Why This Baseball Team Has a 4.2 Million Person Waitlist With Savannah Bananas Founder Jesse Cole
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 th...
14 Apr 1h 5min
Ken Burns and the Art of Telling the Whole Story
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...
7 Apr 54min
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 Lubetzk...
31 Mar 54min
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 ign...
24 Mar 1h 5min
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...
17 Mar 45min
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...
10 Mar 43min
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...
3 Mar 58min
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. I...
24 Feb 54min
