The Power of Positive Destruction

Chapter 6 Develop Your Unique Selling Proposition

After my short stint on the West Coast, I was determined to pursue something big—something transformational. I was also unemployed, which meant I had a lot of free time.

But coming up with my next big idea felt very pressing. It was the late 1990s and I was 39—already old by Silicon Valley standards, where I had just tried to make a go of it. At that time I didn’t know most entrepreneurs start their first company in their 40s. At the time, I felt like a failure. Selling Merrin Financial was a big disappointment for me. It was not the huge success I had planned for or envisioned, and it certainly wasn’t the payoff I had invested 10 years of my life toward. I knew the truth; I had no choice other than to sell it, and I felt like I had sold out. I was depressed and anxious.

I set up weekly meetings with Eric LeGoff, whom I first met when he was tasked with implementing the order management system (OMS) at Heine Securities and who later joined Merrin Financial. He introduced me to his friend Steve Apkon. Our goal was to brainstorm the next big thing. Steve was renovating the Jacob Burns Film Center in Pleasantville, New York, just north of New York City, and every week we met in one of the desolate offices in the building. Our conversations were all over the place. We had a lot of ideas, but none were very good.

It was more of an exercise. We were flexing our brain muscles, and that work did lead us to ask a lot of questions about ...