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Jonathan Bales

Tennis with a Frying Pan (Feat. Adam Levitan)

It’s no secret I like prop bets with friends—usually as a useful motivational tool, but sometimes as a good spot to make money, or even just for fun (since going through life without risking your hard…

Why I Bet on Trump to Win $75,000

Many of you know I made a bet that Donald Trump would become our president – I wrote about it at 4for4 a year ago, although the bet was made months before that – so I just wanted to talk a…

Should You Work for Free?

Back in college, I tracked every play in every Cowboys game and charted them into like 50 different categories: every motion, audible, pass length, formation, personnel, and so on. It took me like 10-…