A Bit of Optimism

A Bit of Optimism

My career is an accident. It started when I set out to rediscover my passion and reignite a spark I’d lost — and that journey led me to the work I do now. If you know me from my books or my speaking, you know I’m fascinated by why people do what they do. What makes someone find joy and meaning in their life, or pursue something far greater than themselves? I started A Bit of Optimism to explore those ideas and expand my own perspective. This podcast is a trove of honest conversations, with people who challenge me, teach me, or simply help me see things in a different way. Some guests are household names, and others you may be meeting for the first time. But each one of them has something to share that can help all of us grow. So if you’re looking for a spark — some insight, inspiration, or just a reminder that good things are possible — join me on A Bit of Optimism! Let’s grow together.

Episodes

Stop Telling Us Everything Happens for a Reason with Anti-Victim Tom Nash

May 12, 2026 • 62 mins
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 behind Last Meal with Tom Nash wh...
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The Real Reason You Feel Empty (Even When Life Looks Good) with Musician Mike Posner

May 5, 2026 • 52 mins
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 heard on this show. Mike wal...
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The Real Reason Young People Don't Have 'The Hunger' for Work (And What Leaders Need to Hear) with Generations Expert Dr. Eliza Filby

April 28, 2026 • 85 mins
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 bestseller: Inheritocracy. And wi...
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The Leadership Advice Nobody Follows (But Everyone Should) with Top Leadership Expert Don Yaeger

April 21, 2026 • 54 mins
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 Times bestsellers, and a former Ass...
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Why This Baseball Team Has a 4.2 Million Person Waitlist With Savannah Bananas Founder Jesse Cole

April 14, 2026 • 65 mins
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 entertaining version of baseball. But...
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Ken Burns and the Art of Telling the Whole Story

April 7, 2026 • 54 mins
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 answers. From The Civil War to The ...
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What Happens When You’re Naive Enough to Try with KIND Founder Daniel Lubetzky

March 31, 2026 • 54 mins
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 their values? KIND Bars are now a h...
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AI Can Do Everything… Except This (Why Humans Still Win) With Restaurateur Will Guidara

March 24, 2026 • 65 mins
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 the age of AI. Will helped transform...
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Revisited: What Dying Teaches Us About Living with Death Doula Alua Arthur

March 17, 2026 • 45 mins
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 being open about our deaths meant we co...
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Revisited: The Kennedy Family and the Search for Self with Journalist Maria Shriver

March 10, 2026 • 43 mins
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 born into the legendary Kennedy and S...
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Revisited: How to Turn Stress Into Creativity With Grammy-Winner Jacob Collier

March 3, 2026 • 58 mins
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 build something new or break what ...
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The Confidence Conversation We Need to Have with Scott Galloway

February 24, 2026 • 54 mins
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, bestselling author, and larger-than-life soci...
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28 Years on the Force: Chief Angela Averiett on What It Really Takes to Change Police Culture

February 16, 2026 • 65 mins
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 while advocating for a healthier p...
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When Pop Fandom Becomes a Force for Good with AJR’s Adam Met

February 10, 2026 • 61 mins
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, they create extraordinary momentum. Ad...
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What Grit Really Teaches Us About Happiness with Professor Angela Duckworth

February 3, 2026 • 56 mins
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 make sense of that tension than to...
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Matthew McConaughey on How to Fall Back in Love with Your Life

January 27, 2026 • 59 mins
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 stepping away from romantic comedies at t...
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Revisited: Trevor Noah Makes My Brain Hurt

January 20, 2026 • 56 mins
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 former host of The Daily Show, a bes...
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Revisited: Kids (And Employees) Know More Than You Think with Dr. Becky Kennedy

January 13, 2026 • 43 mins
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 grounds for leadership. Dr. Becky Kennedy...
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Revisited: The First Steps To Reducing Your Anxiety with Author Mel Robbins

January 6, 2026 • 57 mins
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 conversation answers an important question: h...
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Revisited: The Beautiful Brilliance of Boredom with Creative Polymath Elle Cordova

December 30, 2025 • 63 mins
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 chasing, let boredom settle in, and...
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