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When entrepreneurs talk about expansion, most conversations focus on revenue, opportunity and growth. Very few people talk about the operational pressure that comes with opening a second location. That pressure is where many businesses start to break down.

I have seen this happen in healthcare and in other industries. A founder builds a successful first location through hard work, close oversight and personal involvement. Then they assume the same formula will automatically work somewhere else. What they discover very quickly is that success tied to one person rarely transfers cleanly to another location.

When my brother Stephen and I started expanding our healthcare businesses, we realized something important. If the business only worked because we were physically present every day, then we did not actually have a scalable company. We had a demanding job with a good revenue stream.

That realization forced us to approach expansion differently. Before opening another location, we began asking ourselves a set of questions designed to test whether the business could truly operate at scale. Over time, those questions became our version of a franchise test. Here are the seven questions I believe every founder should answer before expanding.

1. Can someone else run your operation successfully?

This is the first and most important question. If the business depends heavily on your personal oversight, your second location will struggle from the beginning.

In our early years, I stayed involved in nearly every decision. I reviewed operations constantly, solved issues personally and approved far more than I should have. At the time, I thought that level of involvement protected quality. In reality, it created dependency.

Expansion requires the opposite. Your systems must allow competent people to operate successfully without constant intervention from the founder. A simple way to test this is to step away temporarily from day-to-day operations. If progress slows dramatically during your absence, your business still depends too heavily on you.

2. Have you documented your core processes?

Undocumented success does not scale. Many founders carry operational knowledge in their heads. They know how to onboard customers, resolve issues, manage scheduling or maintain quality because they have repeated those actions hundreds of times. The problem appears when another team tries to replicate the process without direct access to the founder.

When we started growing our healthcare businesses, documenting processes became one of the most valuable things we did. We created standard operating procedures for onboarding, scheduling, communication, staffing and patient workflows. That documentation created consistency across locations.

One exercise I recommend is identifying the five most critical systems in your company and documenting them step by step. Keep the instructions simple, practical and repeatable. A scalable SOP should allow another capable person to produce the same result consistently.

3. Does your culture exist beyond you?

A strong first location often reflects the founder’s personality and energy. Employees respond directly to your leadership style, standards and communication. The challenge comes when you attempt to recreate that environment somewhere else. Culture must become operational, not personal.

In our companies, we learned that culture requires reinforcement through hiring, training and leadership development. You cannot assume people automatically understand your standards because they spent time around you.

Before expanding, ask yourself whether your values are clearly communicated throughout the organization. Your team should understand how decisions are made, how customers are treated and what behaviors define success inside the company. When culture only exists through the founder’s personality, expansion creates inconsistency very quickly.

4. Do you have leaders ready to grow with the company?

A second location creates leadership pressure immediately. Someone has to oversee operations, manage people, solve problems and maintain standards while you divide your attention across multiple sites. One of the biggest mistakes founders make is expanding before building leadership depth.

I learned this personally as our businesses grew. Early on, too many decisions still came back to me because leaders had not fully developed ownership within their areas. That slowed growth and limited scalability.

Before expanding, identify whether you already have strong leaders capable of running operations independently. If you cannot clearly name those individuals today, leadership development needs attention before expansion. One practical step is assigning increasing responsibility to existing team members before opening another site — give them ownership over projects, operations or departments now so you can evaluate how they lead under pressure.

5. Can your systems handle more complexity?

Growth always increases complexity. Communication expands. Scheduling becomes harder. Staffing pressure increases. Financial oversight becomes more demanding. Without strong systems, complexity turns into chaos very quickly.

One of the best decisions we made during expansion was investing in automation and operational systems early. We evaluated repetitive tasks and asked whether technology could improve efficiency and consistency. Scheduling, communication, billing and documentation all became areas where systems reduced operational strain. This is not about replacing people — it is about creating structure that allows people to perform at a higher level.

Before opening another location, evaluate where your current systems already feel strained. Expansion magnifies weaknesses that already exist.

