Bill Green spent 23 years at Merck before turning 50 and going all in on his own consulting practice. Then COVID hit, the phone stopped ringing, and he spent the better part of three years wondering if he was really an entrepreneur or just pretending to be one. In this conversation he unpacks what finally broke the stall, why leading with values isn't woo woo, and what he means when he tells other founders to burn the boat.

Kenny Pointer once sat in a hotel lobby wearing a sweatsuit while a group of people a few feet away rehearsed how they would greet him. He was the person they were there to impress, and they never recognized him. As Chief Services Officer at Mariner, Kenny has spent a career watching the way people shift when they find out his title, and he has made a point of not shifting back. That thread, being the same human in every room, runs through his conversation with Sam Sapp.

Kevin Kwok named his digital marketing agency J29 Creative after Jeremiah 29:11, a verse his family leaned on through immigration, loss, and starting over. Airing the day after Christmas, this conversation with Sam Sapp moves through Kevin's arrival from Hong Kong at age six, a software engineering degree he picked up during the dot com era, a Cajun restaurant bar he closed after his father died of cancer, a bankruptcy he filed in his early twenties, and the long climb back that eventually put him at the front of a marketing agency.

Lindsay Howerton calls herself a scalpel. Some operators are machetes. Some fall somewhere in the middle. She's the one you hand a stalled business to when sales can't keep up with operations, or operations can't keep up with sales, or the leader just knows something is off and can't name it. In this conversation she walks through how she learned to read people and process early, why she almost didn't want to be tied to her Missouri hometown, and how she and her husband now buy and rehab blighted houses there on purpose.

About ten years ago, four women in Kara Viatori's family sat down and chose a new last name together. They went looking for something that meant more, and landed on a Latin word for traveler. Kara carries that name now as Director of Information Technology at MOCSA, a Kansas City nonprofit countering sexual violence, and the story is the doorway into a conversation about social engineering, burnout, and why curiosity is the real IT skill.

Krista Shelton will tell you that only an accountant could catch Al Capone, and she can quote the poster that still hangs in IRS offices to prove it. She spent 13 and a half years at the IRS, three and a half as a revenue agent auditing small businesses and the next ten as a federal special agent carrying a gun, kicking in doors, and working drug conspiracies next to the DEA. She now runs Focus Forensic Solutions from a sixth-generation family farm in Maryville, Missouri, and she's convinced that most fraud isn't clever. It's just unwatched.