In this panel discussion, presented at the Fourth Annual Olin Family Business Symposium at Olin Business School at Washington University in St. Louis in October 2018, Tugboat Institute members Alaina Macia and Penny Pennington offer insight into their companies’ approaches to ownership and leadership through the Evergreen lens. Alaina offers the perspective of assuming leadership in and growing her family business, MTM Inc., while Penny, Managing Partner of Edward Jones Financial, shares insights around leading a nearly-100-year-old firm. These inspiring Evergreen leaders speak to what it takes to steward strategic ownership and thrive in the long term.