In this episode of The Grit Mindset, Matt Rosen takes us back to 2002, when the tech bubble burst and he traded IT sales for bar ownership in Dallas’ Lower Greenville. He shares the wild ride of opening Dirty Daves—from build-out headaches, parking problems, and too many free drinks… to debt before opening day, missing daiquiri machines, and hiring the DJ as manager.

Matt gets real about the mistakes, the lessons learned, and how those early challenges shaped his move into consulting. Along the way, he reflects on working with his brother, why personal guarantees can be risky, and the dos and don’ts of going into business with friends. It’s an honest, entertaining, and educational look at grit, risk, and finding the silver lining when things don’t go as planned.