Christos Garkinos has lived several lives—and nearly lost one along the way. From a lonely childhood as a gay Greek kid in Detroit to running marketing for Virgin Megastores, launching fashion lines on HSN and becoming Bravo’s “Robin Hood of Fashion,” Christos seemed unstoppable…until addiction, financial collapse and grief brought everything crashing down.

In this episode, Christos and I talk about what happens after you lose everything—and how rebuilding can become more powerful than the original dream.

We dive into the making and launch of his memoir Covet the Comeback, including how he orchestrated a book rollout that looked more like a rock tour than a traditional publishing plan: celebrity-filled dinners, sold-out events across the country, a five-month LA billboard that landed directly above an ATM from his darkest days and a community that showed up in ways he never imagined.

Christos opens up about sobriety, ego, surrender and the surprising emotional weight of being seen—by strangers, by longtime fans and by the people who once underestimated him. He shares how storytelling transformed not just his public image, but his business, his relationships and his sense of legacy.

Episode Highlights

· Why Christos refused a “normal” book launch and built his own rules

· The billboard moment that made him believe in something bigger than himself

· How sobriety reshaped his instincts, leadership and creativity

· What happens when your community turns your story into their own

· Why a book isn’t about sales—and what it actually gives you instead

Walter Clarke has spent more than 30 years advising wealthy families—and he’s seen firsthand how money can quietly destroy relationships, identity and mental health when people aren’t prepared for it. A former investment manager turned financial educator, Walter didn’t set out to write books to build a brand. He wrote them because he’d lived the consequences of not understanding risk.

In this episode, Walter and I talk about what happens when success arrives before education—and how one catastrophic business failure reshaped his philosophy on wealth, parenting and legacy.

We unpack his first book, The Big Risk, which chronicles a painful chapter involving regulatory action, bad advice and the moment Walter lost his firm—and why owning the narrative was the only way forward. He shares how writing the book transformed shame into authority and positioned him as someone who teaches from experience, not theory.

We also dive into his second book, 401Kid, and the radical idea that financial education should start at birth—not adulthood. Walter explains why kids lose their parents’ influence around age eleven, how money is actually a byproduct of value creation and why avoiding “entitlement” conversations does far more harm than good.

This conversation is part cautionary tale, part parenting guide and part roadmap for building wealth that lasts across generations. It’s about learning the hard way—and making sure the next generation doesn’t have to.

Episode Highlights

• Why sudden wealth is more dangerous than lack of money
• How writing The Big Risk helped Walter reclaim his story
• The moment that inspired 401Kid—and why the title just clicked
• Why money conversations must happen before age eleven
• How books elevated Walter’s authority and opened entirely new business doors

When we published Right for the Role, I figured John would sell a few books, make a couple of actors cry and call it a day. Instead, the four-time Emmy-winning casting legend turned it into a full-blown second act. His memoir didn’t just tell the story of his decades casting ER, The West Wing and Shameless—it completely rewired his creative life.

After decades shaping other people’s performances, John finally stepped into the spotlight. The book sparked a podcast, packed acting schools, earned a spot in the Studio City Barnes & Noble window and somehow made him Instagram-famous (his words, not mine). At 78, he’s directing plays in New York, reconnecting with old collaborators and discovering that telling his own story was the most powerful casting choice of all.

In our conversation, John opens up about how writing forced him to drop his trademark privacy, what it’s like to relive your life with a co-writer on Zoom and how Right for the Role became both a calling card and a creative revival. He says the book didn’t give him a new life—it gave him his old one back. Which, for someone who’s spent decades defining what it means to be “right for the role,” feels about as poetic as it gets.

Episode Highlights

• How Right for the Role became a podcast, a tour and a rebirth
• Why John swears he “discovered no one” (but, come on, he totally did)
• What it’s like to publish your first book in your seventies and go viral for it
• The Smoke House signing that turned into an LA industry reunion
• Why he believes creative people need to tell their own stories
• How a memoir turned a quiet retirement into a full creative renaissance
• Why he now feels right for every role—including grandfather