From Grants to Greatness: Matthew Lesko on Personal Branding, Boldness, and the Power of Being You

Our guest: Matthew Lesko – America’s most flamboyant grant guru, bestselling author, and media veteran with over 100 major TV appearances.

Known for his question mark suits and riotous personality, Matthew Lesko has been helping Americans access government funding for over 50 years. With more than 4 million books sold and a reputation as a professional guest on everything from Oprah to Larry King Live, Lesko joins Nicholas for a rollercoaster conversation on personal branding, failure, heart-led business decisions, and why joy should be your guiding light.

Key Takeaways

This episode isn’t just about government grants—it’s about how to live a life of purpose, play, and real personal power. Lesko shares how dressing like a cartoon character helped him get more airtime than most A-listers, and why being “weird” might just be your greatest superpower.

He reminds us that success isn’t a formula—it’s trial and error, authenticity, and the guts to get up again after each faceplant. Matthew’s infectious energy is a wake-up call to stop hiding behind expectations and start leading with heart. Whether you're building a business or building yourself, this episode will help you laugh your way to clarity.

Chapter Summaries

Lesko the Legend and personal branding

Nicholas kicks things off with a bang, matching Lesko’s wild energy in a conversation about personal style and first impressions. From being too outrageous for QVC to making people smile at Starbucks, Matthew explains how his eccentric wardrobe isn’t a gimmick—it’s who he is.

Navigating Grants in a Changing America

Grants might be getting chopped under new administrations, but Lesko doesn’t sweat it. He shares his method of ignoring political noise and instead focusing on the 500+ programs that always pop up to replace the old ones. It's all about keeping your head down and doing the work.

From Navy Man to Media Star

Before becoming a TV personality, Lesko drove ships in the Navy and built software companies in the 70s. But none of it stuck—until he stopped listening to the "experts" and started doing what actually made him happy. That’s when the magic (and the grants) started flowing.

The Birth of the Question Mark Suit

His flamboyant brand wasn't born overnight—it was a response to failure and frustration. Lesko couldn’t afford advertising, so he leaned into media and figured out how to be entertaining enough to get invited back again and again. The suit? It got people to stop channel surfing. The rest was down to preparation, energy, and joy.

Joy, Heart & Hustle

Now in his 80s, Lesko still works daily, driven by what he calls "the smarter organ"—his heart. He believes joy is underrated in business and that your most “weird” trait could be the one thing that sets you apart. It's not about being perfect; it’s about moving forward, mess and all.

Brand Like a Human

Matthew doesn’t buy into sterile branding strategies. He thinks the best brands come from looking inward—not at the market. His advice: forget what others think, double down on your quirks, and let your true self shine through. If people don’t like it, it’s a win—you’ve saved everyone some time.

On Working Long & Living Well

Lesko doesn’t see what he does as “work.” He sees it as giving. And that’s his real definition of success—how much of yourself you give to others, how much joy you bring, and how alive you feel doing it.

Conclusion

Matthew Lesko is a living reminder that you don’t have to tone yourself down to build something meaningful. Quite the opposite. With every laugh, story, and outrageous jacket, he challenges us to show up more fully, share what’s truly in our hearts, and stop waiting for “perfect” before we start. Whether you're applying for grants or figuring out your personal brand, Lesko’s message is loud and clear: be brave, be weird, and be generous.