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In pursuit of manliness, author Joel Stein gambles as a day trader in Chicago

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The Joel stein ‘man made’ book tour

† 6 to 8 p.m. Wednesday (signing books until 7)

† ARTango Center, 4203 N. Ravenswood

† Free admission includes complimentary wine, food and entertainment

† RSVP at starkraving

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Updated: October 23, 2012 8:33PM

When journalist, Time magazine columnist and professional smart-ass Joel Stein set off to augment his ever-flagging manliness for a book titled “Man Made: A Stupid Quest for Masculinity” (Hachette Book Group, $26.99), he spent time in the wilds with unwashed Boy Scouts, rode alongside burly firefighters, endured boot-camp rigors with U.S. Marines and tooled around in a zillion-horsepower Lamborghini.

But one of his greatest challenges involved gambling with another man’s hard-earned dough as a Chicago day-trader. He undertook this nerve-racking endeavor for the noblest of reasons: “I want to feel the rush of making lots of money,” Stein reveals in his self-mocking book, “and then snorting cocaine off a hooker who is snorting cocaine off another hooker.”

Really, though, who doesn’t?

A post on the Wall Street gossip site eventually landed him a taker: 25-year-old Matt Nadel, “the man of immense b---- I’ve been hoping to find.”

A financial whiz at Chicago’s Great Point Capital, Nadel agreed to show Stein the ropes and then let him loose behind supercomputers with a pile of invisible, but very real, cash at his disposal.

“At 8:30 a.m. in Chicago the opening bell goes off in the New York markets,” Stein writes, “and everyone in this quiet, dark room instantly gets Tourette’s.”

Which is to say they cussed a lot and with vigor.

The now “13 percent” manlier author — who’ll be in town Wednesday at ARTango Center in Lakeview (proceeds support Meals on Wheels Chicago) — talked about his thrilling and often nerve-racking experience.

Q: What made you come to Chicago in the first place? Couldn’t you have had your pick of traders in New York?

A: Absolutely not. Because I’d been really working hard on trying to get someone to give me a pot of money to day trade. And I got a couple of guys on the phone who were into it … and then they would check with their lawyers. There’s a lot of SEC rules about trading, and the lawyers never want to take a risk. So they all shut me down.

Q: Did you have to somehow indemnify yourself before gambling with Matt’s money?

A: I signed some things. I don’t know what they were. What did I have to lose? It was someone else’s hundred thousand dollars. I knew I wasn’t responsible for it.

Q: While trading, you’re in this dark room that seems really depressing.

A: Really depressing. I felt that way about poker. If you sit in that poker room for like 12 hours and grind it out, it’s not very glamorous. You’re eating a bad sandwich and stuck in this room and no one’s really talking and it’s slow. It’s not for me, that’s for sure.

Q: Matt seemed able to shut off his uber-competitiveness outside the trading room. Was he an anomaly?

A: I didn’t spend enough time with enough of them to know, but I think [day traders] can turn it off a little bit more the way that poker players or anyone who plays a game with really defined rules and really defined hours can.

Q: Especially during the first crucial hour-and-a-half of trading, you’ve got to be ultra-He Man.

A: It’s exciting. The room I was at in Chicago — I didn’t meet them all, but they seemed like a really nice group of guys. And then they just got Tourette’s for that hour. Because I was reading back some of the stuff this one guy said, and he’s like, [quiet voice], “You can’t put my name on that. I can’t believe I said that.” He just had no idea.

Q: What was the most intimidating part of the whole experience?

A: It’s gambling, so the big opportunities required a lot of risk. And it was moving very, very fast. My first hour, I had trouble just getting the buttons right.

Q: Is adrenaline coursing? Are you trembling?

A: Yes, yes. It’s like any gambling: you get a big adrenaline hit and it’s super fun. Like, really fun. I was really shocked at how much I enjoyed it … I left there that day just pumped to go do something or gamble on something. Or bite something.

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