The Digital Contrarian

TDC #083 Part 4: The "Contrarian Canon" (Continued)

• Ryan Levesque • Episode 83

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0:00 | 4:02

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 life or business that you've never told publicly—but probably should? Drop it in the comments.


Key Take-aways

  • Storytelling is becoming the ultimate differentiator in a post-AI content landscape
  • Raw, imperfect moments create tension—polished AI content can't replicate that
  • Three story types give you a framework for any situation
  • Stories sell faster than features (a $130 profit in 20 minutes proves it)
  • OpenAI launching ads in ChatGPT—predicted back in Issue 20


Timestamped Outline

0:00 – Introduction: The Contrarian Canon Part 4
0:08 – Embarrassing mistake: Getting "canon" wrong
0:46 – ChatGPT can't make human mistakes
0:52 – OpenAI launches ads (predicted in Issue 20)
1:08 – Kids building retail arbitrage business
1:27 – $130 profit in 20 minutes using stories
1:54 – How stories made the sale happen fast
2:06 – Focus: Storytelling and selling your stuff
2:26 – Most scalable post-AI business skill
2:35 – Why storytelling creates connection
2:44 – Polished AI content vs. raw human stories
3:00 – Bear in the woods: Raw moments create tension
3:13 – Three story types breakdown
3:24 – Practical storytelling toolkit for business
3:37 – Link to full issue in description
3:46 – Closing thoughts and sign-off


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Credits

Host: Ryan Levesque © 2026 RL & Associates LLC. All rights reserved.

The Contrarian Canon Part 4, and how to use stories in unconventional ways to sell your stuff. Something happened this week that was a little embarrassing. A client sent me a note to let me know that in this series, The Contrarian Canon, I had been using, in some places, the wrong form of canon.

I was using the one with two N's, i.e. the one for firing cannonballs. And while I wish I could say that there was a clever double meaning behind it, alas, it was just a mistake from a bleary-eyed writer working hard to finish his book, Manuscripts, in my case, for my upcoming book, Return to Real. Now, the only saving grace is that at least you know that my writing hasn't come from ChatGPT, which, I don't know, would have gotten wrong.

By the way, in case you hadn't heard, ChatGPT's creator, OpenAI, just announced this week that they are launching ads. This is a pretty big deal, and something that we predicted way, way, way, way, way back in Issue 20 of The Digital Contrarian, and something I'll have more to say about what this means and the opportunity it presents once I get through this manuscript. Speaking of which, while I've been deep in manuscript mode these past few weeks, my kids have been deep in the process of building a little business.

They're learning about retail arbitrage, finding items locally that they can flip on eBay and Poshmark for a profit, like the Fall Raven parka in this photo. It retails on the website for $535. They found it locally on Clearance for $169 and were able to sell it on eBay for $329.

In fact, it sold within 20 minutes of posting, and they made a cool $130 profit after fees. So they are quickly seeing firsthand that being a business owner can be a lot more lucrative than getting a J-O-B. How did the item sell so quickly? Well, they're learning the power of using stories to sell in their listings to make their postings more memorable and stand out, which brings us to the focus of today's newsletter, storytelling and how to use stories to sell your stuff.

Building on where we started in part one, part two, and part three of the Contrarian Canon 1N series from the last three weeks, I've pulled yet another one of the most powerful but overlooked key ideas that I wrote about this past year, and one that I think is worth doing a deep dive into today. This one is all about why storytelling might be the most scalable post-AI business skill from issue number 56. Storytelling isn't just the path to connection.

It might just be the most scalable skill that we have left. In this issue, we make the case that in a world increasingly drowning in polished, optimized, and increasingly AI-generated content, story is what cuts through the clutter. And because stories don't just inform and educate, they connect.

Now we start with a vivid real-world moment, a bear in the woods, me wearing Crocs with socks, and a crusty old stick, to show why raw human scenes create the kind of tension that makes people lean in. Then we turn storytelling into something that you can actually use. We break down the three story types and share five contrarian tips for making your stories more compelling.

What you'll get if you double-click is a practical storytelling toolkit that you can immediately apply in emails and marketing and sales pages, even simple listings, so your message stops feeling generic and starts feeling true. We'll make sure we link to the full issue in the description with this episode so you can dive right in right now. Okay, I will leave you with that for today.

Back to manuscript editing for me. Have a great rest of your day. Remember to hug the ones you love.

And until next week, I wish you all my best. Take care and talk soon.