Some leaders build companies. Others build legacies. Charles Tate did both. From investment banking to outdoor hospitality, his story isn’t about following a formula. It’s about trusting your instincts, taking bold risks, and choosing to lead differently when the easy option would be to stay the same.

Throughout his career, Charles has shown that doing things differently isn’t just about innovation. It’s about connection. Whether navigating Wall Street or creating new kinds of businesses from the ground up, his success comes from asking better questions: What emotion is my business solving for? How does this decision actually serve people, not just numbers?

For Charles, business is deeply human. The most successful companies, he says, don’t just sell a product; they solve an emotional need. Think of FedEx restoring trust, Starbucks creating community, or Buc-ee’s redefining comfort in the most unexpected way. When you understand the emotions that drive people, you start building something that lasts.

In this episode of Rethink Change, Charles chats with Ward about what it really means to lead differently. You’ll hear how clarity, courage, and emotional connection come together to build not just great businesses but meaningful ones, as well as how to surround yourself with the right people who can take your business to the next level. When it comes to entrepreneurship, it takes a lot of grit to keep pushing through challenges. But it also takes a lot of heart to create something impactful for your ideal audience.

CHAPTERS:

00:00 – Passion, Persistence, and the Entrepreneurial Mindset

02:15 – Doing Things Differently: The Power of Bold Decisions

05:10 – Reinvention: Pivoting Toward New Opportunities

08:00 – Innovating Capital: Rethinking Private Equity Strategy

11:00 – Building Beyond Yourself: Transition and Legacy

14:00 – Strategy Through Emotion: Rethinking What Business Solves For

17:00 – FedEx, Starbucks, and Buc-ee’s: Lessons in Emotional Strategy

20:00 – Newton Nurseries: Turning Insight Into Competitive Advantage

24:00 – Time as Currency: Building Around Customer Efficiency

27:00 – Outdoor Hospitality: Designing Emotion Into Experience

31:00 – Leadership Clarity: Focus, Management, and Purpose

Topics Discussed: 

• Making a difference in entrepreneurship
• Constructing your company as solving an emotional problem 
• Balancing persistence and passion in leading a business
• Navigating the plateaus of business by trying something new 
• Why having good management is the difference maker

About Rethink Change:

When growth is stagnant, culture’s a mess, the brand’s adrift, and the board wants miracles by Monday, Pennebaker’s podcast, Rethink Change, is where innovators and disruptors go for clarity.

Hosted by Founder Ward Pennebaker and President Matt Pennebaker, this podcast delivers sharp insights from battle-tested leaders who’ve navigated chaos and turned challenge into momentum. You’ll hear from executives from startups to global behemoths, from a wide range of industries. No fluff. All results. These conversations reveal what actually works, enabling you to think differently and act smarter.

Get Connected with Rethink Change:

• Website: https://www.pennebaker.com/podcast
• LinkedIn: https://www.linkedin.com/company/pennebaker/ 
• Facebook: https://www.facebook.com/pennebakerbrand
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