

The Digital Contrarian
Ryan Levesque
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.
Episodes
Mentioned books

Oct 4, 2025 • 8min
TDC 068: Your $20/month AI tool is about to cost $500: The Coming AI Price Shock...
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 SummaryIn 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, and understand why a 25x price increase is inevitable when the subsidy ends.Question of the Day 🗣️How dependent is your business on artificially cheap AI tools? What's your contingency plan if prices increase 25x?Key Take-awaysOpenAI loses $1.35 for every dollar of revenue despite its $500 billion valuationThe AI sector exhibits textbook bubble behavior with negative unit economicsCurrent AI pricing is artificially low, subsidized by venture capital fundingA 25x price increase (like Netflix's evolution) is inevitable when subsidies endBuild contingency plans now before your AI-dependent business model breaksTimestamped Outline ⏱️00:00 – The $500 AI price shock is coming01:04 – Inside the town hall: What we covered01:58 – OpenAI's terrifying financials revealed03:13 – The math problem that makes no sense03:58 – When the AI subsidy ends05:30 – What this means for your business06:03 – The Netflix playbook: $8 to $200/month07:22 – Build your contingency plans nowLinks & Resources 🔗Issue #062 of The Digital Contrarian – "Is the AI Bubble Bursting??" → https://ryanlevesque.net/is-the-ai-bubble-bursting/Subscribe to The Digital Contrarian newsletter → https://thedigitalcontrarian.comConnect & CTA 🎯👉 Enjoyed this? Subscribe & leave a review on Apple Podcasts.🎁 Join 100 000+ digital entrepreneurs who get Ryan's "Strategic Insights for Digital Entrepreneurs Who Think Differently" every weekend: https://ryanlevesque.net/join-the-digital-contrarian/CreditsHost: Ryan Levesque © 2025 RL & Associates LLC. All rights reserved.

Sep 27, 2025 • 4min
TDC 067: 3-Part "RTR" AI Business Model Opportunity
TDC 067: 3-Part "RTR" AI Business Model OpportunityThe 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 coming back to earth, and uncover the three-part RTR AI business model opportunity that most entrepreneurs are completely missing.Question of the Day 🗣️Have you noticed any shifts in your market over the last few months? What are you seeing that others might be missing?Key Take-awaysPaid media costs on Meta are at their lowest levels in over a year for the first time in nearly two yearsMajor AI infrastructure deals (300BOracle−OpenAI,300B Oracle-OpenAI, 300BOracle−OpenAI,100B NVIDIA-OpenAI) signal a fundamental market shiftA three-part RTR AI business model opportunity exists for those who take action nowMost entrepreneurs are unaware of this shift, creating a major competitive advantageLive town hall registration is capped at 300 attendees and expected to fill quicklyTimestamped Outline ⏱️00:00 – Welcome to Episode 6700:33 – Six major market observations taking shape00:58 – Paid media costs finally coming back to earth01:40 – Major AI infrastructure deals reshaping the landscape02:25 – The market shift most people are missing02:58 – Announcing live town hall event03:25 – Three important registration details04:05 – Keeping today's episode shortLinks & Resources 🔗Issue #064 of The Digital Contrarian – "Surprising (Non-AI) Trend Taking Shape" → https://ryanlevesque.net/surprising-trend-taking-shape/$100 Billion OpenAI deal with NVIDIA → https://www.cnbc.com/2025/09/24/nvidia-openai-investment-in-cash-mostly-used-to-lease-nvidia-chips.htmlMeta's 'Vibes' Short-Form Video Feed of AI Slop → https://techcrunch.com/2025/09/25/meta-launches-vibes-a-short-form-video-feed-of-ai-slop/Connect & CTA 🎯👉 Enjoyed this? Subscribe & leave a review.🎁 Join 100 000+ digital entrepreneurs who get Ryan's "Strategic Insights for Digital Entrepreneurs Who Think Differently" every weekend: https://ryanlevesque.net/join-the-digital-contrarian/CreditsHost: Ryan Levesque© 2025 RL & Associates LLC. All rights reserved.

