I walked away from my conversation with Amy Oliver thinking about how much of life comes down to what we do when we're afraid. Amy, the owner of E-Bike Alley in Williamsburg and Norfolk, Virginia, has faced some pretty big moments of uncertainty. And what I love about her story is that she didn't always know how things would work out. She just kept finding a way forward.
Four Months in Europe and a Pair of Scissors
After graduating from the University of Dayton in 1988, Amy couldn't find a job that excited her. Her stepfather suggested traveling through Europe, so she worked three jobs, saved about $3,000, and went alone when none of her friends wanted to join her.
A couple of weeks into the trip, she was frightened enough to call home. Her stepfather encouraged her to meet people, and a conversation with two students from Yugoslavia helped her find the courage to continue.
Then her emergency credit card expired. Running low on money, Amy bought scissors and started cutting hair in youth hostels to earn the $10 a day she needed.
I loved this part of her story. Before she ever opened a bike store, Amy was learning to trust herself, find customers, and solve problems without knowing exactly how things would turn out.
The Bike Ride That Changed Everything
Amy had already tried several careers, including running a food truck and working in real estate. But the idea for E-Bike Alley arrived during a family trip to California.
She and her husband, Kevin, rented electric bikes with their children and her brother's family and spent eight hours exploring Angel Island. Even with four teenagers along for the adventure, everyone had a wonderful day.
When the rental bill came to more than $600, Amy was surprised by her own reaction. She would happily do it again.
And then she realized something. Hampton Roads didn't have that same experience available, and she believed people would love it.
Sometimes a business idea doesn't begin with a formal plan. Sometimes it begins with one wonderful day and the realization that other people might enjoy it just as much.
Six Months of Crickets
When Amy opened her first store, she expected customers to come pouring through the doors.
Instead, she told me it was six months of crickets.
So she started offering $5 group rides along the Elizabeth River Trail. People could rent a bike, ride with her, and discover for themselves what made the experience special.
Those riders began buying bikes. Then came destination rides, accessories, and a growing community of people who enjoyed getting outside together.
What stands out to me is that Amy didn't wait for customers to understand her product. She found a way to let them experience it.
Choosing Her Own Direction
Amy originally operated as a Pedego electric bike dealer. When market conditions changed and that business model no longer worked for her, she faced a frightening decision.
She left the dealership arrangement and created her own brand, E-Bike Alley.
With leases to meet, her home on the line, and a home equity line of credit helping keep the doors open, she had plenty of reasons to be afraid.
But she kept learning. She researched manufacturers, educated herself and her staff, and eventually built a business carrying fifteen brands.
Amy told me that building E-Bike Alley hadn't necessarily changed who she was. It had given her more room to be herself.
I think there's something wonderful about that.
Fear Doesn't Get the Final Word
Amy was also diagnosed with breast cancer in 2013. She spoke honestly about how fear stayed with her for years afterward, and how it wasn't until her five-year checkup that she stopped constantly looking over her shoulder.
That experience, her solo travels, and her business challenges all connect to something she said during our conversation. When life presents a fork in the road, she'd rather choose a direction where she can help create the outcome.
And her favorite quote?
"Just do it."
If you've been waiting until you feel completely ready to pursue your own dream, I hope Amy's story encourages you to think differently. You can be afraid, still have things to learn, and still take the next step.
Visit e-bikealley.com to learn about Amy's stores, rentals, and group rides in Virginia. She also welcomes questions at amy@e-bikealley.com.
Keep dreaming. And never forget, the world always makes way for the dreamer.