News & Politics

The ‘Free Money’ Guy on How He Got His Start—and Those Crazy Suits

Matthew Lesko took his MBA and decided to have fun.

Photograph courtesy of Matthew Lesko.

If you don’t remember the name, you might remember the suits. Matthew Lesko—the infomercial pitchman offering consumer advice on how to get free money from the government for everything from small-business grants to credit-card payments—became a staple of late-night TV and a bestselling author thanks to his question-mark-emblazoned suits and hyper­active antics. While his operation has mostly moved to YouTube, he’s still at it at age 81. We met up with the Adams Morgan resident to find out where that style sense came from and how he got his start as a media personality.

“The first suit I made, it was actually in Montgomery Mall. A lady used to embroider hats and shit, so I got a cheap suit and had her embroider it. I used to travel a lot, and every step was like walking on eggs. I was so self-conscious! As a guy growing up in my generation, everyone is so macho, but the more I did it, the more I saw people who loved it. The only time it used to piss me off was in Adams Morgan on a Saturday night. Especially young men—they’re drunk and trying to say something nice, and they don’t know how to do it. It’s a gauntlet. Now I miss the suit if I don’t have it on.

“I remember hiring a young guy at AU. He was in marketing and needed a job as credit, so I said, ‘You should [work for] me!’ I didn’t know how to do publicity, so I got a list [of media outlets]. I said, ‘Let’s try a small town. Call ’em up and see if they can get me an interview.’ I’d go to town—everyone was looking for a guest on the 4 pm news. From that, I went on to Oprah, to Letterman.

“But it wasn’t because of what I was saying, it was how I said it. You’re on the Today show and it’s ‘Up next we have Matthew Lesko to talk about government information.’ Well, if you have the show in the morning, [viewers] will go, ‘I’m gonna go brush my teeth.’ So I have to get you out of the bathroom. When someone asks me a question, I explode [with energy]. I imagine people all over the country going, ‘What’s that asshole talking about?’ while brushing their teeth.

“My parents didn’t admit I was their kid for the first ten years I did this, because I acted like a maniac, until I went to their retirement village and someone was like, ‘Is that your son? I saw him on Larry King!’

“In the ’70s, I had a software company that failed. I had another business that failed. I told myself: I’m doing everything the way I was taught in MBA school, but I’m failing, I’m not having fun. So the next time I do something, I’m gonna have fun doing it. If I fail, f— it, it doesn’t matter.

“I’m having fun now instead of eating shit for ten years to maybe have fun in ten years. You find out by failing, and there’s no perfect thing out there. You have to do it yourself.”

Arya Hodjat
Editorial Fellow