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One of America’s Greatest Business Leaders Started as a Paperboy

Our American Stories / Lee Habeeb
The Truth Network Radio
February 13, 2026 3:02 am

One of America’s Greatest Business Leaders Started as a Paperboy

Our American Stories / Lee Habeeb

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February 13, 2026 3:02 am

Jerry Stead, a successful business leader and philanthropist, shares his life lessons learned from his early days as a newspaper delivery boy in Iowa. He reflects on the importance of honesty, being present in the moment, and taking care of every individual customer, while keeping the bigger picture in mind.

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Shop the new spring collection at 20% off $75 or more with code iHeart20. And we return to our American stories. Joining us next is Jerry Stead. May be the most impactful business person you've never heard of. At least, not yet.

Jerry has never sought the spotlight, not during his tenure serving as CEO or chairman of ten publicly traded companies, perhaps the first in history to accomplish this, and not during his philanthropic work, where he has given well over half a billion dollars to charity. Kerry is also unique in that he never had a contract as CEO or chairman. Jerry wanted his performance, not a piece of paper. to be the reason why companies trusted him with command. To give you an idea of how successful Jerry's leadership has been, consider that a $1,000 investment in his good friend Warren Buffett's Berkshire Hathaway 38 years ago would be worth $1 million today.

That same $1,000 investment in Cherry's companies would be worth $8,800,000 today, more than eight times greater. In this story, Jerry shares with us how his lofty business career began many years ago at the age of nine, delivering newspapers in the early morning hours. in Iowa. Three AL That's when I rise every morning. Never set an alarm since I was nine years old.

Growing up in Iowa, you'd think I had been brought up as a farmer's son. While my parents did assist farmers throughout using their startup insurance company, we didn't work the land or herd any livestock. I was a newspaper boy. At the age of nine, I welded the Des Moines Register like nobody's business. I had 51 daily newspapers, 65 Sunday newspapers, every morning seven days a week.

I'd rise from my bed, Get myself together, eat a quick breakfast, pedal to the railroad station where newspapers were thrown from the rail car. Thought newspapers would land alongside the tracks. I carried my trusty wire cutters that were so important because in those days they always bundled the papers with wire. I placed the papers in heavy canvas bags on either side of my bike's rear wheel. It was quite the load, but once I had the papers on and I hustled to make it all happen.

I had to be at Wally's by 4.20 a.m. and Stand's by 4.30 a.m. Those were the two taverns in town that were just three blocks apart. Both of them received three copies of the Register, and if I didn't arrive by four thirty with the Register Sports Sections, I'd hear about it. I can still remember Wally yelling at me once for being three minutes late.

None of us liked to be yelled at, and I sure didn't either. I scheduled my time and arranged my route so the taverns were always first.

Sometimes I'd arrive at the railroad station right on time as always, waiting for my papers, but the train would be late. Often it was 10 to 12 minutes late. Then I really had to scramble. I peddled like crazy to get the papers to the taverns, get these two customer orders dropped off, and go on to do my normal route before school. Yeah.

By the end of February in Iowa, I'd be on roads where snow was taller than me.

sometimes as high as five feet high on each side of the road. I couldn't get my bike to customers' front doors. the snow and icy roads would double the amount of time I had to deliver the papers.

so I quickly learned how to toss each paper to its expected spot. I became very adept at throwing over snow piles. I used rubber bands to hold the papers together. Every customer wanted their newspaper in the same location each morning. It was a unique exercise in target practice and finesse.

all while trying to pull my mind from the strict schedule. Thankfully no one minded me throwing the papers when the weather was bad. I'll never forget one day, one winter day. My dog, Sandy, who always came with me on my route, was following behind me. Car came over the hill.

It was still dark. Sandy was hit and killed within seconds. a helpless feeling for me, the most I'd ever had. I cried. but I also felt a deep responsibility to get the papers delivered.

I had to quickly think through what to do, working through the emotion of that terrible moment, alone and in the cold. I ended up moving Sandy to the side of the road. got my paper route done and went home so my father could help me gather up Sandy and we buried him near our home. Yeah. Interacting with customers was always fun and satisfying for me as a young man.

I had to go door to door once a week to clack. but I like getting to know the people around our town.

Sometimes collecting could be very tricky. Every now and then I'd call on a customer and they'd literally hide in their house. They'd refused to answer the door. I really dreaded those moments, not only because they were uncomfortable, but I was the one out of the money. I had to pay for every paper myself.

