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Bike Bets (part 1)

This is going to be a series of posts about bike bets. It starts with Dan Bilzerian’s infamous bike challenge. After having a discussion with David Silverman about it in May (maybe?) - he told me I should really write about this because the whole story was really interesting. I thought that was a good idea, but you know how it is with stuff like that. It goes on the to-do list but you never seem to get around to it. I put it off for a little while and then during the WSOP there was just 0% chance of me getting this done. But now I have some time chill-axing down in Brazil and here we are.


I bet on Dan Bilzerian to complete his bike bet vs. Bill Perkins. The bet was Dan had 48 hours to ride a bike from the Las Vegas sign to his house in the Hills in LA or vice-a-versa. He could use a number of bikes, and have a crew to support. So I hear about this bet like everyone else and am thinking... Wow what a crazy bet!! Within a couple days, I get a call from Dan and Bill asking me to arbitrate a couple issues for them. One question is about what happens if Dan gets pulled over by the police and arrested, and the other was about the exact route Dan had to take, e.g. does he have to take the highway (which is a shorter route start-to-finish, or can he do the same distance but on side roads where it's 100% legal). I make my arbitration which I think was really the fair resolution to the situation. I think it was also something all parties were amenable too, so it was nice that nobody left heading to the bet with a bad taste in their mouth about the situation they were in. Over the next couple weeks, thinking about the bet I decide Dan has a major advantage and want to bet. I ended up making a series of bets with Bill and some other people. The first couple bets I made were with the exact same rules as Dan and Bill’s original bet, and the later bets were with the modifications that I would lose if Dan died or was arrested, and that no time was added on the clock for any reason. At the time, it was the most I’d ever wagered on a prop bet. Because I’m friends with Dan, I called him at various times to ask him how his training was going. He seemed pretty confident and I liked what I was hearing. I kept placing more bets and was really in for a good sweat on this one. The challenge came and Dan crushed it. There was some controversy about the drafting, but I believe Dan won the bet fair and square.


A few weeks later in mid-April in a poker game at Aria, discussion about Dan’s bet comes up on a Friday evening. Another player (who will remain nameless but isn't Bill Perkins - who wasn't in this game anyways) says that it would be immensely difficult to do Dan’s challenge without training OR drafting. I agree that it would be very difficult but think it could be done. He challenges me and asks me to think of odds I would take to do it. I think about it for a while and say 10:1. He says he thinks he would lay 10:1 against but wants to think about it more. No bet is made, but the groundwork has been laid. We play all day Friday and into the night, and do the same on Saturday and Sunday. Despite having these discussions, after every grueling day of playing poker for 10-14 hours, I don’t do any kind of physical activity or training.

An aside now about my bike experience:

I had a bike as a child and biked around the neighborhood to friend’s houses. As an adult I only biked at Burning Man for the last 3 years, and had just bought a bike for the first time as an adult in February 2016 with my wife. We bought 250$ cruisers. I had never biked more than 6 or 7 miles in my life, and had never biked on a road bike or recumbent bike.

On Monday, he brings it up again and he feels a bit more confident on his side it would appear. We hammer out stipulations: he is laying 10:1 against my doing it. If I buyout beforehand for any reason, I owe half of what I would lose. If I die, it’s a wash. If I have a freak accident (like hit by a car, tornado, earthquake), it’s a wash. I have 48 hours from when I start, no time added for any reason. I can have support cars, but no drafting. I have to bike 280 miles in total, or walk the bike. I can choose the route, but it can’t be overall much net downhill, so he would need to approve it first.

I’m a bit nervous, as it seems like he thinks I can’t do it. He's a smart guy and he's had a few days to think about it and/or talk to someone. Given my healthy respect for Baysian inference as a poker player that makes me worry a little bit. That said, over the last few days I had talked with Dan Bilzerian and one of his coaches, Nate, and they seemed to think that with these conditions I would be 25-40%. That made it a good bet getting 10:1. I knew this would be extremely tough and it would be my life for this week. I also thought it would be fun to challenge myself like this and I was getting long odds. So I gathered up my courage, shook his hand late Monday night, and we had a bet. I would have to do it by Friday midnight , unless I played until 5AM Tuesday morning, in which case I would have until midnight Saturday to leave. I decided to give Dan a piece of the bet, in return to have him set up my support team (the same crew he used), take care of the logistics, use his recumbent bikes, and provide any other help possible. I played until 5AM Tuesday morning (!!) and quit the game. First strike against me, I had been playing poker for 14 hours a day for 5 days straight Thursday-Monday on a bad sleep schedule doing NO exercise!

