

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

Dec 20, 2025 • 12min
TDC 079: The Tension Between Resistance & Productive Procrastination: How to Know When It's Time to Ship
TDC 079: The Tension Between Resistance & Productive Procrastination: How to Know When It's Time to ShipWhen productive procrastination crosses the line into destructive resistance—and the simple test to know when you must finally ship.Episode SummaryIn 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 avoidance, discover why original thinkers are "quick to start but slow to finish," and uncover a simple litmus test for knowing when your creative window is closing.Question of the Day 🗣️What's the one project you've been "productively procrastinating" on—and if you're honest with yourself, has it crossed the line into resistance?Key Take-awaysProductive procrastination is idea incubation, not laziness—it's where creative magic happensOriginal thinkers feel doubt but keep it pointed at the idea, not themselvesThere's a thin line where incubation quietly turns into avoidance and resistanceCreative windows don't stay open forever—market conditions change and energy wanesSimple test: Is your procrastination producing new insight or just new excuses?Timestamped Outline ⏱️00:00 – Introduction: The tension between resistance & productive procrastination00:27 – My biggest unfinished project: The Return to Real book01:00 – Why I've been procrastinating (my string of excuses)02:31 – At some point you just need to ship the damn thing03:19 – James Clear: "Writing a book is not good enough is good enough"03:48 – The power of productive procrastination04:28 – Adam Grant's core argument: Idea incubation05:20 – The truth about creative work and windows06:15 – How do you know when it's time to ship?07:27 – When resistance rears its ugly head08:15 – The simple litmus test: Insight vs. excuses08:56 – Three rules of thumb for when to ship09:52 – Pressfield's rally cry: The more scared, the more sure10:07 – Your pep talk: Get your butt in gear and ship10:34 – Holiday wishes & winter solstice message11:02 – January 8th Town Hall event announcementLinks & Resources 🔗Issue 060 of The Digital Contrarian – "Inside a Room with 40+ Million-Copy Bestselling Authors" → https://ryanlevesque.net/inside-a-room-with-40-million-copy-bestselling-authors/Issue 027 of The Digital Contrarian – "Building Your Strategic Content Ecosystem" → https://ryanlevesque.net/strategic-content-ecosystem/Join the Return to Real Book Waitlist → https://ryanlevesque.net/return-to-real-book/Apply for Return to Real Agency (February 2026 Cohort) → https://www.ryanlevesque.net/applyConnect & 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 © 2026 RL & Associates LLC. All rights reserved.

Dec 13, 2025 • 15min
TDC 078: 12 Days in Austin: Business Lessons, Dad Fails, and Why the AI Backlash is Coming
TDC 078: 12 Days, 12 Takeaways: Lessons from Austin That Will Change How You Think About Business & LifeThe last mile is the one that matters most—and why most entrepreneurs quit right before their breakthrough.Episode SummaryIn 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 backlash requires immediate brand strategy shifts, discover the 4-step plan for raising multi-millionaire kids, and understand why hosting dinners beats Facebook ads for ROI.Question of the Day 🗣️What's one habit that's keeping you small right now and no longer serving who you want to become?Key Take-awaysStanding ovations happen in the last 60 seconds—most people remember sentences, not booksA committed group will raise the average together when focused on shared improvementThe AI backlash is coming as 162,000+ layoffs create anti-AI sentiment—prepare your brand nowHosting dinners for friends offers better ROI than spending the same cash on Facebook adsIf it requires daily discipline, it's a badly designed system—successful people need less willpowerTimestamped Outline ⏱️00:00 – Introduction: 12 Days, 12 Takeaways00:54 – Day 1: The Last Mile Matters Most02:42 – Day 2: A Committed Group Raises the Average03:25 – Day 3: Laugh at Yourself in Public04:15 – Day 4: Enjoy the Mess Before It's Gone05:00 – Day 5: The AI Backlash is Coming06:18 – Day 6: Dinners Beat Facebook Ads07:11 – Day 7: Heart, Humor, Humanity & Hilarity08:05 – Day 8: How to Raise Multi-Millionaire Kids10:28 – Day 9: What Strengthened, Surprised & Needs Evolution11:00 – Day 10: No Deal Goes in a Straight Line12:34 – Day 11: Daily Discipline = Bad System Design13:17 – Day 12: A Man Admits His Mistakes14:56 – Closing Thoughts: Who Needs Your Hug?Links & Resources 🔗Issue #077 of The Digital Contrarian – "True Self vs. Strategic Self"→ https://ryanlevesque.net/true-self-vs-strategic-self/→ https://youtu.be/Va41rZ3TJCMWork with Ryan's agency to build your Strategic Content Ecosystem → https://www.ryanlevesque.net/applySubscribe 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© 2026 RL & Associates LLC. All rights reserved.

