The Herd with Colin Cowherd - The Favorites - Can You Bet On Politics?

Episode Date: June 24, 2022

Are you a news junkie? Do you wish you could bet on election outcomes or world events? Today's guest Alex "Keendawg" Keeney is an expert in doing just that. He joins Action Network hosts Chad Millman and pro gambler Simon Hunter to discuss the world of online prediction markets, and how thousand of traders invest millions of dollars in markets as diverse as the next GOP presidential nominee to the margin of victory in a mayoral primary. Keeney is the founder of Star Spangled Gamblers and host of their popular podcast, which has become the leading source of information about political prediction markets. Prior to founding SSG, Alex was a screenwriter in Hollywood, a policy advisor in the U.S. House of Representatives, and a marketing executive for Jordan Belfort, better known as the real Wolf of Wall Street. Follow him on Twitter @keendawg #HerdSee omnystudio.com/listener for privacy information.

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Tennessee redline is 1,800-889-9-9-87889, 1-800-2-2-470-0 in Wyoming, or visit 1-800gambler.net in West Virginia. Welcome to the favorites, the podcast from the Volume Podcast Network. I am Chad Milman, Chief Content Officer of the Action Network. I will be joined, as I always am, by my BFF, my companion, my compadre, professional. better. Simon Hunter. Hello, Simon. Chad, brother.

I'm excited for today's episode. You know how much I love talking politics. Listen, I'm glad you're previewing it. So we have a special guest on today. Alex Keeney, who is better known as Keen Dog and host of the popular star spangled gamblers podcast, he is a veteran in the up-and-coming world of online prediction, markets. We have been talking about this at action for years. Since we launched, we have been writing stories about really the political betting markets, which is where a lot of this

interest comes in. And for news junkies or those interested in betting on or investing in the world of politics, world events, betting exchanges have become a go-to way to invest and profit on the stuff we see every day in the news. And I will tell you right now, and I'm going to want to ask Alice about this, like the 2020 presidential election and the 2016 presidential elections, those markets were predicting what the outcome was going to be long before the polls were showing it and were in some cases more predictive than the polls, both with Trump and with Biden. Alex, I feel like doing a podcast like this is a long time coming, especially now when there's

so much heat in political markets, and I know this is broader than that. Tell me how you get into this. How did I get into it? Well, first of all, Chad, Simon, thank you for having me on to represent all of the political gambling degenerates out there in the Twitter sphere. I got into it probably the way a lot of people do, which is they clicked on a link that they thought was a joke and it turned out to be real. So my first trade was I was betting on whether or not Brett Kavanaugh would make it onto the Supreme Court, if you can remember that kind of nasty and contentious period in politics. And I made like triple my money on my first trade.

I just figured gambling was going to be easy. Picking winners was going to be easy. It would always be that way. And it turns out that it's, you know, harder than that. but I was hooked by success as many, many betters probably are. And what is like, what's your background? Are you a trader by trade? Are you a gambling fiend?

Like how do you even decide to click on that? No, no, I'm like actually terrified of gambling. Like it literally keeps me up at night, but I know that I win more often than I lose so I can put myself back to sleep. Do you have a real job? I do. I do. I live in LA, so I do all that like fake LA stuff, like content marketing and digital media and whatever. But I actually worked in politics for a while in my career. And I got into TV and

didn't feel like people loved me enough in TV. So I thought I'd kind of prove them wrong by, for some reason, I thought betting on politics would be a good way to prove the haters wrong. But you know, it's my competitive side. That'll show them, Alex. Right, right. Show those beta cucks. that's an industry term. I know we're going to talk about the difference between prediction markets and betting on a game at a sports book. And before we get into sort of the details of this specifically, can you shed any light on what you saw in 2020 with specifically the presidential market between, Joe Biden and Donald Trump.

Well, this is, experience with that. This is a very sensitive subject. I might trigger some political gamblers here. Well, the thing that was so funny about the 2020 election was, is that all the, you know, professional big time winners, $100,000 a year of winnings, all these guys thought it was going to be a blowout election and all the kind of meatheads that they wrote off as they used to call them MAGA money.

