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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.
39 Episodes
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TDC #083 Part 4: The "Contrarian Canon" (Continued) In this episode of The Digital Contrarian, host Ryan Levesque makes the case for storytelling as THE differentiator in a post-AI world—and shares a practical toolkit you can apply immediately. You'll learn the three story types every creator needs, five contrarian tips for compelling stories, and how his kids flipped a $169 parka for $329 on eBay in 20 minutes using nothing but storytelling. Question of the Day What's one story from your...
TDC 082: Part 3: The "Contrarian Cannon" (Continued) In this episode of The Digital Contrarian, host Ryan Levesque tackles the dilemma every entrepreneur eventually faces: Do you build for the hyper-engaged 100, the silent 100,000, or orient everything around a single person? You'll discover why optimizing for scale creates drift, why over-serving your superfans leads to burnout, and why centering around "the one" sharpens your message and simplifies every decision. --- Question of the Day...
TDC #081: The “Contrarian Cannon” (Part 2) & The Surprising Nature of Breakthroughs. The moment you feel most stalled might be the exact moment you're closest to your next big shift. Episode Summary: In this episode of The Digital Contrarian, host Ryan Levesque explores the surprising pattern behind how breakthroughs actually happen—and why they rarely arrive when you're grinding hardest. You'll learn why creative block often precedes insight, what a 200-year-old sugar maple teaches about...
TDC #080 - The Contrarian Canon (Part 1): 5 Overlooked Frameworks for 2026 What if the most powerful business ideas aren't the newest ones, but the ones you missed? Episode Summary In this episode of The Digital Contrarian, host Ryan Levesque shares five overlooked frameworks from the "Contrarian Canon"—powerful concepts buried in past newsletter issues. You'll learn how to optimize around permanence instead of change, why struggle creates satisfaction, and discover advanced pricing psy...
TDC 079: The Tension Between Resistance & Productive Procrastination: How to Know When It's Time to Ship When productive procrastination crosses the line into destructive resistance—and the simple test to know when you must finally ship. Episode Summary In this episode of The Digital Contrarian, host Ryan Levesque dives into the critical tension between productive procrastination and destructive resistance. You'll learn how to distinguish between creative incubation and fear-based avoida...
TDC 078: 12 Days, 12 Takeaways: Lessons from Austin That Will Change How You Think About Business & Life The last mile is the one that matters most—and why most entrepreneurs quit right before their breakthrough. Episode Summary In this episode of The Digital Contrarian, host Ryan Levesque shares his biggest lesson from each of 12 days spent in Austin, Texas—covering five back-to-back events, dozens of private dinners, and nearly 50 hours of sessions. You'll learn why the coming AI backla...
TDC 077: The 4 Types of Driven Entrepreneurs (And Why You're Secretly Seeking Validation) Four archetypes, one painful realization, and 14 words that could change everything. Episode Summary: In this episode of The Digital Contrarian, host Ryan Levesque shares a vulnerable story from Front Row Dads Live about a moment he's not proud of as a father. You'll learn the difference between your True Self and Strategic Self, discover which of the four archetypal patterns drives your behavior, and un...
TDC 076: Worldviews from Viewers: Real Perspectives On How to Make Sense of this Post-AI World... World views from readers reveal what's really shaping how thoughtful people navigate today's chaos. Episode Summary In this special episode of The Digital Contrarian, host Ryan Levesque shares thought-provoking reader responses to last week's worldview challenge. You'll discover seven diverse principles shaping how people make sense of this moment in history, explore frameworks for navigating com...
TDC 075: How To Craft Your Worldview With AI What I learned at Tony Robbins and Dean Graziosi's $250,000 private mastermind this week. Episode Summary In this episode of The Digital Contrarian, host Ryan Levesque dives into building a comprehensive worldview and why it's your hidden operating system. You'll learn how to surface your existing beliefs, discover the three levels of reality that shape decisions, and explore a six-step AI-assisted process for crafting worldviews that drive r...
TDC 074: The First Trillion Dollar Thought Leader: Being Known for How You Think, Not What You Consume Why being known for how you think beats influence every time. Episode Summary In this episode of The Digital Contrarian, host Ryan Levesque dives into the critical distinction between influencers and thought leaders in the AI era. You'll learn why chasing followers is the wrong game, how thought leadership transforms ideas into equity, and discover the unsexy immediate next step to start bui...
