Why Humble Beginnings Often Build the Strongest Leaders

Over the years, I have been fortunate to hold some incredible leadership roles. I served as National Marketing Director for Little Caesars during its high-growth years, led five divisions as a Vice President for a $3-billion convenience store organization with more than 1,400 locations, and eventually became President of Jimmy John's before launching Gray Cat Enterprises in 2004.

But none of those opportunities happened overnight.

Long before the executive titles, the boardrooms, and the strategic planning sessions, I started at the absolute bottom. And not just metaphorically.

I literally scraped mold off cheese for a living.

The year was 1986. I was living in Denver and trying to break into the retail world. I figured if I was going to earn $3.25 an hour, I might as well experience the madness of holiday retail during peak shopping season. So, I started applying everywhere—sporting goods stores, clothing retailers, music stores—you name it.

Then I found a magical land of summer sausage, gift baskets, crackers, and cheese: Hickory Farms.

It seemed perfect. Holiday shoppers everywhere. Festive displays. Endless gift boxes. I was hired almost immediately and proudly handed my first magenta apron. I assumed I was on my way to becoming retail royalty.

Instead, I was assigned to the cheese counter.

At first glance, the display looked impressive with rows of cheddar, Colby Jack, Edam, Swiss, and every other cheese imaginable stacked neatly for holiday customers. But there was a problem quietly growing beneath the surface.

Mold.

Lots of it.

Apparently, my primary responsibility was not customer service or sales. It was mold management.

Armed with a knife, plastic wrap, and questionable confidence, I carefully opened packages of cheese throughout my shift, scraped off the mold into a bucket, rewrapped the product, and moved on to the next block. All of this, of course, had to happen discreetly so customers did not witness the behind-the-scenes realities of holiday cheese retail.

For two straight weeks, that was my life.

And honestly? It was one of the best lessons I could have learned.

Because starting at the bottom teaches you things success never can.

It teaches humility. It teaches work ethic. It teaches resilience. It teaches you how organizations really function from the ground up. Most importantly, it teaches appreciation—for opportunities, for growth, and for the people doing the hard work every single day.

Ironically, I must have done a decent job scraping mold because management began training me on store paperwork and discussing a management track. But eventually, I decided not to pursue that path in Denver. Instead, I packed up my newly acquired “cheese expertise” and moved to Chicago, where I landed a position at Little Caesars.

Again, I did not start in a glamorous role.

I started as a manager trainee working inside a single restaurant six days a week making pizzas, handling customers, and learning operations firsthand. From there, opportunities gradually opened:

• Community Marketing
• Marketing Manager
• Regional Marketing Director
• National Marketing Director

Eventually, I was overseeing field marketing initiatives for more than 1,600 franchise and company-owned stores across 35 markets throughout the United States.

But none of that happens without first learning the fundamentals.

Too often today, people want the title before the experience. They want the outcome without embracing the process. But leadership, growth, and career development rarely happen in giant leaps. More often, they happen one difficult, unglamorous step at a time.

The truth is, there is value in every role—even the messy ones.

The people who become effective leaders are often those who understand what it feels like to work at every level of the organization. They understand operational challenges because they have lived them. They respect frontline employees because they once were one. They value hard work because they know what it took to climb.

Starting at the bottom is not a setback. It is preparation.

Every difficult role, frustrating task, long shift, and uncomfortable learning experience builds perspective and character. Sometimes the job itself is not the destination—it is simply the training ground for what comes next.

Looking back now, scraping mold off cheese was never really about cheese. It was about learning perseverance, humility, and the willingness to do whatever job was necessary at the time.

Those lessons carried me far beyond the holiday retail floor.

And they still matter today.

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