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A Bit of Optimism

A Bit of Optimism

By: Simon Sinek
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 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. Career Success Economics Personal Development Personal Success
Episodes
  • The Real Reason Young People Don't Have 'The Hunger' for Work (And What Leaders Need to Hear) with Generations Expert Dr. Eliza Filby

    The Real Reason Young People Don't Have 'The Hunger' for Work (And What Leaders Need to Hear) with Generations Expert Dr. Eliza Filby
    Apr 28 2026
    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 with more generations in the workplace than at any point in history, she is precisely the person we need to show us a new way to win… together. In this conversation, Eliza makes connections about how generational change is reshaping work, wealth, and modern life that I’d never thought to connect. She might just change how you see the world (and people) around you. In this episode you'll learn: ➡️ Why calling Gen Z "entitled" is the wrong diagnosis (and what's really driving the behavior leaders complain about most) ➡️ How retirement planning and eldercare became the new midlife crisis ➡️ How the economy changed after 2008 + quietly rewrote the rulebook for every generation that followed ➡️ Why belonging is becoming increasingly rare (even though we need it) ➡️ Why Millennials + Gen Z are more likely become homeowners by being loyal to their parents than by being loyal to their jobs ➡️ 3 things no AI will replace in the workplace… ➡️ What’s driving hyper-individualism + how do we fix it We all may have strong opinions about one another, but it’s time to focus on building greater understanding. This conversation is a good place to start. This… is A Bit of Optimism. + + + To buy a copy of Dr. Eliza Filby’s bestselling book Inheritocracy: It’s Time to Talk About the Bank of Mum and Dad, head to: https://www.elizafilby.com/books Want to hear more from Eliza? Check out her It’s All Relative Newsletter: https://www.elizafilby.com/newsletter + + + Chapters 00:00:00 Rethinking the Generational Divide at Work 00:01:35 How Dr. Filby Became a Generations Expert 00:04:33 Defining Generations: Why They're Getting Shorter 00:08:42 The Fragmentation of Shared Experience 00:14:29 Conspiracy Culture Infiltrates the Workplace 00:16:16 The End of Job Security and the Rise of the Solopreneur 00:18:02 What Leaders Must Offer in the Age of Uncertainty 00:20:31 The Bank of Mom and Dad: Living in an Inheritocracy 00:28:23 Why Young People Don't Have 'The Hunger' for Work 00:31:35 The Changing Life Cycle: Delayed Adulthood and Pressured Midlife 00:41:45 Rising Individualism and the Loss of 'We' at Work 00:47:02 Gen AI: The Next Generation in the Workplace 00:50:44 The Solution: Let Humans Do What Can't Be Counted 01:00:42 Disrupting the Path to Mastery and Nurturing Human Skills 01:03:02 How the Generations Can Come Together + + + Simon is an unshakable optimist. He believes in a bright future and our ability to build it together. Described as “a visionary thinker with a rare intellect,” Simon has devoted his professional life to help advance a vision of the world that does not yet exist; a world in which the vast majority of people wake up every single morning inspired, feel safe wherever they are and end the day fulfilled by the work that they do. Simon is the author of multiple best-selling books including Start With Why, Leaders Eat Last, Together is Better, and The Infinite Game. + + + Website: http://simonsinek.com/ Live Online Classes: https://simonsinek.com/classes/ Podcast: http://apple.co/simonsinek Instagram: https://instagram.com/simonsinek/ Linkedin: https://linkedin.com/in/simonsinek/ Twitter: https://twitter.com/simonsinek Facebook: https://www.facebook.com/simonsinek
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    1 hr and 25 mins
  • The Leadership Advice Nobody Follows (But Everyone Should) with Top Leadership Expert Don Yaeger

