
The Digital Contrarian
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.
The Digital Contrarian
TDC 061: The AI "Personal Branding Paradox" ??
TDC 061: The Personal Branding Paradox in the Age of AI
The more AI you use to scale your personal brand, the less personal it becomes.
Episode Summary
In 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 π£οΈ
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-aways
- The Personal Brand Power Law: only a tiny handful capture most attention while everyone fights over scraps
- The 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 everywhere
- One weekly "source of truth" content piece trumps dozens of AI-assisted posts
- Small strategic rooms create more opportunities than mass-market approaches
Timestamped Outline β±οΈ
00:00 β Intro: Birthday reflections and farm life
00:42 β Recent events and AI developments
02:30 β The Personal Brand Power Law explained
03:29 β The Great AI Paradox revealed
04:23 β The "Fewer, Deeper, Less" framework
05:12 β Move #1: Source of Truth content strategy
06:05 β Move #2: Show your struggle to build trust
06:58 β Move #3: Small rooms and strategic absence
09:11 β Personal Branding AI Summit invitation
Links & Resources π
- Get on the Return to Real Farm Event waitlist β https://ryanlevesque.net/vermont-farm-mastermind-waitlist/
- Register for Mike Kim's Personal Branding AI Summit β https://youarethebrand.ai/join?am_id=robby397
- Issue 025 β "Tipping Points" β https://ryanlevesque.net/half-baked-ideas-contrarian-advantage-ai-era/
- Issue 027 β "Your Strategic Content Ecosystem" β https://ryanlevesque.net/strategic-content-ecosystem/
- Issue 035 β "Why the Struggle is the Solution" β https://ryanlevesque.net/why-the-struggle-is-the-solution/
- Issue 055 β "My Contrarian YouTube Strategy" β https://ryanlevesque.net/my-contrarian-youtube-strategy/
- Issue 056 β "Storytelling: The Most Scalable Post-AI Business Skill?" β https://ryanlevesque.net/storytelling-the-most-scalable-post-ai-business-skill/
- Issue 060 β "Inside a Room With 40+ Million-Copy Bestselling Authors" β https://ryanlevesque.net/inside-a-room-with-40-million-copy-bestselling-authors/
Connect & CTA π―
π Enjoyed this? Subscribe & leave a review on Apple Podcasts.
π 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
Β© 2025 RL & Associates LLC. All rights reserved.
The Personal Branding Paradox in the Age of AI and Lessons Learned from the Latest Hermosi Launch. So this week, it was my birthday. 43 and feeling pretty free.
And no, I did not celebrate by watching their Hermosi launch, although the scale and volume was certainly impressive. Now more on that in just a moment. Instead, I spent the day on the tractor moving 50 round bales of hay into the barn, which in turn will feed our herd of cattle over the winter.
Now, you know, IRL instead of URL. Speaking of which, last week, as you may remember, I was in Nashville at an amazing author mastermind that I wrote about in issue number 60 of the Digital Contrarian, inside a room with 40 plus million copy best-selling authors. It's worth checking out.
And next week, I'm delivering the opening keynote at the 2025 Newport Global Summit in Newport, Rhode Island, alongside Barbara Guggenheim, Steve Forbes, and Alan Patricoff, the legendary venture capitalist. And by the way, a huge thank you to my private client, Diana Orly, for inviting me to be part of the summit. Then in three weeks from now, Tyleen and I are hosting the inaugural Return to Real Mastermind Experience at our farm here in Vermont.
Now, this event, unfortunately, is 100% sold out, but you can still get on the waitlist for the next events that we host here on the farm. And I'll make sure that we include a link to the waitlist page in the description with this episode. So all to say, it's been a busy few weeks.
And more importantly, it's also been a really busy few weeks in the world of AI. We've seen open AI's GPT-5 rollout and user backlash around personality loss, i.e. people grieving their AI companions changing overnight. Yeah, it's pretty wild.
Google Gemini adding memory to personalize conversations even more. And states in the United States, like Michigan, for example, tightening deepfake laws by criminalizing the use of deepfake AI in certain circumstances. Now, the headlines would suggest that on one hand, we want AI with a personality that feels more human.
But then on the other hand, we want to be protected from deepfake technology that feels too human. Now, I'm not sure that we can have it both ways, but I find this to be a fascinating parallel to the focus of this week's episode of The Digital Contrarian, which is the personal branding AI paradox. As we explored back in issue number 25, it's never been easier to get into the game, but it's never been harder to stand out.
And I think the Hrimozi launch this past week is a perfect example of this because it demonstrates what I describe as the personal brand power law. Now, the personal brand power law means that in any crowded space, only a tiny handful of voices capture the vast majority of attention while everyone else fights over the scraps. Now, it makes sense, right? Which is why it's never been more important to build your personal brand so that you can get a piece of the action and you're not left with nothing.
