The Most Important Business Lesson I Ever Learned Was at Sixteen Years Old
The Product Was Never the Product
At 5:45 am on some Saturday mornings, a tricked-out truck in a drive in theater parking lot was all darkness.
A few vendors sat or slept in their trucks waiting for the gates to open.
One of them was 17 years old.
He had a box full of defective shirts, a handful of cardboard signs, and absolutely no idea he was getting the best business education of his life.
The shirts came from my father’s fledgling company, Contessa of Hollywood.
Inside a small production facility in Hollywood, artists stood in front of easels airbrushing. They created roses, sunsets, beach scenes, rock and roll artists and every other California inspired design imaginable onto dresses and shirts destined for boutiques across the country.
Not every piece survived the process perfectly.
A little overspray here.
A small loose thread there.
Maybe a stencil shifted slightly.
The boutiques did not want them.
The manufacturer did not want them back.
So, into a box they went.
And eventually, into the back of my truck.
A couple of weekends each month followed the same routine.
Get there before everyone else.
Claim the best spot for foot traffic.
Wait for the gates to open to pay and get your stall, which was merely a parking spot for a movie at night.
Nobody handed out maps explaining that.
Nobody taught it in a classroom.
It was simply obvious after watching customers stream through the gates while vendors three rows deeper spent half the morning wondering where the crowds were.
Same shirts and prices.
Different results.
By nine o’clock the flea market (swap meet) would come alive.
Families.
Collectors.
Bargain hunters.
Young couples.
Tourists.
People looking for something they needed and plenty of things they didn’t.
The cardboard signs weren’t fancy.
Most looked like they had been made the night before because sometimes they had.
Buy two, get one free.
Special today.
Perfect gift.
Nothing revolutionary.
Just enough to get someone to stop walking.
That was the real challenge.
Not selling the shirt.
Getting someone to stop long enough to look at the merch.
Like a barker out front of a strip joint, “look at these beauties on sale here!”
The interesting part came after that.
Most shoppers could not find the defect.
Many stared at the shirt for a minute or two before asking where the problem was.
I would say “if you cannot find it then neither can I.”
A tiny paint mark.
A slight stitching issue.
Something so minor it disappeared the moment the shirt was worn.
The conversation usually became more important than the shirt itself.
A woman shopping for her daughter or a husband looking for a birthday gift.
Maybe a grandmother buying something colorful for a granddaughter.
The shirt opened the discussion.
The discussion often made the sale.
Christmas was a completely different world.
The exact same shirts suddenly became gifts.
The cardboard signs became seasonal colors, with a bow, or a wrapping paper around it.
Traffic increased and sales increased. Even the energy increased.
A teenager making seventy-five to one hundred and fifty dollars on a Saturday suddenly discovered that December could be a very profitable month, doubling or tripling the payout. The money mostly went toward furthering the look of my tricked-out truck.
Looking back, what stands out isn’t the money.
It isn’t the shirts not even the flea markets.
What stands out are the people.
The products changed over the years.
Selling and delivering newspapers from my bike.
Airbrushed apparel.
Chevrolets.
Banking services.
Technology.
Different industries, customers and decades.
Yet one thing seemed remarkably consistent.
People wanted to buy from someone they liked, that seemed genuine.
Someone who listened to them and who treated them fairly.
I would take the time to answer a question instead of rushing in to close a sale, also listening to the buying signals.
The shirt was rarely the entire story, also the car selling wasn’t either.
Neither was the bank account, the software or the stock.
The product was often just the beginning.
Trust did most of the heavy lifting.
Funny how a box of rejected shirts taught that lesson long before Silicon Valley, banking, entrepreneurship, or investing ever entered the picture.
This content is for educational and informational purposes only and should not be considered financial advice. Investing involves risk, including the potential loss of principal. Always do your own research before making investment decisions.




I like this article a lot! Previous life experiences in any kind of sales will make one a better listener/negotiator/problem solver/etc. It's interesting to think that it's not really about the product itself but rather how it is sold/who it's sold by. Reminds me of waiting tables and connecting with the customer on any level before they even think about ordering, always makes the "sale" of food and beverage easier and usually more profitable! Also learning new things about your dads upbringing is always fun too! Thanks for sharing, another great read pops!
Some people are just born with it! You definitely are Phil. The desire to connect with people , find a need and fill it, and really explore your entrepreneurial spirit! I think those of us that grew up helping out in our parents business, and really using that experience to help us develop our own business sense was a real gift. You did such an amazing job at writing this article and it allowed for me to create a visual of the whole thing. Wish I had been around to buy a shirt from you.! You would've sold me😂