Life can change in an instant. One day you’re shopping at Saks Fifth Avenue, and the next you’re sitting in your car with everything you own, and everyone you love, wondering what happens now.

Joan Howard grew up in Beverly Hills with every advantage until a series of crises left her homeless and living in her car with her mother and three dogs. What helped her rebuild wasn't luck or charity. It was kindness, consistency, and one simple weekly practice of being in service to others.

Today, Joan is a long-time volunteer for Food on Foot, the very organization that helped her decades ago. Food on Foot is more than a meal line—it’s a community built on dignity, kindness, and practical support for people experiencing homelessness in Los Angeles. Their model helps people find work, save money, build confidence, and move forward with independence.

In this episode, we talk about what homelessness actually looks like, why service can be transformative, and how organizations like Food on Foot help people not just get back on their feet, but build a future.

This is A Bit of Optimism.

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To learn more about Food on Foot, visit their website!

https://www.foodonfoot.org/

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What if a great business was built like a handmade mixtape? A lovingly crafted experience that is as much a love letter from its founder as it is custom-tailored to its audience.

Before Jeni’s Splendid Ice Creams became a household name, Jeni Britton was a 22-year-old art school dropout scooping her ice cream creations at a farmers market in Ohio. She didn’t have investors, connections, or a playbook. What she did have was a vision - not just for ice cream, but for connection.

Jeni believed her bold ice cream could be a conduit for something bigger: a place where people feel seen, conversations happen naturally, and strangers become community. Over the next two decades, she bootstrapped her way from a small counter to a nationally recognized brand by doing everything the slow, hard, old-fashioned way — one customer, one flavor, and one act of service at a time.

She refused shortcuts. She prioritized people. And she built her company like a handmade mixtape — crafted with intention, risk, rebellion, and love.

In this conversation, Jeni explains what true entrepreneurship really is: not hype, not hyper-growth, and not chasing venture capital, but the courage to follow a vision long enough for it to start leading you. We talk about the creative process, the power of service, the lessons learned from young employees, the myth of “scalable ideas,” and how walking in the woods helped Jeni discover her next chapter - Floura.

Jeni’s story is a reminder that the best things in life - and in business - take time, heart, and a willingness to make something beautiful even when no one is watching.

This is A Bit of Optimism.

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This episode is brought to you by the Porsche USA Macan

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Visit Jeni's Splendid Ice Creams: 

https://jenis.com/

Check out Jeni’s newest venture — Floura: 

https://www.floura.com/

Who would’ve guessed that one of the world’s best company cultures was hiding behind a can of WD-40? Of all the places to find a leadership masterclass, the blue-and-yellow can in your garage probably wasn’t on your list - but it’s time to put it there.

Garry Ridge - an Australian who brought his charm and curiosity across the Pacific  - joined WD-40 Company in the late ’80s and rose through the ranks, eventually serving as CEO for 25 years. But he didn’t start out as the culture-building expert he’s known as today. Early in his career, he lived by the old mantra: “be brilliant, be brief, be gone.” He had to unlearn that mindset and rebuild himself into a leader who centers people, learning, and belonging  - an evolution that reshaped WD-40 from the inside out. His new book, Any Dumb Ass Can Do It, captures that journey.

In this episode, we break down how Garry built a company where people genuinely love coming to work  - even through recessions, pandemics, and all the external chaos leaders can’t control. We dig into the systems and behaviors that fueled WD-40’s rise, from psychological safety to accountability to building internal consistency no matter what the market is doing.

Garry and I both believe that people deserve to love their work - even if they don’t like it every single day. People want to feel seen, heard, and valued. And Garry is one of the rare leaders who knows exactly how to make that happen.

This is A Bit of Optimism.

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This episode is brought to you by the Porsche USA Macan

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Check out Garry’s new book.

https://thelearningmoment.net/any-dumb-ass-can-do-it/

And his coaching work with The Learning Movement. 

https://thelearningmoment.net/

What if great friendships aren’t found by luck but built through effort?

