Today we talk to Greg Bennick—writer, speaker, punk rocker, coin collector, juggler, and the first ever returning guest on the podcast.

Greg is one of those people whose passion is contagious. He can make anything interesting—coins, kindness, counterstamped nickels from 1860—and somehow ties it all back to living a life that actually means something. Our first conversation was the episode I recommended most when people asked what this podcast is all about, and this one might be even better.

We talk about the terrifying beauty of taking creative risks, the unexpected power of noodles in a hotel lobby, and why staying in the game—whatever your game is—might be the most important decision you ever make. He also shares what it’s been like to release his first book into the world, and why the chapter he almost left out might be the one that changes everything.

This conversation is about passion, purpose, and possibility.

Please enjoy, Greg Bennick.

Key Takeaways

• “Do it your way.” Greg shares how skipping the networking events at a major speaker conference—and eating Pad Thai alone in the hotel lobby—led to the most authentic connections of his career.
• Writing his first book taught him that vulnerability is part of the process—and that success often starts with just staying in the game.
• The chapter he almost didn’t include—on kindness—became the one readers connected with most. Sometimes others see the heart of your work more clearly than you do.
• Creativity isn’t magic—it’s a muscle. The breakthrough moments come after you’ve put in the reps, not before.
• Greg’s obsession with rare coins isn’t really about the coins—it’s about history, relationships, and finding connection in unlikely places.
• Comparison will kill you. We all assume everyone else has it figured out, but the truth is most of us are just doing our best to stay curious and keep going.
• Greg’s advice for anyone looking to start something new: Leap into the dark—not to fear failure, but to embrace the possibility of success.
• Purpose doesn’t have to be some grand external mission. Sometimes it’s sitting quietly in the lobby with a bowl of noodles, choosing to live a life that’s yours.

Connect with Bob Mathers

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The Restless Leader Newsletter on Substack: https://bobmathers.substack.com/

Greg’s website: https://www.gregbennick.com/

Greg on LinkedIn: https://www.linkedin.com/in/gregbennick

Greg on Instagram: https://www.instagram.com/gregbennick

Today we talk to Emily O’Brien, founder of Comeback Snacks, a company she launched while serving time in federal prison for drug smuggling. And if that alone isn’t enough to get you to listen, I give up.

Emily is raw, funny and vulnerable about the choices she made that landed her behind bars. She talks about the moment she saw her parents in the courtroom for the first time, the shame she carried, the strength she found, and the mindset shift that helped her recalibrate her life.

Today, Comeback Snacks is carried in over 1,100 stores across the country and employs a number of formerly incarcerated people. Everyone deserves a second chance, and Emily is proof that joy, humor, and intention can show up in the most unlikely places.

Please enjoy, Emily O’Brien.

• Emily’s story is a powerful reminder that no matter how far off course we get, we can still come back—and sometimes stronger than before.
• Despite growing up in a supportive household, Emily’s descent into addiction and toxic relationships shows how quickly things can unravel—no matter your background.
• Her time in prison became a personal “recalibration,” where she read 82 books, kicked substance use, and began sketching the plans for what would become Comeback Snacks.
• Emily reframes reinvention as recalibration—not becoming a new person, but returning to the good core that was there all along.
• With Comeback Snacks, she’s hired over a dozen formerly incarcerated individuals and developed a reintegration program to help others start businesses post-prison.
• Her “Comeback Blueprint” offers a framework for transformation: Commit, Own it, Be Accountable, Educate others, and Lead with Values.

Links and Resources

Comeback Snacks Website: https://comebacksnacks.com/

Emily’s instagram: https://www.instagram.com/emz.obrien

Comeback Snacks Website: https://www.instagram.com/comebacksnacks

Emily’s LinkedIn: https://www.linkedin.com/in/emily-o-brien-b628a4132/

Connect with Bob Mathers

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Today we talk to Lacey Heels —writer, creative strategist, and the author of The Rebirth Rituals.

This wasn’t a planned conversation. In fact, a few short weeks ago, we’d never even met. But after a few chance encounters (and some beautifully-timed serendipity at a retreat in the woods), Lacey’s book landed in my hands—and I couldn’t put it down.

We talk about that strange, messy, powerful space in between who we’ve been and who we’re becoming. Lacey opens up about the collapse that led her to start over, the fears that come with shedding an old identity, and how journaling and creativity helped her find clarity, healing, and direction.

If you’re sitting in the “what’s next” part of your life or career, this conversation is for you. It’s about rediscovering the parts of yourself you’ve left behind, honoring the discomfort of not knowing, and trusting that the through line will appear—if you just keep going.

Please enjoy, Lacey Heels.

Key Takeaways

The magic of in-between moments: Lacey describes the “liminal space” we all find ourselves in when one chapter ends and the next hasn't fully begun—and why learning to sit with the discomfort is essential.

Being known for one thing... and craving something else: Many of us reach a point in our lives or careers where we feel the urge to reinvent ourselves, even when we’re unsure what comes next.

The collapse before the rebirth: Lacey shares her experience of burnout after shutting down her business, and how letting go of what no longer fit made space for something new to emerge.

Start messy and trust the process: Whether it's journaling, creating, or starting a new path, Lacey encourages us to begin before we have it all figured out—the clarity comes in the doing.

Journaling is self-leadership: For high performers who are used to intellectualizing everything, journaling can be a powerful tool for self-awareness, emotional regulation, and reconnecting with purpose.

Run small experiments: Instead of waiting for “the answer” to appear, Lacey suggests taking small, low-stakes steps toward the life you want. Try something. See how it feels. Adjust.

You’re allowed to start over: Sometimes we need to be reminded that it’s not only okay to pivot, it’s necessary. Reinvention isn’t a failure—it’s part of being human.

Creativity as a healing force: Whether it’s writing, gardening, painting, or music, making space for creative expression helps us integrate our experiences and find meaning in them.

Connect with Bob Mathers

Website

LinkedIn

Instagram

The Restless Leader Newsletter on Substack: https://bobmathers.substack.com/

Links & Resources

Lacey on Linkedin: https://www.linkedin.com/in/laceyjheels/

Lacey on Substack: https://www.awildhoney.com/

Lacey on Instagram: https://www.instagram.com/awildhoney/

The Rebirth Rituals: https://www.amazon.ca/dp/B0F931KTTQ