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Socratic Assassin

Meet Jan Helfeld, Internet provocateur.

1:05 PM, Mar 26, 2014 • By JIM SWIFT
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Helfeld has been doing these interviews for years. Being the son of a lawyer certainly seems to have inspired him. “When I was very young, I liked to argue, say 10 or 11 or whatever, and I realized something interesting: If you catch another person in a contradiction, you won the argument.” Contradictions play a big role in Helfeld interviews, which employ what he calls the “Socratic interviewing” method.

“In order for the Socratic interviewing to work,” says Helfeld, “you have to know your stuff. You have to know why you think what you think. What your premises are, what the relationship is. You have to have an integrated philosophy, at least in that area, where you understand what principles depend on what principles or what conclusions depend on what conclusions.”

He worked as a lawyer for a while before transitioning into business. “I did mortgage financing and property development at a small time level. And a few other small businesses, like a restaurant I had, this or that, inconsequential stuff.”

Helfeld then submitted a request to do television on a local variety show. “I had a little section there which was called the happiness section. It’s kind of like philosophical, I did like a little tip, a little analysis about something in life.” Helfeld’s section on the show led to him being offered his own show, called What's your Philosophy? On his new show Helfeld landed his first big interview—Jaime Benitez, chancellor of the University of Puerto Rico. “The guy was talking philosophic nonsense. Every time I tried to offer him a way out, he just dismissed it out of hand.... He was an arrogant son of a bitch.”

Benitez gave his father his first job as a law professor. But, Helfeld recalls, “I said ‘Aw, hell, my commitment is to the truth, f— it.’ I did the best to help him out... He doesn't want any help? Down you go! And so from then on, that was when I have been committed to the truth, and that's what I try to pursue.” Helfeld is most happy when “everything ends amicably, it’s friendly,” he says. “You know, that’s what I’d prefer. But I’m not about to let the truth go down the drain to keep a friendship in an interview.”

“For 30 years, [Benitez] was an institution in Puerto Rico,” he continued. “He was a friend, so I had to take him home in the car to his house after I crucified him. So then afterwards I went to celebrate at a discotheque. And I was thinking, ‘You know, I kind of like this. This is fun. It's like trying to catch a greased pig.’ … That was the image that came to my mind and I said, ‘You know, I like this, I am going to continue with this career.’”

Helfeld later hosted a radio show in Puerto Rico and did some interviews in New York, but made his way to Washington in the mid-nineties to host a show on a now-defunct small political network. The offer fell through after the proposed contract changed, and Helfeld pursued freelance opportunities instead. In Virginia, Helfeld created a show called The Bottom Line on cable access, and proceeded to interview a whole host of elected officials. Much of his viral content came from his cable access show.

Cable access shows have always been a good source for interesting content that normally wouldn’t get airing on normal television channels, but they don’t last forever. After all, time and bandwidth are finite. Helfeld still goes with the title of his show these days, since what he’s after is “the Bottom Line.”

The Internet has been good to Helfeld, but it has changed what he does.

On one hand, the costs of getting his interviews out to viewers have been reduced dramatically, thanks to YouTube. (Helfeld only posts clips of most interviews, but his website does sell some of the full ones.) Before the proliferation of Internet video, Helfeld had to copy his own tapes to get them out there. “Man, was that a pain in the ass,” he tells me. On the other hand, it would stand to reason that it makes it harder for Helfeld to get interviews, since he’s a Google search away from being denied an opportunity by a rightly skeptical press secretary.

But Helfeld disagrees. He recounts the story of Mike Wallace connecting him with his agent in New York. “The agent said, ‘You have a good gimmick here, Jan. But I don't think it's going to work because the people will not want to do interviews with you.’” Jan wasn’t worried.

“Some people are careless. Some people are good—they admit being wrong. Some people overestimate—‘Oh, the other guy got screwed, but wait til I get him. I'll show him a thing or two.’ And the last thing is there are so many people, the universe is big.”

How did Helfeld get all of those congressmen and senators to sit down and talk to him in their offices? He started a nonprofit group in Puerto Rico called Rational Solutions, Inc. and back when he was doing The Bottom Line on cable access, he and this nonprofit “would send out hundreds of invitations to do interviews, explaining who I was, the interviews, subject matter, and most people would just ignore it, some people would get back to me.”

So far as direct mail campaigns go, this one was pretty successful.

Helfeld's first viral hit, he thinks, was a Harry Reid interview on whether taxation was voluntary.  A friend of his put it online at his request, but another blogger with more influence recognized its potential and posted it to YouTube. There, it got 2 million views. Jan feels that the initial lack of credit this blogger gave him was downright impolite, but he didn't pursue any legal action; he seems at peace about it. He tells me he tries “to contribute to the political and philosophic discussion in America, and therefore, to its development.”

“You know, what I do is pretty hard.” Helfeld says. “There’s a lot of tension and conflict sometimes, that wears on you psychologically. So, there’s a sense of satisfaction of doing a good job… you know... I think I’m not the only one that’s doing these exposes, I don’t know who the other people are, so, somebody’s gotta do it, but it’s not what I’d call pleasant.”

The grind of finding people to interview wears on Helfeld, he admits. He hopes that with his body of work, interested parties could set up some of the interviews for him, concluding, “It seems to me that I could be very useful to people that have a particular agenda that is consistent with mine, and they need me to interview a particular person.”

An ideological, journalistic hit man for hire. But Helfeld doesn’t want just to kill the interview subjects with kindness—he wants to kill them with reason.

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