6. Is your first location consistently profitable?

Some founders pursue expansion too early because growth feels exciting. The danger is that a weak first location creates two weak locations instead of one strong company.

Your original operation should demonstrate stability before expansion begins. Revenue should be predictable. Margins should support growth. Operational issues should feel manageable rather than constant.

When we expanded into additional healthcare businesses, we focused heavily on operational consistency before adding complexity. That discipline created a stronger foundation for future growth. A useful exercise is reviewing the last 12 months of performance — look for operational stability, team consistency, customer retention and financial predictability. Expansion works best when the original location operates from strength rather than momentum alone.

7. Are you expanding strategically or emotionally?

This may be the hardest question of all. Opening another location can absolutely transform a business — it can create leverage, expand impact and position the company for long-term growth. But expansion amplifies everything inside the organization, including weaknesses.

That is why I believe the franchise mindset matters so much. Franchises succeed because they create repeatable systems, documented standards, leadership consistency and operational discipline. Founders who approach expansion with that same mindset dramatically improve their chances of sustainable growth.

The goal is never just opening another location. The goal is building a business that operates successfully beyond the constant presence of the founder.

If you tell someone you’re an entrepreneur, they’ll assume you’re from one of the anointed cities: New York, Silicon Valley, maybe Austin or Miami. Start a company outside of these major metros, and the general read is that you’re a farm league founder.

I know otherwise. I’ve built seven companies, all in my hometown of Lexington, Kentucky. I travel regularly, and when I tell people I’m from Kentucky, they often look surprised and say, “What’s going on in Kentucky?” Those who live here know there’s a lot going on. Lexington may be a mid-sized market, but it’s one that has a flourishing entrepreneurial community.

My friend Scott Shapiro, Lexington’s former Chief Innovation Officer, has done research on what he calls “University Cities” — mid-sized markets like Lexington, Madison and Ann Arbor, which are built around major research universities.

His data shows that these cities match the largest metros in talent, entrepreneurship and economic resilience at a fraction of the cost. The bottom line is this: Markets like Lexington give founders advantages that simply don’t exist in big cities.

Failure is survivable

Everyone loves a good entrepreneurial success story. The same can’t be said about the stories of failure. But even the most successful founders leave a trail of failures behind them. It’s inevitable.

I’m no stranger to failure. In 2017, I was running a clothing brand called Provisions, a Kentucky apparel brand built around giving back. We had a great product, customers and momentum. Then there was a market shift that impacted our licensing, and the ground disappeared out from under us. There was no pivot to make. The business was done.

In the end, that failure cost me a few hard months and a bruised ego. A year and a half later, I started Bolt Marketing, the agency I run today. If I’d been carrying San Francisco rent and payroll when Provisions went down, that story would have ended differently. In Lexington, the failure was tuition.

This is where the math comes into play. Housing, salaries, office buildouts and daily living expenses in mid-sized markets are a fraction of what they are in major metros, and all of it rolls up into one critical number: how long you can keep going before the money runs out. Lower costs mean more runway on less capital. When a failed idea costs you a few months instead of everything, you can afford to try, miss and try again.

You can make a name for yourself

In Silicon Valley, there might be thousands of businesses doing exactly what you do. You can produce excellent work for years and never make real headway. But in a mid-sized market, you can become the big fish, and if you do it right, you can get there fast.

Produce great work, make it visible, and the word gets around. Less competition and a tighter community mean a reputation actually builds, and a strong local reputation is something that will convert directly into revenue.

Networking in big cities is transactional. Everyone is hunting for their next opportunity, and genuine business relationships are hard to come by. I’ve seen this first-hand in bigger markets and have come to understand that mid-sized ones run on a completely different operating system. The business community is tight enough that real, collaborative relationships form on their own. Founders here look for ways to help each other. Those relationships become the most dependable source of referrals and new business you’ll ever have.

At Bolt, we regularly host happy hours, panels and events to bring the Lexington business community together. Nobody’s pitching anybody. People show up to learn from each other and enjoy the company, and lasting relationships come out of that. It can be harder to replicate that in a transient city of 8 million.

