Why I Killed a $150,000 Passive Income Stream

Sometimes You’ve Gotta Burn Your Boats

An audio version of this story, read by the author, is available here »

There’s an expression, to burn your boats. It originated with a military strategy. Hernán Cortés famously “burned the boats,” after arriving in the New World to conquer the Aztec empire. (He actually “scuttled” his ships. He sunk them.)

I recently burned my boats, when I killed off a $150,000 passive revenue stream.

The birth of a passive income muse

In March of 2007, I was sitting with some friends on the cable-locked chairs and tables — at two in the morning — on the porch of a closed restaurant in Austin, Texas.

We were doing the kind of thing that we did at the time, after a night of parties at the SXSW conference: We’d sit around and talk about our ideas. Facebook and Twitter were still fringe services — most of the mainstream world knew nothing about them. The internet seemed full of opportunities.

The subject of my dating life came up. I was terrible at finding a girlfriend, but I was good at finding dates. I described in great detail to my friends the way I had optimized my process of online dating. I had something to say about what you should write in your profile, what your pictures should be like, and what to say in your messages.