Bestselling novelist Fredrik Backman, the mind behind A Man Called Ove (adapted into the Tom Hanks film A Man Called Otto), Anxious People, and the beloved Beartown series, has spent his career writing about the quiet power of ordinary people. But in his real life, he learned one of his most important lessons from his best friend of 30 years: meaningful friendship is a skill you develop, not a lottery you win.

Despite being a self-described introvert, Fredrik discovered that you don’t need hundreds of friends. You only get a few humans who truly shape your life. His newest book, My Friends, is a tribute to those relationships and the daily work of showing up for the people who matter most.

In this candid and inspiring conversation, Fredrik and I talk about the healing power of friendship, why differences make relationships stronger, the value of having friends who edit us, and the joy of being genuinely happy for someone else.

If you want to become a better friend and build deeper connections, this episode offers heartfelt lessons from one of the world’s most compassionate storytellers.

This is A Bit of Optimism.

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This episode is brought to you by the Porsche USA Macan

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To check out Fredrik’s newest book, “My Friends,” visit: 

https://www.simonandschuster.com/books/My-Friends/Fredrik-Backman/9781982112820

Find the full-length speech Fredrik gave for Simon & Schuster here: 

https://www.youtube.com/watch?v=NSuSyZ92Cjg

If you feel stupid while learning something new, you’re doing it right. But if you keep doing the same thing over and over hoping it’ll suddenly make sense - that’s on you. The trick isn’t to push harder; it’s to find a new teacher, a new explanation, a new way in.

That’s exactly how Matthew Broussard approaches comedy - and everything else. A stand-up comedian, math nerd, and former financial analyst, Matthew is obsessed with learning and cracking the formula behind how things work. He treats every joke like an equation, testing, refining, and solving for laughter.

He’s the creator of Monday Punday, a puzzle webcomic and app, and has been featured on The Tonight Show with Jimmy Fallon, Conan and Comedy Central’s Roast Battle. He’s also made appearances on The Marvelous Mrs. Maisel and The Mindy Project. His storytelling, including his viral tales about his mother-in-law, proves that logic and vulnerability can live in the same sentence.

In this episode, we explore the overlap between comedy and leadership—the art of experimenting, iterating, and connecting through honesty. We talk about the hidden work beneath success, the difference between purpose and perfection, and why laughter might just be the purest form of optimism.

This is A Bit of Optimism.

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This episode is brought to you by the Porsche USA Macan

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Check out Matthew’s Youtube page for his full comedy special “Hyperbolic”: https://www.youtube.com/@mondaypunday

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I’ve long imagined a world where people wake each morning inspired, feel safe wherever they work, and return home fulfilled by what they’ve created. That vision once felt like a dream - until I met Bob Chapman, CEO of Barry-Wehmiller, who quietly built it into reality. Over five decades, Bob has grown a humble Midwestern manufacturing company into a global business success story, proving that leadership grounded in humanity can scale across the world.

Bob sees the people in his company not as line items, but as human beings within his span of care -  individuals he feels responsible to help become healthy, fulfilled, and whole. His belief is simple yet profound: when people are cared for at work, they create happier families, stronger communities, and a better world. He captured this vision in his book Everybody Matters -  which I’m proud to have published -  inspiring leaders everywhere to imagine a kinder form of capitalism.

In this episode, we return to BW Papersystems in Phillips, Wisconsin where Bob first brought me fifteen years ago where he showed me what his Truly Human Leadership movement looks like. There, I speak with Amber Meyers, Randall Fleming, Lance Johnson, and Jared Nelson, each at different points in their journey with Barry-Wehmiller - some just three years in, others more than twenty-five. Through their eyes, we see the company’s evolution and the lasting power of care in action. What I once thought was idealism, I now know is possible: proof that capitalism can, in fact, be kind.

This Is A Bit of Optimism. 

For more of Bob’s work check out: 

Bob's book, Everybody Matters https://www.barrywehmiller.com/bobchapman/b

Chapman & Co. Leadership Institute: https://www.ccoleadership.com/

Barry-Whemiller: https://www.barrywehmiller.com/

We don’t usually look to Hollywood for lessons in career longevity. But it might be the perfect place to study it. Few industries move faster or cast people aside more quickly, and yet Rob Lowe has spent more than four decades defying those odds. His story isn’t just about surviving fame—it’s about overcoming adversity, finding joy in the work, and proving that authenticity is the only path to a career that lasts.

