This Is... A Bit of Optimism

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

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, and told us what resonated. This week, w ...  Show more

LISTENER PROBLEM: Feeling Unfulfilled Despite Achieving My Goals In today's episode of Join Up Dots, we dive into a listener's story of achieving financial freedom, only to find themselves feeling unfulfilled. We explore why reaching the top of the mountain can sometimes leave yo ...  Show more

LISTENER PROBLEM: Feeling Unfulfilled Despite Achieving My Goals (Follow Up) In this episode of Join Up Dots, we dive into more stories of listeners from around the world who, despite achieving financial freedom, still struggle with feelings of emptiness and a lack of purpose. Fr ...  Show more

On this episode of the GaryVee Audio Experience, Im sharing a recent book signing I recently did for my new kids book Meet Me in The Middle. I share a bit of the journey of creating VeeFriends. We start with a look back at my childhood inspirations and how the 80s icons like H ...

In this special episode, I had the opportunity to speak with a group of young students about entrepreneurship, mindset, and the importance of curiosity. We talked about my early days as an entrepreneur—selling lemonade, knocking on doors, and finding what I loved. I shared how ...