Bite-Size Episode Show Notes

In this bite-size episode of The Inner Entrepreneur, Paul sits down with wealth strategist and author Garrett Gunderson to explore the idea of “sacred cows” in money — the widely accepted financial beliefs that rarely get questioned, yet quietly shape how people save, invest, and think about wealth. Garrett shares the unlikely origin of his work: a grassroots study group built on one simple principle — question everything, and don’t try to be right, just try to find out what’s right. That mindset led him to challenge conventional retirement planning, hidden fees, and the myths embedded in systems like pensions and 401(k)s.

The conversation moves beyond financial products into mindset, identity, and value creation. Garrett explains why the wealthy don’t see money as a zero-sum game, why playing not to lose keeps people stuck, and why investing in skills, relationships, and financial intelligence compounds far more powerfully than chasing returns alone. He also reflects on personal loss, burnout, and how stepping back to realign with family and purpose ultimately gave rise to his bestselling book and long-term.

About the Guest

Garrett Gunderson is a wealth strategist, entrepreneur, and New York Times bestselling author. He is best known for challenging conventional financial advice and helping entrepreneurs and high-income professionals build wealth through value creation, financial intelligence, and personal alignment. Garrett is the author of Killing Sacred Cows, What Would the Rockefellers Do?, and The Algebra of Wealth, and has advised thousands of business owners on building wealth that supports a meaningful life.

About the Host

Paul Ryan is the host of The Inner Entrepreneur Podcast, where he explores the inner world behind entrepreneurial success — purpose, mindset, wellbeing, and the deeper questions that surface as businesses and careers evolve.

Work With Paul

To learn more about Paul’s mentoring, programs, and frameworks — including The Life Code and The One-Hour CEO — visit:pauljryan.net

Why Success Breaks Entrepreneurs and What to Do About It – Sherry Walling #151

Episode Summary

In this episode, Paul sits down with clinical psychologist and entrepreneur Dr. Sherry Walling to explore what really happens after the big business exit. They discuss why a financial windfall often triggers an identity crisis, how over-identifying with your company fuels loneliness and burnout, and why presence—not provision—is what our families truly want from us. Sherry also shares simple practices for emotional steadiness, including journaling, free-writing, and gratitude, along with her personal journey through grief, MDMA-assisted therapy, and ayahuasca. From stress habituation to heart-centred leadership and plant medicine, this conversation digs into what it means to stay human while building big things.

Key discussion points:

• Why exits often trigger depression, disillusionment, and relationship strain
• How fusing identity with your business sets you up for an existential crash
• The loneliness that comes with extreme success or high achievement
• Why many entrepreneurs unconsciously delegate the family to their partner
• Burnout as a repetitive-strain injury of the mind
• Habituation: how chronic stress becomes invisible
• Journaling, Morning Pages, and seeing yourself on paper
• The neuroscience behind gratitude and why it matters
• Building a company without martyrdom or 70-hour weeks
• The role of humility in leadership and delegation
• Sherry’s clinical work with trauma and the promise of MDMA-assisted therapy
• Her personal story of grief and how plant medicine supported her healing
• What ayahuasca actually is—and why it feels like medicine, not recreation

About the Guest — Dr. Sherry Walling

Dr. Sherry Walling is a clinical psychologist, author, and founder of ZenFounder, where she supports entrepreneurs through burnout, emotional resilience, trauma, and life transitions. She is also the author of The Entrepreneur’s Guide to Keeping Your Sht Together*, Exit Strategy (co-authored with her husband Rob Walling), and Touching Two Worlds, and integrates creative movement and aerial arts into her work. Learn more at zenfounder.com and touchingtwoworlds.com.

About the host:

Paul Ryan is an entrepreneur, 8 figure business owner, mentor, podcaster and creator of the 1-Hour CEO and Life Code Program. As a CEO, Paul has a depth of 'real life' experience of what it takes to be successful in business and life.

Connect with the host:

Pauljryan.net

https://www.linkedin.com/in/paul-ryan-9a98774/

In this bite-size episode, Damion Lupo dismantles one of the most dangerous myths in entrepreneurship: that failure is something to be avoided. Drawing on decades of experience across more than 70 businesses — including losing everything and starting again — Damion reframes failure as the tuition fee for wisdom. He explains why most businesses don’t survive, not because of bad ideas, but because of a lack of real commitment. There is no “trying” in entrepreneurship — only deciding, persevering, and learning fast. Those who succeed are not luckier or smarter; they are more resilient, more decisive, and willing to move before everything feels certain.

Damion also explores the deeper evolution required to build lasting wealth and freedom. He argues that true financial security isn’t about accidentally reaching a number, but about becoming the person capable of recreating it. From knowing when to persevere versus when to quit, to understanding why environment, mentorship, and vision shape outcomes more than tactics, this conversation is a masterclass in long-term thinking. It’s a powerful reminder that almost nothing in business is fatal — and that growth comes from action, not waiting for perfect conditions.

Links to full episode:

https://open.spotify.com/episode/599FJBEVZyGGbhAazhSqD6?si=GsbLxGN0Rja0GVkqdR-8wA

https://youtu.be/N0r-qol9MU4?si=Gija1CEUNzE2c71s

About the Guest Damion Lupo is an entrepreneur, investor, and financial educator who has founded and operated over 70 companies. After experiencing both extreme success and complete financial collapse, including a period of homelessness, Damion rebuilt with a deep focus on resilience, decision-making, and sustainable wealth creation. He is the creator of the Turnkey Retirement framework and is known for helping entrepreneurs think differently about money, risk, and long-term freedom.

About the Host Paul Ryan is the host of The Inner Entrepreneur Podcast, where he explores the inner world behind entrepreneurial success — mindset, resilience, purpose, and personal growth. Through candid conversations with founders, investors, and thought leaders, Paul helps entrepreneurs build businesses that support a meaningful, well-lived life. Learn more at pauljryan.net.