Dec 6, 2025 • 11min
TDC 077: The 4 Types of Driven Entrepreneurs (And Why You're Secretly Seeking Validation)
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 uncover how childhood wounds show up in your business today.Question of the Day 🗣️Which of the 4 archetypes do you most identify with—The Lone Wolf, The Fighter, The Knight in Shining Armor, or The Achiever?Key Take-aways:Your True Self serves your needs; your Strategic Self serves others—there's no Choice CFour archetypes emerge from childhood: Lone Wolf, Fighter, Knight, and AchieverThe Achiever pattern drives hyper-performance while burying parts you learned to hateThe ASK Method can cause you to lose yourself by always serving market needs first"When you're busy seeking validation of the few, you cannot impact the many"Timestamped Outline ⏱️00:00 – Introduction: True Self vs Strategic Self00:50 – This episode will be different (more personal)01:25 – A question to begin all questions02:07 – Front Row Dads Live event context02:41 – Something I did as a dad I'm not proud of04:04 – Your True Self vs Strategic Self explained05:49 – The four archetypes for coping with unmet needs07:11 – My pattern: The Achiever playbook09:25 – Philip McKernan's 14 words to live by10:37 – Final thoughts & wrap-upLinks & Resources 🔗Issue #044 of The Digital Contrarian – "Top 10 Contrarian Business Frameworks" → https://ryanlevesque.net/top-10-contrarian-business-frameworks/Issue #067 of The Digital Contrarian – "3-Part RTR AI Business Model Opportunity" → https://ryanlevesque.net/3-part-rtr-ai-business-model-opportunity/Related video: "3-Part RTR AI Business Model" → https://youtu.be/HhystvcW2B8Issue #074 of The Digital Contrarian – "The First Trillion-Dollar Thought Leader" → https://ryanlevesque.net/the-first-trillion-dollar-thought-leader/Related video: "The First Trillion-Dollar Thought Leader" → https://youtu.be/Sz4ZKYT2yRwSubscribe 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© 2026 RL & Associates LLC. All rights reserved.

Nov 29, 2025 • 8min
TDC 076: Worldviews from Viewers: Real Perspectives On How to Make Sense of this Post-AI World...
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 SummaryIn 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 complexity, and hear perspectives that might challenge your own assumptions.Question of the Day 🗣️Which of these seven worldview principles resonates most with you? Where do you agree or disagree?Key Take-awaysYour body often knows the truth before your mind admits it—physical responses reveal when you're performing vs. being authenticHistorical patterns repeat; understanding the past helps us recognize dangerous parallels in current eventsHumans aren't inherently good or evil but have capacity for both—the need to belong drives most decisions99% of people are kindhearted when encountered one-on-one; hate comes from creating "us vs. them" dynamicsNothing in the universe happens randomly—everything is cause and effect, we just haven't found the pattern yetTimestamped Outline ⏱️00:00 – World views from readers introduction00:42 – Why today's episode is different01:40 – Principle #1: Brad Did - When your body tells the truth02:10 – Principle #2: Kurt Varner - Those who forget history02:45 – Principle #3: Kristen Carter - Neither all good nor all evil03:45 – Principle #4: Andrew Skinner - 99% of people are kindhearted04:17 – Principle #5: Randall Porter - Nothing happens at random05:03 – Principle #6: Damien Bowler - Tribe 2.0 and vertical economies05:51 – Principle #7: Jane Olinder - A new balance is coming08:01 – Final thoughts and invitation to reflectLinks & Resources 🔗👉 Issue 076 of The Digital Contrarian: "How to Craft Your Worldview with AI"📄 https://ryanlevesque.net/how-to-craft-your-worldview-with-ai/🎥 https://youtu.be/tOjQruLODlMBook mentioned: "1929: Inside the Greatest Crash in Wall Street History" by Andrew Ross Sorkin → https://www.amazon.com/1929-Inside-Greatest-History-Shattered/dp/0593296966Connect & 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.

