The Paperboy

The Paperboy

Everything I ever needed to know about business I learned as a nine-year-old paperboy...

The Paperboy... Its 5AM, its pitch black out, and its 34 degrees and sleeting. The wind is screaming, you’re 9 years old, and you have to deliver the papers. You get up, put on 3 pairs of sweat pants, and 4 sweatshirts. 60 lbs of papers have just been dropped off, and you grab your flashlight and a razor to open the bindle. You spend the next 30 minutes in your garage folding the papers into tight packets and you load up your paper route bags which are tied to your bike.

You head out into the snow, and walk your bike the first half of the route which has 3 monstrous hills. The bike eventually becomes light enough to ride and the cold becomes less and less horrible. It takes over 2 hours to deliver a paper to each of your 160 customers. Barely enough time to get ready and get to school.

This was my daily ritual 7 days a week for 3 years delivering the Boston Globe in Winchester, MA. The job was hard but lucrative and it taught me everything I ever needed to know about business. My paper service provided a $5,000 dollar college scholarship which you were entitled to for three years of service. $5,000 in the late early 90s was a lot of money for college. My undergrad degree from Bentley University was $75,000 and I minimized that further by receiving grants to play Division II Football as an Offensive Left Tackle, and working 20 hours a week at a Dotcom startup, e-Dialog, where I discovered Linux in 1997, and sent me on the trajectory I find myself on today at

Delivering the Globe taught me the value of hard work and how life is linearly rewarding. The more you put into something the more you get out of it. Anything worth doing is hard, and strength can be manifested in character and body. My paper proceeds were invested in the nicest X-men comic book collection in the North East.

At times I felt like Sisyphus. My 80 pound bike was a boulder and I was a bit of a trickster who in fact had cheated death. I spent the better part of my 3rd year in Children’s Hospital with a wicked infection in my right ankle which massive amounts of antibiotics could barely control.

Both of my parents had paper routes, and I was always a business man. My paternal grandfather Daniel R. McGonagle Sr. put three kids through college selling flashlights door to door. He opened one door at a time and emptied his car trunk literally every day seven days a week.

I quickly discovered there was a side business opportunity for a paper boy walking dogs. I had a business called Pet Care Extradinaire, and my tagline was: If you have something to do and your pets being a pest, give me a call and Ill do all the rest.

In the afternoons I had the keys to 15-20 houses and would walk their dogs. Some were good dogs and some were bad. And I was lucky I wore 4 sweatshirts as dog attacks are a hazzard of the paper route and dog walking professions. The worst and last one was very bloody, and I always carried a can of mace, and a wrench afterwards.

Today, I value the hard work that I put into that paper route. It taught me so many valuable lessons that I still use today. I am sure there are other jobs that have done this for others and I’d love to hear about them.