It’s easier to hold onto top talent

In hyper-competitive markets, your best people are always one recruiter call away from leaving. There’s always going to be a better offer somewhere. This means frequent turnover and constant pressure to keep your team intact.

In markets like Lexington, fewer businesses are competing for the same employees, and people live here on purpose. Family, affordability, lifestyle. When someone can buy a house, raise kids and still do work that interests them, they have far less reason to shop around.

This stability compounds. Institutional knowledge stops walking out the door every 12 months. Culture has time to form. People grow within your company, rather than treating it as a layover.

It’s not all easy

The advantages of mid-sized markets are very real — but there are downsides to any geography. You can’t have a surfing company in Omaha. But even beyond the obvious mismatches, if your business depends on large outside investment, the coastal metros give you more shots at that funding. And your local market in a smaller city is automatically smaller, which means some businesses have to think beyond their home geography from day one.

But these constraints push you toward building a stronger, more financially sound company from the beginning. The limits of a mid-sized market sharpen you as an operator.

Choose the unexpected location

I love big cities. There’s an energy about them that is infectious, and you can’t help but want to create. But energy doesn’t pay the bills; opportunity does, and it lives in more places than people think. The most interesting thing you can do as a founder is the thing people don’t expect, and building a thriving company in an “unexpected” place is exactly that. It makes you distinctive. It lets you build a team with hometown pride. It connects your journey to a community that will show up for you in ways a major city never will.

And the case for building business in unexpected geographies keeps getting stronger. In a post-Covid world, remote work erased the last real argument for coastal geography. Your clients, your talent and your capital no longer require a specific zip code. You don’t have to move to where people think founders should go. You can build a successful business right where you are. Pick a mid-sized market, plant your flag, and get to work. To some, you may look like a farm league founder — but the farm league is where the big leaguers come from anyway.

If you tell someone you’re an entrepreneur, they’ll assume you’re from one of the anointed cities: New York, Silicon Valley, maybe Austin or Miami. Start a company outside of these major metros, and the general read is that you’re a farm league founder.

I know otherwise. I’ve built seven companies, all in my hometown of Lexington, Kentucky. I travel regularly, and when I tell people I’m from Kentucky, they often look surprised and say, “What’s going on in Kentucky?” Those who live here know there’s a lot going on. Lexington may be a mid-sized market, but it’s one that has a flourishing entrepreneurial community.

My friend Scott Shapiro, Lexington’s former Chief Innovation Officer, has done research on what he calls “University Cities” — mid-sized markets like Lexington, Madison and Ann Arbor, which are built around major research universities.

Y Combinator (YC), a well-known startup accelerator that helped launch companies like Reddit, DoorDash and Airbnb, has invested in more than 5,000 startups since 2005. Now YC leaders note that founders seem to be outsourcing writing their applications to AI. 

The YC application requires founders to explain how they selected their idea, identify competitors in the space and outline their plans to generate revenue. Some tell-tale signs reveal that many tech-focused founders have recently decided to use AI to write answers to these questions.

One giveaway is the longer responses that AI produces. According to YC partner Tyler Bosmeny, YC applications have increased in length by 60% over the past three years. “I wonder what could explain that…” he wrote on X earlier this week.

Another YC partner, Pete Koomen, spent a week reading applications. He wrote in an X post this week that “back in my day (one year ago) founders didn’t talk like this.” He shared a chart showing that the percentage of applications containing the word “wedge” went from less than 1% in spring 2025 to greater than 20% in summer 2026. 

Meanwhile, em dashes, another AI giveaway, started growing in use in 2023 and “really hit their stride in 24,” Koomen said. According to the data he shared, by summer 2025, more than 50% of YC applications used em dashes. 

Koomen emphasized that the spacing of those em dashes was important. Em dashes with spaces around them spiked in use in summer 2025, around the same time that the word “wedge” became more popular. These signs of AI use coincided with the launch of Anthropic’s Opus 4 AI model, he said. 

