The Digital Contrarian

TDC 056: Storytelling, the most scalable post AI business skill worth building

• Ryan Levesque • Episode 56

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#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 need to master, and find five contrarian tips for telling better stories that cut through the noise.

Question of the Day 🗣️

Where might you tell a story instead of simply dropping more content this week?

Key Take-aways

  • Stories travel and stick while other content gets forgotten quickly
  • While the best things in life don't scale, stories absolutely do
  • Three story types needed: first person (you), second person (someone you know), third person (out there)
  • Start with maximum tension, not context or setup
  • The parts you're tempted to skip are what audiences crave most

Timestamped Outline ⏱️

00:00 – The most scalable post-AI business skill
00:08 – Face-to-face with a bear (in crocs with socks)
01:13 – Why stories create deeper connection than any other content
03:51 – What 145 stories taught me about scale and connection
04:55 – The Winnie the Pooh effect: why stories scale across generations
09:30 – The power of shared stories as connective tissue
10:36 – Harari's insight: how stories built human civilization
13:00 – What makes a story captivating (not just nice)
18:19 – The three story types you need to master
24:44 – Five contrarian tips for telling better stories
28:18 – The one question to ask yourself this week

Links & Resources 🔗

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Credits

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

Storytelling, the most scalable post AI business skill worth building. Crocs, socks, and a crusty old stick. So last night, just before dark, when I was out on the farm doing my final rounds for the evening, I noticed something was eerily off with the cows.

Every single one of them was frozen, eyes locked, not on me, but on the woods. Just seconds before I'd been checking the hives, the bees quietly humming their evening lullaby. When suddenly, the unmistakable sound of branches breaking echoed out of the darkness, my heart started to thud in my chest.

And there it was, a massive shadow, lumbering closer and closer and closer to me through the trees. It was a bear, and not a small one. Now, there are certain moments when reality becomes surreal.

And there I stood alone in the darkness, face to face with an adult black bear. Armed with nothing but a crusty old stick, and of course my deeply regrettable fashion choice, crocs with socks. It was a moment that made me feel wildly unprepared, vulnerable, and exposed.

But it also brought me instantly back to another moment, one that you might remember from issue number 23 of the Digital Contrarian. The secret power of being unprepared. A moment when I found myself wide awake at 127 AM in a UK hotel room, my heart pounding for a completely different reason.

Staring at the ceiling, realizing I was hours away from stepping onto a stage with an unfinished keynote for Chris Ducker's event, in front of over 100 paying attendees. Now, both stories share a single uncomfortable truth. There's something deeply raw and real about being unprepared.

And when you share those kinds of stories, the messy, the authentic, the unfiltered ones, people can't help but lean in. The proof? Well, according to my Google Analytics account, issue number 23, the one where I tell that play by play story of being massively unprepared before my UK keynote, is one of my all time highest time spent on page issues of the Digital Contrarian. Because a compelling story doesn't just capture attention, it creates a connection between you and your reader.

In fact, I believe storytelling isn't nearly a nice to have skill in this post AI era. In our fractured, distracted, and increasingly disconnected digital world, I believe that it might just be the single most scalable skill that you can develop. Because stories travel and stories stick.

Stories are how you sell products. Stories are how you raise money. Stories are how you recruit employees and partners.

And as you've all know, Harari argues in Sapiens, stories are what enabled humans, a mere hairless ape, to transcend small tribes and scale up to global civilizations. We cooperate, we coordinate, and we collaborate at massive scales, not because of logic or force, but because of the common fictions, narratives, and stories that we share. So today I want to dive into the skill and science of storytelling.

Because as someone who spent the last week curating the stories that I'm going to be telling in my upcoming book, Return to Real, I've realized something profound. If the best things in life don't scale, one thing absolutely does. And that is stories.

And that makes storytelling arguably the most valuable skill that we can refine as entrepreneurs, because in this world of fractured realities and short attention spans and AI-generated content, he or she who can cut through the clutter and tell the best story wins. So let's talk about how. What 145 stories taught me about scale, connection, and Winnie the Pooh.

Over the last week, with the help of Chad Cheapy T, I've been neck deep in curating stories for my upcoming book. And right now I've got over 145 stories, and counting, that have passed through my fingertips, each one a snapshot of life, of business, or a moment when someone chose to take the road less traveled. It's been an illuminating process, because as you may know, one of the contrarian principles in the Return to Real is, the best things in life don't scale.

