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June 24, 2022 • 29 mins

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

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Speaker 1 (00:00):
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(01:06):
in Wyoming or visit one eight hundred gambler dot net
in West Virginia. Welcome to the Favorites, the podcast from
the Volume Podcast Network. I am Shad Mellman, Chief Content
Officer of the Action Network. I will be joined as

(01:30):
I always am, by my bff, my companion, Michael Padre
Professional Better, Simon Hunter, et Oh, 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 uh.
We have a special guest on today, Alex Keeney, who

(01:53):
is better known as Keen Dog and host of the
popular Star Spangled Gamblers podcast. He is a vet in
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

(02:14):
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

(02:36):
every day in the news. And I will tell you
right now. And I'm gonna want to ask Alice about this,
Like the twenty presidential election and the presidential elections, those markets,
we're predicting what the outcome was going to be long
before the polls were showing it, and we're in some

(02:59):
cases more predictive than the polls, both with Trump and
with Biden. Um, 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. Uh, tell me how you

(03:20):
get into this? How did I get into it? Well?
First of all, Um, Chad Simon, thank you for for
for having me on to represent all of the political
gambling degenerates out there in the Twitter sphere. Um. 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, UM,
my first trade was I was batting on whether or

(03:42):
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, you know, gambling
was going to be easy. Picking winners was gonna be easy.
It would always be that way, And it turns out
that it's you know, harder than that. But uh, I
was hooked by success, as many many betters probably are.

(04:05):
And what is like what's your background? Were you? Are
you a trader by trade? Are you a gambling fiend? Like?
How do you even decide to click on that? I'm
like actually terrified of gambling, like it it like 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? Um?

(04:28):
I do? I do. I live in l A, so
I do all that like fake l A stuff um
like content marketing and digital media and whatever. But um,
I actually worked in politics for m a while in
my career, and I got into TV and didn't feel
like people love me enough and 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

(04:49):
to prove prove the haters wrong. But you know, it's
my competitive side that'll show them, Alex right right, show
those beta cuts. That's a that's an industry term, like
I know we're going to talk about like the difference
between prediction markets and betting on a game at a

(05:10):
sports book. And before we get into sort of the
details of this specifically, can you shed any light on
what you saw in um with specifically the presidential market
between Joe Biden and Donald Trump. Well, this is experience

(05:32):
with that. This is a very sensitive subject. I might
I might trigger some political gamblers here, um that. Well,
the thing that was so funny about the election was
is that all the you know, professional big time winners,
hundred thousand dollars a year of winnings, all these guys
thought it was gonna be a blowout election, and all
the kind of meat heads that they wrote off as
they used to call them, maga money, you know, they

(05:54):
just love Donald Trump and would bet on them everywhere,
kind of had a right that it was going to
be a really close election and um, not a blowout.
So the pros I think actually lost money or or
really underperformed in that election. Um 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,

(06:18):
John King were predicting. Uh, it was a fairly close election,
so it was there was a lot of um, A
lot of money was made by people who were written
off as idiots. This 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 present. That's
why the big flip happened. Where these pros they saw
what was happening At two three in the morning that

(06:39):
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 were Democratic. I mean, that was again,
we'll never see it again because I don't think wellever
another election like that with COVID obviously, but that was

(07:02):
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 two fifty
of the peak all of a sudden six am, seven am.
It's minus was like, holy sh it, Like this whole
thing flipped like from that three am till seven am
in the morning. That was pretty wild, right, right, Like

(07:22):
the way that the markets are kind of real time
up and down, there was the chance, I think that
three o'clock before dawn to start buying you know, Joe
Biden to win Georgia, Joe Biden to win Arizona. Uh,
you know, and uh 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

(07:46):
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? Well, first of all, you
don't have to be right to win money, um, and
you can the answer in advance, so you don't necessarily
even need to like watch the game to know how
it's gonna end. So what I mean by that is, um,

(08:07):
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, Uh,
the odds of just 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 Joe Manson just
said from the Senate did he really mean what he

(08:29):
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. Um. 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

(08:51):
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 ad the answer in advance and win.
So it's um. I think in some ways it's actually
a great deal easier than sports betting. Where can I
do it? Uh? The biggest betting exchange that's legal is

(09:12):
a website called predict it uh, and we have a
promotion on Star Spangled Gamblers to get you like two
of matching money to start, So there's the promotional content.
Predicted 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, uh, prices,

(09:34):
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. Uh, it's 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

(09:55):
that d gens like myself know about and used, but
it's I don't think you can using the United States
anymore called poly market. It is blockchain to nominated, but
they post fascinating and profitable markets as well. So those
are your three big players. I know I want something
to jumping because I know he's got some question for you.
But you say you can find the answer before. I

