From my first entrepreneurial endeavor in the nightclub business at the age of 17, I’ve been motivated by glory. To me throwing nightclubs was the coolest thing one could possibly do. People new my name and would shout it insistently from the long line they had to wait in to get in. Hundreds, if not thousands, of kids in LA wanted to be my friend. But it was more than fame that I sought. I was trying to prove myself to all those who had judged me and criticized me before. More importantly I was trying to prove myself to myself. Trying to escape a sense of unworthiness that I’ve felt since I was a kid. Success soothed a deep seated insecurity for a moment or two.
When I moved back to LA from New York I was motivated by Glory once again. I wanted to build a huge business that would make the papers. So that everyone I had worked for in New York, everyone I had gone to school with, would be left envious. Again, I was striving for relief of my own insecurity, trying to prove to myself that I was in fact good enough.
But a few things happened in the process of building the business over the past two years, that have made me less attracted to glory. To begin, the glory hasn’t come with TaskUs, in the same way that it did with Access (the all age nightclubs I used to throw). The stakes and expectations were way higher with TaskUs than they had been in the nightclub days. Throwing Access was like having a summer job. I wanted to have fun and make a little money. I ended up making a ton of money, but had I made a few hundred dollars every night instead of a few thousand, I would have been just fine. This time I needed to make enough money to support myself. And not just support myself now. I needed to build a business that could make enough money to support myself in 10, 20 and 30 years. Enough money to support myself with a family, put my unborn kids threw college and pay for the hospital bills when I die.
Building this business proved to be way more challenging than throwing nightclubs. I had to learn all about technology, websites, international labor laws, cultural differences and exchange rates. Perhaps more importantly the strategy behind the business was only half thought through. This was entirely my responsibility and I struggled for the first 12 months in business as a result. This challenge led to working 16 hour days for nothing, zip, zero. I was making no money and working harder than I ever had. I was sacrificing my early twenties and earning nothing. Something didn’t add up.
The most important thing that happened, however, was meeting Tom. Tom is a wildly successful, self made entrepreneur. And yet he hardly ever works. He does yoga. He meditates. He hangs out with his family and his friends. He occasionally takes trips to see stores and takes the time to think through the major strategic decisions of his business. But he barely ever works. This model clashed so boldly with my traditional view of success – working long hard hours to provide an upper-crust lifestyle for a beautiful (perhaps slightly dysfunctional) family. Tom isn’t the richest person I’ve met since moving back to LA. But he can buy whatever he wants, do whatever he wants. travel to where ever he wants, eat where ever he wants, and he actually had the time to enjoy all of these things.
Meeting Tom made be stop and reconsider my why. Why did I want to be an entrepreneur. What did I really want to achieve. This led me to realize I want Freedom.