    The Leadership Advice Nobody Follows (But Everyone Should) with Top Leadership Expert Don Yaeger
    Apr 21 2026
    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 Associate Editor at Sports Illustrated. Don has worked alongside the greatest athletes of our generation: Michael Jordan, Serena Williams, Michael Phelps. But no relationship shaped him more than the 12 years he spent as Coach Wooden's mentee. Whether or not you're a sports fan, I promise you: the lessons Don shares are as universal as it gets. We explore what it really means to win in business and in life. The greatest leaders in history already figured this out. The question is why the rest of us aren't following their lead. In this episode you'll learn: ➡️ Why the winningest coach in college basketball history never talked about winning (and what he focused on instead) ➡️ The Bill Walton story that reveals how great leaders hold standards without exceptions (even for their best people) ➡️ How one conversation with John Wooden transformed Don's marriage & the weekly habit he's kept for 16+ years ➡️ What Delta CEO Ed Bastian's "virtuous cycle" can teach any leader about putting people before results ➡️ What a great mentor actually look like and how to know when you’ve found one If you've ever chased the short-term win at the cost of the long game… this episode is the reset you didn't know you needed. This… is A Bit of Optimism. + + + If you want to read a free chapter from Don's upcoming book The Business of Storytelling, head to: https://www.donyaeger.com/chapter/ Join the Leaderful app! Listeners can use promo code: STORY30 when you download the app or sign up at simonsinek.com. + + + Chapters Chapters 00:00:00 The Power of Appreciation: What You Look For, You Find 00:02:02 From Delivering Newspapers to Sports Illustrated: Don's Journey to Journalism 00:04:21 Don’s 12-Year Mentorship with Coach John Wooden 00:06:50 Coach Wooden's Philosophy: Pyramid of Success 00:09:00 The Bill Walton Haircut Story: How Wooden Managed Ego and Held Everyone to the Same Standards 00:10:33 Building Better Humans, Not Just Better Players 00:14:36 The Love Letters That Changed Don's Marriage 00:19:35 Looking for Things to Love: The Mindset That Changes Everything 00:22:23 Leading with Employee Care Over Customer-First Mentality 00:33:55 What True Mentorship Really Means: It's Not Transactional 00:47:07 Why Aren't More Leaders Following Coach Wooden's Example? 00:53:17 The Best Storytelling Advice: Know Your Audience + + + Simon is an unshakable optimist. He believes in a bright future and our ability to build it together. Described as “a visionary thinker with a rare intellect,” Simon has devoted his professional life to help advance a vision of the world that does not yet exist; a world in which the vast majority of people wake up every single morning inspired, feel safe wherever they are and end the day fulfilled by the work that they do. Simon is the author of multiple best-selling books including Start With Why, Leaders Eat Last, Together is Better, and The Infinite Game. + + + Website: http://simonsinek.com/ Live Online Classes: https://simonsinek.com/classes/ Podcast: http://apple.co/simonsinek Instagram: https://instagram.com/simonsinek/ Linkedin: https://linkedin.com/in/simonsinek/ Twitter: https://twitter.com/simonsinek Facebook: https://www.facebook.com/simonsinek + + + Photo/Video credits for this episode: https://tinyurl.com/ycxdw52s
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    55 mins
  • Why This Baseball Team Has a 4.2 Million Person Waitlist With Savannah Bananas Founder Jesse Cole

    Why This Baseball Team Has a 4.2 Million Person Waitlist With Savannah Bananas Founder Jesse Cole
    Apr 14 2026
    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 with the fan experience. Jesse calls his approach Fans First and it’s more than a slogan and the title of his book… It’s a standard. Every minute of the two-hour games are crammed with attention grabbing spectacle. It’s a full-blown live experience designed for every seat in the stadium: players dance, fans are part of the show, trick plays defy the laws of physics, there are multiple sing-alongs… all during an actual baseball game. In this conversation, we talk about building something new for others, from embracing years of failure (including selling just two tickets in the first three months), to creating experiences that make people feel included, joyful, and valued. We also discuss how he took inspiration from Disney and PT Barnum, the importance of affordable in-person experiences, and how his team reviews every single detail after every show to get better the next day. Because what Jesse’s building goes beyond just entertainment. It’s a place where people can feel seen for generations to come. And in a world that often moves too fast to build things with care… Those human details might be what matter most. This… is A Bit of Optimism. --------------------------- To learn more about the Banana Ball League or sign up for the ticket waitlist, check out: https://bananaball.com/ Or if you want all things Savannah Bananas, head to: https://thesavannahbananas.com/ ---------------------------
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    1 hr and 6 mins
All stars
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I find Simon so inspirational to listen to - no matter how many times I hear the same lectures/ted talks I love his optimism, consistency in his approach to inspiring in leadership.

So lovely to hear him chatting to other such amazingly successful people.

Love Simon Sinek

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Great consistency of storeys giving positive actions we can all use in most parts of our lives.

Inspiring positive actions.

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Simon Sinek’s critical thinking and ability to extract the story, shines through every episode. Excellent content every time.

Simon Sinek is not the star, he makes sure every guest is!

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This is the best podcast for people that are looking deeper into their life and purpose,

The best podcast

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Every week, Simon talk to a different person about something that is thought provoking, and gives you a lot to reflect on, no matter what your background is..

always thought provoking subjects

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