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 than credentials, and understand how to make all roads lead naturally to you.

Question of the Day 🗣️

Which of these three questions is hardest for you to answer powerfully in your market?

Key Take-aways:

• Category of One positioning requires answering three questions in your market's mind
• "Why now?" establishes urgency by showing the old paradigm is obsolete
• "Why this?" positions your novel solution against conventional approaches
• "Why you?" creates natural authority where no other provider is worth considering
• Strategic content ecosystems can syndicate across 37 formats and channels

Timestamped Outline ⏱️

00:53 – Results from the framework approach
01:14 – Agency work and strategic content ecosystems
02:09 – The three questions framework introduction
02:13 – Question 1: Why NOW?
02:29 – Question 2: Why THIS?
02:47 – Question 3: Why YOU?
03:05 – Reflection prompt for your business

Links & Resources 🔗

• Priority waitlist for agency clients → https://www.ryanlevesque.net/apply
• 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/

Credits

Host: Ryan Levesque
© 2025 RL & Associates LLC. All rights reserved.

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 information gain rate principles that make AI systems choose your content over competitors'.

Question of the Day 🗣️

Have you tested whether ChatGPT recommends your brand when asked questions in your niche? Try it and share what you discover in the comments!

Key Take-aways

• ChatGPT usage doubled to 16 min/day while Google search time declined to 18.2 min/day
• Optimize content for concepts and semantic meaning, not just keywords
• AI models often stop after reviewing just 100 lines of content
• Vector embeddings measure semantic similarity using cosine angles between text
• Entity graphs reveal how AI connects your brand to relevant concepts and competitors

Timestamped Outline ⏱️

00:00 – Cold open & hook
01:14 – The data proving ChatGPT is eating Google's lunch
02:09 – Why AEO is the new SEO
03:01 – Key Concept #1: Vector Embeddings explained
04:22 – The paradigm shift: Keywords → Concepts
04:53 – Key Concept #2: Entity Graphs
06:33 – How to do an Entity Graph Gap Analysis
07:00 – Key Concept #3: Information Gain Rate & Time to Answer
08:46 – How to optimize IGR and TTA for your content
09:30 – Final thoughts: The first mover advantage
10:22 – Building your strategic content ecosystem

Links & Resources 🔗

• Apply for Strategic Content Ecosystem → https://www.ryanlevesque.net/apply
• Google Natural Language API → https://cloud.google.com/natural-language
• Subscribe to The Digital Contrarian newsletter → https://thedigitalcontrarian.com
• Private Advisory (7-8 figure business owners) → https://ryanlevesque.net/1-1-vip-waitlist/
• Strategic Mastermind (6-7 figure entrepreneurs) → https://ryanlevesque.net/strategic-advisory-group-mastermind-waitlist

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.

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 lessons resonates most with you? Drop a comment and let me know!

Key Take-aways

• Custom AI dashboards beat vanity metrics – track engagement scores, not just opens and clicks
• Less AI in writing process correlates directly with higher reader engagement scores
• Creative fecundity is essential – you never know which piece will break through
• Buffer days between writing and sending prevent newsletter stress and missed deadlines
• Make it great before you make it grow – optimize for impact, then scale

Timestamped Outline ⏱️

01:26 – Lesson #1: Let data drive decisions (AI dashboard reveal)
05:03 – Lesson #2: Less AI = More engagement (the shocking data)
06:38 – Lesson #3: Creative fecundity is the key to success
08:38 – Lesson #4: Keep your cutting room floor
09:20 – Lesson #5: Build in a buffer day
11:25 – Lesson #6: Make it non-negotiable (decide to win)
13:25 – Lesson #7: Make it great before you make it grow
14:26 – All 7 lessons recap