One word decreased in popularity

YC co-founder Paul Graham wrote in an X post in April 2024 that someone sent him a cold email suggesting “a novel project.” Then he noticed that the email used the word “delve.”

“My point here is not that I dislike ‘delve,’ though I do, but that it’s a sign that text was written by ChatGPT,” Graham wrote in the post, which has been viewed 2.6 million times. 

He added a chart created by researcher Philip Shapira, which illustrated that the word “delve” has jumped from nearly zero to nearly 18,000 instances in published papers and articles from 1990 to 2024. 

“No one uses it [delve] in spoken English,” Graham wrote. “It’s one of those words like ‘burgeoning’ that people only use when they’re writing and want to sound clever.”

Founders using AI to write applications have recently stayed away from “delve.” Koomen found that the word only spiked in 1.25% of applications in the winter of 2024, before Graham’s post. 

Graham said more recently, in an X post in May, that “a lot” of emails from founders now adopt “a hard-hitting journalistic style.”

“I know they’re written by AI, because no founder ever wrote this way before,” he wrote, adding, “It feels like being lied to.”

Y Combinator (YC), a well-known startup accelerator that helped launch companies like Reddit, DoorDash and Airbnb, has invested in more than 5,000 startups since 2005. Now YC leaders note that founders seem to be outsourcing writing their applications to AI. 

The YC application requires founders to explain how they selected their idea, identify competitors in the space and outline their plans to generate revenue. Some tell-tale signs reveal that many tech-focused founders have recently decided to use AI to write answers to these questions.

One giveaway is the longer responses that AI produces. According to YC partner Tyler Bosmeny, YC applications have increased in length by 60% over the past three years. “I wonder what could explain that…” he wrote on X earlier this week.

A few years ago, I helped start a company called Kitchen Data Systems. At the time, ghost kitchens were exploding. Delivery was booming, and it felt like the kind of opportunity you move on quickly. We had some traction and real revenue early, but the business never scaled the way we expected. So we pivoted.

Instead of building delivery-only food brands, we explored a buyers’ club model for independent restaurants. Large chains like Domino’s can negotiate far better ingredient pricing because they buy on a massive scale. Smaller restaurants often serve great food but pay more because they lack that purchasing power. Our idea was to aggregate demand so independent operators could access similar pricing advantages.

It was a smart pivot, but we couldn’t execute the model well enough, and eventually we ran out of time and money. From the outside, that might look like failure. From the inside, it was a lesson in how businesses actually evolve. Almost every founder will face a moment where an idea doesn’t work the way they expected — you can’t avoid those moments. The real test is how you recover when they happen.

Conduct an honest post-mortem

The first step after a setback is analyzing what actually happened. Many founders either skip this step or let emotion dominate the process. A proper post-mortem is about identifying which assumptions were wrong and where execution fell short. Sometimes the market is not ready. Sometimes the product fails to meet the customer’s needs. Other times, the strategy is solid, but the team cannot execute it quickly enough.

In our case, the concept of helping independent restaurants with purchasing power had merit. The problem was execution — we were not able to build the system quickly enough for the model to work at scale. If founders misdiagnose failure, they often carry the wrong lesson into the next venture. The goal of a post-mortem is to understand the real cause so that the next decision improves.

Separate emotion from evidence

Building a company is deeply personal. Founders invest years of effort, reputation and energy into something that may or may not succeed. When the outcome falls short, the emotional response can be strong. That reaction is natural, but it also clouds judgment.

A common mistake founders make is convincing themselves they just need more time. Others double down on a strategy that clearly is not working because walking away feels like admitting defeat. A better approach is to step back and evaluate the situation objectively. Look at the numbers. Look at customer behavior. Look at the growth trajectory. If you were evaluating the opportunity fresh today with the information you now have, would you still pursue it?

If the honest answer is no, continuing to pour resources into the same strategy won’t improve outcomes. Discipline in entrepreneurship often means recognizing the difference between persistence and stubbornness.

