What can leaders and business owners learn from moonshiners? More than you might think.

Jon Umstead has spent more than 30 years leading teams and organizations, from startups to Fortune 500 companies, in roles ranging from COO and CMO to transformation leader. In this episode, Jon and Diana reconnect after working together more than 17 years ago to talk about leadership, navigating change, entrepreneurship, and why getting things done often means keeping things simpler than we make them.

• Why reaching out and making the ask can create unexpected opportunities

• Building a career around curiosity, variety, and knowing yourself

• What leading through organizational change and M&A can teach you

• Why process for the sake of process creates unnecessary complexity

• Treating people like people as a foundation for effective leadership

• Why plans need to change when reality changes

• Using volunteer and board service to build new skills

• What moonshiners and bootleggers can teach businesses about distribution and innovation

• How entrepreneurial thinking can exist inside large organizations

• Why leadership doesn’t require direct reports

⏳ Timestamps 00:00 Meet Jon Umstead and why making the ask matters 06:09 Against the Grain and Jon’s new book 07:50 From corporate executive to mobile tap business 10:51 Building a career around variety and curiosity 15:03 Lessons from organizational change and M&A 20:51 Why business problems are more alike than we think 23:08 Where leaders create unnecessary complexity 26:31 Why leadership starts with caring about people 28:59 Growing from leading small teams to large organizations 34:05 Building experience through board service 40:44 Business lessons from moonshiners 43:34 What bootleggers can teach us about distribution 49:13 Entrepreneurial thinking without starting a business 50:46 How to spot a genuinely entrepreneurial workplace 54:05 Bringing real-world leadership experience into teaching 55:24 Rethinking what leadership needs to look like 57:39 Where to find Jon and Against the Grain

💡Take Action 🔥 Subscribe for future episodes → [https://www.youtube.com/@dianaalt] 📖 Grab my Resume Don’ts Guide → https://www.dianaalt.com/resumedonts ❌ Avoid these common job search mistakes → https://www.jobsearchmistakes.com 🚪 Wondering if it’s time to walk away? → https://www.isittimetowalk.com 💼 Work with me → https://www.dianaalt.com

📢 Connect with Jon Umstead 🌐 Website → champaignshine.com🔗 LinkedIn → https://www.linkedin.com/in/jonumstead/ 📲 Follow Jon on Social Media: Facebook → https://www.facebook.com/champaignshine Instagram → https://www.instagram.com/champaignshine X → https://x.com/jonumsteadAgainst the Grain: Business Lessons From the Still by Jon Umstead → https://www.amazon.com/dp/B0H6G8VMCS

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