The stuff that truly fills us up in what much of the world is craving, the meaningful relationships, the slow food dinners, the deeply rewarding work, doesn't come from optimizing, or automating, or scaling to the nth degree. It comes from depth, it comes from being present, it comes from being intentional with your time. The very things that digital tools, as seductive and convenient as they are, often strip away.

But as I've dug deeper into these 145 stories, I've realized something fascinating. Stories may be the exception to that rule, because while the best things in life don't scale, something I truly believe, stories at their core actually do. Take a story, for example, that we all know, Winnie the Pooh.

The story of Christopher Robin, the 100-acre wood, and a honey-loving bear. It's a familiar narrative shared by millions of us around the globe. In fact, there are 50 million copies sold of the original book, and it's one of the best-selling books of all time.

Now the text that I'll read here in just a moment, written by an anonymous Reddit user, and which I originally discovered from a Brent Lindeke piece, is heartfelt. It's poignant, and it demonstrates why this story is so powerful. So here goes.

At the end of the Winnie the Pooh story, Christopher Robin takes Pooh to the enchanted place at Galleon's Lap, and basically lets Pooh know in ambiguous terms that this is the end of their adventures together. You see, began Christopher with a long sigh, it's like sleeping for a long, long time. Christopher Robin was surrounded by his friends under his favorite tree.

It rested on the top of a hill overlooking the entire 100-acre wood. He was older now, and he knew that he didn't have much more time left with them. But going to sleep means that someday you'll wake up, Pooh said with a smile.

Precisely, Owl exclaimed, and we'll be here when you do, Kanga added. I'll even make you breakfast. Christopher couldn't help but smile.

I would very much like that, but you all have to understand that it will be a very, very long time. Ho, ho, ho, we're great at waiting a long time. Rabbit here waits every year for the carrots to grow in the garden, Tinker chimed in.

And every year you destroy them, Rabbit snarled. But Christopher, Roo interjected, jumping into Christopher's lap. What are we going to do when you're gone? I won't be gone, Roo.

I'll be right here. Christopher placed his finger over Roo's heart. Roo giggled and scrunched up into a ball.

We'll be just fine, muttered Eeyore. I'm used to being alone anyway. None of you will be alone.

You're family now. And while I'm gone, you will all take care of each other. But you'll be right back, Christopher, stuttered Piglet.

Christopher let out a soft sigh and looked around at all his friends. It was going to be difficult to help them to understand, and they probably never would. Sometimes good things come to an end.

But here's the secret, everyone. Come close. And they all huddled together underneath the tree to listen to Christopher's secret.

Memories are forever, he whispered, and tapped Poo on the nose. Memories, said Poo? Well, I have plenty of those, like the time we saved you from the heffalumps. Or when you helped me fix my garden, cried Rabbit.

Or when you organized my library for me, exclaimed Owl. Or that time you built me the new house out of those sticks that you found in the woods, Eeyore added sullenly. It didn't last the night, but I remember it.

Yes, yes, all those are memories, and you will have them forever. Just like I will have my memories of all of you, Christopher stood up and took one last look over the 100-acre wood. The sun was setting in the orange autumn sky, and the trees were beginning to lose their leaves.

It was time he went home. Christopher gathered all of his friends together and began walking back down the hill. They were all busy discussing the memories that they had with each other.

Christopher, Poo said, looking up at Christopher as they walked hand in hand. You aren't coming back, are you? Christopher looked down at the ground and took a moment before he responded. No, Poo, I won't be coming back this time.

They walked in silence, listening to the sound of the crunching leaves underneath their feet. Poo suddenly stopped and looked intently into the ground. I believe I'm going to miss you, Christopher, he said with a soft, broken voice.

Christopher leaned down and took his lifelong friend into his arms. I will miss you too, Poo. I will miss you very, very much.

This is not just a cute children's tale. Stories like Winnie the Pooh become so powerful precisely because they scale across countries, cultures, and generations. They're viral before the word viral even existed, and yet their virality isn't digital, it's human.

In the case of Winnie the Pooh, it's a story about growing up, about the end of childhood, about death, about grief. It's about saying goodbye to the ones we love. And it's the shared stories like these that form the connective tissue that binds us together as a species.

Now in issue 54 of the Digital Contrarian, the breakdown of shared reality, I explored how we've lost so much of this connective tissue in our society. With the fragmentation of traditional media, the splintering of shared narratives, and the algorithmic echo chambers we found ourselves trapped in, our shared reality has frayed and fractured. But contrast that with what Yuval Noah Harari argues in his book, Sapiens.