Links & Resources 🔗

• Issue 001 of The Digital Contrarian – "An Embarrassing Confession" → https://ryanlevesque.net/authentic-business-communication-confession/
• Issue 027 of The Digital Contrarian – "Your Strategic Content Ecosystem" → https://ryanlevesque.net/strategic-content-ecosystem/
• Issue 058 of The Digital Contrarian – "Bombshell Week in AI" → https://ryanlevesque.net/bombshell-week-in-ai/
  • Related video: "Bombshell Week in AI" → https://youtu.be/BAnNrTQC47M
• Issue 062 of The Digital Contrarian – "Is the AI Bubble Bursting??" → https://ryanlevesque.net/is-the-ai-bubble-bursting/
  • Related video: "Is the AI Bubble Bursting??" → https://youtu.be/153Y_LP2oYc
• Issue 066 of The Digital Contrarian – "A Crazy Person's Guide to Living Life" → https://ryanlevesque.net/a-crazy-persons-guide-to-living-life/
  • Related video: "A Crazy Person's Guide to Living Life" → https://youtu.be/tbDx0R2j0GQ
• Private Advisory (7-8 figure business owners) → https://ryanlevesque.net/1-1-vip-waitlist/
• Strategic Mastermind (6-7 figure entrepreneurs) → https://ryanlevesque.net/strategic-advisory-group-mastermind-waitlist

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.

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 between major AI players, and uncover a potential opportunity hiding in OpenAI's recent job postings that could rival the early days of Facebook Ads.

Question of the Day 🗣️

Where do YOU think we are on the AI bubble curve? Share your perspective in the comments below!

Key Take-aways

Enterprise AI adoption has fallen from 14% to 12% between June and August 2025—unprecedented for any new technology
The NASDAQ curves from the dot-com bubble (1998-2001) mirror today's AI-driven market almost identically
Circular AI deals between OpenAI, Nvidia, and AMD echo the financial engineering that preceded past bubble crashes
A single ChatGPT algorithm change wiped out $8 billion in Reddit's market value by reducing citations 86%
OpenAI's recent job postings suggest an ad-supported model may be coming sooner than expected

Timestamped Outline ⏱️

00:00 – The AI bubble question everyone's asking
00:08 – Why you can't see bubbles from the inside
01:40 – Where are we on the AI hype cycle curve?
02:12 – The late-stage bubble evidence piling up
03:04 – The circular AI money shell game explained
04:07 – Why 95% of enterprise AI pilots are failing
04:42 – The anti-bubble argument (and why it matters)
06:41 – Unprecedented volatility: AMD up 35%, Reddit down 22%
07:36 – The neuroscience of staying calm in chaos
08:23 – OpenAI's next move: The biggest opportunity since Facebook Ads?
08:59 – New agency service announcement

Links & Resources 🔗

Issue #068 of The Digital Contrarian – "Why Your $20/month AI tool is about to cost $500..." → https://ryanlevesque.net/your-20-month-ai-tool-is-about-to-cost-500/

Issue #039 of The Digital Contrarian – "Right Thesis, Wrong Timing?" → https://ryanlevesque.net/right-thesis-wrong-timing/

Derek Thompson's "This Is How the AI Bubble Will Pop" → https://www.derekthompson.org/p/this-is-how-the-ai-bubble-will-pop

Bloomberg's circular AI money flow diagram → https://www.bloomberg.com/news/articles/2025-10-08/the-circular-openai-nvidia-and-amd-deals-raising-fears-of-a-new-tech-bubble

Return to Real Agency waitlist → https://go2.bucketforms.com/sf/8a8a42b9

1:1 VIP Client waitlist → https://ryanlevesque.net/1-1-vip-waitlist/

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.

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, 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-aways

• OpenAI loses $1.35 for every dollar of revenue despite its $500 billion valuation
• The AI sector exhibits textbook bubble behavior with negative unit economics
• Current AI pricing is artificially low, subsidized by venture capital funding
• A 25x price increase (like Netflix's evolution) is inevitable when subsidies end
• Build contingency plans now before your AI-dependent business model breaks

Timestamped Outline ⏱️

00:00 – The $500 AI price shock is coming
01:04 – Inside the town hall: What we covered
01:58 – OpenAI's terrifying financials revealed
03:13 – The math problem that makes no sense
03:58 – When the AI subsidy ends
05:30 – What this means for your business
06:03 – The Netflix playbook: $8 to $200/month
07:22 – Build your contingency plans now

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/

Credits

Host: Ryan Levesque
© 2025 RL & Associates LLC. All rights reserved.

