Matthew Lesko enters a café wearing a neon green suit jacket bedecked with question marks, a collared shirt adorned with yellow smiley faces and red hearts, and a bright polka-dot bow tie. “I’ve even shown up to weddings and funerals dressed like this,” he begins our interview. “Although I always call in advance to make sure it’s OK.”
Right then, a server stops at the table to take our order and chimes in, “Can you come to my wedding dressed like that?”
Probably not, but Lesko can certainly help that waiter earn more cash than his current barista job pays.
Starting in the 1980s, Lesko became a B-list celebrity for his late-night infomercials, in which he dressed in eccentric clothes and hawked books like Free Money for Everybody: How to Get Government Grants for the Whole Family! Over the decades, he appeared on The Oprah Winfrey Show and The Late Show with David Letterman. In the digital era, those infomercials have largely given way to a social media presence including 190,000 YouTube followers on his channel, @MatthewLesko.
None of it is a scam.
The government offers countless financial opportunities and grants, which most people don’t even know about, in areas ranging from college tuition to down payments for your house. Lesko’s job is to compile all that information in one place — and, in his words, “sell it to people for as much as I can get.”
It all started when Lesko was an American University MBA student, when a 1973 oil embargo caused prices to surge. “Most companies, in the ’50s and ’60s, all they had to worry about was stuff inside the company,” Lesko says. “That was the first time that many companies really had to think about what was happening outside the company.”
So he started his own business, originally intended to help struggling small businesses better avail themselves of government grant opportunities. His venture later expanded to include both bestselling books and counseling to individual clients. “I didn’t know anything about government,” Lesko recalls of those early days. “I only knew the DMV and the IRS.”
Now living in the Adams Morgan neighborhood of DC, Lesko turned 80 in May. Even at his age, he still seeks out novel opportunities in life, like visiting Burning Man dressed in his famously outlandish outfit. “Nobody noticed me. I was wallpaper!” Lesko laughs. “I mean, there were people there dressed as giraffes.”
He leaves our interview with some parting words. “You’re a freelance writer. You know who hires more freelance writers than anybody else? The government.” He pauses. “Although most of it is EPA brochures about how to avoid slipping in the woods.”
Feature image of Matt Lesko with former president Barack Obama, White House photo, public domain
This story originally ran in our September issue. For more stories like this, subscribe to Northern Virginia Magazine.