Sep 20, 2025 • 11min
TDC 066: A Crazy Person's Guide to Living Life in an AI World
TDC 066: A Crazy Person's Guide to Living Life in an AI WorldEach ChatGPT usage category reveals what humans are desperately craving in an AI-saturated world.Episode SummaryIn 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 heart, humor, and humanity and not more artificial intelligence.Question of the Day 🗣️Which of the seven wedges resonates most with YOUR life right now? Where are you craving more "real" and less "artificial"?Key Take-awaysEvery AI usage category reveals where people are yearning for what's deeply human and authenticPersonal writing (18%) shows hunger for genuine voice—opportunities in storytelling and book clubsTutoring (10.2%) reveals desire for someone who sees you—think micro schools and apprenticeshipsHealth/fitness (5.7%) shows craving to feel alive—outdoor adventure travel is fastest growing tourismThe subtext of all AI usage: people want more time doing what's really meaningful and preciousTimestamped Outline ⏱️00:00 – A crazy person's guide to living in an AI world01:16 – OpenAI's groundbreaking usage study revealed02:30 – The overlooked angle everyone's missing03:27 – Why each AI vertical reveals human hunger04:08 – Wedge #1: Personal Writing (18%) - Heart, Humor, Humanity04:50 – Wedge #2: Tutoring (10.2%) - Hands in the Dirt05:06 – Wedge #3: How-To Advice (8.5%) - Going Analog05:46 – Wedge #4: Health & Fitness (5.7%) - Best Things Don't Scale06:17 – Wedge #5: Translation (4.5%) - Oxytocin Over Dopamine07:03 – Wedge #6: Programming (4.2%) - Category of One07:51 – Wedge #7: Products (2.1%) - Between Death and Danger08:26 – The real subtext behind all AI usage09:03 – Why I stay up past midnight beating this drum09:42 – Your call to action: Bang your drumLinks & Resources 🔗OpenAI ChatGPT Usage Study (NBER Working Paper) → https://www.nber.org/system/files/working_papers/w34255/w34255.pdfThe Digital Contrarian newsletter → https://thedigitalcontrarian.comConnect & CTA 🎯👉 Enjoyed this? Subscribe & leave a review on Apple Podcasts.🎁 Join 100 000+ digital entrepreneurs who get Ryan's "Strategic Insights for Digital Entrepreneurs Who Think Differently" every weekend: https://ryanlevesque.net/join-the-digital-contrarian/CreditsHost: Ryan Levesque © 2025 RL & Associates LLC. All rights reserved.

Sep 13, 2025 • 7min
TDC 065:The AI Battle Brewing Beneath the Surface Plus 27 Vermont Farm Mastermind Takeaways
TDC 065:The AI Battle Brewing Beneath the Surface Plus 27 Vermont Farm Mastermind TakeawaysEpisode SummaryIn 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 the Day 🗣️What's your biggest takeaway from the 27 Vermont insights? Which one could transform your business?Key Take-awaysThe $1.5 billion Anthropic settlement signals a shift from the "Napster era" to the "Spotify era" of AIYouTube may be the next AI battleground as the last non-AI powered search engineSingle source of truth content can generate viral breakthrough results (27K+ views in 18 weeks)Strategic content ecosystems outperform shallow algorithm gaming every timeVermont Farm Mastermind revealed 27 transformative business and life insightsTimestamped Outline ⏱️00:00 – The AI battle brewing beneath the surface00:48 – $1.5 billion Anthropic settlement breakdown02:15 – From Napster era to Spotify era of AI03:40 – YouTube as the next AI battleground04:30 – Town Hall announcement: October 2nd05:35 – Unexpected YouTube breakthrough explained06:35 – Vermont Farm Mastermind experience07:25 – 27 takeaways from Maeve Ferguson's perspectiveLinks & Resources 🔗Issue #055 of The Digital Contrarian – "My Contrarian YouTube Strategy" → https://ryanlevesque.net/podcast/tdc-055-my-contrarian-youtube-strategy-building-a-strategic-content-ecosystem-part-2/Issue #031 of The Digital Contrarian – "Cultivating Influence vs. Chasing Attention" → https://ryanlevesque.net/cultivating-influence-vs-chasing-attention/Vermont Farm Mastermind Takeaways → https://maeveferguson.substack.com/p/27-takeaways-from-ryan-levesquesCheck if your videos were scraped → https://www.theatlantic.com/technology/archive/2025/09/youtube-ai-training-data-sets/684116/The Digital Contrarian newsletter → http://thedigitalcontrarian.com/Connect & CTA 🎯👉 Enjoyed this? Subscribe & leave a review on Apple Podcasts.🎁 Join 100 000+ digital entrepreneurs who get Ryan's "Strategic Insights for Digital Entrepreneurs Who Think Differently" every weekend: https://ryanlevesque.net/join-the-digital-contrarian/CreditsHost: Ryan Levesque © 2025 RL & Associates LLC. All rights reserved.

