You Are More Like Grammy-Winner Jacob Collier...

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 Guid ...  Show more

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 mos ...  Show more

Today we have part two of Bruce Headlam’s conversation with YouTube sensation turned five-time Grammy winner Jacob Collier. We left off our last episode with Jacob talking about what it’s like to perform to an audience of thousands of people after spending years growing his fan b ...  Show more

Stevie Wonder may be our modern day Mozart. A child prodigy, he joined Motown as a preadolescent where he was marketed as “Little” Stevie Wonder. He wowed audiences with his virtuosic command of the piano, harmonica, drums and of course, vocals. At just 13, he had his first numbe ...  Show more

A sweet and searching conversation between Krista and the man behind Bon Iver at this year's On Air Fest, full of wisdom and revelation. He is a person who experiences deeply, who metabolizes creatively, and who just keeps growing. He opens up with Krista about the strangeness of ...  Show more

Whether you're a fan of Taylor Swift or not, no one can deny her success as both a music star and businesswoman. Her career has been a masterclass in everything from customer connection to innovation, decision-making to digital adaption, offering lessons for people in any industr ...  Show more