Want to lose money on the election? There’s a podcast for that

‘Election Profit Makers’ is back to chase that 2016 feeling

Putting money into PredictIt isn’t “gambling,” but the highs and lows are real. (Christopher Furlong /Getty Images)
Putting money into PredictIt isn’t “gambling,” but the highs and lows are real. (Christopher Furlong /Getty Images)
Posted March 5, 2020 at 5:00am

Like a gambler who can’t leave the table, the “Election Profit Makers” podcast is back for another campaign season, despite a 2016 that ended in tears.

Billed as “your guide to winning and losing money” on elections, the show returned in time for Super Tuesday. The mood may be different, but the hosts are the same: political cartoonist and artisanal pencil sharpener David Rees, investor Jon Kimball, and “This American Life” veteran Starlee Kine.

Each week the gang splashes out money on PredictIt, a kind of stock market for politics. Think you know who will win the Democratic presidential nomination or whether Michelle Obama will suddenly hop into the race? Buy some shares tied to your predictions. 

It’s not an online gambling site. It’s technically a nonprofit research project, but that doesn’t make the thrill (or the risk) any less real.

Rees, who has been friends with Kimball since they were kids, calls the show a “critique of conventional punditry,” where the pundits put their money where their mouths are and “suffer consequences if they’re wrong.”

And in 2016, they were very, very wrong. The day after the general election, the trio dropped an episode titled “This is what it sounds like when Daves cry,” in which they worked to come to grips with Donald Trump’s shocking upset (and a loss of thousands of dollars). It’s a brutal listen. “It was a slog,” says Rees. “It really sucked.”

I asked Rees how he dried his tears and whether he’s changing his strategy this time around.

HOH: Why come back for 2020?

DAVID: Gluttons for punishment. [Laughs.] In a way, it is cathartic to be able to talk about this stuff with friends. And we really do want to make back the money we lost in 2016.

HOH: How much was it?

DAVID: Jon lost about $4,000. That was a disappointing night for us for lots of reasons, and losing all that money was the diarrhea icing on the s--- cake.

When the new election was coming up, these guys at Radio Point, [a sister company of “Inside Amy Schumer” producer Irony Point,] asked if we’d be interested in bringing it back and having a little support on the back end in terms of production and recording and stuff, so it wasn’t just the three of us in our apartments doing it all ourselves. 

Over the years a lot of people have asked us to bring it back. Politics is fundamentally about groups and tribes, especially now. But simultaneously, it can also make you feel very isolated and lonely. Political podcasts … can be useful if they help you feel less alone. 

I don’t know. Basically, we just miss talking to each other.

HOH: In 2016 pundits didn’t take Trump very seriously. Obviously in 2020, that’s not the case. So was there any trepidation about doing this? Because it is kind of a light-hearted approach to politics.

DAVID: It is light-hearted, but it’s not like we’re agnostic about the realities that are underpinning these trades. 

This season, Starlee has said, “I am not going to bet on things that I don’t actually want to happen. I’m going to keep betting with my heart.” 

I’m a little more broken now, and I am just going to “bet” on ways that make money with the full acknowledgement that this is a ghoulish and strange way to process politics.

It is a market, and this is the glory and the horror of capitalism. I agree that if I just heard there was a podcast where people were betting on political outcomes, I’d be like, “Those people are sociopaths.”

HOH: Can you take us back to that morning after the election in November 2016?

DAVID: I think we were all pretty confident that Hillary was gonna win. 

HOH: Did you think about not doing the show?

DAVID: No. The whole hook of the podcast had been, “This podcast will end the day after the election.” It was just like, “Now we’ve got to see it through.”

It just sucked, man. It was just a bummer. Jon was heartbroken for many reasons. Neither of us are rich. Like, $4,000 is a lot of money. He lost a s--- ton of money.

HOH: What other changes are you making for 2020?

DAVID: We’re going to have guests come on and bet using their money — not just be comedians, but also political writers or people we found on Twitter who we think are really insightful.

I grew up in North Carolina. So one of the things I’m going to be focused on for this season is the North Carolina Senate election, because Republican Thom Tillis is up for reelection. Trump has been in Charlotte trying to drum up support for Tillis. I think that seat could flip. Jon is very skeptical. [He] currently lives in North Carolina.

HOH: You can hear pundits sometimes talking themselves into believing certain things.

DAVID: These prediction markets are subject to that hive mind mentality too. That’s how Jon first got started in PredictIt, even before the first season of the podcast. He was on PredictIt and realized the Trump supporters were just so diehard.

Turned out they were right. But back in the summer or spring of 2016, that was a hive mind, and Jon could short those “bets” and make good money. He was right and they were wrong all the way up until election night. And then there was a reckoning.

This conversation has been edited and condensed.