I sat down with entrepreneur and business coach John Glon for a conversation about something I've experienced personally—and something I see happen to so many founders: the moment when hard work, grit, and determination that once built the business start becoming the very things that hold it back. John shared his journey from running a successful electrical manufacturing business to realizing that his deeper calling was helping leaders and their teams communicate, execute, and lead better. We explored what happens when founders become the person everyone depends on, why "I'll just do it myself" becomes such a dangerous habit, and how growth can eventually demand an entirely different skill set than the one that created the business in the first place. I also shared a deeply personal story about a painful decision I made with a business partner, the consequences of stepping too far away from my own company, and the years of costly mistakes that eventually helped me develop a better way forward. At the heart of this conversation is a simple question: What if the solution to your business problems isn't working harder, but learning how to lead differently? John and I unpack structure, vulnerability, curiosity, presence, accountability, and the importance of creating a business where everyone understands their role, knows the North Star, and has the freedom to do their best work. If you're a founder or leader who has built something successful but feels like the business is demanding more and more of you, this conversation may help you see your situation—and your next move—in a completely different way. Highlights (01:32) – John explains the philosophy that guides how he shows up: love, care, and compassion, and how his entrepreneurial journey led him toward helping other leaders. (02:52) – Why John walked away from a seemingly reliable and profitable business path after realizing that success wasn't filling his cup or allowing him to help enough people. (05:32) – We explore the idea of turning years of costly mistakes into a shortcut for other entrepreneurs, so they don't have to spend years learning the same lessons the hard way. (05:59) – I share a powerful storytelling lesson: how saying "I worked so hard to figure this out, and now I have the shortcut for you" can transform painful experiences into authority. (08:23) – John reveals the three things he believes make his coaching different: structure, vulnerability and curiosity, and being fully present with the people he serves. (10:34) – Why vulnerability can unlock a completely different level of trust inside an organization—and why admitting that you don't have all the answers can actually make you a stronger leader. (13:05) – The warning signs that a founder may be operating out of alignment: the business is growing too quickly, the wheels are falling off, or the owner desperately wants more time away from the business. (15:04) – We uncover a major trap for high achievers: you can't outwork every problem in your business—and you definitely can't outwork problems in your family. (17:29) – Why entrepreneurs often need someone outside themselves to help break habits, patterns, and "scar tissue" that keep them stuck in the same leadership cycle. (18:14) – John describes what becomes possible on the other side: genuine smiles, more engaged employees, higher-level work, more personal freedom, and a team that is finally rowing in the same direction. (20:02) – John tells the story of a painful decision to exit a business partnership—and how acting from shame and frustration created consequences that went far beyond the original conflict. (22:52) – A powerful lesson about the danger of using an "easy button" in business: stepping too far away can cause you to lose touch with the heart and soul of the culture you created. (24:36) – John discovers that his results-driven approach was alienating employees who had been drawn to the company because of its heart-centered culture. (26:18) – An emotional conversation with a key employee forces John to confront a difficult realization: he was no longer operating in alignment with his own values. (28:59) – John looks back on a period when his business finally felt joyful—employees were laughing, money was flowing, the team was connected, and he was able to create balance outside of work. (31:25) – I tell the story behind my own transformation, beginning with the question that stopped me in my tracks: "Why do we need to babysit you?" (34:00) – I reveal the process I developed through years of painful mistakes: creating structure, vulnerability, curiosity, and presence so leaders can bring their businesses and lives back into alignment. (35:53) – John reacts to hearing his story reflected back to him—and explains why experiencing a story can sometimes create more transformation than simply intellectualizing a problem. (37:53) – John shares why storytelling has become such a powerful leadership tool for him, and why the best speakers don't always need slides or complicated frameworks to make an impact. (38:59) – John shares his closing thoughts and where you can connect with him and learn more about his work.