After leaving the game, I did 30 minutes on a stationary bike at Panorama at about 5:30AM before going to my home in Summerlin and sleeping – my first “day” of training. Later that day (Tuesday), I met up with Dan, rented a road bike, and went back to his place. I met up with Bob McCall there (Bob is a long time biker who runs a cycling company Cycle Vegas and who helped train Dan on the bike for his challenge in Vegas) and took Dan’s orange recumbent bike “orange sherbert” out and rode back and forth on a relatively flat Las Vegas street for a total of 18 miles that night (Tuesday). Riding a recumbent bike is a lot more comfortable when spending many, many hours riding, and would be the primary bike I would use on this ride. You avoid serious pain on your rump from sitting on the small road bike saddles, and in your upper back from leaning over when tucking. On a recumbent you sit back in relative comfort and pedal (think of the stationary bikes in the gym where your legs are extended out in front of you). The only drawback is that your legs are up and it’s a bit tricky to ride and balance at first when you are used to riding more traditional bikes. Learning how to ride on a recumbent bike was a bit tricky at first, and I did almost crash once going like 12 miles an hour (which might have turned out badly for the bet!). Afterwards, I got a massage and was pretty surprised at how good my legs felt. That was more than double the longest distance I had ever ridden. I was expecting more soreness.

Bob and Nate also were discussing with me exactly how I should ride, which is a pretty interesting topic. Doing a super-endurance challenge like this is different than other types of athletic activities. The goal would be to keep my heart rate in the 110-120 zone. Here you can usually have a conversation fairly easily, and should not be sweating a lot. If someone like me pushes myself a lot harder than this, than I would have problems going 280 miles!! I'd want to have a high pedal cadence and be constantly eating and drinking to make sure I didn't have a calorie deficit (you need A LOT of calories for something like this!!). I was reasonably fit, but I was by no means an amazing athlete of any sort. That said, there was some good news... I had a resting heart rate of around 55-60 bpm, which was good for this, as it meant that I had more leeway before breaking through this "working zone" of 110-120 bpm.

The next day (Wednesday) I took the bikes out to Red Rock and rode 18 miles again on the recumbent, this time with some wind and small grades. I rode back to Dan’s house on the road bike at night, mostly downhill, about 10.5 miles. All in all, that was almost 30 miles of riding! My legs were a little more sore that evening, but still much less than I expected. I got a massage again and was feeling really good about my bet. This would be the last day I could ride seriously as I’d have to let my legs totally recover in order to leave Saturday and not have any soreness or lactic acid buildup. By now my coach Nate had found the route, and it had already been approved. I would be riding south on the Pacific Coast Highway (route 1) in California. While it isn’t totally flat, there are no difficult climbs, and I would have a tailwind for the entire ride. Those are some huge advantages.

(Here's a pic of me riding that day out at red rock on "orange sherbet", Dan's recumbent bike)

To my surprise, that evening I had some talks with the gentleman I made the bet with and it looked like he wanted to buy out. I went to bed thinking about it.

At this point, I felt very confident that my chances were well above the 25-40% that Nate had told me. I had done almost 30 miles the day before (Wednesday), and it wasn’t that tough. I could also see how useful the recumbent bike would be for the comfort of a 40+ hour ride as opposed to the road bike. With the training that I was given, it seemed to me that biking 280 miles would be really arduous, but something that I could do. I know that I have a lot of heart when I set my mind to something, and there was no way I would ever give up. I would push through any pain and deal with issues as they came up with the team that I had (bike coach, masseuse, nutritionist, etc...). It felt like I had all my bases covered, and I thought I was a decent favorite to win the bet. Apparently the gentleman I bet with thought the same and really wanted to buy out. I didn’t really want a buyout, but he really wanted one, asked for mercy, and gave a generous offer (about 46% of the total amount I could win) considering the initial odds. Dan and Nate thought I should take that offer for sure. At this point, I had also mentally psyched myself up to do this damn thing. I believed I could send it, and was excited to push myself as hard as possible, see what I was capable of, and just fucking do it. In the end though, it seemed like he really wanted to buy out and I didn't want any hard feelings. I thought I was giving up $$, but I decided to grant him the buyout Thursday.

Because I had been training for this bike bet, I didn't have a seat in the game on Thursday. But the gentleman instant pays on Thursday the entire amount of the buyout, which I go collect before going to the Olivier-JC fight (where I meet Dan and give him his share). That was amazing gambling ethics, and I have lots of respect. I wish everyone operated like this. No haggling, slow-pay, or anything of the sort. After the fight, later that night a seat opens and I go back to Aria to play for a while that night and all day Friday. I'm gonna have a Churrasco (Brazilian style BBQ) at my place on Saturday and invite Dan for that and to go on a bike ride after. That's where the story about the third bet, the one where I did the ride, goes down!

Next, head over for the most interesting part of this whole saga in Bike Bets Part 2, the in-depth look at the 3rd bet, the one where I attempted the bet myself...

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