Barstool Nate and Smitty Making a Run at WSOP: Recapping Our Week in Vegas

I’m a huge fan of Barstool Sports. I’ve been visiting the site since 2011, became good friends with Smitty awhile back, and do a fantasy football podcast there. It’s the most unique site I’ve ever seen with the most engaged audience in the world.

About a month ago, I had an idea for my DFS analytics platform FantasyLabs to send one of Barstool’s former poker players – Smitty or Spider Monkey Nate – to play in the WSOP Main Event. We set up a death match heads-up challenge for the right to play in the World Series of Poker Main Event:

 

This is an atypical type of deal for Labs, so why did we do it? A few reasons:

– I viewed our “return” on this as a long-term branding play with a wide range of outcomes – and honestly a decently high probability of moderate success with some smaller chance it blows up. Thanks in large part to the guys smashing Day 1, I think it’s blowing up. I think this is probably a top 5 or 10% outcome already with a nice path to top 1%.

– Like I said, Barstool is the most engaged site I’ve ever seen. I mean look at their Reddit discussing the event, or the Barstool Radio episode debating who is getting what money, or the comments on blogs like this one. Or just search “BarstoolNate” on Twitter. It wasn’t a huge stretch to assume Stoolies might help blow things up and get WSOP, ESPN, and others to notice.

– All the content, content, content.

– And content, content, content.

– And content, content, content.

– And content.

– We have some connections in poker and figured it could be good for the game, which would in turn help things spiral out of control. It’s been great getting guys like Joey Ingram involved. He did a pre-WSOP podcast with the guys and a skit with Nate on Barstool.

– It seemed fun. And it has been.

 

Recap

We arrived in Vegas on Friday and headed straight to the suite. It was supposed to be a quiet night. We ended up at Surrender and won some money playing blackjack. Somehow $75 of my chips ended up in the pool, which seems about right. I also ran into Manz and taught him vodka + water is a thing. He didn’t make it out the next day.

Saturday started like this:

 

And ended like this:

 

I also got a little footage of Angry Nate:

Sunday was The Great Lost Day. I did head to Umiya with Levitan and Joe Ingram and learned their $25 all-you-can-eat sushi is the best deal known to man. Highly recommend.

Obviously, yesterday was all about the guys running it up on their Day 1 of the Main Event. It was a wild run.

Couldn’t be prouder of my dudes. I think there was a decent chance of them getting coverage no matter what, but it obviously helped that they both played so well.

And then, today, all hell broke loose.

There’s a bunch of threads about this on Barstool’s Reddit page and on the Barstool Rundown, so I’ll just direct you there for now 🙂

Otherwise, it’s been a great run so far and any time you can see the spider monkey on ESPN, that’s a win.

 

The Bet

I was in Denver this past weekend for the wedding of one of my best friends and FantasyLabs co-founder Peter Jennings. We had about half of the FantasyLabs team there, which was awesome.

wedding

 

Don’t mind the fact that I packed light brown shoes with a dark gray suit – nothing to see there folks. Completely normal attire that doesn’t look ridiculous in the least.

It was a spectacular wedding at a spectacular venue – Arrowhead Golf Club – and everyone had a fun time blah blah blah…onto the story.

Peter invited so many DFS players that we honestly could have held a fantasy sports convention. In addition to the Labs guys, there was dinkpiece, Kcannon, EmpireMaker, SaahilSud, Davis Mattek, Jeremy Levine, BirdWings, and a bunch of other top players and business guys.

It was no surprise, then, when props started popping up on the day of the wedding on certain events that would take place. Will Peter or Ashley cry? How many times will Jesus be mentioned during the ceremony? And the big one that got all the action: the length of the best man’s speech.

The best man is Peter’s friend Beckmann and I believe early bets were coming in at over/under five minutes, but the total quickly jumped to 7 min 30 sec. Beckmann is definitely an outgoing person, but that’s a long time for anyone to talk in front of over 100 people. I got my money in on the under. I actually had a really nice potential arbitrage opportunity pop up when I heard someone was taking bets at 6 min 30 sec. I tried to get the over on that – in which case I would break even if the speech fell short of 6 min 30 sec or went over 7 min 30 sec, but win both bets if it fell between those numbers – but I ultimately couldn’t get that number.