What allows humans to cooperate at scale isn't reason or instinct. It's fiction. It's our capacity to tell shared stories.

And Harari makes a compelling case. We're not the fastest or strongest species. We didn't rise to dominance by raw power or logic alone.

Instead, we humans built civilizations, empires, global communities, because we learned to create shared imagined realities, stories. Money, nations, religions, these aren't objectively real entities. They're stories that we've collectively agreed upon, and they work because they scale.

In other words, storytelling isn't just a soft skill. It may just be the single most powerful and scalable technology that humanity has ever developed. So here I am, deep in these 145 stories for the return to real.

And it strikes me that in this post AI world that we find ourselves in, storytelling might just be the most valuable skill for us to focus on. Because after all, in a fragmented world that's grown increasingly disconnected from the real and the true, he or she who can both seek and speak truth, and in the process tell the best story, may just win. And that's why storytelling is something I'm personally working on, getting better at, to refine, and ultimately to master.

Because the story I shared about my own bear in the woods experience, croc socks, stick and all, is reminiscent of something that we explored together way back in issue 20 of the Digital Contrarian, Going Analog, the ultimate post AI zig. And in that issue, we explored the following. For people to trust you, they need to see three things.

They need to see your heart, your humor, and your humanity. Look, the world is hungry for all three right now. The world is hungry for connection.

The world is hungry for what's real. And because of that, in this post AI technical race to the bottom era that we find ourselves in right now, storytelling isn't just the path to connection. It might just be the most scalable skill we have left.

But the question is this, what makes a story captivating and not just nice? Now on paper, issue 23 of the Digital Contrarian, the secret power of being unprepared was a complete mess. Look, there was no framework, there was no hook, and there was no clear call to action. It was just the story of me, sitting wide awake at 1.27 AM in a Cambridge UK hotel room, my heart racing, staring into the dark, completely unprepared for the keynote that I was due to deliver in less than eight hours.

And yet it is still one of the highest time on page issues that I've ever published in the Digital Contrarian. Why is that? Because it was a compelling story. And as humans, we're wired for stories in ways that we rarely stop to consider.

Consider the opening scene. Sunday, November 17th, Cambridge UK. It's 1.27 AM, and I wake up with my heart pounding out of my chest.

I'm set to speak on stage in less than eight hours. My slides are not finished, my presentation is not done. I have a rough idea of what I want to cover, but I've never done this talk before.

This is brand new material. And on top of that, it's my first time ever delivering a keynote in the UK. And I'm starting to panic.

There are over 100 people from all over the world who have paid to be at this event. And Chris Ducker, my friend and organizer of this event, pictured with me, is counting on me to deliver. My heart starts racing as I lay there in bed, wide awake, staring into the abyss.

I could hear a lifetime of voices in my head. My mom, my wife, my business partner, my dog. Why do you always do this? Why do you always wait to the last minute for everything? There's no more time.

I need to wake up. I need to figure out what I'm going to say. Now, contrast this with your typical optimized content.

It's well-structured, it's polished, it's perfectly formatted. Sure, it might be useful, but memorable? Compelling? Not usually. It feels clinical.

It leaves no mark. The reality is this. When storytelling is absent, your content, no matter how tactical or strategic, feels sterile and generic.

Readers skim, they click away, and they forget. There's no emotional hook. There's no shared resonance.

There's no lasting impact. The mirror neurons are not firing, and no oxytocin is released. No connection is formed.

And connection is everything. It's the very thing Yuval Noah Harari argues in Sapiens allowed our species to build those civilizations and empires and global communities. Our ability to create and share these imagined reality stories is the true currency of human cooperation.

In fact, Will Storr, in his book The Science of Storytelling, describes the human brain as essentially a storytelling machine. Our brains don't simply record experiences, they encode them in narrative. As Storr explains, stories help us simulate experience, build meaning from chaos, and understand ourselves and our world.

He points out that great stories activate a chain reaction in the brain that pulls us into the minds of others, creating empathy and helping to make sense of complex realities. At its core, a story is a cause-and-effect simulation that we genuinely care about. Our minds don't just passively listen, they actively participate.

And that's why stories become sticky. They imprint on us emotionally, neurologically, and deeply. Now, compare that kind of narrative experience to, say, memes.

Sure, memes are fun. They compress ideas and they rapidly propagate, grabbing attention. But memes don't deepen understanding.

