Why I Started with a Liberty Tax Franchise

In 2012, I opened a Liberty Tax franchise on a corner in Tampa. Not because I loved taxes. Not because I had read a book about franchise networks. I did it because I was broke, I knew I needed to learn how to run a business, and a franchise—with its systems already built—was the fastest way to do that without going bankrupt in the process.

I'd been in Tampa since 2007. I'd flipped a few houses, closed some deals, but I hadn't built anything that moved money predictably month to month. I didn't know how to hire. I didn't know what cash flow seasonality meant. I didn't understand the difference between being busy and being profitable. A franchise, it turned out, was exactly the business school I needed, and I'd get paid while I learned.

The Franchise as a Tuition Check You Get Paid For

People ask why I didn't start something "cooler." An app, a tech company, a flipping operation scaled across three states. The answer is simple: I wasn't ready.

A Liberty Tax franchise teaches you three things fast. First, systems. The parent company gives you the operational playbook—software, marketing templates, hiring standards, filing procedures. You don't get to invent the wheel. You get to run the wheel. That constraint is actually a feature. It forces you to focus on execution, not on perpetual planning.

Second, seasonality. Tax season is real. You're slow October through December, then it's flat-out from January through April, then it's quiet again. That swing taught me more about cash flow forecasting than any MBA could. You have to reserve cash in the busy months to cover the slow months. You have to hire ahead of the rush. You have to let people go or keep them lean. That's not cruel—that's how you stay solvent when your revenue swings 40 percent month to month.

Third, volume. At a tax franchise, you process hundreds of returns a season. You deal with customers, vendors, employees, quality control, workflow problems. Every one of those interactions is data about how to run something bigger. Who stays on board? Who quits after three weeks? What process breaks first when you're understaffed? What system wins you customer loyalty even when you're slammed?

Those three lessons—systems, seasonality, volume—lived with me into every business I built after.

What Liberty Taught Me That I Reused

When I started Star Insurance in 2014, I was only two years into running the tax franchise. I wasn't remotely ready. But I borrowed the operational DNA that Liberty had given me.

Insurance, like taxes, has seasonality. You get surges around renewal windows. You have to staff ahead of demand and manage through the dips. You have to forecast cash. I'd already learned that lesson at Liberty, so I didn't panic when January to March looked different from July to September.

More importantly, I understood systems. Insurance requires compliance, training, checklists, and repeatable processes—or you'll lose your license. I didn't reinvent compliance from scratch. I built on the framework I'd learned at Liberty: write down how things work, train people to that standard, measure whether they're following it, fix what breaks.

By the time we got to 10,000 customers at Star, I wasn't surprised at the hiring challenges. Scaling from 5 people to 30 people was hard—but Liberty had already taught me that hiring is not about finding geniuses, it's about finding people who'll follow the process and catching the ones who won't within the first 30 days.

The same logic carried into construction and real estate. When I started buying buildings for the Johnson Foundation of Florida, I wasn't learning for the first time how to manage a team, hit compliance deadlines, or navigate seasonality. I was remixing lessons I'd already paid tuition to understand.

Why I Didn't Chase the Sexy First Business

This is where I'll be direct: I see a lot of first-time founders skip the foundational business and go straight for the thing they want to run. They start a podcast before they've sold anything. They build an app before they've managed five employees. They raise money from friends because it feels more legit than bootstrap a franchise.

The franchise teaches you what it costs to stay in business. Everything else builds on that foundation.

It's not the path everyone takes, and I'm not saying it's the only path. But I watched what happened to the people who didn't take it. They hit a cash crisis at month 18 and suddenly they're learning about reserves and burn rate in an emergency. They hire their first 10 people all at once and don't know why seven of them quit in two months. They launch into a new market without understanding what happens when demand spikes.

The tax franchise cost me nothing except my time. I didn't raise capital. I didn't bring in partners with big ideas. I just showed up, ran the playbook, and paid close attention to everything that broke.

Would it have been cool to say I started a real estate syndication in 2012? Sure. Would it have probably failed? Almost definitely. The franchise didn't make me look smart. It made me capable of not failing when the bigger bets came.

The Unsexy Business as Capital

This is what people miss about franchises, and why I think they're underrated as a first business. They generate capital—not just cash, but the kind of operational capital you can't get from a book. You learn when to hire. You learn when to cut. You learn how to keep people. You learn what your own attention span is for—what works when you're managing it directly versus what needs systems.

That capital then transfers. By the time I was scaling Star Insurance to 10,000 customers, I wasn't learning how to manage people. I was learning how to manage more people with the same principles I'd already tested at 50.

By the time the Johnson Foundation bought its fourth building with 150 tenants, I wasn't figuring out what a lease means. I was debugging a system I'd already built.

If you're thinking about starting a business and you're not sure if you're ready to go all-in on the thing you really want to build, a franchise—or something like it, some low-risk operation with a tested system—is not settling. It's tuition. And unlike most tuition, it pays you while you go.