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May/June 2019

Matthew Lesko, The ‘Free Money‘ Man: Asking the Right Questions

Maybe you caught him on Oprah, or when he talked with Larry King, or when he turned up on Letterman or Vice TV. But the odds are you’ve seen Matthew Lesko at some time somewhere. You know, the wiry guy with the round glasses and shock of hair, wearing those neon-colored suits with question marks all over them? Sticking his face almost maniacally into the camera and nearly shouting at you about how to get “free money” from the government?

If you have seen him, odds are also that you thought he was nuts. After all, that’s his media persona, and he’s crafted it carefully. But beneath it, he’s really saying that you may be nuts if you’re not taking advantage of the thousands of governmental programs that provide all kinds of assistance to Americans at no cost.

What you may not know is that Lesko also is an often reflective, self-deprecating man who says he genuinely wants to help people—especially veterans. He’s a Vietnam veteran himself, a former U.S. Navy spy-ship driver who sailed the South China Sea in the mid-1960s. Gathering information, you could say, has always been at the center of his working life in one form or another. And he’s loved it.

Lesko didn’t always love his clients, though. Not in the beginning. In fact, it took being a success at helping people who didn’t need help to realize what he really wanted to do. At the top of his list: “I think veterans should be first in line for every fucking program we have,” Lesko said. But over the decades he’s been in business, Lesko has found that veterans, like a lot of other people, don’t know where to look for those programs.

A Problem with Authority

Lesko was born and raised in Wilkes-Barre, Pennsylvania, and attended Marquette University in Milwaukee, eventually earning an undergraduate degree in business. Recalling his days as a less-than-stellar student, he said, “I was on probation every semester. I studied like hell one semester, and it didn’t get me anything. So I figured, why work that hard? I did just enough to get by. And I did, just barely.”

It was 1965. The Vietnam War was underway, as was the military draft. Lesko applied for graduate school, “but I was too terrible a student.” Having no interest in “camping in the jungle,” as he put it, he joined the Navy before the Army came for him. “I went in wanting to fly, but the recruiter said, ‘Go to Officer Candidate School first.’”

It didn’t take long for his problem with authority to surface. “I got one foot off that bus and I thought, ‘I want outta here soon as I can! People telling you what to do! What the hell is that?’”

After OCS, as a newly minted ensign, Lesko found himself aboard the U.S.S. Oxford, an intelligence-gathering ship similar to the U.S.S. Pueblo, which later became infamous when North Koreans seized it in January 1968, accused it of spying, and held its crew hostage for almost a year. But nothing so dangerous happened during Lesko’s tour on the Oxford. “We’d just travel up and down the coast of South Vietnam, listening. And we’d put into port every fifty days,” he said.

Half the crew—Lesko’s half—operated the ship, while the other half did the listening, and often the twain never met. “There were separate places on the ship that we couldn’t go in,” he recalled. He didn’t mind. Nor did he have much of an opinion about the war at the time. “I never really thought about it, so I had no particular feelings about it. I grew up in the fifties, ‘My country right or wrong’ sort of thing. There were sometimes discussions on board among the officers, but not me.”

Lesko focused instead on learning his assigned duties. “I became the ship’s navigator only because when I got on board, I was the most junior officer, and it’s a skill,” he said. “They thought since I’d just got out of OCS, I knew how to do it. But I had to learn it. It was not computerized then. At least not on the South China Sea. You had to use the sextant and consult books and things.”

Except for being told what to do, Lesko found his time in the Navy rather pleasantly remarkable in that, as he said, “I never had more responsibility again the rest of my life. The military is incredible—they give a billion-dollar ship to a 22-year-old kid to drive around. Just amazing.” He almost signed up for another tour in Vietnam—this time on gun boats—but ended up finishing his military career as a diplomatic courier in the U.K.

As it was for so many others, coming home was not what Lesko expected it to be. “I was pissed when I came back because I was thinking, ‘Hey, I’m a military man, an officer! I’ll have a chick on both arms!’ And I come back home, and I was just looked at as something dumb. Like, how did you not get out of it? I thought I’d come home as a hero.”

Acting Like a Fool

A civilian again and without much of a plan, Lesko decided to accompany a buddy and his wife who were moving to the D.C. area. Once there, he enrolled in the Master of Business Administration program at American University. “I got an MBA and I started a software company in 1975 or so,” he said. “Basically, it was an information business for guys coming home from the war. They’d been out of touch and didn’t really know anything. So, it was an information service to help them. But it didn’t really go anywhere.”

After several more unsuccessful attempts at information brokering, Lesko found his niche with large corporations. “They were interested in competitors and markets,” he said. “And you could get that information in Washington. Some company called and said they wanted to start a chain of pasta stores and wanted to know what’s the market for pasta. I found a guy in the Commerce Department who studies the pasta industry. That’s all he does.” Lesko got all the information and charged the company for his efforts.

