He’s not chasing wholesale reinvention. He’s looking for the next small improvement that compounds over time. Better call documentation. Slightly faster claims turnaround. One more training opportunity for the team. None of those things make headlines individually, but stacked across months and years, they create a company that’s measurably better than it was last quarter.
It’s the same discipline as the four-singles strategy applied to operations. Incremental. Consistent. Compounding. And very hard for competitors to replicate, because there’s no single big move to copy—just a relentless accumulation of small ones.
Building Something That Outlasts You
Most small business owners don’t talk about succession planning until they’re forced to. A health scare. A buyout offer. A sudden realization that the business can’t function without them at the center of every decision. By then, the planning is reactive rather than strategic, and the outcomes are rarely what anyone wanted.
Sean is doing it differently. On the podcast, he shared that he’s actively preparing his CFO and President to take over New Leaf within the next five to seven years. Not in a vague “someday” sense. In a structured, intentional way that involves progressively handing off responsibilities, building their decision-making muscles, and creating the conditions for a leadership transition that doesn’t destabilize the organization.
This is consistent with everything else in Sean’s leadership philosophy. Long-term thinking over short-term convenience. Investing in people before you need the return. Building systems that don’t depend on any single person, including the founder.
The ESOP plays a role here too. Because employees own 30% of the company, the succession plan isn’t just about who sits in the CEO chair. It’s about protecting the value that every employee-owner has built. A smooth transition preserves that value. A chaotic one puts it at risk. Sean is planning the handoff not just for himself, but for everyone who has a stake in what New Leaf becomes next.
For other small business owners listening to the podcast, this might have been the most valuable takeaway. Succession planning isn’t a sign that you’re done. It’s a sign that you built something worth continuing. And starting the process five to seven years before you need it is the difference between a graceful transition and a scramble.
Key Takeaways
- You don’t have to be a born entrepreneur to build something meaningful. Sean’s “accidental entrepreneur” path proves that corporate experience and startup grit can coexist.
- Hit singles. Consistent, incremental growth through steady client acquisition builds a more resilient business than chasing one transformational deal.
- ESOPs aren’t just retention tools—they’re wealth-building programs. A $35,000 average account balance is changing financial futures for young professionals.
- Pay people to learn. A $1,000 annual education stipend is a small investment that signals the company cares about the person, not just the role.
- Treat mistakes as data, not disasters. A culture that learns from failure compounds improvement faster than one that punishes it.
- Start succession planning years before you need it. Five to seven years of intentional grooming protects the value everyone has built.
The Bottom Line
The service contract industry is growing toward $83 billion. The companies that capture that growth won’t be the ones with the flashiest technology or the loudest marketing. They’ll be the ones that invested in their people, stayed disciplined about how they grew, and built organizations that can thrive without any single person at the helm.
Sean Hicks didn’t set out to be an entrepreneur. He set out to build a company where everybody wins when the company succeeds. Fifteen years later, New Leaf’s employees own a piece of what they’ve built. They’re getting paid to learn. They work for a leader who thinks in terms of 1% daily improvements rather than overnight transformations. And the next generation of leadership is already being prepared to carry it forward.
Not bad for an accidental entrepreneur who started with a Verizon internet box.
Learn more about New Leaf Service Contracts: trynewleaf.com