How Throwing Newspapers Taught Me Everything About Business

I didn’t know it at the time, but this was my introduction to becoming an entrepreneur. 

From the time I was eleven, I made money. 

My first job was as a paperboy. And it all started with me talking to our paperboy. The conversation started by just saying “Hi” to the kid. He told me he got a new, better paying job and was leaving the Jersey Journal. He asked, “Why don’t you take over my route?”

“How much money can I make?” I asked.

“You’ll make about $70 per week,” he said.

When he told me this, all I could think about was freedom. I could do whatever I wanted to do. Buy whatever I wanted to buy. My allowance at the time was about $2 per week. This job would blow that away. 

He told me where to go to apply for the job. I went there and the only question the delivery boss asked me was, “Are you twelve years old yet?”

“Heck, yeah,” I answered. I lied and got the job.

“What do I do now?” I asked.

“Come here at 4 o’clock on Monday with a grocery basket. We’ll load the newspapers you need to deliver into the basket. You’ll then deliver the papers with the help of the guy who is leaving. He will help you on the first day. Then it’s up to you.”

I left happy that I got the job. He was happy he’d found someone who could fill the route. 

I got home from school and swiped my mom’s grocery basket. I headed to Jackson Avenue to the delivery storefront of the Jersey Journal. I was so excited.

They pointed to a stack of papers and told me to count out 166 and put them in my basket. The guy that was leaving was there, but he wasn’t helping at all. He just stood there and talked to the boss about who knows what. But he wasn’t helping me is all I knew.

Then off we went. 

In Jersey City where I grew up, there were two-story, two-family houses on both sides of the street. He showed me how to deliver the first ten houses on one side of the street, then grab a handful of papers and deliver them to the houses on the other side of the street. 

He said, “People want their papers before they have dinner. This means you have to go fast or the people toward the end of the route are going to complain. If they complain, they will probably cancel their paper, and you’ll make less money.”

“Yikes,” I thought.

I began delivering the papers to the houses he pointed to. I ran. I didn’t want anybody to complain. I wanted all the money I could make.

It took over two hours to deliver all those papers. I was exhausted but exhilarated. I did it. 

He said to me, “Now you know how to do it. Here is a list of all the people you delivered to. It has their names and addresses. Good luck.”

And that was the last time I ever saw that guy in my life.

Wednesdays.

When I showed up at the delivery office on my first Wednesday, I noticed something that scared the heck out of me. Each paper ballooned to over five times the size of the papers I delivered on Monday and Tuesday. “What the heck is this?” I asked.

“It’s ad day,” the boss said.

“But my basket won’t hold all the papers I need to deliver,” I said.

He said, “Take what you can. Deliver them. Come back and pick up some more. Then deliver them. Keep doing this until you’ve delivered all the papers.”

“That’s going to take forever,” I said.

“If you don’t want the job, I’ll find someone else that does,” he answered.

I worked until 8 pm that night. It took me twice as long to deliver those big, fat newspapers on that first Wednesday.

Getting paid.

At the end of the week, my first Saturday, I got up the nerve to ask my boss, “When do I get paid?”

“When you collect the money for the papers,” he said.

“What? What does that mean?” I asked.

He explained, “After you deliver your papers on Saturday, you go back to the first house, knock on the door, and ask them to pay you the $2.50 for the week’s subscription.”

“That can take all day,” I said.

“That’s how you get paid, “he said. “You have to pay me for all the papers you deliver. Then, whatever is left is yours. If people don’t pay you, I don’t care. You still have to pay me for the papers you took from this office. If you want to make the most money you can, you have to collect the $2.50 from everyone you delivered to.”

So I was thinking, “This is going to take a lot of time, but then at least I get my money.” 

Not so fast.

Going door to door asking for money is not as easy as it sounds. Some people weren’t home. Other people lied to me and said they never ordered the paper. Some told me they didn’t have the money but needed the paper to find a job. And the excuses went on and on. 

When I finally collected all I could, I went to the boss with the money. He counted it in front of me. He then counted out what I owed him for all the papers I delivered. Then he counted what was left. This was mine. It came to $33.30

“But the guy who used to deliver the papers told me I would make $70 a week. I want the rest of my money,” I demanded.

“That’s now how it works, son. You want to make the $70, you have to be better at collecting the money. A lot of people didn’t pay you. Go back and get that money from them that they owe you and it’s yours. You already paid me for the papers.” 

Over time, I got better and better at collecting the money. In fact, I was relentless. It was my money. I delivered the papers. They took them. They owed me the money. I stopped accepting excuses. Their problems weren’t my problems.

Then came cancellations.

The tougher I got on collections, the smaller the route became. I was down to the people who were paying me for the papers, but I was making $40 per week and not $70 per week.

I asked my boss, “How can I make more money?” 

He answered in a flash, “Sell more subscriptions.” 

“How?” I asked.

“You go door to door and ask people if they would like you to deliver the Jersey Journal every day. If they say ‘Yes,’ you’ll make more money.”

Off I went. I knew the houses I was delivering to, so I set aside time to go to the houses that didn’t get the paper. I knocked on the door, introduced myself, then asked them to subscribe. 

“Why would I do that?” they would ask. And then they would say things like:

“I don’t care about the news.”

“The Jersey Journal is a crappy newspaper.”

“I don’t have the time to read it.”

“It’s all bad news, and I don’t want to read it.”

“It cost too much.”

This was my first experience selling. I went back to my boss and told him what people were saying. He gave me a few sales tips and sent me on my way. 

Selling is really hard. 

And then came Wednesday again

This time I was ready. I had two baskets. I had to buy one for $15, but I was ready for the increased size of the paper. But dragging two heavy baskets proved to be my undoing. 

The next Wednesday, I hired a couple of younger kids to work with me. One would pull the lighter basket, and I would point to the houses that needed delivery. The kids were following my instructions. This proved to be the best way to go, but now I was making just a little less because I had to pay these kids.

Then the complaints came.

My new employees were not as diligent as I was. They were throwing the papers on porches, and a good wind would blow them apart. They left them exposed to the rain. They would miss a house or two and hide the papers somewhere not knowing where to leave them. 

People started to complain. Either I would not be paid by these people, or I would only get paid for the papers they received. 

The newspaper delivery business was my first experience at making money. And you know what? I loved it. Making money was something I really enjoyed. I liked that it came with challenges. I liked that I was rewarded when I solved these challenges. I solved someone’s problem, and I was paid to do it. I had money and the freedom that came with money. I loved it.

From the moment my boss counted out that $33.30 and gave it to me, I was hooked. I spent the rest of my life looking for ways to make more and more money. And in every case it included:

• Picking up a product or making a product

• Delivering it

• Collecting money

• Selling more people

• Customer service

And that is what business is all about. Nothing more complex than a Jersey Journal delivery route.