Now, naturally, most people to do this are leveraging AI at this very moment. But when it comes to using AI to help build and grow and expand your personal brand, the great AI paradox is this. The more AI that you inject into your personal brand to scale your reach, the less personal it becomes.
And paradoxically, the harder it becomes to stand out. In other words, scaling your output with AI tends to flatten your voice and pushes you toward looking, sounding and tasting the same as everyone else. Now, on one hand, your personal brand is less about what you say and more about what other people say about you when you are not in the room.
But on the other hand, if what you say gets completely ignored because it's lost in the sea of sameness online, well, nobody's going to be talking about you and your brand in the first place. So the question, naturally, is what's the solution? Well, this takes us to part two. A personal brand playbook in the age of AI.
Three quick moves. One of the shifts that my forthcoming book, Return to Real, advocates for is shift number three. The best things in life don't scale.
Fewer, deeper, less. Now, this is a strategy to not only stand out in the sea of sameness, but to also give yourself a strategic advantage in the AI era. And while we began exploring this shift in issue number 56, Storytelling, the Most Scalable Post-AI Business Skill, what we haven't explored in detail are some of the tactical moves that you can begin immediately implementing in your business to start making this shift starting as early as this week, beginning with move number one, which is an example of fewer.
And this is produce one weekly piece of what I describe as source of truth content that comes straight from your brain and straight from your heart. Now we explored this in issue number 55, My Contrarian YouTube Strategy. This idea is all about publishing fewer pieces of real, unsanitized source of truth content yourself directly from your mind and collapsing the gaps between that content exiting your body in the form of writing and speaking, etc, and entering into your prospect's brain.
This can look like publishing one piece of content weekly. My weekly email newsletter is an example of this in lieu of dozens of pieces of AI-assisted content in the same time frame. This takes us to move number two, which is an example of deeper.
Show your struggle, show your work, to show that you're the real deal. Explored in issue 35, Why the Struggle is the Solution, this is all about letting people see the messy behind-the-scenes reality of your life, not just the highlight reel, but the real reel as I've previously described it. Because when you share more deeply your failures and the unvarnished process, it builds trust because this is hard to fake.
In an AI-saturated world, proof-of-work receipts, i.e. the equivalent of those hay bales in the barn or an emergency room visits on the farm along the way, not only builds trust, this helps become part of your brand moat and it shows people that you are the real deal. And this takes us to move number three, an example of less. Small rooms plus strategic absence will give you more reach than trying to go big and be everywhere.
Coming off a launch like Hormoses, it's natural to think, well, maybe it's worth trying to emulate the whole go big and be everywhere personal brand approach. But remember, what you're seeing in that launch is the personal brand power law at work. And then on top of that, the level of relentless maniacal focus to be everywhere for years leading up to a singular big launch like this demands a decade-long level of sustained intensity, sustained execution, and sustained sacrifice that few are capable of, not to mention the years and years and years of 12 to 18-hour workdays, seven days a week.
So instead of trying to go big and be everywhere and running the risk of burning out and running out of resources along the way, a more sustainable approach, arguably, is to put yourself into a series of multiple smaller rooms that not only build powerful relationships, but which are strategically aligned with your goals, i.e. your equivalent of the million-plus copy bestselling author event or the Newport Global Summit or the Vermont Mastermind Experience that we're hosting here on our farm. Just a few rooms like that can make all the difference in the world to your business and can open up incredible doors. And the beautiful thing about this approach and not trying to go big and be everywhere is that depth compounds.
And what I mean by that is getting yourself into just one or two rooms like this can be all that it takes to create a domino effect that opens up bigger and bigger opportunities. So the power of strategic absence explored in issue number 27, your strategic content ecosystem explains this concept in more detail. Okay, so where does AI fit into all this? And how do you deal with the whole personal branding AI paradox that we introduced a few moments ago? Well, that brings us to part three, how to amplify your personal brand using AI without losing your authenticity or your audience.
Did you see that headline right there? Yeah, the one that you just heard me articulate out loud. Yeah, that's a headline that I helped craft for a private client of mine, Mike Kim. Now you see, this week, Mike is hosting a personal branding AI virtual summit that explores the very question that we've been discussing at the heart of this week's episode.
And by the way, I highly, highly recommend registering for the summit. If you're not too late, it's 100% free, and you can pick which sessions that you want to attend. In fact, as I told Mike earlier this week, there are at least three sessions in this summit that I immediately myself identified as can't miss and that I've already marked off in my calendar.
In addition to the session I'm leading, of course, to kick off the entire summit. By the way, we'll make sure to include a link with this week's episode to register for the summit if you are interested. Okay, I'm going to leave you with that for now.
Now, I know there's much, much more to be said on this topic, but it's getting late here, and I got to wrap. So let's do this. Let's pick up the conversation in my virtual session with Mike on the personal branding AI summit.
For those of you who are interested in going deeper, and for everyone else, in the meantime, I want to wish you a great rest of your week. Remember to hug the ones that you love. And until next week, I wish you all my best.
Take care, and we'll talk soon.