Dorie Clark is a Wall Street Journal bestselling author of The Long Game, Entrepreneurial You, Reinventing You and Stand Out. She's a keynote speaker and teaches executive education at Columbia Business School. She's also been named three times as one of the Top 50 business thinkers in the world by Thinkers50.

In this episode, Chris and Dorie talk about what it really takes to build a sustainable business over the long-haul. They dive deep into what it means to lead for the long term, how to stay grounded in a noisy world, and why delayed gratification is the ultimate superpower for leaders.

Dorie shares the behind-the-scenes story of how her books Entrepreneurial You and The Long Game were born out of her own questions about income, impact, and integrity.

If you’ve ever struggled with distraction, burnout, or the pressure to move faster than you want to, this episode will give you the perspective shift you didn’t know you needed.

IN THIS EPISODE YOU’LL LEARN:

• Why impact doesn’t always equal income (and what to do about it)
• How to sell with integrity without feeling like a used car salesman
• The truth about thought leadership and how long it really takes to build
• Why leaders are more in control of their time than they think
• What George Michael can teach us about finding your calling

EPISODE TIMESTAMPS:

• 02:11 - Dorie Clark on Long-Term Success
• 04:23 - Building a Sustainable Business
• 07:46 The Importance of Strategic Patience
• 11:01 - Challenges of Modern Leadership
• 20:28 - Balancing Work and Personal Life
• 23:02 - Balancing Priorities in Relationships
• 27:30 - Hobbies and Musical Theater
• 31:51 - Personal Projects and Simplifying Life

RESOURCES MENTIONED IN THIS EPISODE:

• Pre-Order The Long-Haul Leader
• Connect with Chris on Instagram
• Connect with Dorie on Instagram
• Check Out Dorie's Book, The Long Game

SUBSCRIBE & REVIEW:

Be sure to subscribe and leave a review on Apple Podcasts (or your favorite podcast player) — it helps more long-haul leaders like you discover the show and join the journey.

Thanks for listening to The Long-Haul Leader podcast. See you next week with more insights to help you lead with purpose, resilience, and impact.

Ryan Levesque is a 7-time Inc. 5000 CEO & Founder, and 2-time #1 National Best-selling Author. He's generated over $100M in revenue and has successfully sold two of his companies.

His work has been featured in the Wall Street Journal, Harvard Business Review, Forbes, Entrepreneur, and NBC News. Today he serves as a Strategic Advisor to multiple businesses, is working on his next book, and writes a weekly email newsletter “The Digital Contrarian” offering Unconventional Business Wisdom to over 100,000+ subscribers.

In this episode, Chris and Ryan explore the seismic shifts shaping the world today, and what they mean for long-haul leaders and creators.

From economic upheaval to environmental pressure to existential questions raised by AI, Ryan breaks down the "three colliding forces" reshaping life and business as we know it. He also shares why he chose to relocate his family to a 100+ acre farm in Vermont, and how that decision represents more than just a lifestyle choice.

IN THIS EPISODE YOU’LL LEARN:

• The three massive forces (economic, environmental, and existential) colliding right now
• How Ryan is preparing his family for an uncertain future
• Why a return to nature, simplicity, and “what’s real” is both a personal and business strategy
• How Ryan blends hands-in-the-dirt farming with high-level digital entrepreneurship
• Why doing the unscalable thing may be the smartest move you can make today

EPISODE TIMESTAMPS:

• 04:39 - The Changing World Order
• 06:01 - Economic Forces and Big Debt Cycles
• 10:33 - Environmental Forces and Climate Change
• 14:20 - Navigating the Future: Strategies and Concerns
• 15:53 - Balancing Optimism and Fear in the Age of AI
• 20:33 - Entrepreneurs and AI: Embracing Opportunities
• 24:56 - Transitioning to a Rural Lifestyle
• 30:35 - Balancing Modern Skills with Traditional Practices
• 37:00 - The Value of Unscalable Efforts

RESOURCES MENTIONED IN THIS EPISODE:

• Pre-Order The Long-Haul Leader
• Connect with Chris on Instagram
• Subscribe to Ryan's Newsletter
• Connect with Ryan on Instagram

SUBSCRIBE & REVIEW:

Be sure to subscribe and leave a review on Apple Podcasts (or your favorite podcast player) — it helps more long-haul leaders like you discover the show and join the journey.

Thanks for listening to The Long-Haul Leader podcast. See you next week with more insights to help you lead with purpose, resilience, and impact.

Jenny Wood is a New York Times bestselling author of Wild Courage. She's a speaker, former Google executive, and former Harvard Business School researcher who knows that real success isn’t about following the rules or waiting your turn.

Her practical, no-nonsense approach empowers ambitious people to break the mold, be better leaders, build influence, and reach their full potential.

In this episode, Chris and Jenny dive deep into the realities of building a meaningful business that supports your life, not the other way around.

Jenny shares how her relationship with money and success has shifted since leaving the corporate world, why she’s scaling back on keynote speaking, and the powerful mindset shifts that helped her find peace and profitability in her next chapter.

IN THIS EPISODE YOU’LL LEARN:

• Why success without sustainability isn’t real success
• How Jenny restructured her business model after leaving Google
• A fresh perspective on money, freedom, and what’s “enough”
• How to spot the invisible fears that sabotage progress (failure, uncertainty, judgment)
• How to reclaim traits like selfish, shameless, and manipulative for good
• The one belief she had to unlearn from corporate life to truly thrive

EPISODE TIMESTAMPS:

• 04:10 - From Google Exec to Entrepreneurship
• 08:02 - Rethinking Financial Goals and Business Strategy
• 15:06 - Overcoming Imposter Syndrome and Embracing Shamelessness
• 19:52 - Struggles of Balancing Work and Family
• 22:48 - Prioritizing Mental and Physical Health
• 24:12 - Transitioning from Corporate to Entrepreneurial Life
• 27:21 - Effective Coaching and Building Demand
• 30:31 - Launching Group Coaching Programs
• 35:19 - The Power of Influence and Relationships

RESOURCES MENTIONED IN THIS EPISODE:

• Pre-Order The Long-Haul Leader
• Connect with Chris on Instagram
• Pick Up a Copy of Wild Courage
• Connect with Jenny on LinkedIn

SUBSCRIBE & REVIEW:

Be sure to subscribe and leave a review on Apple Podcasts (or your favorite podcast player) — it helps more long-haul leaders like you discover the show and join the journey.

Thanks for listening to The Long-Haul Leader podcast. See you next week with more insights to help you lead with purpose, resilience, and impact.