Me and the Chicago Tribune.

I started life parked in a stroller at Amway Global and Prepaid Legal Services events my parents frequented. Subliminal indoctrination into the world of entrepreneurship. My siblings still joke about my first words “buy low and sell high” and there are pictures of me perusing the stock section of the Tribune (yes that’s me in the picture). But the real scene of the crime took place in the summer of 1986 or 1987, so I was 5 or 6ish, in a little southwestern suburb of Chicago, IL called Palos Heights.

My father was the head-honcho (owned and operated) of a little automotive detail shop called Hi-Tech Auto where we both worked… and lived. For me, those years were pretty impressionable. A lot happened, my parents split (long story for another time), I lived in a garage with my sister, father and some random employees who worked for him. I slept in cars and showered in a toilet stall with a hose Macgyvered to the sink, but being 5 you don’t really know any better and just roll with it. I bring this up because the most amazing part is that my father knew how to make “chicken soup out of chicken shit” and somehow made it feel normal. He always went out of his way to make me comfortable, no matter the situation. There was always a hustle going on and was a constant source of inspiration for me as a young entrepreneur. It’s great to remember where you came from, a humbling reminder as I write this.

The stand

Right before my parents split, I got my dream birthday present, a toy only an entrepreneur would want. Took me a while to figure out what this little piece of nostalgia was called, but I found them eBay recently called Playskool Pipeworks. Think lifesize Tinker Toys. I had vision to turn it into a lemonade stand, I’m not sure why I remember it so vividly… I think it may be the commercial I’m remembering. Anyway, after a couple of extra chores, and a lot of begging they finally appeared but were quickly packed up, moved between parents and forgotten. Until a year later when that dream (or commercial) would become a reality.

As the story goes, or at least from my mom’s recollection, my father offered to loan me some money, with interest, to fund my beverage stand startup. We made a trip to Aldi to buy some cups, premix powdered lemonade, and the essentials. I anxiously unpacked and built my stand, stirred up some Country Time lemonade, and squeakily markered up a sign on poster board to open for business. Lunchtime rush brought empathetic foot traffic. My dad’s employees and mechanics next door lined up, dollar bills in hand. (I believe I was charging 0.50 – 0.75c a cup but I can’t remember that far back) and by late afternoon I was SOLD OUT. What a day and a wad of singles! My success, and first thumb through the day’s take were quickly interrupted, a moment I won’t soon forget. My father’s glasses at the tip of his nose as he blabbered something my greedy Uncle Sam, a lease agreement for the space that my 4′ stand occupied plus interest on the original loan? The greenbacks now near half the pile I ended my shift with.


Over the years, while others would find ways to cut costs and reduce their budget so they could save up or afford something, my perspective was always to find a way to have my cake, and eat it too. My inner voice always rambling “how will I make more to afford this” rather than “what can I cut out of my budget” or “how long will I have to save up”. Don’t get me wrong, I had a budget plan early on and always made great money for my age. There has ALWAYS been a side hustle (or 2 or 3) and anyone that knows me from my earlier entrepreneurship years would say “what business are you into now?”. I had always wondered when and where that mindset started for me and didn’t really recognize it until I started writing this.

So back to the story. I made a little money, got slapped with reality, and a new perspective began to evolve in my brain. My first of many, entrepreneurial seizures. How do I replace what Uncle Sam took? What if I could sell snacks like the coin-operated criminal (vending machine) that sold $1.50 bags of chips (that is like $3.50 in today’s money). Subtract X from Y, count the number of sales I had to make each day, raise prices. I was hooked.

Entrepreneurship 101

Hi-Tech Auto (My lemonade stand was set up in between the two last bays on the right)

Over that summer my father and I made several successful Aldi runs, expanding my empire to include Arnold Palmers, flavored lemonade, chips, cookies and then pizza, hot dogs, bratwurst. I even owned a hot dog warmer, a pizza oven, and a microwave. We settled up at the end of every day, with a note pad and some real-world math. The lessons I had previously struggled to master in a classroom (math, spelling, etc…) I had now grown to love. I learned to prospect by canvassing the local construction site, strip malls and car wash with Xerox’d copies of my menu. I bartered my big blues to drive in more buyers and learned the art of persuasion (sales). While other 6-year-olds were playin’ ball and riding bikes around the hood I was taking orders and flipping burgers.

By midsummer, my little lemonade stand grossed nearly $3,000 ($7K in today’s money), an amazing feat for a young restaurateur. My stand had garnered the attention of our local community, nearby hospital staff, police, and, apparently, the city’s department of health and food safety… I had taken a noticeable share of the lunchtime crowd from local hot dog stands, or at least that is how I like to remember it, which may have gotten some unwanted attention and awarded me my first “Cease and Desist” notice from the city. Ok, ok, it wasn’t that formal or serious. I think what went down was that my father had been warned that we would need a permit and some health and safety protocols or we had to close up shop. Lessons learned about navigating permits, regulatory and compliance, and local competition.

Just as fast as it started, it was over. The funny thing is that I don’t remember being that upset about it. At the sunset of the summer, I took my money and invested in a full-sized, coin-operated arcade game, Buck Rogers The Planet of Zoom, and some baseball cards that were going to be used as prizes for my new arcade startup. A business that would later become my first big failure, and another great lesson learned from entrepreneurship 101.

The original hustler

The exercise of writing about my journey in entrepreneurship has reminded me of where I came from and some of the events that shaped who I would eventually become. When I read it back to myself, I think of how many paths I could have taken, and ways this story could have ended. I was fortunate to have amazingly loving, supportive, and entrepreneurial parents and amazing mentors along the way. But out of all of them, I raise a glass of lemonade, in honor of my father who was the original rise and grinder, hustler and entrepreneur who made this story a part of my life.