You know, they just loved Donald Trump and would bet on them everywhere. Kind of had a right that it was going to be a really, close election and not a blowout. So the pros, I think, actually lost money or really underperformed in that election when Joe Biden, you know, did not talking conspiracy theory level, almost losing an election, but compared to, you know, what the mainstream media, Chuck Todd, John King, were predicting. It was a fairly close election. So it was a lot of money was made by people who were written off as idiots, is the truth. Yeah, I would say most professionals said that if there wasn't the whole right in ballot, probably would be a different

president. That's why the big flip happened where these pros, they saw what was happening at two, three in the morning, that election night, the ballots started coming in that were mailed in. And that's where they got off. So again, you're right. A lot of pros I know did lose big. But man, did they get it back? Once the info came out there like, dude, there's millions of votes being counted. And guess what? A lot of them are Democratic. I mean, that was, again, we'll never see it again, because I don't think we'll have another election like that with COVID, obviously. But that was really cool watching Lifetime, like Chad talked about, the Action Network. I kept refreshing the homepage and just kept watching Biden's odds go from, what was it, like,

plus 250 at the peak, all of a sudden, it's 6 a.m., 7 a.m., it's minus 200. It was like, holy shit. Like this whole thing flipped like from that 3 a.m. until 7 a.m. in the morning. That was pretty wild. Right, right. Like the way that the markets are kind of real time up and down, there was the chance, I think, at three o'clock before dawn to start buying, you know, Joe Biden to win Georgia, Joe Biden to win Arizona, you know, and a lot of his money was made while the world was

sleeping. So explain the difference between the exchanges and the sports books and where it's legal and sort of how betting in this framework is different than betting on a game. Well, can I tell you the best part first? Yes. Well, first of all, you don't have to be right to win money. And you can find the answer in advance. So you don't necessarily even need to watch the game to know how it's going to end. So what I mean by that is a lot of times you're betting against, you know, you just need to be a step ahead of the news because we're trading on effectively a stock market.

Right. And so every time a new news story comes out, the odds adjust, you know, you're dealing with human beings who are on the other side of the trade. They're panicking. They're wondering if they, you know, read Joe Biden wrong or if that thing that, that Joe Manchin just said from the Senate, did he really mean what he just said? So people are freaking out in real time. You have the opportunity to sell or to buy more. And really, you just need to be smarter than the average trader in that particular market. So you don't have to be right. You just

have to be a little bit smarter than the other people who are playing. And sometimes that's not that hard. And then in some cases, you can just learn the answer. I mean, there's a bet right now on whether or not Donald Trump will be indicted in Georgia by a grand jury that doesn't have the legal authority to make a criminal indictment. You can get the answer in advance and win. So it's, I think in some ways it's actually a great deal easier than sports betting. Where can I do it? So the biggest betting exchange that's legal is a website called Predict It. And we have a promotion on Star-Spangled gamblers to get you like $200 of matching money to start. So there's the promotional content. Predict it is the largest legal betting exchange. They offer several

hundred bets, mostly on elections, but also on like a wide variety of other things. Again, it's a stock market. Prices you can sell, you can buy, you can sell in and out at your level of comfort. There's a website called Calci that has a serious amount of Silicon Valley, funny money, that's building a wider net of prediction markets. So literally like the weather, like truly degenerate stuff, but also, you know, CNBC type stuff too, in addition to CNN type stuff. And then there's a third website that DGents like myself know about and use, but it's, I don't think you can use in the United States anymore called Polymarket. It is blockchain denominated, but they post fascinating and profitable markets as well. So those are your three big players. I know I want some than jump in because I

know he's got some, a question for you, but you say you can find the answer before. I don't really know what that means. Well, can I give you an example? Yeah. Okay. Most people are really bored by the United States Senate. Like, are you kind of bored by the time the word comes out of my mouth, U.S. Senate? I'm getting some nods here. Okay. And most people are really bored by like, you know, your average cabaret secondary, you know, Janet Yellen at the treasury or something. Well, when Joe Biden was nominating people to be in his, in his treasury, secretaries, and labor and whatever, it got to a point where, you know, every bet has an expiration date. It has to hit by a certain date and then it pays out. And it got to the

point where if you added up the amount of time using Senate procedure that it takes to confirm a nominee, it's all written down. It's all written down somewhere. And you start adding up the time for each nominee, you could reach the conclusion that most of them were not going to be confirmed, at which point the smart thing to do was to buy bets at a 10, 20x multiple that, you know, that paid like a slot machine. So again, the point is, you know, if you know the question and you know where to look for the answer, oftentimes you can get a tremendous edge with, you know, just a couple hours work. You're just betting on the fact that other people aren't going to do this work.

Right. Or that, you know, you know, politics is probably like sports in the sense that people are into it tend to think they know everything. And, you know, of course, no one knows everything. So, you know, you're batting against people's hubris. Literally, you know, it's a paramutual bet. You're betting against the guy on the other side of the trade. What are some examples of the market you can trade in when you're doing this?