Nov 22, 2025 • 20min
TDC 075: How To Craft Your Worldview With AI
TDC 075: How To Craft Your Worldview With AIWhat I learned at Tony Robbins and Dean Graziosi's $250,000 private mastermind this week.Episode SummaryIn 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 real results.Question of the Day 🗣️What's one principle that deeply shapes how you see the world, and where did it come from?Key Take-awaysYour worldview is the combination of what you believe is true, patterns you notice, and how you actThe world operates cyclically not linearly—learn the cycle and phase to predict what's nextEnergy is the base layer of everything; capitalism is just turning energy into useful stuffThere are three levels of reality: objective, subjective, and inter-subjectiveGreen fruit marketing focuses on nurturing prospects over time, not just picking ripe fruitTimestamped Outline ⏱️00:00 – Cold open & hook00:39 – Your hidden operating system: why worldviews matter02:38 – Deep convictions loosely held: three lenses04:11 – The world operates cyclically, not linearly06:47 – Energy is the base layer of human experience07:52 – Three levels of reality: objective, subjective, inter-subjective09:01 – Lessons from a $40 million product launch11:23 – How to build your worldview with AI11:52 – Step 1: Surface what you already have12:33 – Step 2: Articulate 5-10 strong beliefs loosely held13:26 – Step 3: Choose your faculty of thinkers15:00 – Step 4: Stress test with dissonance15:48 – Step 5: Connect worldview to real decisions17:14 – Step 6: Create a review rhythm18:24 – Your turn: one principle reshaping your worldviewLinks & Resources 🔗👉 Issue 046 of The Digital Contrarian: "Brace for Impact"📄 https://ryanlevesque.net/brace-for-impact/ 👉 Issue 022 of The Digital Contrarian: "How to See Hidden Patterns"📄 https://ryanlevesque.net/hidden-patterns-others-completely-miss/ 👉 Issue 028 of The Digital Contrarian: "The Return to Real Movement"📄 https://ryanlevesque.net/the-return-to-real-movement/ 👉 Issue 042 of The Digital Contrarian: "How to Keep Your Head Straight…"📄 https://ryanlevesque.net/how-to-keep-your-head-straight/ 👉 Get on the waitlist for "The Return to Real": https://ryanlevesque.net/return-to-real-book/ 👉 Subscribe to The Digital Contrarian newsletter: https://thedigitalcontrarian.com Each week, I share frameworks and contrarian strategies for finding meaning and building resilience in both business and life.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.

Nov 15, 2025 • 10min
TDC 074: The First Trillion Dollar Thought Leader: Being Known for How You Think, Not What You Consume
TDC 074: The First Trillion Dollar Thought Leader: Being Known for How You Think, Not What You ConsumeWhy being known for how you think beats influence every time.Episode SummaryIn 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 building your own trillion-dollar personal brand.Question of the Day 🗣️Are you planting fruit trees or ordering DoorDash with your content strategy? What's one idea you could turn into an email this week?Key Take-awaysInfluencers rent attention from algorithms; thought leaders build mental real estate in decision-makers' mindsMarkets already treat certain personal brands as multi-billion dollar assets (see: Elon Musk's pay package)Thought leadership lives in the "important but not urgent" quadrant—it's fruit tree behavior, not DoorDash behaviorMost people never build one because they chase quick hits instead of planting for generationsStart with one email about one idea you have energy around right now—then do it weekly for 12 weeksTimestamped Outline ⏱️00:00 – The trillion dollar thought leader shift00:21 – Influencers vs thought leaders: The wrong game01:36 – Elon Musk's trillion dollar personal brand02:06 – What thought leadership actually buys you today02:22 – Company value and deal flow (Edelman LinkedIn data)03:31 – Optionality: When opportunities find you04:07 – Talent magnetism: Attracting operators who think04:34 – Durability: Personal anti-fragility05:32 – Why doesn't everyone build one?05:47 – The fruit tree vs DoorDash behavior07:06 – The "no shortcuts across the green" rule08:20 – Your small unsexy immediate next step09:34 – Closing thoughtsLinks & Resources 🔗Issue #022 of The Digital Contrarian – "How to See Hidden Patterns Others Completely Miss" → https://ryanlevesque.net/hidden-patterns-others-completely-miss/Issue #028 of The Digital Contrarian – "The Return to Real Movement" → https://ryanlevesque.net/the-return-to-real-movement/Issue #042 of The Digital Contrarian – "How to Keep Your Head Straight…" → https://ryanlevesque.net/how-to-keep-your-head-straight/Issue #046 of The Digital Contrarian – "Brace for Impact: 3 Converging Forces…" → https://ryanlevesque.net/brace-for-impact/Strategic Content Ecosystem Service → https://www.ryanlevesque.net/apply"Return to Real" book waitlist → https://ryanlevesque.net/return-to-real-book/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.

