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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.
30 Episodes
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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...
TDC 063: 5 AI Infographics That Will Blow Your Mind Five shocking AI infographics reveal hidden truths about data centers, jobs, and what AI is doing to your brain. --- Episode Summary In this episode of The Digital Contrarian, host Ryan Levesque shares five mind-blowing AI infographics from his personal collection. You'll discover hard evidence that AI is killing jobs for young people, learn why data centers now consume more power than entire countries, and see shocking MIT research on ...
TDC 062: Is the AI Bubble Bursting? My Keynote Insights + MIT's Shocking 95% Failure Rate While 65% of all VC flows into AI, the real opportunity lies in the barbell approach. --- Episode Summary In this episode of The Digital Contrarian, host Ryan Levesque dives into AI bubble dynamics and enterprise failure rates. You'll learn why 95% of AI projects fail, how billionaire investors view current market concentration, and discover the barbell strategy for hedging against bub...
TDC 061: The Personal Branding Paradox in the Age of AI The more AI you use to scale your personal brand, the less personal it becomes. Episode Summary In this episode of The Digital Contrarian, Ryan Levesque explores the personal branding AI paradox and why scaling with AI often flattens your voice. You'll discover the "Personal Brand Power Law," learn the three-part "Fewer, Deeper, Less" framework for standing out, and understand why small rooms beat trying to be everywhere. Question of the...
TDC 060: Inside a Room With 40+ Million-Copy Bestselling Authors Seven powerful lessons from the literary equivalent of the NBA All-Star team. Episode Summary In this episode of The Digital Contrarian, host Ryan Levesque shares profound insights from his private gathering with 40+ million-copy bestselling authors including James Clear, Jamie Kern-Lima, and Hal Elrod. You'll discover why good enough isn't good enough for books, learn the secret to short-form content success, and understand why...
TDC 059: Live Wild or Die Boring: The Urgent Case for Reconnecting with the Natural World (Part 1) Why nature isn't just good for your soul—it's essential for survival, creativity, and breakthrough innovation. Episode Summary In this episode of The Digital Contrarian, host Ryan Levesque shares insights from recording his upcoming book Return to Real and reveals shocking research about our digital lifestyle. You'll discover how concrete environments increase early death by 12%, learn why natur...
TDC 058: A Bombshell Week in AI and an Eventful Week on the Farm Microsoft's groundbreaking AI job impact research reveals which careers are most vulnerable. --- Episode Summary: In this episode of The Digital Contrarian, host Ryan Levesque breaks down Microsoft's explosive AI job impact research paper analyzing over 200,000 AI interactions. You'll discover which jobs are most at risk from AI displacement, learn about satisfaction scores that predict future automation, and ...
TDC 057: The Rise of the Generalist: An Unexpected Side Effect of the AI Era Why AI might reverse 200 years of specialization and reward cross-domain thinking. --- Episode Summary In this episode of The Digital Contrarian, host Ryan Levesque explores a counterintuitive insight from Lex Fridman's interview with Google CEO Sundar Pichai. You'll discover why AI may favor generalists over specialists, learn how cross-domain connections create unique value, and understand why yo...
#056: Storytelling: The Most Scalable Post-AI Business Skill Worth Mastering In a world of AI-generated content and fractured attention, your ability to tell compelling stories may be your greatest competitive advantage. Episode Summary In this episode of The Digital Contrarian, host Ryan Levesque dives into why storytelling is the most scalable post-AI business skill worth developing. You'll learn how stories create deeper connection than any other content, discover the three story types you...
#055: My Contrarian YouTube Strategy: Building a Strategic Content Ecosystem My contrarian YouTube strategy creates 500K+ annual views with just ONE piece of original content per week. Episode Summary In this episode of The Digital Contrarian, host Ryan Levesque dives into the evolution of his strategic content ecosystem six months after first introducing it. You'll learn how one weekly "source of truth" piece creates a sustainable content system that respects family time, discover the long-f...
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