Like presidential nominees, world events? Oh, yeah. I mean, you name it. Right now, of course, you know, who's going to be president or, you know, is Ron DeSantis going to win? Mask mandates on airplanes. That's one. You can bet on who's going to be the mayor of Philadelphia? I don't know that you can bank that exact trade right now.

But if there's an election pending, you will eventually be able to, yes. The mayor of San Jose is a trade right now. And it's a good value play, too, if I may say so. Well, like the mayor of San Jose, before you decided that was going to be something you wanted to participate in, how much research had you done? What made you realize there was value? Well, you know, there are trends in politics. There's trends in every marketplace. One of the trends in politics right now are kind of very liberal cities becoming frustrated.

with sort of progressive leadership, not trying to pass judgment here. That's not what we do. But you can see the trend in other cities like San Jose. And you look at a, you know, a marketplace that is giving like an eight to one shot to the, you know, Harvard grad with experience in the business community against sort of hacky city hall insider. You know, you can start to see the tape replaying from some of these other news stories we've seen. So, you know, it's sort of that level of awareness that you probably have as a sports better for, you know, your own, you know, your own value buys. This baseball season turned K's into cash and big hits into big wins with Fanduel

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You don't need to do a lot of research before you decide to invest. Yeah, absolutely. I worked on Capitol Hill for five years. So I feel like I have a pretty intuitive understanding of how a senator will vote or, you know, if the Congress is interested in something or if they're just blowing smoke up the sort of ass of proverbial voters. But, you know, it's nothing that people can't learn. You know, it's all, everything's public. Like there's, it's all public information. You know, if you care enough to read the New York Times or Wall Street Journal in the morning, you've already got an edge over. for most of the people who are betting, because they are not doing that, believe it or not. What is the amount of money you can trade on these exchanges? So the granddaddy of them all predicted is capped by the government, unfortunately, at $850 a bet. Now, there's workarounds, but Kalshi, the Silicon Valley money bags company, their limit is 25K. polymarket out there in blockchain Netherlands, there's no limit there. So just depends on what you want to bet on and where the action is cleared. So the biggest market predicted has a limit of

$850. Right. The next one, which is sort of the venture-backed high flying startup, you can bet up to $25K. So do you do this for a living? Is this how you make the majority of your money? No. No. Okay. I don't have the, I don't want to sound like a weenie, man. But I couldn't imagine being one of those guys pushing around, you know, like one, two, you know, million dollar bankroll trying to grind out a couple grand a week on the, you know, that hustle is a tough one.

Someone's got to do it, brother. You're talking to you, you're talking to one of them. Yeah. Respect to you, man. Thanks, brother. So in these exchanges then, the reason I ask these questions is because are there sharps? Are there squares? Like, how does the market work?

Yeah, there are a number of people who, there aren't a lot. There are a number of people who are probably earning in the $100,000 to $300,000 range during this full time. There are, they're, wonderful nicknames for the squares out there. There was the, first was the mag of money. Trump's out of office, so the kind of dumb mag of money has receded. Now it's the Biden squares. The Biden squares are the people who, you know, made easy money betting on Joe Biden, but in the election and just been giving it back. So, yeah, I mean, any time that you can bet against especially a partisan lightning rod of a candidate or someone that's got kind of a cult around them like Bernie Sanders or something like that, you can always get good odds.

You just got to know where to look for it. Yeah, I think a lot of political betters talk all the time about how easy it is if you just, like you talked about, pay attention to your history, you read up on what's happening. It's never a surprise where, you know, Bush, we've all seen the movie Vice. We saw how this man kind of got reelected. He did his eight years. It was no shock that went over. Obama came up, he was probably going to win. And then after Obama was done, a lot of pros said,

you know, mathematically, it's probably a 70% chance that a Republican will win after a Democrat has just served eight years. That's not because they actually thought Trump was going to win. They're just looking at straight math off the book of what historically has happened in this country. So I like that I just broke it down there where it's like a lot of tea leaves. Like these guys who put in the Times, they can make money off of it. Yeah. Like you talk about, it's hard because most of these books are going to have to be offshore. Like, it's just America hasn't legalized it yet. And it's like very slow for them to figure out how to really take bets on these political stuff. So it is kind of cool how he's telling people like, there are ways around it in this country. I didn't even know about

these sites. Let me put a finer point on it. It's, it's legal with constraints. The constraints can be a little bit suffocating for a, you know, a company like predicted and a company like CalShia. The activity is more limited than you might like. So, assume, mean, our audience aren't really political insiders. What would be the attraction of an exchange to a regular everyday better? What does a sound investment strategy look like on these kind of sites? Again, I don't think that people should be deterred by not being an insider. I mean, if you think about some of the worst, the worst political predictions, you know, they tend to come from within the political system. Right. We had the White House telling us there was no inflation just a couple of months ago.