Protect the relationships built along the way

When companies struggle or shut down, it can feel safe to retreat. Founders stop returning calls, investors move on and teams scatter. That instinct is shortsighted. One of the most valuable assets in business is your reputation during difficult moments.

Entrepreneurship is a long journey. The people you work with during one venture often appear again later in your career. A former employee may become a founder you invest in. An early investor may support your next idea. A partner from a failed project may introduce you to a future opportunity.

Because of that, how you handle difficult moments matters. Communicating honestly, acknowledging mistakes and treating partners fairly during setbacks builds long-term trust. People understand startups fail — what they remember is how you behaved when things became difficult. Maintaining those relationships ensures that one failed venture does not close the door on future opportunities.

Extract one strategic lesson

Rather than generating a long list of abstract lessons, a more useful approach is to identify one lesson that genuinely changes how you operate moving forward. Maybe it is about testing demand earlier, before building infrastructure. Maybe it is hiring differently or focusing on a different customer segment. Sometimes the lesson is simply about speed — early-stage companies cannot afford to wait long for proof. If the data is not moving in the right direction, adjustments must happen quickly.

Entrepreneurship rarely follows a straight path. Many successful founders tested several ideas before discovering the one that gained traction. Each attempt produces information that helps refine the next decision. If you walk away with one clear adjustment in how you evaluate opportunities, the setback has already paid for itself.

Re-enter the arena with calibrated conviction

The final step after a setback is returning to the arena. After experiencing failure, a drop in confidence is common. Doubt creeps in. Survival urges us to avoid risk or wait for certainty before trying again. But entrepreneurship and certainty are seldom bedfellows. Sales conversations begin with rejection. Investors decline pitches. Customers say no. Progress comes from continuing to ask, test and move forward. You may even have to face failure again before you finally find a company that takes off.

I was reminded of this recently by a story from one of my interns. He was standing in line at a Wetzel’s Pretzels and noticed the person ahead of him was Anthony Kiedis from the Red Hot Chili Peppers. He debated whether to ask for a photo, then decided to go for it. The worst outcome would have been a polite no. Instead, he walked away with a photo and a story he will remember for years.

Entrepreneurship works the same way. Most opportunities start with a message, a meeting request or a simple question that could easily be ignored. Occasionally, that attempt opens the door to something much bigger. After a setback, don’t forget what happened — apply the lessons while maintaining the courage to try again.

The end is up to you

Setbacks are an unavoidable part of building companies. Ideas fail, strategies miss the mark and sometimes the timing simply does not work. Those moments are sometimes brutal. They’re discouraging. It can feel like the end. But failure in entrepreneurship is only final if you stop learning from it.

Founders who recover well approach setbacks with discipline. They analyze what happened honestly, separate emotion from evidence and protect the relationships built along the way. They extract one lesson to inform the next decision, then return to the market with renewed focus.

A few years ago, I helped start a company called Kitchen Data Systems. At the time, ghost kitchens were exploding. Delivery was booming, and it felt like the kind of opportunity you move on quickly. We had some traction and real revenue early, but the business never scaled the way we expected. So we pivoted.

Instead of building delivery-only food brands, we explored a buyers’ club model for independent restaurants. Large chains like Domino’s can negotiate far better ingredient pricing because they buy on a massive scale. Smaller restaurants often serve great food but pay more because they lack that purchasing power. Our idea was to aggregate demand so independent operators could access similar pricing advantages.

It was a smart pivot, but we couldn’t execute the model well enough, and eventually we ran out of time and money. From the outside, that might look like failure. From the inside, it was a lesson in how businesses actually evolve. Almost every founder will face a moment where an idea doesn’t work the way they expected — you can’t avoid those moments. The real test is how you recover when they happen.

When Michael Browning Jr. tried to launch a trampoline park in 2011, every bank and investor rejected him. His age was a factor — he was 26 years old at the time. Investors said he was too young and that his idea would never work. 

Undeterred, Browning went to his parents and asked for their help. His dad had a construction background and said he could help Browning build the facility. His parents also invested in the venture. 