(10:19):
don't really know what that means. Well, can I give
you example? Okay? Um, 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? Us, Senate,
I'm getting some nods here, okay, And most people are
really bored by like you know, your average cavert secretarary,

(10:40):
you know, Janet yelling 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 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 the nominee, it's

(11:01):
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, you know, bets at the ten
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, um,

(11:23):
oftentimes you can get a tremendous edge with you know,
just a couple of hours work. What are you're 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 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

(11:43):
you're batting against people's hubrists. Literally, you know it's a
paramutual bet. You're betting against the guy on the other
side of the trade. What are some example of the
market you can trade in when you're doing this, like
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 it's Rhonda Santis is

(12:04):
gonna win um mass mandates on airplanes? That's one you
can bet on. Who is gonna 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, they will
eventually be able to. Yes, the mayor of San Jose
is a trade right now, and it's it's it's it's
a good value plate too, if I may say so. Well,

(12:26):
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, um, you know there are trends
in politics. There's trends in every marketplace. One of the
trends in politics right now we're kind of very liberal

(12:47):
cities becoming frustrated with um, sort of progressive leadership. Not
trying to pass judgment here, that's not what we do. Um.
But you can see the trend in other cities like
San Jose and you look at, you know, a marketplace
that is giving like an eight to one shot to
the Harvard grad with experience in the business community against
sort of hockey city hall insider. You know, you can

(13:10):
start to see the tape replaying from some of these
other news stories we've seen so um. You know, it's
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(14:55):
or visit one eight hundred gambler dot net in West Virginia.
Are there markets where you feel like you can see
enough patterns over time you don't need to do a
lot of research before you decide to invest. Yeah, yeah, absolutely. Um.

(15:18):
I worked on Capital Hill for five years, so I
feel like I have a pretty intuitive understanding of how
a senator will vote or uh, you know, if the
Congress is interested in something or if they're just blowing
smoke up the sort of mass of proverbial voters. Um.
But you know, it's nothing that people can't learn, you know,
it's all everything. It's public, like there's is all public information.

(15:40):
You know, if you if you care enough to read
the New York Times or Wall Street Journal in the morning,
you've already got an edge over 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 grand daddy of

(16:01):
them all predicted is capped by the government unfortunately at
eight fifty of that. Now there's workarounds. But Calci the
Silicon Valley you know money bags company, Uh, their limit
is k and um Polly market out there in blockchain Netherland.
There's no limit there. So um just depends on what

(16:24):
you want to bet on it where the action is cleared.
So the biggest market predicted as a limit of eight
and fifty bucks right, the next one, which is sort
of the venture backed, high high flying startup, you can
bet up K. So do you do this for a living?
Is this how you make the majority of your money? No? Okay,

(16:46):
I don't have the I don't want to sound like
a weenye man, but I couldn't imagine being one of
those guys pushing around, you know, like one to million
dollar bank roll, trying to grind out a couple of
grand a week on the You know, that hustle is
a tough one. Someone's got brother, you're talking You're talking
to one of them respect to you man, So in

(17:07):
these exchanges, then the reason I ask these questions is
because are there sharps? Are there squares? Like? How does
the market work? Yeah, they're there are a number of
people who there aren't a lot. There are a number
of people who are probably earning in the hundred thousand
dollar range during this full time. Um, there are they're
they're wonderful nicknames for the squares out there. There was

(17:29):
the first is the maga money. Trump's out of office,
so that kind of dumb maga money has proceeded. Now
it's the Biden squares. The Biden squares are the people
who made easy money betting on Joe Biden but in
the election and just been giving it back. So uh yeah,
I mean, any any time that you can bet against,
especially a partisan lightning rod of a candidate or someone

(17:49):
that's got kind of a cult around them, like Bernie
Sanders or something like that, you can always get good odds.
You just gotta know where to look for. 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

(18:10):
man kind of got reelected. He did his eight years.
It was no shock that when Obama came up, he
was probably gonna win. And then after Obama was done,
a lot of pro said, you know, mathematically, it's probably
a seventy percent chance that a Republican will win after
a Democrat has just served eight years. That's not because
he actually thought Trump was gonna win. They're just looking
at straight math off the book of what historically has

(18:32):
happened in this country. So I would like to 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, Like you talked
about it's hard because most of these books are gonna
have to be off shore. 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

(18:53):
telling people like there are ways around it in this country.
I didn't even know about these sites. Let me put
a fire point on it, it's it's legal with constraints.
The constraints can be a little bit suffocating for you know,
a company like Predicted. In a company like Calcy, the
activity is more limited than you might like. So, assuming
our audience aren't really political insiders, what would be the

(19:16):
attraction of exchange to our regular, every day better What
does it sound investment strategy look like on these kind
of sites. And 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

(19:36):
inflation just a couple of months ago. Well, like we
all knew that onen'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, batting against cult like candidates,
batting against something happening, Usually nothing happening is the most

(19:58):
likely outcome. Put liquidity into the marketplace for bets that
you know are closing in a month and the outcomes
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,
bilo sell high Like do you do a lot of

(20:19):
that same stuff? Yeah? Yeah, absolutely. I mean I feel
safe for doing it because I can lay off my
risk anytime I want. You know, I know about the
most I'm gonna 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, and that the

(20:43):
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 auto is that isn't interested in betting.
That's not the case in politics, right, everything is about prediction. Prediction,

(21:07):
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 and do
you see these markets having an impact on how elections
can be discussed or potentially determined. Political gambling isn't really new.