Well, we all knew that wasn't true. Look, you can't make someone. be a gambler. You can't make someone become an investor. But if you pay cursory attention to what's going on, you know, there's simple ways that you can grind out returns. You know, like I said, betting against cult-like candidates, batting against something happening, usually nothing happening is the most likely outcome, putting liquidity into the marketplace for bets that, you know, are closing in a month and the outcome's already decided, but the bet itself doesn't, you know, stuff like that, easy ways to generate returns pretty passively. So would you say there's a lot of parallels between sports betting, political betting? Like, you're gathering trust info, signal versus noises,

by low, sell high. Like, do you do a lot of that same stuff? Yeah, yeah, absolutely. I mean, I feel safer doing it because I can lay off my risk anytime I want, you know, I know about the most I'm going to lose if I, if I pull the ejection seat. What's interesting about betting on politics is that unlike sports, even though it's legal, there's still a little bit of a church and state separation in that the betting isn't explicitly discussed during the game. It's not explicitly discussed during the pregame shows. The broadcast companies are still worried about alienating part of the audience because it's still the majority of the audience that isn't interested in betting. That's not the case in politics, right? Everything is about prediction, prediction,

That is the vernacular. That is the window through which all of this is viewed. Could there be a concern with bigger money compromising these markets? And do you see these markets having an impact on how elections can be discussed or potentially determined? Political gambling isn't really new. I mean, it's like new as a consumer phenomenon. But, you know, if you go to work in a shiny suit on K Street or you, you know,

you're involved in your local, you know, political scene in your hometown. Those people's jobs are putting money in pockets of politicians, making bets, hedging their interests so that when the election settled, everyone's taken care of. So I, you know, if you, if we want to play a war of memes, I think that this is just a consumer, consumers doing what political insiders already do. But I think it's useful for, you know, for the national dialogue. We only talk about things that are real. We don't talk about memes.

we don't talk about conspiracy theories. We don't blame, you know, immigrants or the white working class or whatever the newest thing that we're supposed to dislike for, you know, things happening in the world that are, we perceive as bad. Like, you have to be right. Like, if you're going to be in a casino, like, if you're going to put money on the line, you have to be really honest about what's going on. So I think there's a lot of utility for that.

And frankly, it's more fun. Like, when you, when you were playing in a casino and not a government building, you are having fun. So I would love to see more of that in a political discourse. And that's what we do at Star-Spangled gambling. What are strategies, okay, if you're sort of being successful here, what are the strategies that successful traders are using within these predictive marketplaces? You've mentioned one or two, sort of being ahead of the news or really digging into the arcane details. What are other ways

in which you can execute successfully? Well, I think you've got to know your limits, too. I mean, do you guys bet on everything or are you just, you know, just football and basketball? but never hockey or like how do you guys do it i bet it all but i'm getting really good information so it's a little different yeah yeah yeah like if a guy i trust hits me up he's like hey there's a cricket tournament starting india in two hours it's england versus whoever whales bet bet bet bet england in this tournament but it's a seven day long bet it's like i'll bet it and then all of a sudden in seven days i'll see the plus a thousand in my account but yeah it's it might be a little different i know chad Chad bets a decent amount, especially because he works for a gambling company,

but we're probably a little different than most. Yeah, I, like I am mostly football, NFL football, than NBA. And I usually let my fandom dictate my betting habits. Not to mean that I'm betting on teams that I love, but those are the sports that I'm watching the most. That's where I feel most comfortable about my level of information versus what the market is predicting. And so that combined with the information I can glean from experts like Simon or experts like

Matt Moore, who's one of our NBA analysts, like I can start to get a better sense of what makes me comfortable. And then like the other stuff, you know, college basketball, I'll usually just tail people and see sort of where I'm comfortable. But I'm usually doing that at a much lower limit. That sounds exactly right for, you know, what we're doing over here. here batting on politics, you know, know your strengths, know your weaknesses, and make good friends to, you know, help offset the gap in between the two. And I always wondered, can trading in

these markets make you like a smarter or more informed citizen or will it simply make you more cynical? I don't know. I feel like that depends on the type of person you are. Do you think you would become a happier, a jollier person degenning with us? No, like I stay away from politics because I feel like it's such a miserable world to be in because it's like, not that we, we've all experienced it, but we've all been there where you're at a family party and you're just stuck with the two crazy uncles going back and forth where it's like, God, it doesn't matter. Can we just enjoy this dinner? But I can't imagine bedding on it because you're in it 24-7. Like you're always hearing the rumors, always hearing the news.

