The Man Who Proved Me Right with CEO Bob Chap...

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 listen ...  Show more

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 Jan ...  Show more

In this powerful Saturday Mashup, we tackle one of the most common struggles—burnout. This episode brings together an incredible lineup of guests, including Sebastian Maniscalco, Rob Dyrdek, Alan Stein Jr., Inky Johnson, and more. Together, we dive deep into the symptoms of burno ...  Show more

In this high-energy episode, Sean Whalen joins me to deliver an unfiltered deep dive into success, failure, and the mindset needed to win in business, fitness, and life. We discuss the dangers of ego-driven decisions, the power of taking massive risks, and why ...

In this episode, we dive deep into the journey of Keven Undergaro, the visionary founder of After Buzz TV, and explore the intersections of failure, success, and the courage to pursue one's dreams against all odds. 

From facing the fear of failure head-on to pioneer ...

Ryan Holiday unpacks the subtle and not-so-subtle messages life sends us—and what happens when we ignore them. From mismatched tattoos and injured ankles, Ryan reflects on the lessons he’s learned about preparation, awareness, and humility. Using examples ranging from personal mi ...  Show more