The Pleasures and Perils of Arbitrage

(Quick note that more teaser-trailers for Lyca will be mailed out today. Paid subscribers can request a free copy here. In the following paid-subscriber-only post I talk arbitrage, first presenting a framework for understating how it differers from normal investing, then detailing my own experiences with a successful arbitrage project. This post only exists because of a Twitter DM I received asking for it; if you want to see me write about something let me know. I don’t want to give too much away about what follows, but there will be talk of Weird Al, economics jokes, steak knives, Dutch books, dying dot-coms, and sick puppies.)

In the early part of the new millennia, not long after my attempts to run a web design company in Bolivia had crashed and burned, I shifted my focus from building websites for others to building them for myself. By and large these went nowhere, though I did get one semi-smash hit, which I sold after about a year. While poking around other people’s projects on what was SitePoint Marketplace (now called Flippa), I noticed that some people were engaged in a new form of arbitrage, and I dove deep into figuring out how they were doing it.