What Being Homeless Taught Me About Business

Life-long lessons.

Disclaimer: No AI was used in the production of this story, only HI.

At age 9.5, I was homeless and responsible for my mother, brother, and two sisters. I was now head of household.

First Lessons Learned

When I finally found work, I walked over five miles up and back down El Cajon Boulevard in San Diego, looking for work. Despite being 5'7" and fairly strong-looking, no one would employ me.

I was foraging for food amongst a sea of galvanized trash cans when the owner of the Italian restaurant came out and stopped me. He was a first-generation Italian American who said, “Hey, get a job!” When I explained my circumstances, he said, “Can you wash dishes?”

The lesson learned was that if you can’t offer someone a benefit, there’s no way you’re going to convince them you can help or be of service.

I also learned never to give up. NEVER. I could have just gotten mad, run away, or backed down. I didn’t. I politely stated my circumstances. He saw the human capital in me. This singular lesson served me well in school, the military, and in business. Most especially in business. NEVER give up.

Next Lesson, Accountability

The store owner’s oldest son had just finished college. I was still homeless, but we didn’t have to look for food; the owner agreed to send food home every night when I finished work at midnight. I worked from 4 p.m. to midnight so I could go to school and take care of the other kids and my mom.

Tony, the son, pulled me aside and said, “If you want to get somewhere, always ask, can I do anything else to help you.” He said he learned this in college from a friend. I started asking everyone I worked with if I could help. It paid off. The owner noticed. He started teaching me the business when I was ten. I was the only one outside the family that knew the recipes. I became his go-to guy at night. By eleven, I was 5'10" and weighed around 225 lbs.

If You Follow Through, Others Will Help You

It wasn’t long before the owner’s wife taught my twenty-nine-year-old mother how to be a waitress. She had never worked at anything in her life. She held that job from twenty-nine to forty-four when she died of cancer. She was great at it. People loved her.

Along The Way

Lessons in business, how to do business, how to run a business, how to provide customer service, follow up, and how to get customers for life were ingrained in me from an early age. His sons and I learned it together. They went on to achieve multiple points of distribution in several states. I grew up and left that business by the time I was fourteen.

While I talk about having twenty-seven businesses, those were from when I had just turned twenty-one until I finally sold my last business when I was seventy-five. Not everyone was a winner. But most people would say the work I did, the people we helped, and the places I’ve been have all made me the man I am today.

In my youth, I had a car detail business serving more than 75 apartments in Bell, CA. My father was a tool and die maker working for Bethlehem Steel. I earned half of what he made just working every weekend.

In the military, I sold Rolls Royce and Jaguars (and other new foreign cars). I bought and sold used cars on the side to enlisted Air Force men and women.

For a short time, I co-owned a business at twenty that repaired rentals for a wealthy real estate investor.

Life Changing

My real estate client made his money in insurance. I applied to Mutual of Omaha to sell insurance. After taking all the tests, they sent me a rejection letter to tell me I COULDN’T SELL. Yet another lesson learned: just because you own a large, successful business doesn’t mean you get it right.

The Take-Away And Challenge From This Story

While being homeless, I learned about business, being a dad, a son, a brother, a provider, dignity, character, and the ability to say NO. There were constant opportunities to make more money, sell drugs, run numbers, be a lookout, join a gang, or steal. The list goes on. I was poor and had all of the advantages of being poor.

Yes, advantages. That’s your challenge today. Look at your youth, family, schooling, friends, and work you’ve done in the past. Besides the success and the misery, what did you learn about being in business? What lifelong lessons are you still using today? Use them, write about them, and share those experiences so that others can learn.

This is a shout-out to a few people who have started this movement. Please read their work:

Conceivably Me (first used the term HI), Victoria Kjos, R C Hammond, @Maryan Pelland OnText.com, Michael Koetsier, @CarolF, and many many more. Today, the number of writers is nearly 300 on Medium, all of whom have written about topics for consideration on AI vs. HI.

Please jump on the bandwagon with us to participate.

Thanks for reading,

✍ — I would greatly appreciate it if you give me some feedback and let me know you saw this post. Thank you!

©DR Rawson

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