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.
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In a world of job-hopping, side hustles, and an endless LinkedIn feed, Tim Harris did something almost no one does anymore. He stayed put. Few executives spend an entire career helping build a dynasty. Tim Harris spent 35 years with the Los Angeles Lakers, rising to President of Business Operations and helping transform the franchise into a global brand. Through championship eras, iconic athletes like Kobe Bryant and LeBron James, and decades of change in professional sports, Tim's influence was...
Hello from Team Simon! We're taking a quick break this week and will be back with brand-new episodes of A Bit of Optimism next Tuesday. Until then, we're revisiting one of our favorite episodes — when bestselling novelist Fredrik Backman joined the show to talk about the thing he's spent his whole career writing about: the quiet, radical power of showing up for people. And Fredrik says great friendships aren't found by luck. They're built deliberately, repeatedly, and, sometimes, inconveniently ...
Vanessa Van Edwards, a behavioral scientist, shares her journey from self-proclaimed awkwardness to decoding human interaction. She argues that social skills are learnable, not innate, and provides actionable strategies for navigating social situations, from networking events to personal conversations. The discussion highlights the critical need for intentional social practice, the power of authenticity, and how helping others feel comfortable is the ultimate antidote to one's own awkwardness, leading to deeper connections and career growth.
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 where he asks his guests what their last meal would be if the world en...
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 walked across America, survived a rattlesnake bite, climbed Everest, and c...
Dr. Eliza Filby discusses how generational differences, economic shifts, and the rise of AI are profoundly reshaping work, wealth, and modern life. She explores the erosion of job security, the rise of solopreneurship, and the impact of the “Bank of Mum and Dad” on young people's work perspectives. The episode emphasizes that leaders must offer belonging and purpose, advocating for nurturing unquantifiable human skills like care, collective wisdom, and clear communication in the age of AI to foster a more connected and stable workplace.
Leadership expert Don Yaeger discusses profound lessons from his 12-year mentorship with legendary coach John Wooden, emphasizing Wooden's focus on building character and relationships over winning. He shares powerful anecdotes, including Wooden's universal standards and the practice of love letters that transformed Yaeger's marriage, and highlights modern applications from Delta CEO Ed Bastian's employee-first model. The episode also explores the reciprocal nature of true mentorship and why many leaders still struggle to adopt these proven, people-centric strategies for enduring success.
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 underneath it all is something much more disciplined: an obsession...
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 Vietnam War to Baseball , Ken has shaped how we understand Americ...
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 household name and Daniel achieved his dream of building the cultu...
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 a restaurant into the best in the world, not by reinventing the ...
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 could live happier lives? That’s where Alua Arthur comes in. Alua i...
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 Shriver families, arriving with a script already written for her—a...
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 came before? Perhaps the answer is both—simultaneously. Jacob Col...
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 social commentator. In recent years, his work, which includes his new...
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 path forward. I met Angela through The Curve, my organization focu...
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. Adam Met, best known as the “A” of indie-pop band AJR, believes tha...
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 today’s guest, Angela Duckworth. Angela is a professor of psycholog...
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 the height of his success to sitting with uncertainty when there w...
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 bestselling author, and a stand-up comedian. But his brand of humor ...
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, aka the “Millennial Parent Whisperer,” became an essential voic...
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: how do we push through the days where life can feel overwhelming? ...
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 give our minds room to wander. Elle knows the power of that paus...
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 ideas into your own lives and workplaces. Your support, curiosity, and generosity are what give this...
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 favorite moments from the past year. We’re kicking things off with one of our most popular episodes...
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 decades. To the world, he was thriving, but internally he yearned for fulfillment no paycheck could g...
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 ...
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 ...
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 ...
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 bei...
