A Bit of Optimism

We often comfort ourselves with the idea that things happen for a reason, or define our struggles as a test of strength. Tom Nash might ask you to reconsider. Tom is a speaker, former DJ, and globe-trotting advocate for agency, anti-fragility, and the radical idea that your worst moment might be your greatest asset — as he argued in his TED Talk, "The Perks of Being a Pirate.” He’s also the mind b...

If at some point, you've looked at your life—your job, your relationships, your achievements—and thought: “is this it?” This episode is for you.  Mike Posner had that moment at 30. His life, by every external measure, was extraordinary: he had hit songs, Grammy nominations, millions in the bank. He was a pop star… And he was miserable. What followed was one of the most honest reckonings we've ever...

Admit it, you've complained about at least one other generation. Boomers, Gen X, Millennials, Gen Z—somehow, they all end up with reputations built around what's wrong with them. Dr. Eliza Filby has a different suggestion: stop asking what's wrong with them. And start questioning what world they were handed. Eliza is a contemporary historian, generations expert, and the author of Sunday Times best...

The most successful leaders, coaches, and teams in history share one counterintuitive secret: their main focus wasn’t winning. And yet… they won more than everyone else.  My guest, Don Yaeger, learned this lesson from his mentor: legendary college basketball coach John Wooden. Don is one of my favorite master storytellers, a top business leadership coach, author of 44 books, 13 of them New York Ti...

We talk a lot about building successful things. But what does it actually take to build something people love? Jesse Cole has built an entirely new genre of entertainment: The Savannah Bananas and the Banana Ball League. They’re a viral sensation, selling out stadiums across the country, and have over 4.2 million fans on their  ticket waitlist. On the surface, Banana Ball looks like a wild and ent...

We live in a world that pushes us to simplify everything: right or wrong, good or bad, this or that. It makes things and our place in the world easier to understand. But the truth is rarely simple… in fact, it’s often messy and deeply human. For 50 years, Ken Burns has mastered his craft, becoming one of the most prolific and respected documentary filmmakers. His documentaries notably resist easy...

Naiveté is one of the most powerful assets an entrepreneur can have. In fact, I think some of the most meaningful things in the world only exist because someone was naive enough to try. Daniel Lubetzky would know. In a crowded category and cutthroat industry, Daniel dared to build a company called KIND. He started with a simple question: how can we help people snack healthily without compromising...

As businesses race toward faster systems, smarter tools, and total automation, something critical is getting lost: human connection. And ironically, the rise of AI is making that gap impossible to ignore. In this episode, I sit down with returning guest and close friend Will Guidara, former co-owner of Eleven Madison Park, to explore why humanity is becoming the ultimate competitive advantage in t...

Team Simon here! While A Bit of Optimism is on a short break, we’re revisiting a few episodes you helped make some of our favorites. We’ll be back with brand-new conversations next week, on March 24th, 2026. In the meantime, we’re bringing back an episode that explores a word most people like to avoid: death. We dance around the subject or use vague euphemisms to not hurt anybody. But what if bein...

Hello from Team Simon! We’re taking a short hiatus, but A Bit of Optimism will return with brand-new episodes March 24th. In the meantime, we’re revisiting some of our favorite episodes. Episodes that many of you who listened, shared them, and told us what resonated. This week, we’re bringing back Simon’s conversation with journalist, author, and longtime friend Maria Shriver. Maria Shriver was bo...

Team Simon here! As we take a short hiatus, A Bit of Optimism will return with brand-new episodes on March 24, 2026. Until then, we’re revisiting some of the conversations you loved and we still think about long after the microphones turned off. This week, we’re rewinding to Simon’s conversation with the wildly creative and endlessly curious Jacob Collier. To create something truly original, do we...

Scott Galloway and I don’t always see the world the same way, but our friendly debates almost always lead us back to common ground. It’s probably why we enjoy talking to each other as much as we do. If you haven’t heard my friend Scott’s name before, he’s known for being brilliant, provocative, and unapologetically himself. He’s a professor at NYU Stern School of Business, entrepreneur, bestsellin...

