Chuck Cahn never planned to join the family business. A pharmaceutical job fell through the week he graduated from Rutgers, his mother told him to go work for his father, and he figured he would stay a few months. He stayed decades. In that time he turned a small office supply company into Stewart Business Systems, a 120-person digital imaging and document management operation doing $85 million a year, with more than 500 of New Jersey's 685 school districts under contract. He sold it for $50 million to Global Imaging Systems, which Xerox later acquired, timing the exit almost perfectly ahead of the 2008 crash.

Then came the part nobody saw coming. In 2012, Chuck became mayor of Cherry Hill, New Jersey, a town of 85,000 people, and took the job for a dollar a year so he would never feel beholden to anyone. He tells Bill Green what it actually takes to run a municipality like a business, from discovering that government accounting looks nothing like QuickBooks to spending two years visiting a different neighborhood every single month. He walks through the quiet win almost no resident noticed, a mall reassessment that brought the county's biggest taxpayer to full value, and the very public one, a land swap that saved Woodcrest Country Club from becoming 600 single-family homes and preserved 180 acres in perpetuity.

Along the way there is wine and one very good story about a king. Chuck and Bill taste through three Saddlehill bottles, including the first Chardonnay ever grown and produced in Voorhees, and Chuck recounts the blind tasting at his own dinner table where Saddlehill beat a very expensive Italian bottle in front of fourteen people. He also explains how his home landed on a Homeland Security shortlist as a possible meeting place for the Pope and the King of Jordan, and what happened when only one of them turned up. The episode closes with a Lightning Round on the one trait every entrepreneur needs, the toughest room he has ever had to work, and where he would put $10,000 today if he were starting over.