I really only ever had two official bosses in my life. I worked for myself, and I worked for my father.
My father taught me a lot about retail. He had a very systematic approach to selling. He didn’t exactly teach me how to run a business, but he did teach me how to sell, and how to take big risks. More than anything, he gave me a work ethic. He taught me to hustle.
My dad put me in business twice. The first time, I was about 18 years old. We were living in California, and one day we went to a wholesale warehouse that sold housewares, things like toasters, coffee machines, stereos. We picked out a bunch of items, rented a booth at a flea market, and set up some shelves. Then he left me there to figure it out on my own. I sold what I could and packed up the leftovers every night. The whole operation lasted maybe a month. I couldn’t have been more bored or disinterested.
Back in the early 80s, my father had an art gallery at the Beverly Show Hotel. He ran that from around 1981 to 1986 and became wealthy within the first year.
I didn’t officially go to work for him until we were both back in New York. Around 1991, he opened a new gallery on 57th Street. I was 22. Even though I’d been around his business since I was about 12, I had never actually waited on a customer. One day, while my father was on vacation, I was left in charge.
I’ll never forget this, Ursula Andress, the famous actress, came into the store looking for a carpet. I knew her from a few old movies, though her career was before my time. I was nervous and clumsy, flipping carpets, trying to figure out pricing while pretending I knew what I was doing. Somehow, I kept my composure long enough to quote her a fair price. She bought a $12,000 rug. That was the first time I made a sale from start to finish on my own, and made a profit.
Around 23 or 24, I got into skydiving. My cousin had started jumping upstate, and because we were competitive, I had to try it too. It was the summer of 1992. Every Sunday, we drove upstate and jumped out of airplanes together. Two Jewish kids from Brooklyn with well-off fathers, what could go wrong? It was dangerous, but it was also a break from the ordinary.
By 1994, I had convinced my dad to open another store and let me run it. We found a small space on 57th between Sixth and Seventh Avenue, about 750 square feet, rent $12,500 a month. I built it out myself, filled it with merchandise, and showed up every day, but I felt trapped. I wasn’t ready for the grind or the boredom of retail.
At the same time, I was seeing a woman who had her own problems. We were young, 22, breaking each other’s hearts back and forth. When it finally fell apart in 1994, I couldn’t sit in that store anymore. I was miserable. I told my father I needed to leave. He was furious, but eventually, he let me go.
I was living in a one-bedroom apartment on Sixth Avenue, The Vogue, around 36th Street. The rent was $1,500 a month, brand-new building. I had no furniture, just a bed and metal shelving for my clothes. When I finally gave up the lease, I packed my things into my Bronco and drove upstate to the drop zone. I started skydiving full-time, trying to forget everything.
As winter approached, camping out at the airfield wasn’t going to work. So I drove to Deland, Florida, the skydiving capital of the U.S. My cousin and I had jumped there before. I rented a room from a guy named Paul McGrevey, who worked at the drop zone. He was kind, experienced, and welcoming. Down there, the skydiving community felt like home. If you jumped and talked the talk, you belonged.
That’s when I started my first real business. It was 1995, and I began producing skydiving videos. I advertised them in print magazines and took orders through an 800-number that went straight to my pager. I’d call customers back, take their orders on index cards, stamp them “PAID” when the money came in, and “SHIPPED” when I mailed them out.
That little 3x5 index card box was my first CRM system, and my first true, personally owned business.