This is the first part in an ongoing series where I talk about my history in business, starting all the way back when I was a child to now, my mid-forties. I already wrote part “zero” right here, so you should read that first if you haven’t yet to get some context.

Here we go, part one…

As I talk about in my primary book, I was raised in a financially strapped, lower-middle-class family. My dad, a psychologist, worked for the state government with a low income, and then later started his own counseling business, still at very low income when I was younger. He supported five children, of which I was the oldest, plus my mom, a stay-at-home wife. (Back in the 1970’s and early 1980’s, low income men could actually do that. Today it’s impossible because of our slowly collapsing currency and economy.)

Things were very tight. All of us kids wore cheap hand-me-down clothing, we ate the cheapest food my mom could buy at the grocery store, and we virtually never went out to eat at restaurants, even fast food ones. My childhood was spent asking my mom for certain toys and listening to her complain that she couldn’t afford it, even if the toy I wanted was just two dollars.

I quickly determined that if I wanted money, I was going to have to get it myself, since clearly my parents weren’t going to do it. (Many years later, my dad would indeed become financially successful with his business, but I was already moved out of the house by then.)

The first business I remember starting was when I was eight years old. It was selling newspapers about whales and sharks to the other kids in my class. Whales and sharks were cool to little kids, myself included. I would get big stacks of newspapers either for free (some of them were free!) or for 10 cents each, using pennies and other scraps my parents would give me for my allowance.

I would call up all the kids in my class the evening before and let them know I was going to sell these newspapers to them the very next morning, in class, right after the pledge of allegiance, and to ensure that their parents would give them some change to bring to school so they could buy my newspapers.

The next day, I would sell all or most of the newspapers I brought to class at 25 cents each, a 150% profit (or infinite profit when they were free). I would come home with over a handful of shiny quarters, which back in 1980 was a decent amount of money for a kid.

I would run home, run into my room, lock my door to keep my younger siblings out, and pour all the quarters into a small pile in my bed. Then I would just lay on my bed, staring at them. It was about five dollars in quarters, more money than I had ever seen in my life. It was so exciting! And so… easy! It would have taken me an entire year of begging my mother to give me five dollars, and yet here it was, after just one day of work.

I knew that if I made this money, I could make more.

Thus motivated, I proceeded to do all kinds of things in order to make money, like:

– I continued to sell different kinds of fun newspapers to the kids in my class.

– I secretly sold bubble gum to the kids on the playground like some kind of kid drug dealer (gum was not allowed in my Catholic school). I would just buy packs of gum at the store for 25 cents, unwrap it, then sell each piece for 10-25 cents each, easily quadrupling or quintupling my money.

– At age 9 or 10, I started going around my neighborhood selling Christmas cards to all the moms. I would sell them in September, deliver them in November, and make as much as $100(!) in profit once the orders were fulfilled.

– Later, as I got bigger, I started mowing lawns for various people in the neighborhood, and later this became moving construction debris on residential sites for local contractors. Sometimes I would make as much as $50 a day. Again, this was a shitload of money for a kid in the 80’s, or at least it felt like it to me at the time.

– Then I started babysitting kids on my street. Babysitting was considered a job for girls, but I wanted money so I didn’t care. I did that for many years.

– Finally, at age 10, after what seemed like years of begging, I got my first computer for my birthday, a $40 TI-99/4A my parents could barely afford. I immediately got to work on it, playing games, learning BASIC, and learning how to type fast. A few years later, I convinced my dad to let me do data entry at his small business and to pay me hourly, which he reluctantly agreed to do after I begged him for six months. Being a stressed out Alpha Male 1.0, my dad fired me and re-hired me three different times for various mistakes I made, but I didn’t care… just as long as I was getting paid.

– By age 12 I was selling snacks and computer disks to all the hackers at local computer gatherings, where these guys would bring in their Commodore 64’s and Commodore Amigas and illegally hack-copy games so they could distribute them them to each other.

– At age 14 I was working for my local science center. Unfortunately, it was a volunteer job so there was no pay, but I knew that if I worked there for at least a year, it would look good on my resume. This way, I figured, the split second I turned 18, I could move out of my parent’s house and get my own place and own job without having to go to college. College seemed like huge a waste of time to me; I wanted to make money, not do fucking homework. Why do homework that won’t matter in a few years when I can instead work full-time, get paid, and improve my resume with real-life work experience?

As it turned out, I was right on all counts, but I’ll talk about that in the next installment.

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