2,400 Pushups In 12 Hours for $2K: How FantasyLabs Co-Founder Jonathan Bales Is Betting On Himself

FantasyLabs Co-Founder Jonathan Bales — king of physical prop bets and the 2018 Gambling Olympics gold medalist — has made a straight-up bet that he can complete 2,400 pushups in 12 hours.

I recently had a quick conversation with Bales to get a sense of his mindset entering the event.

A Conversation With Pushup Prop Bettor Jonathan Bales

Matthew Freedman: When you were a little kid growing up, did you always know that you wanted to be a fantasy sports entrepreneur who competed in pandemic pushup props?
Jonathan Bales: Um, that one's tough. (Laughs.) I didn't know I'd be doing that exact thing, but something equivalently weird, I guess.

MF: How did you come to terms on the bet? It's $2,000 on 2,400 pushups in 12 hours. How did you guys negotiate those numbers?
JB: [draftcheat] just put out a tweet about how many pushups could someone do in the next 12 hours if they got $1,000 per pushup.

And Peter Jennings said 3,600 …

… which he then quickly revised to 2,400, which is still a lot.

DraftCheat was looking for action at that number.

And then I came in and suggested a bet of $2,000 at 2,400 and then I would give him $5 for every pushup I was under, and he would give me $4 for every pushup I was over.

But he didn't like that, because he thought he could lose $10,000. (Laughs.) So he rejected that and just did the $2,000 bet.

But now there's this crazy market that's formed. There's a lot of money on it.

MF: Any sense on what the size of the market on this might be?
JB: I don't know. It's tough to tell, because there are a lot of deals going on that I don't know about, but it's easily six figures already, and I honestly think that by Thursday it could be $1 million.

MF: Does that make you nervous?
JB: Uh, yeah, a little bit. (Laugh.) But I don't think that really matters. I can either do it or not. Even if I were nervous, that would just go away. I can either do the pushups or not.

The only thing that would stop me would be if I get hurt or if I have a really bad strategy and just do as many as I can in the first hour and then physically my muscles just give out, which could happen.

But those are the only scenarios. I think I'm near 100% or near 0% to do it, and I can't change that too much.

MF: What are you thinking about in terms of strategies?
JB: I don't want to talk about that until after. (Laugh.)

MF: OK, but you do have strategies, and you're looking at different possibilities for how you can approach this.
JB: Yeah, and I haven't decided. My main strategy will be to be adjustable. So whatever plan I have, there will be variations that are pre-planned based on how I feel. So I'll use the first half hour or hour to determine which direction I need to go, what sort of breaks I need and things like that.

MF: What do you think will be the key point when you'll have a sense for how things are going?
JB: I would say whenever I can get to more than halfway done. I think as you approach 1,000 pushups, it's a real struggle, because doing 1,000 pushups in a day is probably … I don't know, because I've never done it, but it sounds real hard. (Laugh.)

So when you do 1,000 and you're 40% done or whatever, that's not that great.

MF: How many pushups have you ever done in a single day?
JB: 500.

MF: What do you think a fair line would be?
JB: Probably where it is. I can do more pushups than most people, I presume, but there's so much uncertainty. And there's some stuff out there about people who do this many pushups, but all they do is train doing pushups.

I have not done that, at all. There's been no training. (Laugh.)

So it's really difficult to say how my body will react after 1,500 pushups, if I can get there.

So the real line is probably nowhere near where it is, because I can either do it or not. But the line is probably where it should be based on what we know. This line is probably 50/50.

MF: Can you talk about your workout routine? How is it that you feel you've been preparing for this even if you haven't been preparing with this in mind?
JB: I've been working out pretty well this year. I kind of go through spurts where I might work out really well for a few months, and then I might not work out for a month, depending on travel and things like that.

So I haven't been working out all that hard, but I haven't taken more than a few days off probably all year, which is pretty good through three months.

And I work on my chest and triceps, which are the most important thing. Generally doing bench press. Barbell and dumbbell bench press. I do some pushups, but never really more than 50 at the end of a workout. So not too many pushups.

And mostly for chest I lift probably a bit heavier. If I were doing 135 pounds for a whole bunch of reps, that might be more valuable for this. But it's better than doing nothing.

MF: You mentioned the market earlier. What are your thoughts on people who have side action on this?
JB: How the market has developed is really interesting. And there are people on my side who are betting based on not even anything physical but using the logic of "Oh, Bales would only make a sharp bet." I mean … (Laughs.)

I was just trying to have fun. This has completely unraveled. (Laughs.)

It's not like I was trying to fleece draftcheat because I thought this was such an amazing bet. I still bet on myself to do it, but if your sole reasoning for betting on me is that I bet on myself, I don't think that is good.

MF: What's the largest money amount that you know of that's being bet on you by one person?
JB: I don't know what it's up to know, but it's in the $10,000s. (Laughs.)

MF: How concerned are you about form?
JB: There's an honor system. I'm not going to try to angle or anything. I'm going to try to do the exact form that I had in the video.

I hope that there's no controversy with form, but it's so difficult to say that I'm going to have exactly perfect form on the 2,000th pushup.

If I can't do the pushups at a certain point, I think it's just going to end. It seems unlikely that I'll be able to get near 2,400 around 12 hours in and it's a problem. If I get it, and there are some that don't seem that good, it seems like I would be able to do 100 more and have time to do that.

So I don't think form will be an issue. And there are the judges.

MF: How did you guys decide who would be the judges?
JB: We just sort of nominated them. Dan Back and Headchopper — we both know them pretty well, know that they are really honorable and would do the right thing no matter what, but neither one of us is so close with them that their integrity would be compromised.

Manz — we both know Manz. I'm pretty good friends with Manz, but draftcheat was comfortable enough with him and sure that he'd be honorable too.

And the other main consideration was … (Laugh) … "Who's going to be sitting there all day, who's going to be fine with just watching this?"

I thought of you, of course. You're the first judge who comes to mind.

But we couldn't do that, with you at Action.

MF: Do you have any sense of what you might be wearing while doing the pushups?
JB: I haven't thought about that. (Laugh)

A shirt, shorts? I don't know. I'm usually more comfortable when I work out with more stuff on.

MF: I'm just thinking that, after 1,000 pushups, you might want to shed as much weight as possible.
JB: Yeah, I didn't think about that. So a hoodie — I don't know how much that weighs, maybe a pound? That's not inconsequential. And I did think about my weight, because I saw something that said a pushup is roughly 64% of your body weight, so losing even 2-3 pounds, when you're doing 2,400 pushups, that might equate to dozens of pushups, so it's not nothing.

MF: Alright, thanks. Very informative.
JB: You got any bets on it?

MF: Should I? — do you think you can do it?
JB: I really don't know. I think I can do it. I have a lot of additional money on it. (Laugh) So I think I can do it.

It will be a nice payday if I do.