That’s how Browning found himself working alongside his father, building the first Urban Air Adventure Park by hand. They rented forklifts, laid wood and unloaded foam cubes, constructing the trampoline park from scratch. 

“It was one of these things where I just had a huge passion for starting the business,” Browning tells Entrepreneur in a new interview. “The banks didn’t see it, landlords didn’t see it, people thought I was crazy, but I was committed to it, and it all worked out.”

In 2021, Browning founded Unleashed Brands, a unified franchise platform to help children learn, play and grow. Unleashed Brands, which includes Urban Air, The Little Gym, Sylvan Learning, Premier Martial Arts and Water Wings Swim School, has more than 1,600 locations nationwide and serves more than 25 million children. 

Last year, the company did just over $1 billion in revenue, and Browning predicts it will reach that milestone again in 2026. In 2025, Unleashed Brands opened 133 new franchise locations, with more than 200 franchises in development.

The following interview has been lightly edited for clarity and concision. 

Urban Air: from first park to franchise

How long did it take Urban Air to become a franchise?
Our first Urban Air location opened on October 28, 2011, so we’re coming up on our 15th year. Our first franchise opened on December 16, 2014, with a family in Wichita, Kansas, the Beckers, who are still franchisees today and now have multiple locations. Their general manager is opening a Little Gym, and the Beckers renewed their original franchise for another 10 years.

How did you make the first Urban Air location work despite the risk of failure?
It came down to how we viewed problems and adversity. My core operating philosophy is that problems are mile markers on the road to your destiny. People get rattled when problems show up; I see them as expected. You can pull over and quit, or you can go over, under, around or through them. We had to be gritty, curious and innovative. 

When we started, we were only the sixth trampoline park in the country and didn’t really know what we were doing. We ran the business on one mantra: Keep guests safe, keep them happy and make money — in that order. Every decision went through that filter. My family and I worked every position — register, attraction monitor, janitor, party host — until we knew how to do each job with excellence. Then we trained and coached our staff to deliver an exceptional guest experience.

Learning about franchising

When did you realize your first Urban Air location could be a franchise, not just a single business?
I didn’t initially see franchising as a growth path. We had four family-owned locations in Dallas–Fort Worth when a guest, whose sister lived near our first location, kept calling and asking me to franchise the concept to him. The only thing I knew about franchising was from the movie The Founder about McDonald’s. I went and researched it, got mentors in franchising and decided I didn’t want to look back in 15 to 20 years and regret not exploring it. 

Demand for the brand was strong, but I didn’t want to open and operate every location outside Dallas–Fort Worth myself. As I learned more, I realized franchising was an amazing model: people get a “business in a box” they can own and operate locally. I now teach Introduction to Franchising at a local college because I wish I’d understood it earlier. Too many people think entrepreneurship has to start from a blank sheet of paper; I believe franchising is one of the best models in America to stimulate entrepreneurship.

Starting Unleashed Brands

What was happening in your life when you decided to start Unleashed Brands?
I’m an entrepreneur and CEO, but I’m also a dad of three: a 14-year-old daughter, an 11-year-old daughter and a 6-year-old son today. If you rewind to Covid, those kids were roughly 1, 6, and 9 years old. At that time, we were only Urban Air, and we shut down all locations, like everyone else. We used those months to retool and examine what we’d built after years of hypergrowth. I realized we’d created a platform, a machine that knows how to sell, design, market, open and operate franchise businesses, and we had a large, powerful consumer database of families. 

Coming out of Covid, my wife and I were sitting on the couch, both Googling activities for our kids, and I remember thinking: This is really hard and fragmented. Nobody had built a Marriott Bonvoy-like ecosystem for kids’ enrichment. That’s when it clicked: I was going to buy the world’s best youth-focused brands families already trust, connect them on a shared services infrastructure — same point-of-sale system, same tech stack, shared marketing and media — and simplify the youth enrichment journey for parents. It grew out of frustration as a parent. That’s how Unleashed was born.