Across his career, Rob has navigated the highs of teen idol stardom, the lows of very public failures, and the challenge of reinventing himself again and again—all while staying relevant and true to himself. His secret? A willingness to take risks, embrace failure, and laugh at himself along the way.

Rob and I dive into Rob’s philosophy of resilience, authenticity, and joy. He shares how humiliations turned into lessons, why not taking yourself too seriously is a strength, and how authenticity has become the ultimate currency in today’s culture.

You can also see Rob hosting the fourth season of The Floor, airing September 24th on FOX.]

This is A Bit of Optimism. 

The future is something we create, not just something that happens. To guide progress toward real good, we need bold, optimistic visions of what society can become.

Reid Hoffman makes the case for better science fiction - stories that don’t just entertain, but illuminate the futures we can strive for. As a serial entrepreneur and cofounder of LinkedIn, Reid brings a unique perspective on how storytelling shapes technology, society, and innovation. He argues that imagining optimistic futures is essential if we want to create them.

In this episode, we also explore how technology like AI is changing the way our brains work and how our faculties will evolve, why humanity has shifted from focusing on external threats to internal ones, and how optimism isn’t blind faith—it’s a clear-eyed strategy for shaping a better world.

This is... A Bit of Optimism. 

Check out Reid’s new book here: https://www.superagency.ai/

SUPERAGENCY: What Could Possibly Go Right with Our AI Future

We’ve never had more freedom in our relationships—yet many of us feel more disconnected than ever. Marriage, family, and even the workplace have all been reshaped by shifting norms, new technologies, and rising expectations. Happiness, once a nice-to-have, is now the very glue that keeps both couples and teams together.

Few people understand these changes better than Esther Perel. For decades, she’s helped us rethink intimacy, navigate conflict, and reimagine what a healthy connection looks like—at home and now at work with her new conversation inducing game of questions, Where Should We Begin? At Work. 

Esther and I explore how our ideas of love and partnership have evolved, why friendships can be just as life-giving as romance, and why learning to “talk to strangers” may be the most important skill for the next generation. We also dive into the role of play, trust, and risk-taking in building lasting bonds.

If you care about creating relationships that are strong enough to withstand the pressures of modern life, this episode might just be for you.

This is A Bit of Optimism.

To learn more about Esther’s work, visit: 

www.estherperel.com

And to check out Where Should We Begin? At Work here: 

https://game.estherperel.com/products/where-should-we-begin-at-work?gad_source=1&gad_campaignid=21749016432&gbraid=0AAAAA93e13laOUsIrrGSZUodaliBNmZVP&gclid=CjwKCAjw_fnFBhB0EiwAH_MfZtrMmVTRj7QgBn4ER-_HF10aCifdOOpY1DLy9R4dt4K0Sbh2WKJDeRoC2XUQAvD_BwE

Your instincts aren’t just whispers. They’re a compass pointing you toward the life you’re meant to live. But in a world obsessed with speed, metrics, and outcomes, most of us forget how to listen.

Arthur Brooks, bestselling author and Harvard Business School professor, teaches one of the most popular classes on happiness. But his insights come not just from research, but from a life of reinvention: from French horn player to scholar, from think-tank leader to teacher, and even pilgrim on the Camino de Santiago.

In this conversation, we explore why so many of us feel unhappy today, the real equation for joy, and why following your gut is essential. Along the way, Arthur shares how to treat life like a pilgrimage, why AI may strip away the struggle that makes us wise, and why the process - not the outcome - is where happiness lives.

If you’ve ever wondered whether you’re “falling behind,” or if you’re searching for the courage to trust your instincts, this episode will remind you that happiness isn’t something you chase - it’s something you practice, every step of the way.

This is…A Bit of Optimism.

Check out more of Arthur’s work here: https://www.arthurbrooks.com/