Sep 7, 2025 • 5min
TDC 064: The Market Shift Nobody Sees Coming (While You're Distracted by AI)
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 SummaryIn 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 explore what this opportunity means for digital entrepreneurs who are paying attention.Question of the Day 🗣️Are you seeing any unexpected shifts in your paid media costs recently? Comment "TOWN HALL" if you'd be interested in a deeper dive into this market trend!Key Take-awaysPaid media costs on Meta are hitting 18-month lows, defying expectationsThis shift represents a potential major opportunity for businesses paying attentionThe market dynamics are different from last year's "Great Sea Change"Strategic timing matters when everyone else is distracted by AI trendsTimestamped Outline ⏱️00:00 – Cold open & surprising non-AI trend01:00 – The unexpected paid media cost shift01:42 – Why this contradicts last year's predictions02:18 – Balancing multiple commitments and gauging interest03:06 – Digital Contrarian podcast update and gift04:00 – Final thoughts from the farmLinks & Resources 🔗Digital Contrarian Podcast (all episodes) → https://ryanlevesque.net/podcast/The Digital Contrarian newsletter → https://thedigitalcontrarian.comConnect & CTA 🎯👉 Enjoyed this? Subscribe & leave a review on Apple Podcasts.🎁 Join 100 000+ digital entrepreneurs who get Ryan's "Strategic Insights for Digital Entrepreneurs Who Think Differently" every weekend: https://ryanlevesque.net/join-the-digital-contrarian/CreditsHost: Ryan Levesque © 2025 RL & Associates LLC. All rights reserved.

Aug 30, 2025 • 9min
TDC 063: 5 AI Infographics That Will Blow Your Mind
TDC 063: 5 AI Infographics That Will Blow Your MindFive shocking AI infographics reveal hidden truths about data centers, jobs, and what AI is doing to your brain.---Episode SummaryIn 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 what ChatGPT does to your brain connectivity.---Question of the Day 🗣️Which of these five infographics impacts you most, and how are you preparing for the changes they reveal?---Key Take-aways- Data centers are consuming more electricity than entire countries, creating unprecedented infrastructure demands- First hard evidence shows AI is disproportionately eliminating entry-level jobs for young workers- MIT study reveals 83% of ChatGPT users can't recall sentences they wrote minutes earlier- Ten core skills emerge as essential for thriving in the 2030 economy- AI training relies heavily on Reddit data, creating potential accuracy and bias issues---Timestamped Outline ⏱️00:00 – Five AI infographics that will blow your mind00:48 – My infographic collection obsession02:15 – Data centers consuming more power than countries03:40 – First hard evidence AI is killing young jobs05:35 – Ten core skills to master by 203006:35 – Your brain on ChatGPT: the shocking study08:30 – AI gets 40% of facts from Reddit problem09:15 – Which infographic impacts you most?---Links & Resources 🔗- Issue #062 of The Digital Contrarian – "Is the AI Bubble Bursting??" → https://ryanlevesque.net/is-the-ai-bubble-bursting/- Subscribe to The Digital Contrarian newsletter → https://thedigitalcontrarian.com---Connect & CTA 🎯👉 Enjoyed this? Subscribe & leave a review on Apple Podcasts.🎁 Join 100 000+ digital entrepreneurs who get Ryan's "Strategic Insights for Digital Entrepreneurs Who Think Differently" every weekend:*<https://ryanlevesque.net/join-the-digital-contrarian/>---CreditsHost: Ryan Levesque© 2025 RL & Associates LLC. All rights reserved.

