How to change an entrepreneur’s life
I started my first business when I was 6 years old. New York City, 1979: I’d take a pile of books from our house, lay them out on the sidewalk in front of our apartment building, and sell them for whatever I could get.
It was an unbeatable business model for two reasons. One, people find little entrepreneurial kids so cute that they are willing to be absolutely fleeced by them. Two, my cost of goods was zero: I basically stole product from my mom, who let me get away with it [see reason #1].
I became a partner in a business in Miami when I was 23, distributing large-format digital printing supplies to Argentina. “Large-format digital printing supplies” = all the raw materials that go into making giant billboards, or bus graphics, or window signage: giant rolls of paper or adhesive vinyl, giant jugs of toner, etc.
I say “I became a partner in the business” rather than “I started the business” because it would be overly generous to ascribe any level of intentionality, sophistication or skill to what I was doing. I met this older Argentine dude who said I should work for him and he’d give me 20% of the company so I could be an “executive” and a “business owner,” which sounded just fine to me. I thought he had all the answers and I was happy to follow him.
He had a printing company in Buenos Aires that was effectively my only customer. Instead of a glamorous “executive business owner,” I was essentially a glorified purchasing agent, buying, consolidating, and on-shipping the inputs to his South American business. When the printing company went under, so did I.
I became a partner in another company right away, following another man who had answers. We wrote books and produced videos and created a traveling stage show to teach kids and parents how to use computers and the internet.
We were reasonably good at what we did but not good enough. Over time, for all sorts of tiresome reasons, my relationship with my business partner deteriorated. We called it quits right around 9/11.
I was exhausted and broke and moved to Colorado where my sister took me in and fed me. I got a job with a paycheck and hung out for a few years until…