How Time Outside Teaches Us to Live with Uncertainty with Fleet Feet CEO Joey Pointer

Joey Pointer grew up working six days a week on his family’s tobacco farm in rural North Carolina. He shucked truckloads of corn, drove tractors long before he could legally drive a car and learned that the work still had to get done—even when the weather changed or the plan fell apart.

At the time, he hated it. College was his ticket out.

Today, Joey is president and CEO of Fleet Feet, the country’s largest network of locally owned and operated running stores. In this episode, Ashley and Joey explore how the childhood he wanted to escape may have prepared him to lead: teaching him to work hard, contribute to something larger and remain steady in the gray areas where there is no obvious or perfect answer.

Joey also shares what he learned by watching his parents. His mother used her work to strengthen their community, while his father showed him that taking care of people was an essential part of running a business. Joey remembers watching his father pay farmworkers for a full day even when a storm sent everyone home early—a decision Joey questioned as a money-loving kid but understands very differently as a CEO responsible for thousands of employees.

The conversation also turns to the experiences children have when they are given time outside without constant entertainment. Joey tells Ashley about lying motionless in the grass to see whether a vulture would mistake him for something dead. The vulture never came, but Joey now recognizes what the experience required of him: curiosity, patience and the ability to hold one thought for a very long time.

Now a father of three teenagers, Joey is honest about how difficult it is to cultivate those qualities in a world filled with phones, social media and rapidly changing technology. He doesn’t claim to have figured it out. Instead, he is trying to help his children understand the world they are entering while also learning how to turn it off.

In this episode:

Ashley and Joey talk about:

• Growing up on a working tobacco farm in rural North Carolina
• Working six days a week and taking on meaningful responsibilities from an early age
• Joey’s childhood lawn-mowing business and his first experience scaling something
• Why farming taught him to live with weather, uncertainty and circumstances he couldn’t control
• The connection between farm life and Joey’s comfort operating in the gray area
• What Joey learned by watching his parents work, lead and care for their community
• Why his father paid farmworkers even when rain ended the workday early
• How running became a form of meditation and a place to work through difficult decisions
• A seven-week, 12,000-mile family road trip to Fleet Feet stores and national parks
• Why leaders have to stay close to the people doing the work
• Joey’s childhood attempt to lure vultures into the front yard—and what it reveals about boredom, patience and sustained attention
• Why Joey believes harvesting tobacco was harder than completing an Ironman
• The challenge of helping teenagers build grit and resilience in a plugged-in world
• Why children need to understand technology while also developing the ability to turn it off
• The self-doubt Joey experienced after becoming CEO
• What it means to carry responsibility for the livelihoods of thousands of people
• Why Joey now feels drawn back toward dirt, physical work and the tangible rhythm of growing something

A few moments from the conversation

Joey remembers working on the farm from sunup to sundown, beginning when he was around eight years old. The expectations were not necessarily communicated as a list of rules. Work was simply part of family life. Crops had to be planted and harvested, and everyone was expected to contribute.

He also remembers loving money. After earning $40 for spending four hours mowing his grandmother’s lawn, Joey saved enough to buy a riding mower. That allowed him to take on more yards—his first experience growing a business. During the school year, he washed golf carts and collected discarded aluminum cans to earn a little more.

One of the central threads in the conversation is Joey’s comfort with the gray area. Farm life involved weather, machinery and growing conditions no one could completely control. Joey had never directly connected that childhood uncertainty to his leadership style, but he recognizes the parallel: You control what you can, make the best decisions available and keep moving through the storm.

Joey shares an unforgettable story about lying still in the grass to see whether a vulture would fly down to investigate him. It sounds absurd—and his children think it is—but Joey could remain there, quietly holding the same thought, for a remarkably long time. Looking back, he sees a connection between that childhood patience and the resilience required to stay with difficult problems as an adult.

When Ashley asks how he is giving his own children grit and resilience in a world competing constantly for their attention, Joey answers honestly: “Can I just say poorly?” His children have chores, jobs, camps and outdoor experiences, but he acknowledges how hard it is to compete with phones, social media and the expectations of their peers. He wants them to understand technology and AI because those tools will shape their lives. He also wants them to know how to turn everything off.

Joey also talks openly about becoming CEO. Although he had imagined leading a company since childhood, the reality brought fear, insecurity and years of self-doubt. Leadership meant recognizing that people watched his mood, depended on his decisions and trusted him with their livelihoods. He describes the small reminder he placed outside the Fleet Feet office—a mirror with the word “smile”—to help him arrive fully present for the people around him.

Near the end of the conversation, Joey returns to the farm. The work he once wanted to escape now holds a different appeal: sunlight, dirt, physical effort and the satisfaction of seeing something planted, grown and harvested. His work today may never feel fully finished. Farming offered a tangible conclusion—and a connection to the land that he understands more clearly now.

Links & Resources

• Learn more about Fleet Feet
• Read more about Joey Pointer and his path from a tobacco farm to Fleet Feet
• Read about the Pointer family’s seven-week road trip
• Find a Fleet Feet store near you
• Explore America’s national parks
• Subscribe to Raising Wild

About Raising Wild

Raising Wild is a podcast from Wild Idea Media, hosted by Ashley Arnold, about what wild places build in us—and what happens when childhood drifts too far from them.

Every other Wednesday, Ashley talks with writers, scientists, educators, leaders, artists, athletes and parents about childhood, nature, freedom, risk, resilience and the wild, capable kid in all of us.

Together, they explore how time outside shapes us into more capable, curious and connected people—and why the wild places that made us who we are are worth paying attention to, caring for and protecting.

Joey Pointer is president and CEO of Fleet Feet, the country’s largest network of locally owned and operated running stores. He joined Fleet Feet as financial manager in 2004, became chief financial officer in 2012 and stepped into the CEO role in 2017. Today, the Fleet Feet and Marathon Sports platform includes more than 300 stores and nearly $600 million in annual system-wide revenue.

Joey grew up on a working tobacco farm in rural North Carolina before earning undergraduate business and accounting degrees from UNC Kenan-Flagler Business School. He is a runner, an Ironman finisher and the father of three teenagers.