Right, right. And I mean, so much the game is just like not letting yourself react to it while everyone else does. Listen, I worked in politics for years. I know a lot of people who are, you know, high-level political insiders. They're not as smart as the people who were doing this. Like, people who are betting on politics only get paid when they're right. So they really got to be right. And they're from the weirdest occupations. But, you know, as you just described yourself, that the sense of trust that you have,

you know, with the public school vice principal in the Midwest, you know, when he texts you about some random election in Oregon or something, that's like a lot of the fun of it. You know, it's like the community and the trust and, like, the excitement that exists as you develop your advantage in these markets. So you just mentioned something key. And this is, this is the last question, I think, which is you really need to know your stuff in order to win. It does make you a little bit more informed. What are the best places to get this information that allows you to feel informed enough to make a bet? Well, I mean, there's the easy stuff and the hard stuff that, you know, the easy stuff is you just go to Star-Spangled gamblers. You know,

we cover all of this stuff with, you know, all the pros are. contributors. You can learn what they're trading on and what they're not trading on. But, you know, Politico and Punch Bowl, you know, have morning newsletters that are very insider-friendly. Nothing's better than watching C-SPANs that you can actually get into the minds of these people and how they think. And frankly, like watching, you know, shitty partisan news, that's helpful too. You know, you watch Rachel Maddow every night and you'll know what, you know, like white ladies with cats who are upset about stuff, you know, you'll understand how they're thinking. And then you can anticipate how they'll vote.

And, you know, so you can get an advantage doing almost anything. But that's what I would start with Star Spangled Gamblers and then go to Punch Book, Politico, and then whatever that, you know, gets you off. You will never find anybody who's more appreciative of shameless plugs and thoughtful, inline synergistic plugs than me. That was very well done. But I got to tell you, the whole thing is fascinating. And we talk about all the time and it's become something that we cover a lot at action.

Alex Keeney of the Star Spangled Gamblers podcast, I'm very glad you came on to fill us in on all of this. It's only going to get more interesting with the midterms coming up. And then, you know, obviously in 2024, who will be running for president? And will it be Joe Biden? Will it be Donald Trump? Will it be Ron DeSantis? Mayor Pete, who knows? Before we leave, before we leave, is there one?

good bet that we should go on to predict it and make right now. Other than the mayor of San Jose. And there's some dumb song about San Jose, let's play. Do you know the way to San Jose? I've been away so long. That's right. It's almost like you knew to tee me up to sing.

Yeah. All right. I'll give you one D-Gen pick, and I'll give you one like really boring, easy money pick. All right, D-Gen pick. I will either exit this as the biggest genius, you've ever had or the biggest idiot. I think the Senate is going to pass a gun control bill with

a lot of Republican votes. Okay. Underdog pick. It's about a, you know, three X multiple if you hit that right. So I am, I am bigly, to use the former president's term, bigly on a gun control bill passing and might have some egg on my face if, you know, the obvious or the more likely thing happens, which it doesn't. Second, do you remember when Congress passed a like a changing or ending daylight savings bill? Do you remember that weird day on Twitter? I'm taking 80 cents shares on Congress, not on the eve of an election, eliminating daylight savings. I just don't think anyone wants to deal with that. I think that's an easy bet. I'm taking 80 cents shares on daylight savings time remaining as it is. I like it. I like it. Gun Bill

the Pass. Daylight savings remaining as it is Alex Keeney Star Spangled Gamblers podcast. This is fantastic. I love it. This is right up our alley. Thanks for coming on the favorites podcast from the volume podcast network. I am Chad Milman for my BFF, Simon Hunter, for producer Matt Mitchell. Download us from Apple Podcasts from Spotify, wherever you get your podcast, rate reviews, subscribe. Leave us a five-star review. Say whatever you want in the feedback. Feedback is a gift. Until next time, love you. Another podcast from some SNL, late-night comedy guy, not quite. Unhumor me with Robert Smygel and friends. Me and hilarious guests from Bob Odenkirk to David Letterman help make you

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