TDC: The Efficiency vs. Resiliency Dilemma What's the biggest vulnerability in your business right now? Episode Summary: In this episode of The Digital Contrarian, host Ryan Levesque explores the dangerous trade-off between efficiency and resiliency in business. You'll learn why single-channel dependency threatens your business survival, discover how the Irish Potato Famine reveals critical marketing insights, and explore how to build an antifragile strategic content ecosystem that can weathe...
TDC 072: How to Become A "Category of One" Thought Leader. Three questions that separate thought leaders from everyone else in their market. Episode Summary: In this episode of The Digital Contrarian, host Ryan Levesque reveals the Category of One framework that's made his consulting practice oversubscribed and generated 24 speaking invitations in 18 months. You'll learn the three critical questions that establish thought leadership positioning, discover why timing and novelty matter more tha...
TDC 071: How to Get Your Website to Show Up in ChatGPT… The 2025 version of ranking #1 on Google—master these AI concepts before your competition does. Episode Summary: In this episode of The Digital Contrarian, host Ryan Levesque dives into Answer Engine Optimization (AEO) and the advanced AI concepts determining which brands get recommended by ChatGPT. You'll learn how to optimize for vector embeddings instead of keywords, discover entity graph gap analysis techniques, and master informatio...
TDC 070: Seven "Non-Obvious" Email Lessons I've Learned Writing This Email Newsletter Each Week. Episode Summary In this episode of The Digital Contrarian, host Ryan Levesque reveals the seven most impactful lessons from writing 70 consecutive weekly newsletters by hand. You'll learn how less AI usage led to higher engagement, why creative volume beats perfectionism, and discover the custom dashboard metrics that actually matter for email success. Question of the Day 🗣️ Which of these 7 lesso...
TDC 069: The Circular AI Money Shell Game?? | What To Do About The AI Bubble That May Soon Be Coming To an End The AI bubble may be closer to popping than you think—and the evidence is hiding in plain sight. Episode Summary In this episode of The Digital Contrarian, host Ryan Levesque goes into the current state of the AI bubble and where we might be on the hype cycle curve. You'll learn why enterprise AI adoption is actually declining, discover the circular money shell game happening betwee...
TDC 068: Your $20/month AI tool is about to cost $500: The Coming AI Price Shock... The coming AI price shock that could destroy your business model overnight. Episode Summary In this episode of The Digital Contrarian, host Ryan Levesque exposes the broken economics behind OpenAI's $500 billion valuation and the entire AI sector. You'll learn why venture-capital subsidized AI pricing is unsustainable, discover the shocking financials that reveal AI companies lose money on every transaction, a...
TDC 067: 3-Part "RTR" AI Business Model Opportunity The market is shifting beneath our feet and most people have no idea it's happening. Episode Summary: In this episode of The Digital Contrarian, host Ryan Levesque reveals a massive shift taking place in the market right now that connects falling Meta ad costs, massive AI infrastructure deals, and the future of digital business. You'll learn about six major market observations Ryan's been tracking, discover why paid media costs are finally c...
TDC 066: A Crazy Person's Guide to Living Life in an AI World Each ChatGPT usage category reveals what humans are desperately craving in an AI-saturated world. Episode Summary In this episode of The Digital Contrarian, host Ryan Levesque dives into OpenAI's first-ever ChatGPT usage study. You'll learn how each AI usage category reveals human hunger for authentic connection, discover the "Return to Real" opportunity hiding within seven major verticals, and uncover why the world needs more hea...
TDC 065:The AI Battle Brewing Beneath the Surface Plus 27 Vermont Farm Mastermind Takeaways Episode Summary In this episode of The Digital Contrarian, host Ryan Levesque dives into the $1.5 billion Anthropic settlement and its implications for content creators. You'll learn why we may be exiting the "Napster era" of AI, discover the contrarian content strategy behind our first viral YouTube video, and explore 27 transformative insights from the Vermont Farm Mastermind Experience. Question of ...
TDC 064: The Market Shift Nobody Sees Coming (While You're Distracted by AI) Paid media costs are dropping to 18-month lows—here's what this unexpected trend could mean for your business. Episode Summary In this episode of The Digital Contrarian, host Ryan Levesque shares a surprising market observation from his Vermont farm as he prepares to host the first Return to Real mastermind. You'll discover an unexpected shift in paid media costs, learn why this contradicts conventional wisdom, and e...
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