Want Your Business to Succeed? Embrace Uncertainty

Experiment, innovate and grow

As humans, we want to have all the answers right away. But when we’re running a business, there will always be unexpected challenges. They can be as simple as faster-than-expected growth or as extreme as a global pandemic. In those moments, adaptation becomes critical.

For business owners, the trick lies in bravely facing the unknown. When you don’t know the next step for your business, you gain the chance to experiment. Consider leaning into that discomfort—you may come away with an innovative solution.

We’ve partnered with Entrepreneur to highlight three small businesses for their series “America’s Favorite Mom and Pop Shops.” These businesses found themselves at uncertain crossroads—sometimes more than once. Here’s how each spun that uncertainty into gold.

Bobby’s Bike Hike

Today, Bobby’s Bike Hike is the longest-running bike tour operator in the United States. But when Jeremy Lewno first opened the business in Chicago, Illinois, he had to sell his car to buy the tour bikes.

That first bet, placed squarely on himself, set the tone for how he would run his business over the next 20 years. It positioned him for a career of fierce self-reliance and bold risk-taking, in which he pushed himself—and his colleagues—to greater heights.

Expanding the menu

Within a few years of opening, Bobby’s Bike Hike was not only the leading bike tour in Chicago but also looking for ways to expand its offerings. Jeremy and company identified food tourism as a rising trend and decided they would try to tap into it.

With years of tour-leading experience, walking tours of Chicago’s culinary hotspots seemed like a natural fit. 

“There's no better way to experience a city or experience a culture than through its food,” Jeremy says.

But it also meant moving away from the core of the business. “Bike” is right there in the name, after all.

After much deliberation, nknown: eyeing an expansion into other cities that would benefit from BBH’s tours. eremy decided to take the plunge. The response was overwhelming. Customers loved the tours so much that Bobby’s Bike Hike got to put together more of them, design new walking tours focused on the arts and, eventually, organize summer camps for kids.

Exploring the map

For nearly 20 years, Chicago was all Bobby’s Bike Hike had ever known. But after expanding into so many new offerings, there was nowhere left for the tours to grow. So Jeremy took the logical next step into the u

After plenty of research, he identified Miami as a top option. On the one hand, it couldn’t be more different from Chicago. Not only was the climate a polar opposite, but the food scene had completely different influences, and its bike infrastructure lagged a few steps behind Chicago’s.

But that didn’t stop Jeremy. He decided to shelve bikes (at least for now) and focus on the company’s experience with food tours. It was a smart move: when Bobby’s Bike Hike landed in Miami, it received a warm welcome and the business to show for it.

Expanding out of bikes had been one risk that paid off. That experience gave Jeremy the tools to take another calculated risk, trying out a new city. Now, Bobby’s Bike Hike has a playbook for expanding into more cities, diving once again into the unknown and reaping the rewards.

Bond & Bevel

Husband and wife duo Heath and Krista Albers are a classic team. Heath loves making things, and Krista has a unique talent for selling them. Looking for a way to determine their own futures, they joined forces to build Bond & Bevel, a combination cafe and leather goods shop in Caldwell, Idaho.

“Bond & Bevel came from the desire for something different. Wanting to not have a box, wanting to pave our own way, wanting to control our own future,” says Krista.

But things didn’t always look so picturesque.

Learning new skills

Wind the clock back just a few years and you’ll find Heath working as a custom home builder. When COVID-19 lockdowns pushed Americans indoors, it hit his business hard. All of a sudden, he found himself without direction.

Rather than let that rattle him, he took this uncertainty as a chance to learn something new. He started to teach himself leatherworking, using free YouTube videos as his textbooks. It wasn’t long before he realized he’d found a brand new passion—and a business opportunity.

Heath and Krista decided they would wed Heath’s new leatherworking passion to a coffee shop. If that combination seems strange to you, you’re not alone. But it gave the couple something unique in the market, even if it meant learning how to make coffee in the two weeks leading up to Bond & Bevel’s opening day. What’s more entrepreneurial than that?

Letting the money chase you

Bond & Bevel quickly carved out a healthy business in Caldwell, with customers coming in as much for the coffee as for Heath’s handmade leather goods.

Then, one fateful day, Heath designed a leather tote bag that blew up on social media. Demand skyrocketed, and Krista suggested they double down on manufacturing these journey totes.

There was only one problem: Heath wasn’t passionate about making them. He wanted to keep exploring, experimenting and searching for the products that let his leatherworking passion shine through.

“Chasing the dollar means you’re always going after the next project, or the next thing you can sell, rather than having passion in what you’re doing,” says Heath. “There’s a balance in that, but to chase the dollar on everything you’re doing means you're losing the heart and soul of it, and we don’t want to do that.”

Ultimately, the two agreed that it wasn’t worth compromising their vision of self-determination just to chase the money. Instead, they bet that customers would see the quality of everything they made. When that happened, the money would start chasing them. That ethos of experimentation has yet to steer them wrong.

Skull & Combs

When barber Jason Bunce was 35 years old, he felt he’d hit a dead end in life. 

“It was do or die time,” he says.

So with no previous business experience and just $2,000 to his name, he founded the barbershop Skull & Combs in New Haven, Connecticut. That gamble paid off, and he’s since expanded to a second location in nearby Norwalk.

Keeping faith in yourself

Jason started out renting the Skull & Combs space from a landlord who had owned the building since the 1980s. When he first started renting, he built a relationship with the landlord and asked that, if he ever thought about selling, he would give Jason first right of refusal.

About 18 months after Skull & Combs opened, that day came. The only problem was that Jason didn’t have the capital to make the purchase. Without two years of business experience, he couldn’t convince a bank to give him a traditional mortgage on a commercial building.

That left Jason with one option: going directly to the landlord and asking for a private, year-long mortgage. That would give him a chance to build up his experience and return to the banks with confidence. But it also meant betting the farm on this location and convincing the landlord to do the same.

“He agreed to meet and within literally five minutes of having the conversation he agreed to it, we had an interest rate established, and I was elated—over the moon with joy,” Jason says.

Suddenly, Jason had complete creative liberty, giving him a firm base to build his business on. He took that chance and made the most of it, pushing hard for the business he oversees today.

Testing the waters

To this day, Jason rejects complacency. He’s still looking for avenues to improve the business, even in the smallest ways. After all, experimentation doesn’t have to target the core of your business. Even the tools you use in daily work can be a playground for discovery.

Jason had come to know and trust a collection of haircutting and stylist tools and products in his years of work. But he stayed open to trying new ones. He would try out free samples from wholesalers, take note of what worked and refine his tool set.

Over time, Jason found tools that worked even better than the ones he’d known before. They expanded his options, making him a more versatile stylist. And they empowered him to do better work for his customers, raising the bar for their satisfaction.

A strong foundation enables intelligent risk

Embracing uncertainty and charging bravely into risk goes a lot more smoothly if your business already has a firm foundation. Learn more about what Walmart Business can do to help you reshape challenges into opportunities.