convert raw material (client leads, opportunities, and introductions) into a fully formed product (an app, website, logo, whatever our clients wanted) without me lifting a finger. I adopted a mantra. I began to repeat it, over and over. I was “Teflon for tasks.” Never again would I do something that could otherwise be done by someone else.

Chris and I were taking all of these lessons and learning how to operate dozens of businesses at once, ironically, by not operating them at all. After the meddling that I had done myself, and the million dollars flushed down the toilet, we decided on a rather simple management philosophy. We summarized it as follows: when it came to mistakes, we wo

He didn’t need to have the answers to everything; he stuck to what he called his “circle of competence,” the areas in which he was an expert. In fact, he told us that he preferred to avoid stupidity instead of trying to be intelligent.

At conferences, I quickly started to learn that the most important business connections were made in bars, gossiping with drunk executives. Buying a round of drinks often generated a huge return on investment. For instance, there was a big Facebook party in Austin, where I got a crowd of startup founders wasted on my credit card. I must have bought

me how to make friends with just about anyone. Most of my competitors—folks who ran agencies—were nerdy programmers who looked at their shoes when talking to a potential new client. My sales technique was simple: be fun to drink with and ask a ton of questions about whomever I happened to be talking to. It worked surprisingly well.

Over time I also found myself wanting things I didn’t even know I wanted. I’d never worn a watch, and yet I found myself obsessively researching them. I’d noticed that when I met other wealthy businesspeople, they’d often discuss their watches and show them off. I didn’t get it. I had a phone, which told the time down to the millisecond—why did I n

and pathetic than a man who devotes all the hours of the waking day to the making of money for money’s sake.”

When I told him that I managed my own money, he laughed and told me I needed to diversify and he could help. It turned out he was, of course, a wealth manager, which I soon learned was finance speak for “sales guy who knows nothing about investing and puts his clients’ money in mutual funds, then charges them 2 percent a year for life.”

That panorama, which featured countless sailboats, also served as the constant reminder that “the two best days of a man’s life are the day he buys a boat and the day he sells it.” (A lesson I’d learned the hard way years earlier, after I impulsively bought my own sailboat, which promptly turned into a hole in the ocean that ate money.)