It was the swinging 1970s and I was growing up with my sister in the heart of the south side of Chicago – a locale that might strike fear in the hearts of those who only envision “Chiraq” news reports. But my upbringing was more akin to that of Michelle Obama’s, with hardworking and hard drinking parents thrown into the beautiful mix.

My dad was 48 years of age when I was born, with enough years behind him to have seen World War II action – both on the shores of the Philippines when the enemy shelled beaches for three days – causing Daddy to cry out to God and make all sorts of promises – and in the local brothel pictured in a gorgeous black-and-white photo from about 50 years ago that decorates my social media pages.

During the war, Daddy made the most of his get-up-and-grind business smarts, even though the draft had stolen him away from his studies and path to a bachelor’s degree at Tennessee State University at the ripe age of 21. His photography skills were on display in his bunk as he held a row of negatives up to the sun, his rifle evident at his feet. What I wouldn’t give to see those photos today.

Back from war, back to business

After falling in love with Japan and a slender African-American model for Ebony/Jet who had a penchant for basketball players – and whose photos I studied endlessly in the bottom of Mommy’s drawers and via Google Images – Daddy reluctantly left the Land of the Rising Sun and the military. His first wife would eventually leave him, making way for Mommy to fall in love with Daddy and marry him four months after meeting at a party.

“He used to keep a bunch of blank checks in his shirt pocket,” Mommy waxed greedily about the guy who was 10 years her senior and already a successful entrepreneur back in The States.

Love and business go together like God as my witness

In fact, Daddy’s need for a typist helped them hook up on the sweltering day in The Chi that Mommy offered him a beer along with her ability to type about 100 words per minute. I can still hear the buzz and lightning staccato of the IBM Selectric typewriter’s keys that would fill our South Michigan Avenue home over the years.

Daddy worked from 3 p.m. to 11 p.m. at the “Big House,” the prison-like nickname for Chicago’s huge old Main Post Office downtown on Congress Parkway.

But his own tax accounting firm is where he came alive. It was all his, and the income he received from many blacks who ran successful small liquor stores and dress shops around the city paid for the mortgage on our two-story abode, as well as our seemingly outlandish $1,000-per-year tuition at St. Edmund’s Parochial School.

I didn’t even know at first I was witnessing entrepreneurship in action…

“You need to get me something,” Mommy demanded of Daddy in her ironic I-am-woman-hear-me-roar pseudo-feminist kind of way.

No doubt the ERA movement and bra-burning in the streets – along with Daddy’s philandering and penchant for “hanging on stools at taverns,” as she would complain – convinced her that she was no shrinking violet who would suffer at home with the little ones until Daddy miraculously stumbled home at 3 a.m. some weekends.

Thus, Parkway Secretarial Service was born, a small office space near the corner of a black-and-white tiled building overlooking the area of 47th Street and Dr. Martin Luther King, Jr., Drive.

I remember being filled with puffed-up pride upon telling classmates that my mom owned her own secretarial service, no doubt chutzpah passed down from her, in the same way she would later proclaim herself an Executive Secretary with emphasis on the former that let listeners know she considered herself a step above regular secretaries.

Those afternoons after school spent spinning with my sister in swivel chairs in Mommy’s office until we literally saw black space highlighted by swirling stars – along with Daddy’s trots to his office on weekends plus the staplers and file cabinets littering our house – taught me plenty about entrepreneurship.

Entrepreneurship = Hard Work, Long Hours, Freedom, and a Roller Coaster of Financial Situations

One time we spent the entire night at Mommy’s office to make a deadline to get school booklets printed. We became mini entrepreneurs that night, helping her desperately staple booklets in the center.

I learned from the litany of young and interesting secretaries that flowed through the business – including one who left to go follow her boyfriend in a hot band called the Chi-Lites – that employees can change and businesses can fold. Mommy chose the wrong industry in her secretary firm owner role, which at times acted like a cover to sneak away and do her own dirt with a client inside his fabulous Lincoln Continental Mark IV mint green car.

Mommy’s failure at entrepreneurship taught me to start a company surrounding my gift. I mourn the notion that she didn’t turn her amazing sewing and design skills into a house that could have rivaled Versace.

But Daddy’s love of doing taxes stuck, all the way nearly to the day he died in 2011, at age 90, leaving my sister and I to contact any remaining clients with the news.

How I turned a $10 domain name into $3,900

Watching my parents work like dogs taught me directly how to hustle. Before he died, my dad was still showing off his entrepreneurial chops by telling me something about Google Adsense and stuff. I admonished him for spending his little income on get-rich-quick website schemes instead of fixing up the house.

However, after I published my first blog post in December 2005, and later learned that some people actually were making money online, I had to apology to Daddy – and thank him for being so up-to-date on technology, even into his 80s.

I jumped into trying to make money online. Back then, “niche websites” were becoming all the rage and everyone was seemingly selling some kind of course that ended in a seven: either $47 or $97. These days, the courses are much higher. I just scrolled through thousands of words in a transcript from “A Very Sensitive Request From James Altucher” to learn that he’s selling his knowledge for $2,000 per month. I love the guy, but come on!

Anyway, some of that “learning” must’ve stuck, because records show that I registered Redboxfranchisecost.com on May 26, 2011. It was a popular phrase typed by folks searching Google to learn how to get their own Redbox machines, and the domain name was available, so I bought it. Unlike some of the other niche sites I’d set up, that one began making a steady and easy profit – without me having to do much to it.

People loved clicking those Google Adsense links at the top of the website, and by 2014, I was able to boast that the website drew “$8,514.41 total Google Adsense income and counting” with 4,209 unique visitors and $331 earned monthly, as my listing on Flippa noted.

I provided proof of the Google Adsense monies I made each month with the site. I only sold it because American Express was breathing down my neck and I needed to pay off my bills. Thankfully, the site was scooped up for $3,900 – and has apparently been a boon for the buyer, who I estimate has made about three times his investment to date.

Such are the lessons learned along the journey of being a business owner – like the fact that the $29.00 “standard Flippa listing fee” and the “escrow fee of $63.38” that I paid Flippa supposedly didn’t cover the “$195.00 seller escrow fee” that was cancelled, something they claimed I still owed that I don’t completely understand.

“Your account has been suspended temporarily due to potential site rule/guideline violations,” they wrote me years ago. Oh well, if I ever build another bang-up site that I decide to sell, I will throw the nearly 200 bucks their way – but they better get in line behind the IRS. Yeah, that is another valuable lesson learned about being an entrepreneur: Pay your estimated taxes, especially if you run or sell websites!