Interviewed by Michael Nelson and Derek Foster • Article written directly from the recorded transcript using AI, editor-reviewed by Taylor Stone, and subject-verified.

For Steve Rolle, entrepreneurship has never just been about chasing a bigger paycheck. It’s really about building something that lets you call the shots with your time, your choices, and where your life is headed.

The entrepreneur, author, former U.S. Army service member, and host of Rolle With Steve has started 12 businesses, experienced more than a few failures, and built a business responsible for more than $100 million in sales. But his most valuable lesson may not be how to start a business. It’s about building one that doesn’t depend on you to operate. In an interview on Blue Collar StartUp, Rolle shared why starting small, building repeatable systems, and learning to delegate can be the difference between owning a business and creating another job for yourself.

Steve Rolle’s Journey From Military Service to Entrepreneurship

Steve’s take on business ownership goes back far, long before he found success. He grew up in a big family just outside Washington, D.C., and remembers how tight finances shaped what he thought was possible for his own future.

He initially expected to follow a familiar path: find a job, make ends meet, and hopefully retire someday. That changed when he began to see that his decisions could shape his life.

“I realized that my actions can actually affect my future,” Rolle explained.

That lightbulb moment led Steve to the military, where he landed an ROTC scholarship. Thanks to his knack for engineering and a bunch of extra certifications, he found doors opening beyond what he first expected. The military even covered his engineering degree and a master’s that he says is a lot like an MBA, just geared for engineers.

With more time outside his military duties, Rolle began experimenting with business ideas. He went through three iterations of starting businesses while still serving, learning through ventures that sometimes failed and others that developed into something much larger than he anticipated.

After his time in the military, Steve gave the nine-to-five world a shot for about six months before deciding to jump into entrepreneurship full time. Over the past eight years, he’s started a dozen businesses, and he’s the first to admit that most of them didn’t pan out.

But one business that really took off started almost by accident.

Back when Steve was still in the service, his wife pitched in to help her mom move inventory for a company selling those little soaps and shampoos you find in hotels. Steve started looking at the numbers and using his engineering and project management know-how, and before long he spotted a real chance to help the business grow.

His initial goal was modest: reach $150,000 in monthly sales so he could earn extra income without leaving his military career.

That little side project became a business that’s done over $100 million in sales. These days, a team of 25 keeps things running and growing on its own, and Steve hasn’t had to be involved in the day-to-day for more than two years.

That experience changed how Steve thinks about what it means to be an entrepreneur and what a successful business actually looks like.

Why a Side Hustle Can Be a Better Starting Point for Business Owners

Steve sees a lot of folks get hung up on the idea that you have to quit your job, take a big financial leap, and go all in right from the start if you want to build a business.

He pushes back on that, especially for people starting their first business without a pile of outside money to back them up.

Instead, Steve suggests using your current job as a safety net while you build something on the side.

“Your day job is the investor into your side hustle,” he explained.

That steady paycheck gives you room to try out ideas, find your first customers, get a feel for the market, and figure out how to make money over and over again before you ever have to take the leap into full-time business ownership.

For someone working in the trades, this could mean identifying a service opportunity, finding customers, and learning how to consistently win and complete the work while still maintaining their current employment.

Rolle also highlighted a particularly interesting opportunity for people working in commercial construction and the trades: estimating.

He sees commercial estimators as already close to business owners, since they know how to spot projects, price out the work, and bring in customers. If you’ve got access to union labor and know how to win jobs, you might already have the makings of a business.

Steve’s bigger point is that owning a business should be a thoughtful move, not just an emotional leap.

Before you walk away from a steady paycheck, Steve says it’s important to know if your business has a system that works over and over, can actually make money, and if putting in more time will help it grow.

The goal isn’t just to swap your current job for one that’s even more demanding.

Building Systems, Delegating Work, and Making Room for Growth

Steve has noticed that many business owners end up being the biggest thing standing in the way of their company’s growth, even if they don’t mean to.

They handle accounting, sales, operations, customer relationships, and dozens of other responsibilities because they believe no one else can do them as well.

Pretty soon, the whole business depends on the owner’s time and attention.

Rolle experienced this challenge himself. As his business grew, he reached a point where he was selling approximately $2 million annually but couldn’t see how to increase revenue without working even more hours.

That’s when he realized he was the bottleneck.

His answer was to start building systems so other people could take over the important parts of the business.

“Write down what you’re doing,” he advised.

Instead of keeping everything in their heads, Steve says business owners should write down how things get done, explain why it matters, and teach their team to take ownership.

He also encourages owners to let employees improve those systems, not just follow instructions forever.

That way, the company can keep running smoothly even if someone leaves, and the owner gets more time to focus on building relationships, landing bigger sales, hiring, and making the big-picture decisions.

Steve thinks this shift matters even more now that artificial intelligence and automation are tools small businesses can actually use.

He sees a lot of potential for employees to use AI and automation to handle repetitive work, so they can get more done without hiring a bunch of new people.

Instead of seeing AI as something that’s going to take jobs away, Steve looks at it as a way to help employees do more and become even more valuable.

He also points out that keeping good people around takes more than just a paycheck. Business owners need to know what their employees want out of their careers and find ways to help them move up.

For salespeople especially, Steve suggests thinking about long-term incentives like equity or phantom stock. Giving someone a real shot at leadership or ownership is a much bigger motivator than just bumping up their commission.

At the end of the day, Steve believes business owners should build companies where people can grow, pitch in, and really take ownership of what they do​.

That brings Steve back to one of the things he said during the interview that really stuck with us:

“The biggest thing I see holding business owners back from growing into the level that they want to be at is they’re not bored enough.”

For Rolle, time to think isn’t wasted time. It’s an essential part of being an owner. When someone spends every day handling operational responsibilities, there is little opportunity to consider new ideas or identify ways to improve the business.

As he put it, “If the owner is just surviving, then the organization is not thriving.”

The Future You Choose: Entrepreneurship, Freedom, and Impact

Steve’s journey turned into the foundation for his book, The Future You Choose, which you can find on Amazon.

The book explores two connected ideas. The first is personal agency: recognizing that individual actions can influence the direction of one’s life, regardless of where they started.

Second, it’s a hands-on guide for entrepreneurs, walking through how to take an idea, start a side hustle, turn it into a real business, build systems so it can run on its own, and eventually plan your exit.

For Steve, an exit doesn’t always mean selling your company and riding off into the sunset.

He shared that he once turned down a $6 million acquisition offer from a public company because he believed his business still had more room to grow. Later, he used a merger and acquisition strategy to combine the company with a larger organization, retaining an ownership stake and reducing his responsibility for daily operations.

These days, through Rolle Management, Steve works with a small team on select projects and partners with B2B companies that sell wholesale instead of straight to consumers. He’s also still building his personal brand and hosting Rolle With Steve.

Steve’s idea of success has changed right along with his businesses. Sure, financial security is important, but he sees money as a tool, not the finish line.

After someone has found a bit of financial footing, Rolle likes to remind folks that the next chapter is really about the people around you, the community you’re part of, and the difference you can make for others.

For folks thinking about starting something new, especially in the trades, Rolle’s advice is simple but meaningful. Start with what you know best, try new ideas without risking your stability, and look for ways to set up your business so it can grow beyond your two hands.

The idea isn’t to spend decades tied to a job you can’t step away from. It’s really about building something that gives you the freedom to choose your own next steps.