(21:30):
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'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 elections settled, everyone's taken
care of. So I you know, if you if we

(21:52):
want to play a war of memes, I think that
this is just a consumer consumers doing what political insiders
all already do. But I think it's useful, 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

(22:13):
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 gonna 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 the political discourse, and

(22:34):
that's what we do at Star Spangled Gamblers. What are
strategies Okay, if you're 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

(22:54):
arcane details. What are other ways in which you can
execute successfully? Well? Think you got to know your limits too.
I mean, do you guys bet on everything or you
just you know, just football and basketball but never hockey,
or like, how do you guys do it? I've been
at 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

(23:16):
cricket torment starting India in two hours. It's England Verse
whoever whales that betting on 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 of 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,

(23:39):
I like, I am mostly football, NFL football, then n
b A and I usually let my fandom dictate my
betting habits. Not not to mean that I'm 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

(24:01):
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 and see sort of

(24:25):
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? Adding on politics, you know,
know your strengths, you know your weaknesses. Uh, and make
good friends to you know, help offset the gap in
between the two. And I always wanted can trading in
these markets make you like a smarter or more informed
citizen or will it simply make you more cynical? I

(24:48):
don't know. I feel like that depends on the type
of person you are. Do you think you would become
a happier, jolly or person de jailing with us now?
Like I stay away from politics because I feel like
it's such a miserable world to be because it's like,
not that 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't we just

(25:10):
enjoy this dinner? But I can't imagine betting on it
because you're in it seven like you're always hearing the
rumors always here in 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've
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.

(25:32):
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 describe yourself, that the sense of trust that
you have, you know with the public school vice principle
in the Midwest, you know when he texts you about
some random election in Oregon or something. Uh, that's like
a lot of the fun of it. You know, it's

(25:52):
like the community and the trust and like the excitement
that exists as you develop your advantage in these markets.
So you just into something keen. 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. One are the
best places to get this information that allows you to

(26:13):
feel informed enough to make a bet? Well, I mean
there's there's the easy stuff and the hard stuff that
you know. The easy stuff is you just go to
Star Spangled Gamblers. Uh, you know, we cover all of
this stuff with you know, all the pros or contributors.
You can learn what they're trading on and what they're
not trading on. But you know, Politico and Um punch Bowl,
you know, have morning newsletters that are very insider friendly. Uh.

(26:36):
Nothing is better than watching c spans that you can
actually get into the minds of these people and how
they think. Um and frankly like watching you know, shitty
partisan news. That's helpful too. You know, you you watch
Rachel Mattow 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 there's

(26:59):
you can get an advantage. We almost anything. But that's
why I would start with Star Spangled Gamblers and then
go to Punch Book, Politico and then whatever that yeah,
gets you off. You will never find anybody who's more
appreciative of shameless plugs and thoughtful uh inline synergistic plugs
than me. That was very well done. But I gotta
tell you, the whole thing is fascinating, and we talked

(27:19):
about all the time, and it's become something that we
cover a lot of action So, 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 mid terms coming up,
and then you know, obviously in who will be running

(27:41):
for president? And will it be Joe Biden, will it
be Donald Trump? Will be round to Santis 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? The San Jose. I think
there's some dumb song about San Jose which was to

(28:02):
play do you know the way that's almost like new
to team 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 is the biggest

(28:22):
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 you.
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 bigly on a gun control
bill passing, and I might have some meg on my
face if you know the obvious or the more likely

(28:43):
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
eight cent shares on Congress, not on the eve of
an election, eliminating daylight savings. I just don't think anyone
wants to deal with thought. I think that's an easy beat.
I'm taking eighty cent shares on to daylight savings time

(29:04):
remaining as it is. I like it. I like it,
Gun Gun build a 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.

(29:24):
I am Chad Moman for my bff Simon Hunter for
producer Matt Mitchell. Download us from Apple podcast, from Spotify
wherever you get your podcast, rate review, subscribe, leave us
a five star reviews, say whatever you want and the feedback.
Feedback is a gift. Until next time. I love you,
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Colin Cowherd

Colin Cowherd

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Jason McIntyre

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