If someone didn't pay, I paid the price. Thankfully, Christmas came around each year and helped ease my irritation with non-paying customers. I was always showered with candy, baked goods, and even homemade gifts. I still to this day have a few white embroidery handkerchiefs with my initials JLS.

Okay. I loved it when the newspapers would offer special incentives to gain new customers. I enjoy a good challenge and am naturally driven for success.

So the thrill of earning an extra reward was exciting and welcome. I was ten, then a veteran newspaper. Boy and then registered offered a program that allowed me to order five papers free of charge with the intent that I would use them to sell new subscriptions and increase the customer base. I read the rules, quickly realized that I could order extra papers, but I didn't actually have to use them to win the prize. I could win the prize without having to gain new customers.

So I ordered five extra newspapers every week for a month. I piled up the papers in my Nana's workshed, and I won the prize. It seemed so simple, I'd outthought the paper, and it felt good that I'd figured out the loophole.

Soon after that, my father noticed all the papers piled in the woodshed. He asked me what I was doing. I told him that I had outthought the paper and won the prize without actually using the extras they had supplied. You never won a prize if you're not being honest, Dad said. You lose no matter what you gain.

My father's comment about honesty was a wonderful life lesson. I've always operated with his principle in mind. I think through the many business acquisitions, global meetings, reorganizations, philanthropic ventures, and personal matters I've faced. And I always operate with 100% trust of every person. Always.

I also verify my intentions. Yes, I could win the prize, but am I going about it in the right values? Is it ethical? Is it the right way to do business? My dad taught me that shortcuts.

take you places not worthy. of going to Ever. Uh When Sandy died that morning, I cried for 15 minutes. My hurt and sadness could not be stopped for a child who loved his dog. Yes, I had a job to do.

But I also had to allow my human emotions to run the course. Throughout my years as a leader, I've been I continually strive to remember and teach that when people come to work, they're not just walking through the door. There are a hundred different things that they're carrying in their minds and in their hearts. We have to make sure that we relate to them and take the time for the humanness of daily living for every one of our colleagues. The incident with Sandy was a reminder for the kind of culture I wanted to build in every company that I'd led.

A few years ago at the University of Iowa, I met with 25 of the top contributors to the school of the Tippee College of Business. Our host started off our meeting asking each of us what our first jobs were and how they impacted our lives. In that moment, I realized how great an impact my newspaper delivery job had been on my life. Yours is a student, son, brother, husband, father, grandfather, manager. Businessman, CEO, and chairman.

Have been profoundly affected by the simple lessons I learned before dawn making $5 per week. I asked that group, how many of you had newspaper routes when you were younger? Turns out 21 of the 25 attendees had worked a newspaper out as well.

So many of us have shared experiences.

So many around the great country of ours have commonalities that are unspoken.

So many of us strive to do our best every day at work, at home, and in our communities. Yet, so often we're running at our own pace. Following our own to-do list and overlooking the opportunity to interact or share with one another on a deeper level. My goal as a leader always has been to be layered and linear. Be present in the moment.

Listen to everyone. And for the people that you are with, always keep in mind the vision and the end goal. Early mornings as a paperboy taught me to be present for every customer, but to keep in mind the entire route.

So that all would be served, and the enterprise could continue for another day. And a terrific job on the production and editing by our own Madison Derricott. And a special thanks to Jerry Stead, CEO and chairman of 10 publicly traded companies. With that first job as a paperboy, taught him a lot of life lessons, that layered and linear approach to life. Take care of that individual customer, but see the paper route as a whole.

You've got to get to the end. You've got to take care of your best customers, but you've got to take care of all of them. By the way, I had my first job too as a paperboy, delivering the Bergen record. Jerry Stead's first job Here on Our American Stories. At CVS, it matters that we're not just in your community, but that we're part of it.

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You see it instantly. It's Coldwater Creek, the mark of exceptional workmanship, and signature touches inspired by a Mountain West heritage, distinctive styles created from quality fabrics, silhouettes perfected with just the right drape, feel-good fits offering ease of movement, and thoughtful details to elevate your look. For a wardrobe you can count on season after season, visit ColdwaterCreek.com. Shop the new spring collection at 20% off $75 or more with code iHeart20. New year?

New you? Begin at losesweightnow.co and make this the year you finally feel in control. With orderly meds, access proven GLP1 terzepatides starting as low as $149 a month. It's simple, doctor-guided, and delivered right to your home so you can finally focus on feeling healthier and more confident. Get started today at losweightnow.co.

Individual results may vary. Visit losweightnow.co and get started today. That's losweightnow.co. This is an iHeart podcast. Guaranteed human.

Mm-hmm.

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