They don't create the sort of resonant trust that lasts. They're surface-level dopamine hits. They're brief, they're amusing, and they're fleeting.

Stories, especially mini-stories like the Crocs and Socks and Bear story I shared just a moment ago, pack a far more powerful punch. They ground abstract ideas in concrete experiences, emotions, and transformations. They bridge the gap between what is true and what is human.

Just think of the Winnie the Pooh excerpt that you read a moment ago. It's not just a cute story. It's a reflection on everything from growing up to loss to grief and the hard universal truth of saying goodbye.

It connects because it speaks to something universal. It scales because it taps into shared human truths. Stories, real stories, don't just capture attention.

They build connection. And here's why that matters now more than ever. In this era of fragmented realities and infinite feeds and relentless AI-generated content, as we discussed in issue number 49 of The Digital Contrarian, why oxytocin is the new dopamine, the world is optimized for dopamine.

Clicks, likes, quick fixes, cheap thrills. But what are people truly craving? Meaning. Connection.

Ultimately, oxytocin. And that's the power of story. So let's explore a bit more deeply how to tell a better story.

The three story types and why you need all three. After compiling the 145 stories for Return to Real, there's a pattern that I found helpful for thinking about what types of stories are worth sharing. Every powerful, memorable story falls neatly into one of three distinct types.

And as entrepreneurs, leaders, and creators, understanding and using all three is essential to ensuring our stories resonate, stick, and inspire. So here's how to categorize them. Number one.

First, we have first person stories. These are the stories that have happened to me or you in your case. These are your lived experiences, i.e. stories that you've personally walked through yourself.

They carry your unique voice, your unique perspective and vulnerability. They have authority because they're deeply authentic. They've happened to you.

So for example, in my case, being wide awake at 1.27am in the UK, unprepared for a keynote that I had less than eight hours from then. Or facing a bear at dusk this week in my Crocs with socks, armed with nothing but a crusty old stick. These stories resonate because they're real.

The audience feels your tension and triumph directly in your voice from your point of view. When you tell first person stories, you're offering a reader the gift of empathy. Your reader steps into your shoes and feels what you felt.

That takes us to number two. Second person stories. These are the ones that have happened to someone that you know.

Now these stories center around people that you've directly worked with or you know personally. Oftentimes these are going to be clients or customers, colleagues or peers. They're compelling because they add enough distance to highlight clear instructive transformations without sacrificing authenticity.

So for example, Ali Jafarian, a friend of mine and a peer, a founder of MemberDev who transitioned from being a burned out technologist to an outdoor adventure guide and who's now loving his life. Or Melissa Kwan, the founder of a tech company eWebinar, who chose to write openly about the struggles of bootstrapping her startup alone and as a result started getting traction in her business. Now these stories land because they come from direct observation and interaction and guidance.

You're sharing a story that you've influenced or you've shaped or you've witnessed yourself firsthand. When you tell a second person story, you illustrate a transformation. You make an abstract concept immediately relatable, believable and achievable.

That takes us to number three. Third person stories. It happened out there.

These are the stories that you reference from afar. Famous people, historical examples, compelling case studies or powerful ideas. They add weight, credibility and broader context to your message.

So for example, in this Digital Contrarian series of episodes, I've written about and spoken about Nate Hagans, explaining the great simplification and how energy drives our civilization. Or in this segment here, Yuval Noah Harari, describing how shared fictions enabled humans to scale cooperation in his book Sapiens. These stories are powerful because they help you connect the dots on a much larger scale.

They anchor your ideas and context, making your content more relevant, timely and credible. When you tell third person stories like this, you add authority and perspective, broadening your reader's aperture and validating your message. Now, here's why you need all three.

Here's the thing. You don't choose just one of these types of stories. You need all three.

Your first person stories establish intimacy and authenticity. Your second person stories provide practical evidence of transformation. Your third person stories add broader credibility and context.

So together they form a comprehensive narrative that looks like this. First person stories are there to build emotional connection and authenticity. Second person stories demonstrate practical transformation and achievable results.

Third person stories position your ideas within broader societal, historical or cultural context, reinforcing your core insights. And you want to strategically weave together all three types to make your content meaningful, memorable and genuinely impactful. Because when you blend these story types and you do so seamlessly, something powerful happens.

Your message stops sounding like theory. It stops feeling abstract. It starts feeling true and it starts feeling real.