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 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-aways

• Paid media costs on Meta are at their lowest levels in over a year for the first time in nearly two years
• Major AI infrastructure deals (300BOracle−OpenAI,300B Oracle-OpenAI, 300BOracle−OpenAI,100B NVIDIA-OpenAI) signal a fundamental market shift
• A three-part RTR AI business model opportunity exists for those who take action now
• Most entrepreneurs are unaware of this shift, creating a major competitive advantage
• Live town hall registration is capped at 300 attendees and expected to fill quickly

Timestamped Outline ⏱️

00:00 – Welcome to Episode 67
00:33 – Six major market observations taking shape
00:58 – Paid media costs finally coming back to earth
01:40 – Major AI infrastructure deals reshaping the landscape
02:25 – The market shift most people are missing
02:58 – Announcing live town hall event
03:25 – Three important registration details
04:05 – Keeping today's episode short

Links & 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.html
• Meta'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/

Credits

Host: Ryan Levesque

© 2025 RL & Associates LLC. All rights reserved.

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 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-aways

• Every AI usage category reveals where people are yearning for what's deeply human and authentic
• Personal writing (18%) shows hunger for genuine voice—opportunities in storytelling and book clubs
• Tutoring (10.2%) reveals desire for someone who sees you—think micro schools and apprenticeships
• Health/fitness (5.7%) shows craving to feel alive—outdoor adventure travel is fastest growing tourism
• The subtext of all AI usage: people want more time doing what's really meaningful and precious

Timestamped Outline ⏱️

00:00 – A crazy person's guide to living in an AI world
01:16 – OpenAI's groundbreaking usage study revealed
02:30 – The overlooked angle everyone's missing
03:27 – Why each AI vertical reveals human hunger
04:08 – Wedge #1: Personal Writing (18%) - Heart, Humor, Humanity
04:50 – Wedge #2: Tutoring (10.2%) - Hands in the Dirt
05:06 – Wedge #3: How-To Advice (8.5%) - Going Analog
05:46 – Wedge #4: Health & Fitness (5.7%) - Best Things Don't Scale
06:17 – Wedge #5: Translation (4.5%) - Oxytocin Over Dopamine
07:03 – Wedge #6: Programming (4.2%) - Category of One
07:51 – Wedge #7: Products (2.1%) - Between Death and Danger
08:26 – The real subtext behind all AI usage
09:03 – Why I stay up past midnight beating this drum
09:42 – Your call to action: Bang your drum

Links & Resources 🔗

OpenAI ChatGPT Usage Study (NBER Working Paper) → https://www.nber.org/system/files/working_papers/w34255/w34255.pdf
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.

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 the Day 🗣️

What's your biggest takeaway from the 27 Vermont insights? Which one could transform your business?

Key Take-aways

• The $1.5 billion Anthropic settlement signals a shift from the "Napster era" to the "Spotify era" of AI
• YouTube may be the next AI battleground as the last non-AI powered search engine
• Single source of truth content can generate viral breakthrough results (27K+ views in 18 weeks)
• Strategic content ecosystems outperform shallow algorithm gaming every time
• Vermont Farm Mastermind revealed 27 transformative business and life insights

Timestamped Outline ⏱️

00:00 – The AI battle brewing beneath the surface
00:48 – $1.5 billion Anthropic settlement breakdown
02:15 – From Napster era to Spotify era of AI
03:40 – YouTube as the next AI battleground
04:30 – Town Hall announcement: October 2nd
05:35 – Unexpected YouTube breakthrough explained
06:35 – Vermont Farm Mastermind experience
07:25 – 27 takeaways from Maeve Ferguson's perspective

Links & 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-levesques
• Check 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/

Credits

Host: Ryan Levesque
© 2025 RL & Associates LLC. All rights reserved.