My First Job: Customer Service & Entrepreneurship Through Newspaper Delivery

There’s a popular series of articles circulating on LinkedIn right now where mega-successful people discuss their first jobs and what they learned. While I don’t fall in the ranks of the mega-rich, mega-successful business people, it might still be somewhat educational and entertaining to talk about my first job. I figure us regular guys deserve a chance to tell our stories, too (and why should all the bigger names get all the fun).

I grew up in Parma, Ohio in the 60s and 70s, where I proudly served as a paper boy for both The Cleveland Press and The Cleveland Plain Dealer. Delivering newspapers was still a kid’s job then and it gave me plenty of spending money. It also taught me a number of valuable lessons from an early age, including:

Show up or bow out – For the Press, the truck was there every day Monday through Saturday (no Sunday delivery) on Pearl Road near Ripepi’s Funeral Home at 3 PM. The driver threw the paperboys the papers. I had to sometimes assemble the papers and haul them up and down Dresden Avenue and a small part of Pearl Road, until they got delivered. If I didn’t feel well, I either had to do it anyway or find a substitute. We were on deadline and I’d lose the job if I missed a day. There were no sick days for a paper boy (a small business franchisee). I still don’t take a sick day unless I absolutely have to.
Customized personal service pays – Back then, I had to ask every customer where they wanted the paper delivered. The Press didn’t let me just throw the paper on their driveway. I had notes and had to remember that 7840’s paper went in the milkchute, 7920’s paper went in the rear door up the back stairs, or that 7410’s paper went in the front door. Those houses with unusual delivery locations gave better tips. Custom service pays.
Don’t be afraid of the dogs and the mean kids – Some houses had dogs. Big barking mean dogs. But I still had to deliver the paper. Someone told me that if you don’t show fear, the dogs will leave you alone. It worked and I use that lesson up until this day. Same thing applied to the mean kids who didn’t think delivering papers was too cool.
You gotta ask for your money – As a Press boy, I was responsible for collecting the subscription money and turning it in every period. On a Saturday, I had to trudge up and down the street (again) with my big steel loop that contained my collection cards. Had to knock on each door and ask for the paper’s money. I also kept track of who paid by using my hole punch to put a mark next to that period’s collection box on the collection card for each customer. If I didn’t collect the money from a customer, I had to go back again and again until they paid. If I didn’t do it, I didn’t get paid and someone else would take my route.
You gotta prospect for new business (but you’ll get something for it) – One night, my adult Account Manager showed up at my house and tells me we’re going to go and sign up new customers. I don’t want to do it but my parents tell me I have to. We go house to house on the street signing up new accounts and I’ve got another ten customers by night’s end. The Account Manager reaches into the back seat and gives me a fishing rod as an award. For putting a little effort into it, I got more accounts and revenue and received a sales commission. That was sweet.
Know the community – I really became part of the neighborhood and I knew most families in most houses. Nothing gets you more connected and more successful than knowing your customer base.

Looking back on it now, the paper route was excellent training for the adult world. I learned responsibility, customer service, dealing with difficult situations, prospecting, how to get paid, and hanging on to what was yours. It’s a shame that we don’t let our kids do this anymore (or they don’t want to do this) but it laid the groundwork for a lot of my success in later years.