And by the way, if you have a unique and compelling return to real story, or you know a business or a leader that you admire whose story deserves to be shared in my upcoming book, please send me an email and tell me about it. I'm finalizing the list of stories for the book right now as we speak. And I'd love to hear from you.

And that takes me to five practical and somewhat contrarian tips for telling better stories. So by now we've covered why storytelling matters and the three core types of stories that you need in your toolkit. But how do you actually tell better stories? Now, I'm not going to give you fluffy advice like, you know, be authentic or be vulnerable or anything like that.

Although that's very important. But instead, I want to give you some practical contrarian tips that you can put to use right away. So here are five of them to get you started right now.

Number one, start with the moment of maximum tension. Most storytelling advice suggests starting at the beginning. Set the scene, provide context, build slowly, etc.

But here's a contrarian take. Forget that context. Skip the setup.

Drop your reader straight into the moment of maximum tension. Just like how I opened issue 23 at 1.27 a.m. Wide awake, heart racing. Don't ease into your story.

Instead, go for the cold open. When your heart was pounding, when the stakes felt highest, and then quickly fill in the gaps. This immediately grips attention, raises questions, and pulls readers along to find out what happens next.

This takes us to number two. Don't polish too soon or too much. Now, the common advice that you'll hear is to edit ruthlessly.

Polish until perfect. But perfect stories are predictable. And predictable, frankly, is boring.

Instead, keep the awkward details. Remember, embrace your heart, humor, humanity. Reveal your embarrassing choices like Crocs with socks.

Yeah, I know, trust me. Let readers see the messy edges of your experience. Because the imperfections, the genuine details that others might remove are what make your story feel human.

And raw and real stories are always going to be more compelling than sanitized ones. Number three, say the part most people skip. Most people edit out the uncomfortable details, the moments of doubt, vulnerability, or raw honesty, thinking that they're too distracting or too personal.

Like in this image caption with issue number 23, the one where I'm sharing the story of my keynote in the UK, feigning a fake social media smile after not sleeping the night before on my flights as I walk into my hotel in Cambridge, praying to God that my hotel room is ready and they're not going to make me sleep in the lobby. Now, I didn't have to include this photo or that caption, but it adds a little bit of color to kind of demonstrate what was happening in the moments leading up to the event. Because here's the counterintuitive truth.

The parts that you're tempted to skip are precisely the parts that your audience craves most. Don't censor yourself. If a detail feels slightly uncomfortable or slightly too revealing, you're likely onto something powerful.

So lean into it, share it. It's these raw, overlooked moments that give your story emotional depth and authenticity. That takes us to number four.

Choose details that seem irrelevant but aren't. So typical storytelling advice focuses on efficiency. Stick to the relevant details.

Cut anything extraneous. But the contrarian truth, the details that initially seem irrelevant, Crocs with socks and Krusty 6, are exactly what make the stories memorable. Irrelevant details make scenes vivid and tangible.

They ground your reader in sensory experiences and they anchor emotion in physical reality. The reason why I chose to make the Crocs with socks and the Krusty old stick the hero of that story is because it really demonstrated with just a simple mental image how unprepared I was to be standing face to face with a giant black bear just a few feet away from where I was standing. And that takes us to number five.

Know the transformation even when it's subtle. So most advice suggests dramatic transformations and you hear some of these stories. Big life-changing moments.

Hollywood-level stakes. But here's what's counterintuitive. The most powerful transformations are often subtle.

They're quiet. They're internal. Maybe you didn't slay the dragon or overcome impossible odds.

Maybe you simply learned something small but profoundly important. Perhaps you changed your mind or saw a familiar situation in a new way. Even subtle transformations matter deeply because readers see their own lives reflected more clearly in quiet truths than epic adventures.

The bottom line is this. Good storytelling isn't just about structure or clever turns of phrase. It's about truth.

It's about courage. It's about sharing the things that most people leave unsaid. Because when you do, your stories become not just interesting, they become irresistible.

And readers will hang on to every single word. Before we wrap things up, I'll leave you with one final question to think about this week. And that's this.

Based on everything we've explored together in this episode, where might you tell a story instead of simply dropping more content this week? Think about it. Try it out. See what happens.

And report back to let me know. You might just be surprised at the difference that it makes and the impact that it has on your audience and in your business. Okay, I'll leave you with that for now.

Have a great rest of your day. Remember to hug the ones you love. And as always, I look forward to seeing you in the next episode.

Take care, and we'll talk soon.