The Interview Podcast - Matthew Lesko - Free Money, Big Suits, and a Bigger Heart

You’ve seen him in wild suits covered in question marks — and no, he’s not the Riddler. He’s Matthew Lesko, the energetic and eccentric author and entrepreneur who’s spent decades helping Americans access free money and government grants they didn’t know existed.

In this episode, Craig sits down with Lesko to trace his journey from Navy service to bestselling author, his rise to cult fame in the 80s and 90s, and how he became the loudest voice in the country yelling: “There’s free help out there — go get it!”

Lesko shares stories from his early career, how he built his persona, and why he believes helping others access public resources is the most fulfilling work he’s ever done. He also drops practical tools and websites to find help, start businesses, and fight medical bills — all while railing against predatory search engines, bloated government programs, and corporate greed.

And yes, he still rocks the question mark suits.

Highlights:

Why Matthew Lesko never actually “wrote” his first bestseller

The real reason he started dressing like a human exclamation point

Where to find real help online (spoiler: it’s not Google)

What the government offers that most people have no idea exists

His take on capitalism, community, and the future of work

The one piece of advice he’d give anyone chasing their dreams

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