Hassan Diarra is a two-time NCAA national champion. He began his college career at Texas A&M before transferring to UConn. Known for his relentless defense and clutch play off the bench, Diarra evolved into the Huskies’ go-to sixth man during the 2023–24 season, earning Sixth Man of the Year honors. Today, Hassan sits down with David to talk about his success at UConn and what is next for him in the game of basketball.

Matt Garrett is a global macro strategist and investment advisor with extensive experience in forecasting market trends, managing risk, and developing multidisciplinary research frameworks.His background includes roles as a portfolio manager, trader, and credit analyst. Gerard MacDonell serves as Chief Economist at Front Harbor LLC and is a commentator on monetary and macroeconomic policy. Today they sit down with David and talk about how experience helps in markets, how aging messes with your edge, why relying too much on history can backfire, and the constant fear that maybe you're just faking it.

Gwendolyn Woods, a former A&R executive at Bad Boy Entertainment who worked with icons like Sean “Diddy” Combs and Biggie Smalls, reinvented herself as a food entrepreneur by co-founding The Crabby Shack in Brooklyn with Fifi Bell-Clanton. After two decades in the music industry, Woods channeled her creative energy and business savvy into launching the seafood spot with no prior restaurant experience. Through crowdfunding and a shared passion for crab, she helped turn The Crabby Shack into a thriving, Black-owned business recognized by major outlets and featured in the Netflix documentary She Did That, highlighting her inspiring entrepreneurial journey. Today she sits down with David to talk about her entrepreneurship and what she took with her from Bad Boy Entertainment.