At some point during the reception, the best man found out about the bets on his speech. Beckmann is obviously one of Peter’s best friends and he’s very familiar with the DFS scene, but what he said when he learned of the action goes to show the absurdity of hanging out with high-stakes DFS players:

“How much is on it so far, like $200k?”

There wasn’t anywhere close to that amount on it, but think about how insane it is that his initial reaction to learning about the bets was to assume there were literally hundreds of thousands of dollars being placed on the length of his speech.

Now obviously the bets were tainted with Beckmann learning about them. Maybe I’m saying that because I’m bitter the speech went 8 min 20 sec. Or maybe it’s because some of the guys on the over clapped incessantly every time there was a pause in the speech. Completely normal behavior.

The moral of the story: it’s not really a wedding until you have two dozen grown men pull out their phones and start their stopwatches to time the length of the best man’s speech.

What It’s Like to Party at the Playboy Mansion

If you’ve never been to the Playboy Mansion, it’s pretty much exactly what you think the Playboy Mansion is like, times 10. I was lucky enough to visit for the second time recently after qualifying for the FanDuel MLB Championship. Big shout out to my lineup, which finished 78th out of 80 in the tournament. When you have the chance to finish in the bottom 4% of a championship event, you take it.

This time around was different than last because 1) it was my friend Peter Jennings’ bachelor party and 2) I was being shadowed by a writer for SUCCESS Magazine (Michael Mooney). We had 10 total guys come out for Peter’s funeral, and the best man – Beckmann – suggested we stay at Chateau Marmont. If you’re unfamiliar with the hotel, here’s a rundown. Basically, a lot of celebrities stay there and misbehave and/or die.

Per Beckmann when we arrived at Chateau on Friday afternoon: “This place makes good girls go bad.”

Chateau Marmont looks like an old castle. We stayed in Bungalow 1, which is separated from the main hotel. There are four bungalows – Britney Spears was in another one while we were there, apparently – and they’re very private, with a pool, bar, and ping pong table right out the backdoor. Here’s a look at some pictures, all six of which are from Google because I didn’t actually take any photos.

The bungalow itself is very old. I think Peter was a bit tilted when we first arrived because you aren’t paying $5k/night for luxury; it’s all about the history, privacy, and charm. When we first walked into the bungalow, we saw a bunch of alcohol that we naively thought was complimentary. You know, because we paid $5k/night. Then I saw a $12 small bag of chips and realized maybe, just maybe, the liquor wasn’t on the house. We ended up just hiding that so no one could drink it.

We played a bunch of ping pong the first afternoon, and I’d stack our group of guys up against anyone (who is moderately good at ping pong). One of the guys – Steve Bass – was a professional tennis player, which is relevant because he was part of a bet with poker player Brandon Adams on Tuesday in Vegas. Peter was able to travel out to watch Stephen and Brandon play a match of tennis, and the bet was that Bass had to beat Brandon 6-0, 6-0 to win – and he was around (-145) to do it. I think there was some big money on this thing, and Bass indeed won.

One thing that was really cool, though, was learning how Brandon set up the match to try to tilt the odds in his favor. He was able to choose the court, which was at the top of Cosmopolitan. It’s a really shitty court, apparently, at elevation somewhat (Bass said this matters). They also played at 11am – a time when the shadow of the building was moving across the court. It was just really sharp thinking from BA – who is a really smart guy in general – as he knew he was a dog and wanted to embrace variance as much as possible. Bass is also a sharp guy, so he played a super low-variance strategy in which he simply tried to make shots and force Brandon to continually beat him. I originally thought the line of (-145) was probably about right given that BA plays tennis quite a bit – he’s had some big prop bets with Patrik Antonius in the past – but after watching the match, I think he was probably close to drawing dead.