Aug 24, 2025 • 14min
TDC 062: Is the AI Bubble Bursting?? (The Shocking MIT Study, Key Observations from a Billionaire Summit)
TDC 062: Is the AI Bubble Bursting? My Keynote Insights + MIT's Shocking 95% Failure RateWhile 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 bubble conditions while maintaining human competitive advantage. ---Question of the Day 🗣️ How are you balancing AI automation with maintaining the human elements that make your business unique?---Key Take-aways - 95% of enterprise AI projects are failing according to new MIT research - 65% of all venture capital now flows into AI—the highest sector concentration in history - Geographic distance kills AI effectiveness in most business applications - The barbell approach protects your human core while deploying strategic AI assists - Lead with humanity first, then layer in AI where ROI is obvious ---Timestamped Outline ⏱️ 00:00 – Is the AI bubble bursting? 00:48 – Newport Global Summit keynote insights 02:15 – The shocking MIT study: 95% AI failure rate 03:40 – Sam Altman's market manipulation timing 05:35 – Venture capital hyper-concentration warning 06:35 – Data center overinvestment analysis 07:25 – Why geographic distance kills AI effectiveness 08:30 – The barbell approach: Human core + AI assists 09:15 – 4-step practical implementation framework 11:30 – 30-day sprint you can start Monday 13:15 – The big takeaway: Lead with humanity ---Links & Resources 🔗 - The Digital Contrarian newsletter → https://thedigitalcontrarian.com ---Connect & CTA 🎯 👉 Enjoyed this? Subscribe & leave a review on Apple Podcasts. 🎁 Join 100 000+ digital entrepreneurs who get Ryan's "Strategic Insights for Digital Entrepreneurs Who Think Differently" every weekend:<https://ryanlevesque.net/join-the-digital-contrarian/>---Credits Host: Ryan Levesque© 2025 RL & Associates LLC. All rights reserved.

Aug 16, 2025 • 11min
TDC 061: The AI "Personal Branding Paradox" ??
TDC 061: The Personal Branding Paradox in the Age of AIThe more AI you use to scale your personal brand, the less personal it becomes.Episode SummaryIn 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 Day 🗣️Which of the three moves (Fewer, Deeper, Less) do you find most challenging to implement in your personal brand strategy? Share in the comments below!Key Take-awaysThe Personal Brand Power Law: only a tiny handful capture most attention while everyone fights over scrapsThe AI Paradox: more AI in your brand makes it less personal and harder to stand out"Fewer, Deeper, Less" beats trying to go big and be everywhereOne weekly "source of truth" content piece trumps dozens of AI-assisted postsSmall strategic rooms create more opportunities than mass-market approachesTimestamped Outline ⏱️00:00 – Intro: Birthday reflections and farm life00:42 – Recent events and AI developments02:30 – The Personal Brand Power Law explained03:29 – The Great AI Paradox revealed04:23 – The "Fewer, Deeper, Less" framework05:12 – Move #1: Source of Truth content strategy06:05 – Move #2: Show your struggle to build trust06:58 – Move #3: Small rooms and strategic absence09:11 – Personal Branding AI Summit invitationLinks & Resources 🔗Get on the Return to Real Farm Event waitlist → https://ryanlevesque.net/vermont-farm-mastermind-waitlist/Register for Mike Kim's Personal Branding AI Summit → https://youarethebrand.ai/join?am_id=robby397Issue 025 – "Tipping Points" → https://ryanlevesque.net/half-baked-ideas-contrarian-advantage-ai-era/Issue 027 – "Your Strategic Content Ecosystem" → https://ryanlevesque.net/strategic-content-ecosystem/Issue 035 – "Why the Struggle is the Solution" → https://ryanlevesque.net/why-the-struggle-is-the-solution/Issue 055 – "My Contrarian YouTube Strategy" → https://ryanlevesque.net/my-contrarian-youtube-strategy/Issue 056 – "Storytelling: The Most Scalable Post-AI Business Skill?" → https://ryanlevesque.net/storytelling-the-most-scalable-post-ai-business-skill/Issue 060 – "Inside a Room With 40+ Million-Copy Bestselling Authors" → https://ryanlevesque.net/inside-a-room-with-40-million-copy-bestselling-authors/Connect & CTA 🎯 👉 Enjoyed this? Subscribe & leave a review on Apple Podcasts.🎁 Join 100 000+ digital entrepreneurs who get Ryan's "Strategic Insights for Digital Entrepreneurs Who Think Differently" every weekend: https://ryanlevesque.net/join-the-digital-contrarian/Credits Host: Ryan Levesque © 2025 RL & Associates LLC. All rights reserved.

