Money Stories

Most entrepreneurs track every dollar in and out. Very few stop to ask what the money is actually for. Hunter Terpenny grew up on 40 acres in rural Virginia, watching his dad quietly save for years to pay for college, in a household where you earned what you got and nobody handed you anything. 2008 wiped it out almost overnight. That moment stuck with him and shaped the path that followed, including walking away from a funded startup and spending three years living out of his truck with a climbi

Most entrepreneurs are good at making money. Far fewer are good at keeping it, or knowing what it's actually for. Keith Roberts spent 24 years building Zen Man, a creative agency that grew into a machine that nearly broke him. He traded his time for money, weathered lawsuits, hid foreclosure notices from his employees, and hit rock bottom before finding his way out. In this conversation, Keith shares the full arc from starving artist to agency founder to author and speaker, and the lessons that

Many entrepreneurs achieve success only to realize they are further away from freedom than when they started. Niraj Shah has spent his career building businesses and working closely with entrepreneurs navigating success. Over time, he began to see a common pattern: the pursuit of achievement can quietly pull people away from the life they hoped success would create. In this conversation, Niraj shares how early lessons shaped his thinking about ownership, entrepreneurship, and building wealth tha

Chris Girbés has built a life rooted in intention, family, and meaningful work, yet his journey with money has been anything but simple. In this episode, Chris and I reflect on how success and fulfillment are shaped not just by what we build, but by how we relate to it. We explore why financial growth does not create a sense of enough and how old money stories continue to drive high performers. Chris also shares what it looks like to redefine wealth around values, family, and lived experience. W

Step inside The Inner Circle, where Kevin Dahlstrom and I speak freely and honestly without judgment, challenging each other in pursuit of truth. A single question frames this conversation: What’s the most painful truth you’ve had to accept about yourself? Drawing from different stages of life, Kevin and I share the kinds of realizations that only come with time and self examination. The discussion is honest and raw, with their perspectives converging around growth and self awareness. We explore

Jon Bowerman built and sold a multimillion-dollar agency before realizing that success on paper doesn’t guarantee fulfillment. His story is about rediscovering the artist within and finding that true wealth comes from alignment, not accumulation. Jon shares how growing up with scarcity shaped his drive for success and what it took to walk away from security for a life of greater authenticity and purpose. He reveals how embracing vulnerability helped him reconnect with creativity, joy, and meanin