You tend to rebel against what you grew up with, and for me I was ready to trade in oceanic parking lots, run-down strip malls and well-proportioned town houses for squealing subways, cloud-piercing skyscrapers and cramped apartments. I realized I was too comfortable. I went to the park one day and wrote down all the various goals I had, then went back and circled the ones I thought I could accomplish in one, five and ten years. I don’t have the list anymore, but I remember writing that I wanted to start and run my own company. I saw that I wasn’t getting any closer to that goal by staying in advertising, and the hunger inside me was getting its edges sanded down by the act of coming up with a bunch of ideas to sell products, but rarely getting to affect the experience of the products themselves.
I wanted the lack of employment and stable income to motivate me to do something. I wanted credit card companies pounding at my door about unpaid debts, because it would only be a greater incentive to get out there and hustle. I left my job in fall of 2008, right when the big investment banks were on the verge of collapse. I remember going to our office near Wall Street on my last days of work and walking past news vans parked outside Lehman Brothers.