How to Build Leaders from Within—Rich Ashton | Ep 2 episode artwork

EPISODE · Apr 14, 2026 · 24 MIN

How to Build Leaders from Within—Rich Ashton | Ep 2

from Class of Business · host Wisdom

If you've ever wondered how to hand over your small business without worrying it'll fall apart, this episode is for you. Serial entrepreneur and author Rich Ashton shares his journey of developing leadership talent inside his companies—including the struggles and lessons that shaped his approach. You'll pick up practical ways to create a values-driven culture, why promoting employees too soon can backfire, and how to truly train people for leadership roles. We also get into the nuts and bolts of accountability, employee empowerment, and the real differences between running a small business versus a big one. Plus, Rich walks through his process for writing and teaching the principles in his book. Don’t miss it if you want real-world insight on building teams that last.Connect With Rich AshtonWebsite: https://growingyourown.netLinkedIn: https://www.linkedin.com/in/rich-ashton-397a2b10/If Class of Business speaks to you, consider subscribing so you never miss an episode. And if you have a moment, leaving a review helps more people discover the conversations shared here. Your support truly means a lot.There's more to every story than what you hear on the episode. Join the Class of Business newsletter to receive thoughtful takeaways, episode extras, and personal notes that don't make it into the show. It's a quiet way to stay sharp between listens.Sign up here: https://classofbusiness.com/joinChapters00:00 Meet Rich Ashton—Entrepreneurial Beginnings00:42 Early Inspiration and Father’s Influence01:01 Lessons in Integrity and Customer Service01:33 Leaving to Start a Business01:58 Turning Around a Company on the Brink02:47 The Heart of Healthy Business Culture03:27 Empowering Employees for Retention04:34 Solving the Leadership Dilemma in Small Business05:11 Why Promoting Too Soon Fails06:14 Second Generation Business Challenges06:37 The Origin of “Breaking Through” Leadership Training07:08 Building Confidence in Blue Collar Leaders07:41 Accelerating Growth with Leadership Blogs08:44 Company Culture Takes Off—and a Book Is Born09:38 Turning Blogs into a Legacy Book10:37 Core Principles—Accountability and Extreme Ownership11:23 Proactivity and Intellectual Curiosity12:24 Leading Different People, Different Ways13:13 The Dangers of Promoting Unready Leaders13:47 Universal Leadership Lessons for Small Business14:47 How Owners Can Work on Their Leadership15:16 Making Culture Intentional and Actionable16:06 Connecting With Every Employee—Why It Matters17:58 Small vs. Big Business Leadership—What’s Different18:31 Managing Culture Drift in Larger Teams19:45 Small Business Means Wearing Many Hats20:33 Embracing Delegation and Letting Go21:05 The Realities of Delegating Projects22:53 “You Can’t Expect What You Don’t Inspect”23:45 Final Thoughts and Where to Connect24:27 Thanks for Listening and Next Steps

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How to Build Leaders from Within—Rich Ashton | Ep 2

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