Story of a Successful Generational Change: What Business Owners Really Need | Ideas by Mike™ EP61
Why do so few family businesses make it to the third generation? In this episode of the Ideas by Mike™ Podcast, Mike Milligan, CFP sits down with Jason Shupp, and he 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.
He explains the challenges third-generation leaders face as they balance changing circumstances with the values and reputation built by earlier generations. Together, Mike and Jason explore the practices that helped the business endure: a strong work ethic, professional advisors, and a commitment to stewardship. Jason also explains how advisory boards can help business owners step back from day-to-day operations, think strategically, and find a trusted sounding board for important decisions.
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
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!
Do you have any financial inquiries wanting to get answered?
Leave us an email – contact@mikemilligancfp.com
Call/Text Mike Milligan to help you out – 757-909-7151
Visit our website at: www.1oakfinancial.com
Read our blogs to learn more insights: 1.oak Financial Blogs page
Episode 61 of Ideas by Mike™ with Jason Shupp is also available on YouTube!
Podcast: Play in new window | Download | Embed
