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What Happens When You’re Naive Enough to Try with KIND Founder Daniel Lubetzky
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
AI Can Do Everything… Except This (Why Humans Still Win) With Restaurateur Will Guidara
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 re
Revisited: What Dying Teaches Us About Living with Death Doula Alua Arthur
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
Revisited: The Kennedy Family and the Search for Self with Journalist Maria Shriver
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,
Revisited: How to Turn Stress Into Creativity With Grammy-Winner Jacob Collier
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
The Confidence Conversation We Need to Have with Scott Galloway
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 na
28 Years on the Force: Chief Angela Averiett on What It Really Takes to Change Police Culture
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, i
When Pop Fandom Becomes a Force for Good with AJR’s Adam Met
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
What Grit Really Teaches Us About Happiness with Professor Angela Duckworth
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, ye
Matthew McConaughey on How to Fall Back in Love with Your Life
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 m
Revisited: Trevor Noah Makes My Brain Hurt
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
Revisited: Kids (And Employees) Know More Than You Think with Dr. Becky Kennedy
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
Revisited: The First Steps To Reducing Your Anxiety with Author Mel Robbins
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
Revisited: The Beautiful Brilliance of Boredom with Creative Polymath Elle Cordova
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
A Bit of Optimism Will Return in the New Year
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.
Revisited: Your Unhappy Brain Needs Some Assistance with Happiness Expert Mo Gawdat
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 w
Prepare for the Life You’re Meant to Live With Chaplain John Fox
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 sudde
How Losing Everything Taught Her to Help Everyone: Joan Howard’s Story
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
A Rebel With a Cause (and a Cone) with Jeni’s Ice Cream Founder Jeni Britton
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, Je
The Culture That Converts Even the Biggest Cynics with former WD-40 CEO Garry Ridge
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
Choose Your Seven Humans Wisely with author Fredrik Backman
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 se
The Smartest Way To Be Stupid with comedian Matthew Broussard
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 e
The Man Who Proved Me Right with CEO Bob Chapman and the Barry-Wehmiller Team
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 q
Rob Lowe Names Names: The Power of ‘Screw It’
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
The Future You Avoid Is Riskier Than the One You Face with LinkedIn co-founder Reid Hoffman
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
What Your Love Life Can Teach You About Work Relationships with psychotherapist Esther Perel
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
Your Instincts Know What You Want with Author Arthur Brooks
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 Harv
The Power of Doing One Thing Exceptionally Well with Gymshark Founder and CEO Ben Francis
We’re often told to do more, move faster, and chase the next big trend—but some of the most remarkable successes come from narrowing your focus, obsessing over one thing, and truly understanding the people you’re serving. Ben Francis knows
Simon Goes Nuclear with nuclear energy influencer Isabelle Boemeke
“Nuclear” might make you wince—but the real problem isn’t the energy, it’s the branding. Safe, low-carbon, and scalable, nuclear could be a climate hero—if only we told the story right. Isabelle Boemeke is on a mission to change how we thin
The Brilliance of Boredom with creative polymath Elle Cordova
We’re wired to chase the next spark - scrolling, swiping, refreshing - but some of our brightest ideas sneak in when we stop chasing, let boredom settle in and give our minds room to wander. Elle Cordova knows the power of that pause. When
