When Jeff was fired from radio in 2019, married couple Callie and Jeff launched "The Upside" podcast, which hit #6 on Apple's charts within a week and sold out ad inventory 15 months in advance. The success was lightning in a bottle, but when COVID hit and they were together constantly, creating content became exhausting. Callie negotiated her departure from CNN to join full-time, and they've since pivoted to helping entrepreneurs tell their stories through podcasting. They candidly discuss the fear of both partners relying on the same income stream, the importance of defining roles, and why Jeff's philosophy of dealing with minor annoyances immediately has saved their marriage and business partnership.

Contractor Adrian Williams rebuilt his construction business from scratch after relocating from California to Atlanta with nothing but a beat-up truck, a trailer of tools, and a family of five to support. Having burned through his savings attempting to settle in Chattanooga first, Adrian landed in Atlanta financially desperate but determined. Now leading a team of 18, he shares his unique sales philosophy: looking for red flags to turn jobs down rather than desperately chasing every lead. Adrian discusses the anxiety of being sole breadwinner, his wife's unwavering belief in him, why he invested $700 monthly in construction software when they could barely pay rent, and how self-trust became his compass through the scariest rebuilding phase of his career.

Lace Larrabee, comedian and founder of Laugh Lab comedy school, shares her journey from bartender to Atlanta's leading comedy educator. After a regular customer literally put her on a show poster with three months to prepare, Lace's first stand-up performance at 28 changed everything. Now, 14 years later, she tours as a headlining comedian (including America's Got Talent) while running Laugh Lab, which has taught hundreds of women to find their voice on stage. Lace opens up about her biggest fear: fully committing to scaling her business online and potentially failing. She discusses how divorce became a "new lease on life," navigating a new relationship while building her empire, and why rising tides raise all ships in comedy and business.

Meet your host Jessie! Learn about how she decided to start her own business and this podcast!