Before I started working in the fantasy industry, I was a good fantasy player. Good, but not great. Sure, I did all the research before my drafts and stayed on top of news – which was no small feat back in the late-90s and early-2000s – but there was something missing. Something wrong. Something off. I just couldn’t get over the hump and win fantasy leagues. We’re talking a decade-plus without hoisting a single trophy. I was like the Washington Generals of fantasy football.

It got so bad that on my wedding day, my best man gave a 15-minute speech that focused solely on my complete inability to win in fantasy football. I’m not kidding. He regaled the guests with stories of my many misfortunes including losing by a point when...