My Workout Bets with Peter Jennings & Adam Levitan

***This is an update to a prior post (below) in which I offered an open workout prop bet so I could find motivation to move more than a few dozen feet per day. My buddies Adam Levitan and Peter Jennings were interested in doing the same, so we booked a few bets that we’ll test the weekend of February 17th (the NBA All-Star Break when the entire FantasyLabs crew will be in Florida for a company trip).

All three of us will be competing against each other in the bench press, pullups, and racquetball. I have additional bets with Levitan in a mile run and my brilliant idea of seeing who can jump laterally over a bench as many times as possible in two minutes (hard as shit, immediate regret upon actually trying this).

We are going to go into the mile run, jumps, and racquetball “blind,” so to speak, meaning there isn’t any sort of spread or moneyline. We tested the pullups and bench press and adjusted accordingly. Just for the sake of transparency, Levitan and I did this testing together and Peter filmed his and sent it to us. I will rep 225 lbs, Peter 185 lbs, and Levitan 125 lbs (roughly what we could do for six reps). For pullups, I am -7 versus Levitan and -6 versus Peter (Peter is -1 versus Adam). I originally did nine pullups (wide grip from a total hanging position up to chin above the bar), so if Levitan gets 5 reps, for example, then I’d need to do 13 to beat him.

Given that we’re competing so soon, there’s a decent chance I legitimately won’t improve on anything and just lose all my money. Levitan got a trainer for Christ’s sake. Nonetheless, I need more motivation to work out hard, so I am going to put up more money on myself vs Peter and Levitan for anyone who wants to bet against me. It might be totally free money; I have no idea.

Feel free to message me through here or on Twitter if you want to take part in this bet, have a revised version you’d like to offer, or want to create a prop bet of your own to motivate yourself to do something you’ve been putting off.


A few weeks ago when I was in NYC for the DraftKings Fantasy Football Championship, Saahil Sud and I made a fun prop bet with poker player Joe Ingram.



This might sound really difficult, but 40,000 words is very short for a book—it’s more like a very long essay—and I personally know it can be done because I write my books in a pretty short amount of time (usually around 14 days or so).

The terms of the bet are that Joey must publish and promote a 40,000-word book by the end of January, and that’s basically it. One of the reasons I booked the bet is because I know he takes a ton of pride in his work and he’s not going to publish something shitty just to get it out there. Another reason is the holidays are an obvious hurdle. We were also drinking wine and it probably sounded a lot more fun to him at the time.

The main reason I made the bet, though, is because I actually want Joey to write the book. Is he going to make a lot of money in book royalties if he publishes it? Doubtful, but books are such awesome marketing tools and it’s also just cool to publish a book.

Prop bets can act as really useful motivational—whether it’s due to the money or just pride in winning a bet—and so they can turn into win/win situations. If Joey works hard to write the book and comes up short, he’ll still probably be happy; if you were to ask him if he’d pay the amount we bet to have 50% of a book completed by January 31, for example, he’d probably say yes.

For this reason, betting can be a really pragmatic way to motivate yourself to do shit you don’t normally want to do, like working out, eating healthy, or leaving the house, ever.

I used to work out a lot—I think exercising is incredibly important for overall mental health—but I have either stopped completely or gone through periods of half-assing it for a long time now. I convinced myself it was because of work and I didn’t have the time, but that’s sort of shit because you always have time to do things you want to do. If you don’t do it, then you just don’t want to do it enough; when you’re truly passionate about something, you just make it happen no matter what.