It’s often true that the most challenging conversations are often the ones most worth having. Conversations that bring up strong feelings, different experiences, and questions without easy answers. Policing, and how we can make it better, is one of those conversations. San Leandro Police Chief Angela Averiett has spent nearly three decades in law enforcement, navigating the profession’s challenges...

Fanbases are some of the most powerful forces on the planet. They show up. They buy the tickets. They travel across countries and time zones. They memorize lyrics, study interviews, hunt for Easter eggs, and turn the smallest detail into an entire universe of meaning. They collaborate, they organize, and they care deeply. Fan communities are savvy. They are smart. And when they are invited in, the...

We’re often told that the secret to success is grit - more discipline, more perseverance, more individual effort. And grit does matter. But what if it’s only half the story? In today’s world, we’ve become experts at tracking achievement, yet novices at nurturing belonging - and the cost of that imbalance is showing up everywhere from burnout to loneliness. Few people are better equipped to help me...

In a world defined by constant change, reinvention isn’t optional - it’s essential. We often assume reinvention comes from bold leaps or lucky breaks, but actor and author Matthew McConaughey’s story suggests a quieter approach can be far more powerful. In this episode, Matthew joins me to explore the inner practices that have shaped both his life and his legendary career in Hollywood. From steppi...

Hello from Team Simon! We’ll be back next week—January 27, 2026—with brand-new episodes of A Bit of Optimism. We’re excited to bring you new guests, conversations, and opportunities to learn. Until then, we’re diving back into the archives to revisit one of our favorite episodes from 2024, when comedian Trevor Noah joined the show… to get as serious as possible. Most Americans know Trevor as the f...

Team Simon here! We’re revisiting some of our favorite episodes from 2025. But we'll be back in just two weeks with brand-new episodes of A Bit of Optimism on January 27, 2026. We think you’re going to love them! Today, we’re going back to January of last year when Dr. Becky Kennedy joined us to discuss the hardest job in the world—parenting. It turns out, it’s also one of the best training ground...

Happy New Year from Team Simon! We’re so excited to bring you more new episodes of A Bit of Optimism when we return on January 27, 2026. With your support, we’ll make 2026 an incredible year together. In the meantime, we’re revisiting some of our favorite episodes from last year. We kicked off 2025 with a guest most podcast enthusiasts probably have heard of—Mel Robbins. This insightful conversati...

Team Simon is revisiting some of the episodes you helped make our favorites of the year until A Bit of Optimism returns on January 27, 2026, with brand-new episodes. We’re rewinding back to August, when talented polymath Elle Cordova joined the show and unpacked how we’re all wired to chase the next spark. We scroll, swipe, refresh, and repeat—but some of our brightest ideas sneak in when we stop...

Team Simon here! Thank you for being part of such an incredible year—and for helping us grow the podcast through your support, sharing it with others, and showing up week after week. We love seeing your comments and hearing what resonates with you. A Bit of Optimism returns on January 27, 2026, with brand-new episodes we think you’re really going to enjoy. Until then, we’re revisiting a few of our...

Team Simon here! As the year comes to a close, A Bit of Optimism is pressing pause for a short winter break. The show will return on January 27, 2026 and we can’t wait to be back with you. But before we go, we want to say thank you. Truly. This show exists because of you—the listeners who show up every week, share episodes and clips, leave thoughtful comments, start conversations, and carry these...

Often the biggest transformations we undergo don’t arrive as lightning bolts, but as quiet shifts we’ve been preparing for all along. For John Fox, the transformation from a 25-year career in high finance to becoming a chaplain wasn’t sudden at all. It was a slow burn—shaped by loss, reflection, community, and a deep desire to live a more meaningful life. John’s successful finance career spanned d...

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 w...

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 playb...