Aug 9, 2025 • 6min
TDC 060: Inside a Room With 40+ Million-Copy Bestselling Authors
TDC 060: Inside a Room With 40+ Million-Copy Bestselling AuthorsSeven powerful lessons from the literary equivalent of the NBA All-Star team.Episode SummaryIn 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 there's no single "right way" to achieve massive success.Question of the Day 🗣️Which of the seven quotes hit you the hardest? Leave a comment to let me know!Key Take-awaysThere are many things where good enough is good enough, but writing a book isn't one of themThe secret to short-form video is using series, not just storiesYou're robbing the world of yourself if you pretend to be someone elseEvery person has 5-7 defining pivot points—pick one to start your storyAbove all else, optimize for transformation in your workTimestamped Outline ⏱️00:00 – My invitation to the literary "Dream Team" 01:39 – The standing ovation keynote (and plaid shirt controversy) 02:27 – James Clear on writing excellence 02:43 – Pat Flynn's secret to short-form content 02:58 – Dr. Mike Bechtel on authentic living 03:06 – Don Yeager's storytelling framework 03:20 – Hal Elrod's powerful health decision 04:00 – Alex Witkowski on what makes books readable 04:16 – Joseph Wynn on optimizing for transformation 04:38 – The surprising truth about million-copy success 05:30 – What this means for your path forwardLinks & Resources 🔗Get on the waitlist for Return to Real book → https://ryanlevesque.net/return-to-real-book/Books mentioned: Atomic Habits, Worthy, Building a Story Brand, Launch, Profit First, Two Weeks Notice, Limitless, Don't Believe Everything You Think, The Miracle MorningConnect & CTA 🎯 👉 Enjoyed this? Subscribe & leave a review on Apple Podcasts.🎁 Join 100 000+ digital entrepreneurs who get Ryan's "Strategic Insights for Digital Entrepreneurs Who Think Differently" every weekend: https://ryanlevesque.net/join-the-digital-contrarian/Credits Host: Ryan Levesque © 2025 RL & Associates LLC. All rights reserved.

Aug 2, 2025 • 13min
TDC 059: Live Wild or Die Boring (Part 1)
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 SummaryIn 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 nature walks boost creativity by 60%, and understand why tech founders won't use their own products.Question of the Day 🗣️When was the last time you spent a full day in nature without digital devices? What did you notice? Share in the comments!Key Take-awaysPeople in concrete environments are 12% more likely to die early than those surrounded by natureChildren with limited nature access are 55% more likely to develop depression later in lifeFour-day wilderness trips boost creativity and problem-solving by 50%Nature walks increase innovative thinking by 60% compared to indoor walkingWorld-changing inventions like Velcro and bullet trains were inspired by natureTimestamped Outline ⏱️00:00 – Live wild or die boring00:32 – My experience recording Return to Real 02:10 – How the modern digital way of life has left us dumbed down 04:02 – Rewild your life, rewire your brain 04:49 – The shocking health impacts of nature deprivation 06:22 – Why your next breakthrough will come from nature, not screens 08:18 – The science of nature's effect on creativity 10:09 – Why tech founders don't use their own products 11:43 – The real solution to digital addictionLinks & Resources 🔗Get on the waitlist for Return to Real book → https://ryanlevesque.net/return-to-real-book/Issue 053 of The Digital Contrarian – "Between Death and Danger is the Path"PLOS One wilderness creativity studyStanford walking and innovation researchConnect & CTA 🎯 👉 Enjoyed this? Subscribe & leave a review on Apple Podcasts.🎁 Join 100 000+ digital entrepreneurs who get Ryan's "Strategic Insights for Digital Entrepreneurs Who Think Differently" every weekend: https://ryanlevesque.net/join-the-digital-contrarian/Credits Host: Ryan Levesque © 2025 RL & Associates LLC. All rights reserved.


