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Welcome to The Digital Contrarian, where we explore strategic insights for digital entrepreneurs who think differently. Hosted by Ryan Levesque, 7x Inc. 5000 CEO and 2x #1 Best-Selling Author who has generated over $100 million in revenue and sold two companies, this podcast delivers the audio edition of his popular weekly newsletter.
Each episode examines the intersection of digital business, strategic thinking, and authentic entrepreneurship in our rapidly evolving AI-driven landscape. Ryan shares contrarian perspectives on what's changing, what's working, and what's next for entrepreneurs building meaningful businesses that align with their values.
Whether you're navigating the shift from surface-level tactics to purpose-driven work, exploring the "Return to Real" movement, or seeking to build a category-of-one business in an increasingly noisy digital world, you'll find frameworks and insights designed for second-mountain entrepreneurs ready to think beyond conventional wisdom.
Join over 100,000 digital entrepreneurs who receive Ryan's strategic insights every weekend, now available in audio format for deeper exploration while you're on the move, exercising, or living your return-to-real life beyond the screen.
| Episode | Date |
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TDC #083 Part 4: The "Contrarian Canon" (Continued)
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Jan 18, 2026 |
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TDC 082: Part 3: The "Contrarian Cannon" (Continued)
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Jan 11, 2026 |
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TDC #081: The “Contrarian Cannon” (Part 2) & The Surprising Nature of Breakthroughs.
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Jan 03, 2026 |
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TDC #080: The "Contrarian Cannon" – 5 Overlooked Ideas That Could Shape Your 2026
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Dec 27, 2025 |
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TDC 079: The Tension Between Resistance & Productive Procrastination: How to Know When It's Time to Ship
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Dec 20, 2025 |
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TDC 078: 12 Days in Austin: Business Lessons, Dad Fails, and Why the AI Backlash is Coming
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Dec 13, 2025 |
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TDC 077: The 4 Types of Driven Entrepreneurs (And Why You're Secretly Seeking Validation)
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Dec 06, 2025 |
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TDC 076: Worldviews from Viewers: Real Perspectives On How to Make Sense of this Post-AI World...
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Nov 29, 2025 |
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TDC 075: How To Craft Your Worldview With AI
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Nov 22, 2025 |
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TDC 074: The First Trillion Dollar Thought Leader: Being Known for How You Think, Not What You Consume
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Nov 15, 2025 |
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TDC 073: The Efficiency vs. Resiliency Dilemma: Why Your "Optimized" Business Might Be Dangerously Fragile
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Nov 08, 2025 |
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TDC 072: How to Become A "Category of One" Thought Leader.
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Nov 01, 2025 |
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TDC 071: How to Get Your Website to Show Up in ChatGPT…
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Oct 25, 2025 |
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TDC 070: Seven "Non-Obvious" Email Lessons I've Learned Writing This Email Newsletter Each Week.
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Oct 18, 2025 |
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TDC 069: The Circular AI Money Shell Game?? | What To Do About The AI Bubble That May Soon Be Coming To an End
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Oct 11, 2025 |
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TDC 068: Your $20/month AI tool is about to cost $500: The Coming AI Price Shock...
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Oct 04, 2025 |
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TDC 067: 3-Part "RTR" AI Business Model Opportunity
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Sep 27, 2025 |
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TDC 066: A Crazy Person's Guide to Living Life in an AI World
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Sep 20, 2025 |
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TDC 065:The AI Battle Brewing Beneath the Surface Plus 27 Vermont Farm Mastermind Takeaways
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Sep 13, 2025 |
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TDC 064: The Market Shift Nobody Sees Coming (While You're Distracted by AI)
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Sep 07, 2025 |
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TDC 063: 5 AI Infographics That Will Blow Your Mind
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Aug 30, 2025 |
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TDC 062: Is the AI Bubble Bursting?? (The Shocking MIT Study, Key Observations from a Billionaire Summit)
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Aug 24, 2025 |
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TDC 061: The AI "Personal Branding Paradox" ??
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Aug 16, 2025 |
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TDC 060: Inside a Room With 40+ Million-Copy Bestselling Authors
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Aug 09, 2025 |
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TDC 059: Live Wild or Die Boring (Part 1)
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Aug 02, 2025 |
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TDC 058: Bombshell Week in AI
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Jul 26, 2025 |
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TDC 057: The Rise of the Generalist?
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Jul 19, 2025 |
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TDC 056: Storytelling, the most scalable post AI business skill worth building
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Jul 12, 2025 |
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TDC 055: My Contrarian YouTube Strategy: Building a Strategic Content Ecosystem (Part 2)
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Jul 06, 2025 |
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TDC 054: How AI Breaks Shared Reality
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Jun 28, 2025 |
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TDC 053: Between Death and Danger is the Path Up the Mountain
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Jun 21, 2025 |
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TDC 052: Category of One: A $10M/Year Business Blueprint (How I Made Inc 5000 Seven Times)
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Jun 14, 2025 |
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TDC 051: When Setbacks Become Breakthroughs: The Science of Turning Adversity Into Growth in Business & Life
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Jun 07, 2025 |
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TDC 050: Give Up Good for Great: The Secret to Making Bold Life Decisions
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May 31, 2025 |
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TDC 049: The Trust Molecule: Why Oxytocin (Not Dopamine) Will Define the AI Era.
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May 24, 2025 |
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TDC 048: A 12-Part Framework For Owning Your Category: Truth, Hell, & The Lie They Believe.
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May 17, 2025 |
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TDC 047: Who Are You Really Building For? The 100,000, The 100, or "The One?"
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May 10, 2025 |
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TDC 046: 3 Converging Forces Reshaping Our World As We Know It...
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May 04, 2025 |
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Welcome to The Digital Contrarian Podcast
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May 03, 2025 |