With Fortune 500 companies for clients, Lesko’s business thrived, at one point employing thirty people. “I’d find the experts in government and get all the information, and some fat cat would pay ten grand for just organizing that information. I got excited about the things I was finding to help these people. But then I said, ‘Jeez, rich people don’t need this help.’ And eventually I got sick of helping rich people.”

Lesko wanted to get information to people who genuinely needed help. After mulling some possibilities, he settled on books—and found the idea ironic, given that he had failed English in college. But he wasn’t planning on really writing anything: he’d take governmental information about assistance programs of all kinds, slap it all between covers, and sell it.

He put together his first book—essentially a compendium of federal government assistance programs—then he had to let people know about it. “I went on television and acted like a fool,” Lesko said, laughing. He created the question-mark suit (inspired in part by the fact that his parents had been in the garment industry) and the loud, in-your-face sales pitch. It got him on some talk shows. And his first book hit The New York Times best-seller list.

Since then he’s issued more than twenty books on how to get money from the federal government for, as he’s often said, “just about anything.” Lately, however, as the Internet has claimed more and more of the print business, Lesko sells electronic copies of his wares through his website.

Perhaps not surprisingly, he’s been criticized by some for “promoting welfare,” a criticism he rejects. “It’s what it is,” Lesko said. “I’m not making anything up. The government should be doing what I’m doing—letting people know what’s available.”

The fact that the government doesn’t advertise its programs is, in his view, just one reason why most people don’t know about them. “The other is we’ve been trained to hate the government, and that’s just stupid.”

Over the years, Lesko has done some outreach for veterans. “When we had the first Gulf War, I’d go to Walter Reed and give talks to the people about benefits,” he said, referring to the U.S. Army medical hospital in Washington where many wounded soldiers are treated and rehabilitated. “I let them know that there are thousands of other programs that are better and offer more opportunities than what’s available at the VA.”

Lesko encourages all veterans to pursue VA benefits, but adds, “don’t limit yourselves to the VA. So much depends on knowing not just how things in general work in Washington, but how money works. It flows from D.C. to states and counties. So, your first best bet is the County Veterans Service Officer. This is a vast resource for vets.”

The National Association of County Veterans Service Officers (www.nacvso.org) describes itself as an organization that “aggressively pursues all benefits for veterans and eligible family members through education, training and our advocacy programs.” The NACVSO website can direct veterans to an officer in their area.

Other resources include 211, a national organization dedicated to helping people in need, including veterans. Check out www.211.org/services/veterans And, as Lesko insists, don’t forget your local reference librarian. “Those people know what’s available in the community,” he said. “Talk to them.”

Among the best means of all, according to Lesko, is talking to your Members of Congress. “They’re the only ones in the government who have a motive to help you,” he said. “The VA gets the same amount of money appropriated no matter how much they give you. But your elected official, if he gets you five or ten grand, you’re going to vote for that sonofabitch no matter what. So, they have a motive to help you, and most of their staff are there to solve these problems. They can make calls—to backdoor numbers at federal agencies. And federal agencies want to help elected officials. Why? Because elected officials vote for federal agency budgets.”

When seeking information or help, either from an elected official or a government bureaucrat, Lesko says it’s important to show up in person, if at all possible, especially if the pol’s home state office is nearby, noting that “they’re more likely to help a human than an email.”

Also, he advises not to ask directly for money. “Rather, say, ‘I’m trying to get education’ or ‘I’m trying to get trained for a new job.’ That’s your goal.”

“Don’t pay for some course to teach you how to start a business,” Lesko said. “Every county has a small business development center, and they’ll help for free. They may not give you money, but they can give you other stuff, like free legal advice. Got an invention? Go to them with that, too. Don’t go to a company.”

And don’t fall into the grant trap. “Only 20 percent of the free money that the government gives out is called grants,” Lesko said. “If you’re looking for grants, you’re missing 80 percent of the free money. You may think you need a grant to do what you want to do, but you may not. If you say you want a grant—you’re looking for money—they’ll look at the grant programs and probably see nothing for what you want. But on another list is something called ‘direct payments,’ which they don’t tell you about because you didn’t say anything that would send them there to look.”

Lesko has also been criticized for overselling the availability of “free money” from the government. “Lots of government grant money out there for the taking? Think again,” is a headline on a story mentioning him on ConsumerAffairs.com But, as Lesko acknowledged, “It’s no guarantee that any of this will work. So much of it is learning what’s out there and figuring out the best way to use it. Because if you’re looking for one thing, that just narrows your scope and you miss so many other things that could’ve helped because you didn’t ask the right question.”





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