Scott Ashline: On Vulnerability as the Foundation of Success

In this episode, Pat sits down with Scott Ashline, a longtime friend and colleague. Scott grew up outside Boulder, Colorado, the son of avid mountaineers, and traces his path from a public high school and competitive soccer, to Boston College (chosen partly because his dad banned him from schools on the West Coast), to an unlikely detour: turning down a Wall Street job offer to spend a year and a half teaching finance in Belize as a Jesuit volunteer. That leap of faith, and a Jesuit theology professor who became a lifelong mentor and eventually married him and his wife, set the tone for a career built on values over outcomes.Scott shares how he stumbled into financial services almost by accident, choosing a smaller, more values-aligned firm over a flashier one, and how 34 years later he's built a team of 15 while raising two daughters now thriving in New York City's fashion and media industries. The conversation turns into a wide-ranging discussion about what actually drives long-term success: detaching from outcomes, leading with service rather than self-interest, and the vulnerability required to build real trust with clients. Pat and Scott trade notes on mentors, books, and philosophies that shaped how they think... from Stephen Covey to Herb Cohen to Steven Pressfield...and reflect on comparison, contentment, and what it really means to retire from work you love.