On Friday night we stopped by the FanDuel opening party at the W in Westwood, which is right next to UCLA. That’s where I first met Michael. I thought it might be awkward having someone shadow me for the weekend, but it wasn’t at all; Michael pretty much just became an honorary member of the bachelor party right away.

He immediately met a lot of guys in daily fantasy sports – Dan Back, beepimajeep (Jay Raynor), Tommy G (no idea what the ‘G’ stands for), Cal Spears, and so on. Michael has a poker background, which was definitely a huge plus for me when I first found out he would be writing the story, i.e. since poker and DFS are similar games in a lot of ways, he “gets it” when it comes to daily fantasy.

We ate some food at the W and then headed back to Chateau, where we hung out at the bar for a bit. I think I went back to the room at like 2 or 3am, which I’d love to say contributed to the poor performance of my lineup, but it really didn’t. I could do a breakdown of my team and why I liked it, but who really gives a shit?

So I woke up Saturday, did a little research and set my lineup, and then we all headed to the Playboy Mansion. The best way to describe the Playboy Mansion is through pictures. Once again, I took none of these and just found most on Instagram by searching for the event.

Until you’re there, you really can’t appreciate how many girls are shipped into this thing. It’s kind of insane. I’m not really sure where they come from – I heard something about an app that the Mansion or FanDuel uses to find them – but the place is just crawling with models taking selfies.

If taking selfies is an art, these girls are the Michelangelos and Picassos and da Vincis of our time. I think being in the presence of such incredible artists is what had me so flustered and nervous to converse with them; talking to a hot girl is one thing, but trying to do it while she’s creating an Instagram video of her bending over and twerking in a bikini on the Playboy Mansion driveway – her canvas – is another. You have to respect their craft.

I did take one photo at the Mansion – of a parrot – which is either because I didn’t want to look like a creep on my phone or because I’m a giant fucking pussy, or both. While searching for photos to add to this blog, I did find this video, though…

Eye candy 🍡 Follow my snap for more fun under the sun : 👻marymerkems

A video posted by Mary Rodriguez (@marymerkems) on

Noteworthy because if you were to set odds on which guy would be talking to her, I would take even money on Tommy G, and it’s indeed him. If you’ve ever seen a lion creeping around searching for prey in the wild, that’s kind of like what it’s like to party with Tommy G (if the lion failed on 90% of its targets, but was just so fucking relentless that it always got something to eat because it just keeps going and going and going until it happens upon a wounded animal or an emotionally unstable underage girl). Tommy is the man and does always get girls, so I’m just playing of course.

There are a variety of different areas around the Mansion – the pool/grotto, zoo, basketball/tennis courts, game room, and so on – and it’s really just a lot more expansive than you might think. There’s also an area to sweat the games, although I can’t stress enough how few people actually watch. I think I watched maybe five pitches the whole day, which worked out in my favor given that I scored roughly the same number of points.

I mostly hung out in the zoo looking at birds and monkeys and stuff – there are like 300 monkeys, no lie – but I also lost a lot of money in beer pong and lost to Condia playing pool. Big day for me. Really big day. I feel like Condia is still a mystery to a lot of people, but I’ve been able to hang out with him a bit in San Diego and now LA, and I really like him and think he’s a great guy.

If you’re wondering if Hef ever comes out, the answer is no, but I can tell you it’s weird af knowing the guy is just chilling inside. What’s he doing in there? Does he just nap a lot? Is he still having sex? I swear I saw him look out once, but it was probably just another 90-year-old man in a robe.

After the event, we had an afterparty back at our bungalow. Beckmann asked every girl at the Mansion if they wanted to come back for a pizza party, which he said would work because “it’s innocent and fun.” Girls did indeed come back to the bungalow, although I’m not sure if it was because they were really hungry for pizza or because other people invited them to Chateau Marmont. We didn’t even have any fucking pizza, although someone ordered 100 tacos. I ate roughly half of them.

tl;dr The Playboy Mansion is fun. I highly recommend it.