Nov 8, 2025 • 8min
TDC 073: The Efficiency vs. Resiliency Dilemma: Why Your "Optimized" Business Might Be Dangerously Fragile
TDC: The Efficiency vs. Resiliency DilemmaWhat'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 weather any storm.Question of the Day 🗣️Where is your business most vulnerable right now? Are you overly dependent on a single traffic source, platform, or channel?Key Take-awaysEfficiency often comes at the expense of resiliency, creating massive business vulnerability77% of mobile Google searches now result in zero clicks, effectively killing SEO as a traffic sourceSingle-channel dependency in the post-AI world is an existential business threatStrategic content ecosystems provide the diversification needed for business antifragilityYou can achieve resiliency without complexity by hiring teams to manage your content ecosystemTimestamped Outline ⏱️00:00 – Introduction: The efficiency vs. resiliency dilemma00:31 – The efficiency-resiliency spectrum explained01:46 – Farm optimization: Why we choose resiliency over efficiency02:12 – The Irish Potato Famine: A warning about monoculture dependency03:18 – The shocking truth about global food biodiversity loss03:41 – The zero-click reality killing SEO04:28 – Why single-channel dependency is a business death sentence04:48 – The strategic content ecosystem alternative05:38 – Understanding the resiliency trade-off06:24 – How to achieve resiliency without the complexity06:54 – The Digital Contrarian content ecosystem model07:19 – Final thoughts & CTALinks & Resources 🔗Strategic Content Ecosystem Service Priority Waitlist → https://www.ryanlevesque.net/applyIssue #003 of The Digital Contrarian – "The Zero-Click Reality" → https://ryanlevesque.net/decision-making-framework-for-entrepreneurs/ 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.

Nov 1, 2025 • 4min
TDC 072: How to Become A "Category of One" Thought Leader.
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 consideringStrategic content ecosystems can syndicate across 37 formats and channelsTimestamped Outline ⏱️00:53 – Results from the framework approach01:14 – Agency work and strategic content ecosystems02:09 – The three questions framework introduction02:13 – Question 1: Why NOW?02:29 – Question 2: Why THIS?02:47 – Question 3: Why YOU?03:05 – Reflection prompt for your businessLinks & Resources 🔗Priority waitlist for agency clients → https://www.ryanlevesque.net/applySubscribe 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.

Oct 25, 2025 • 12min
TDC 071: How to Get Your Website to Show Up in ChatGPT…
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-awaysChatGPT usage doubled to 16 min/day while Google search time declined to 18.2 min/dayOptimize content for concepts and semantic meaning, not just keywordsAI models often stop after reviewing just 100 lines of contentVector embeddings measure semantic similarity using cosine angles between textEntity graphs reveal how AI connects your brand to relevant concepts and competitorsTimestamped Outline ⏱️00:00 – Cold open & hook01:14 – The data proving ChatGPT is eating Google's lunch02:09 – Why AEO is the new SEO03:01 – Key Concept #1: Vector Embeddings explained04:22 – The paradigm shift: Keywords → Concepts04:53 – Key Concept #2: Entity Graphs06:33 – How to do an Entity Graph Gap Analysis07:00 – Key Concept #3: Information Gain Rate & Time to Answer08:46 – How to optimize IGR and TTA for your content09:30 – Final thoughts: The first mover advantage10:22 – Building your strategic content ecosystemLinks & Resources 🔗Apply for Strategic Content Ecosystem → https://www.ryanlevesque.net/applyGoogle Natural Language API → https://cloud.google.com/natural-languageSubscribe to The Digital Contrarian newsletter → https://thedigitalcontrarian.comPrivate 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-waitlistConnect & 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.

Oct 18, 2025 • 16min
TDC 070: Seven "Non-Obvious" Email Lessons I've Learned Writing This Email Newsletter Each Week.
TDC 070: Seven "Non-Obvious" Email Lessons I've Learned Writing This Email Newsletter Each Week.Episode SummaryIn 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-awaysCustom AI dashboards beat vanity metrics – track engagement scores, not just opens and clicksLess AI in writing process correlates directly with higher reader engagement scoresCreative fecundity is essential – you never know which piece will break throughBuffer days between writing and sending prevent newsletter stress and missed deadlinesMake it great before you make it grow – optimize for impact, then scaleTimestamped 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 success08:38 – Lesson #4: Keep your cutting room floor09:20 – Lesson #5: Build in a buffer day11:25 – Lesson #6: Make it non-negotiable (decide to win)13:25 – Lesson #7: Make it great before you make it grow14:26 – All 7 lessons recapLinks & 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/BAnNrTQC47MIssue 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_LP2oYcIssue 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/tbDx0R2j0GQPrivate 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-waitlistConnect & 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.