Making strategic acquisitions

How did you launch Unleashed Brands — did it start with acquisitions?
Yes. I started by articulating the thesis: We’re going to acquire the world’s best brands that help kids learn, play and grow. To become a true platform, I needed more than one brand. I targeted two brands my kids had personally experienced. The first was The Little Gym; my wife had taken our first daughter there at a local franchise in Dallas. I asked the franchisee who owned the business, got the owner’s number in Chicago, called and asked if they’d sell. They said The Little Gym wasn’t for sale; I said, “Everything’s for sale” and asked for their number. We worked through it. 

The second was Snapology, a STEM education company. My daughter had done a Snapology camp during Covid and loved it — she learned engineering concepts and built a motion-sensor alarm for her bedroom door without realizing she was coding. I reached out to founder Laura Coe, shared the thesis, and she wanted to be part of it. Those two acquisitions in 2021 really launched Unleashed Brands as a platform.

How many brands does Unleashed Brands oversee now?
We have seven brands, organized under three pillars: Learn, play and grow. Urban Air sits in our play pillar. In the learn pillar, we have Sylvan Learning Centers, Snapology and Class 101, which focuses on college planning. In the grow pillar, we have The Little Gym, one of the largest gymnastics concepts; Water Wings, a swim school; and Premier Martial Arts, which focuses on Krav Maga.

Growth secrets

What tactics have you used to grow? What are your secrets? 
I’m a very marketing-oriented CEO. If you want to be the best-kept-secret no one knows about, don’t market. A lot of people see marketing as an expense; I view it as an investment that takes time. You need reach, or the number of people who see your message, and frequency, or how often they see it, before they’ll act. Many entrepreneurs aren’t gritty or innovative enough in their marketing. When I started franchising, I didn’t know how to sell franchises or do franchise marketing. What I did know was that guests were coming into Urban Air, having a great time and later calling to ask if we could open a location in their town or if they could open one themselves. 

Instead of jumping straight into sophisticated digital campaigns, I leaned into that. I put signs over the men’s urinals and on the backs of bathroom stall doors that said, “Want to be your own boss? Own an Urban Air franchise.” Everyone goes to the bathroom while they’re there, and they’re having a great experience in the park, so that message sticks. I’d bet a large percentage of our first 50 franchisees came from people who sheepishly admitted they saw those signs. It inspired them to consider being their own boss and bringing something fun to their hometown.

Advice for founders

What hard, concrete advice do you have for founders?
You have to be willing to get in the weeds and learn every part of the business. Every “overnight success” takes about 15 years; people only see the result after all the problems and learning. You need intimate knowledge of your company at every level. That means missed holidays, late nights, early mornings and being “on” 24/7. 

There’s a misconception that being your own boss means working less. It’s amazing, but it carries a different weight. You also have to find fun in the daily grind — joy in the work itself, not just in the big deal or big sale. People say if you love what you do, you’ll never work a day in your life, but that doesn’t mean you won’t have problems. You need to love it so much that the problems never stop you, and you must be willing to work very hard.

We don’t get to be young forever, but that’s actually a good thing. Like Pete Seeger of The Byrds sang back in 1962:

“To everything there is a season
And a time to every purpose under heaven
A time to be born, a time to die
A time to plant, a time to reap
A time to kill, a time to heal
A time to laugh, a time to weep”

Of course, those lyrics are even older than that. They originally appeared in the Book of Ecclesiastes, which is part of the Old Testament. If you’re looking for proof of the value in old things, I don’t know where you’re going to find a better example than that.

But this isn’t just a feel-good article for my older readers about how age brings wisdom. The point I’m using those lyrics to illustrate is actually that there are distinct seasons to your career, each of which brings valuable perspective. You just have to acknowledge which season you’re in instead of staying in denial about it.

My priorities when I entered the roofing industry as a teenager were very different from the ones I have today, but that hasn’t hampered my business. My company, Roof Maxx, is presently valued at over eight figures and has dealers selling our roof restoration solution across the country.

