Story of a Successful Generational Change: What Business Owners Really Need | Ideas by Mike™ EP61

Third-generation family businesses often hit a 10% wall that threatens their legacy. Learn why this failure rate happens. In this episode of the Ideas by Mike™ Podcast, Mike Milligan, CFP sits down with Jason Shupp, and he breaks down the common pitfalls facing family-owned enterprises as they transition through generations. Many companies struggle to maintain momentum when leadership passes to the third generation, often due to a lack of clear succession planning or evolving market conditions. Episode Chapters: 0:00 - 4:45 Introduction and the 10% Problem 4:45 - 10:15 Jason Shupp's Personal Path 10:15 - 16:30 Navigating Generational Transition 16:30 - 23:15 The Power of Advisory Boards 23:15 - 28:45 Preserving Legacy and Values 28:45 - 33:05 Communication and Empathy Jason also shares how his family’s St. Louis roofing company navigated generational change—and what business owners can learn from its story. Jason reflects on his grandfather’s beginnings, his father’s role in growing the company, and his own unexpected return to the family business after years away. This episode provides actionable insights for business owners concerned about long-term wealth preservation. By addressing the specific financial planning challenges inherent in multi-generational firms, you can protect your assets and ensure the organization remains sustainable for the future. Subscribe for weekly financial strategy breakdowns, and comment below with your biggest concern regarding multi-generational business management. In this episode, you’ll hear about: Why third-generation family businesses face a difficult path to survival. How work ethic and professional guidance can support a successful transition. What it means to preserve a family business’s values and brand. How an advisory board helps owners gain perspective and plan for the long term. Why a trusted board can reduce uncertainty and build confidence in business decisions. How curiosity and listening can deepen empathy and understanding. About our Guest: Jason Shupp Connect with him on LinkedIn -   / jason-shupp-18b4619b   Weblink of BoardEase Advisors: https://www.boardeaseadvisors.com/ Jason is a podcast host, speaker, and empathic collaborator. Before joining his family’s business, he worked in a range of roles, including as an EMT, whitewater raft guide, snowmobile tour guide, martial arts instructor, and high-works rigger. After nearly two decades helping lead a legacy business, he now brings his experience to advisory work and creative projects. He also hosts From There to Here, a podcast exploring the stories and experiences behind people’s paths. This conversation is for family business owners, founders, and next-generation leaders thinking about succession, growth, and how to build a business that can last. Don’t forget to subscribe and leave a comment below! ________________________________________ More Resources: Also Get the Book "The One of a Kind Financial Plan" on Amazon: https://a.co/d/hAOPAgM Stream all past episode of Ideas by Mike™ Podcast:    • Ideas by Mike™ Podcast — with Mike Milliga...   (Ep. 60): The Hidden Medicare Surcharge That Costs Retirees Thousands | Ideas by Mike™ -    • IRMAA Explained: The Hidden Medicare Surch...   Follow our Socials for more updates: Mike Milligan, CFP® -   / mikemilligancfp   1.oak Financial Website - https://www.1oakfinancial.com/ LinkedIn Company Profile -   / 102585896   Facebook: 1.Oak Financial -   / ideasbymike   Instagram: @1oakfinancial -   / 1oakfinancial   Ideas by Mike on Spotify Podcast - https://open.spotify.com/show/4Nxq9bI... Ideas by Mike on Apple Podcast - https://podcasts.apple.com/us/podcast... Do you have any financial inquiries wanting to get answered? Leave us an email - contact@mikemilligancfp.com Or Call/Text Mike Milligan to help you out - 757-909-7151