Here’s how each season of my career helped me refine my pathway to success — and how yours can do the same for you if you let it.

Spring: New ideas and early growth

The springtime of your career encompasses those early years when you’re busy planting the seeds of new ideas and dreaming of the future. It’s arguably the most conceptual time in an entrepreneur’s life, because it’s all about potential. You’re not yet so invested in anything that you’re thinking only about dollars and cents; the future is a blank slate, and you have enough time ahead of you to dream a little.

Now, the likelihood is that not all of those dreams are going to come true, at least not in the way you thought they would. When I was in my teens and twenties, I had no idea that I was eventually going to start Roof Maxx. I got into roofing with simpler ambitions — of becoming a successful contractor, of working with my family, and of building a recognizable brand in our home state of Ohio that would become my legacy.

That didn’t exactly happen. In fact, I worked for 15 years as a roofing contractor and was on the verge of financial failure for most of that time. But as I grew older and wiser, the dream evolved. Things eventually turned out even better than I could have imagined.

Summer: Long days and late nights

The truth is that big plans aren’t enough to succeed in business. You also need to make smart investments. That’s what the summer of your career is for: cultivating the seeds you planted years ago, then carefully pruning and protecting your business ideas so they can grow.

An investment isn’t just about money, either. Not every early-to-mid-career entrepreneur has cash to spare. The time you invest is equally important. And if you invest your time carefully, my experience has taught me that other resources will often become available.

When Todd and I discovered the Roof Maxx formula, which could extend the usable lifespan of asphalt shingle roofs for years as long as they were in decent condition, we didn’t have much in the way of liquid assets. But we had years of experience as roofers, which allowed us to recognize the market potential for a cost-effective restoration solution in an industry then-dominated by contractors who only sold roof replacements, regardless of whether their customers’ roofs could still be saved.

We also had a company that we could sell, so that’s what we did. The money from that sale allowed us to pivot into the business that would eventually become Roof Maxx. What looked like a new company was actually the culmination of years of effort.

Autumn: Harvesting season

Roof Maxx didn’t succeed overnight, but it did disrupt the roofing industry relatively quickly. Homeowners realized we were offering them a way to keep using their current roofs for years to come at a fraction of what it would cost to replace them, and many were eager to try it for themselves.

Our flagship product had undergone extensive testing at Ohio State University, and our dealers were carefully instructed to inspect each homeowner’s roof for suitability before recommending Roof Maxx. We also included a tune-up as part of our complete roof restoration process, which addressed minor damage like nail pops or isolated damaged shingles before the product was applied. This maximized its efficacy and ensured better results for customers.

As a result, many customers who tried Roof Maxx were happy to leave us positive reviews or refer new business our way. As demand grew, we found ourselves presiding over a national dealer network with a presence in all 50 states.

Winter: Preparing for the future

As I write this article, I’m less than a month away from my 60th birthday. I only have a few years left before I’m at what most people consider retirement age. The winter of my career has finally arrived.

But this doesn’t fill me with apprehension. Winter is a time for taking stock of what you have and preparing for the future. Every December, families gather together to celebrate and prepare for the coming year. Roof Maxx started as a family business, and it’s a legacy I’ll be proud to pass on to the next generation once I’ve made the proper arrangements.

When you’re young, you dream of the future. As you gain experience, your focus turns to time and money. Invest those wisely, and you’ll reap what you’ve sown for years to come. After all that, it’s only natural to think about what you’re leaving to others. To everything there is a season.

We don’t get to be young forever, but that’s actually a good thing. Like Pete Seeger of The Byrds sang back in 1962:

“To everything there is a season
And a time to every purpose under heaven
A time to be born, a time to die
A time to plant, a time to reap
A time to kill, a time to heal
A time to laugh, a time to weep”

Of course, those lyrics are even older than that. They originally appeared in the Book of Ecclesiastes, which is part of the Old Testament. If you’re looking for proof of the value in old things, I don’t know where you’re going to find a better example than that.