✊ Some thoughts on AI, marketing, the internet, and where this is all going


Happy Labour Day, Friends,

It was nearly 30C (86F) this weekend here in Barcelona, but as I sat at one of my weekend cafes to read and journal on Saturday morning, there was no mistaking the slight edge in the air.

The first, sweet tinge of Fall.

Fall is my favourite time of year.

Maybe it's that September is my birth month. Maybe it's that I'm most comfortable wearing wool sweaters and jeans. Maybe it's the smell of roasting chestnuts and woodsmoke on the breeze.

Whatever the reason, I find it to be the most invigorating, creative, and reflective. The time of year when all the problems and questions I’ve been stewing on for months begin to synthesize and coalesce into something concrete, focused, and sharp.

I’m still in the early days of this process, but I wanted to share a few snippets of thoughts I’ve been stewing on about podcasting, content, marketing, business, AI, and where we as creators fit into it all.

Consider this a messy first draft of ideas we'll explore more in the weeks and months (and perhaps years) to come.

This year has been a journey.

And we’re now far enough along that journey, that I can look back and connect the dots to both view its arc, understand my current position, and chart the trajectory forward.

Let's start by connecting some of the key plot points.

Q1: How Things Started...

  • I started the year coming off my best year ever in business from a profit perspective… but edging towards burnout that was systematically built into my business model:
    • Charging too little… which required more clients… which required a bigger audience… which required more marketing… all of which resulted in a compounding amount of time and energy from me to keep the system running.
  • My yearly goal was to create more space in my business and life by:
    1. Raising prices and reducing client count
    2. Overhauling my ops systems
    3. Bringing on some targeted help from contractors
    4. Focus on improving client retention and LTV over increasing sales
  • To help, I started working with an Ops Coach, Joey, who—among many other things—consistently challenged (and continues to challenge) my ingrained impulse to always be doing more (content, projects, offers, etc)… and instead focus only on the one, most important project that will have the biggest impact.

Q2: Systems were built, people were hired, progress was made, then...

  • I read the book Four Thousand Weeks by Oliver Burkeman, which instantly rewired my brain regarding my orientation to work and what it means to spend my (our) time well.
  • After reading the book, I immediately stopped working weekends and quit work hours earlier each day (I often worked until 9 or 10 pm previously), and stopped feeling guilty about not getting more done. Seriously, it was like a switch flipped instantly.
  • The root of the transformation was this obvious truth: No productivity or time management system will ever allow me (or you) to “get on top of everything”.
    • It’s a losing battle where the more time I free up, the more projects I take on, ad infinitum.
    • The only solution in the face of this realization is to accept that I'll never be able to do everything I want to do... and then be hyper intentional about the projects I do commit my limited time and creative energy to.

Underlying all of this, of course, we have AI…

  • I’ve been experimenting with AI for the past 3 years (immediately after Chat GPT was first introduced, I created this website of AI Podcast Marketing Advice as a weekend project) and have been perpetually disappointed.
  • Sure, it’s great at some tasks—a brainstorming and thinking partner in particular. But when it comes to assisting in the actual output that my business operates on—ie. content and offers—I’ve so far come up short.
  • Early in the year I bought a course on training an AI model on your writing to assist in content creation.
    • And while the output was close-ish to my voice… it never quite sounded like me.
    • Perhaps more than anything, however, it lacked a certain energy or momentum to the writing and ideas behind them.
    • What's more, I realized that the value of writing for me (and I would argue for everyone) is not "outputing content" but in being forced to surface, connect, and articulate your thoughts, ideas, and opinions in a way that connects with other people.
    • Outsource this function to AI and you instantly cut off at the knees your ability to develop into a genuine expert, thought-leader, or authority, dooming yourself to a career as a budget, second-rate "expert" forever chasing the real thought leaders who are doing the actual thinking. Yikes.
  • Then came this year’s Podcast Marketing Trends Report where I once again made the annual pilgrimage to ChatGPT to help analyze the survey responses…
    • And was once again wildly disappointed by its inability to accurately tell me how many people mentioned “social media” in their response to a certain question (”216… Oh, sorry about that, you’re right, there are actually 365 responses… Apologies, there are actually 276 responses…”) — Nope. Still wrong.
    • What’s more, I realized (again) that, as with writing, the value of analyzing the data manually is not efficiency or accuracy (though it certainly does achieve that).
    • The value, and perhaps the entire point, is to understand the data in a way that makes my understanding of podcasting, marketing, content, and the trends underlying all of them sharper.
    • And the only way to understand the data is to spend significant time grappling with and attempting to decipher what it is (or could be) saying.

Q3: The Summer of George Life Immersion

  • To this point in my 10 years of self-employment, I'd taken one, single, lonely summer vacation (other than my honeymoon, last year). This summer I took two 😱
    • What’s more, both of these vacations involved weeks of being unplugged, doing hard things while having deep conversations with good people—the first, a two-week cycle tour in Devon and Cornwall in the UK, and the second, walking a week of the Camino Norte here in Spain.
    • Both of these trips further solidified the orientation to work that had already been forming...
  • That approach is perhaps best illustrated by a series of small personal changes scattered throughout the year including:
    • Sometime in January or February, I took all social media apps off my phone and decided to simply not engage as either a consumer or poster any more.
      • I’d already been mostly off social media for 2+ years, but it felt good to officially close the door on that
    • In March, I removed the Gmail app from my phone to break my compulsive email-checking habit.
    • In May, I cancelled my subscription to the New York Times and blocked the site on my phone.
    • Also in May, I started buying and reading physical books (rather than Kindle or audiobooks) and have read pretty much 1/week (entirely non-business-related), since then.
    • In June, I started journaling in a physical notebook, and ultimately moved most of my weekly and daily planning there as well.
    • Then, I wrote the script for the first episode of my new podcast Killer Concept, in my journal, and found the process so creatively enriching and more valuable than writing on my computer, that I’ve written all of the subsequent scripts long-hand as well.
    • Also in June, I stopped sleeping with my phone in the bedroom, leaving it in the kitchen overnight.
    • In July, after spending three weeks without headphones in my ears on the cycle tour, I plugged in my Sony noise-cancelling headphones afterwards and immediately found the experience so disconcerting I've pretty much stopped using them, spending a lot less time trying to drown out the “real” world and a lot more time listening to it.
    • Next up: Breaking my obsession with tracking my daily step-count and taking more walks without my phone.

So Where Does This Leave Us?

If we were to characterize the arc of my year, thus far, it follows a clear trajectory away from the digital, away from the inanity of much of the internet these days (AI slop, formulaic human content marketing slop, shallow hot takes, divisiveness, noise, regurgitations, etc) and toward the more grounded, real, analog.

When I started the year, I thought the biggest gains of time and space in my business would come from hiring, systemizing, and reducing my client count.

In reality, the biggest gains of spaciousness have come from disconnecting from the noise, distractions, and expectations.

What’s more, I feel more creative, more focused, more clear on my direction, less worried about AI, tech, video podcasting, etc.

Which I think hints at something interesting for all of us as creators going forward.

My Assessment of the Current Situation for Creators

I’m probably in the top 0.1% of “most online” people in the world.

I run an online business and create online content to market it.

I consume an insane amount of content every week (mostly podcasts, articles, newsletters, and YouTube).

Having (until recently) traveled full-time for 8 years, nearly all my close relationships play out online (Zoom, WhatsApp, DMs, emails, communities, etc). What’s more, most of them wouldn’t even exist without the internet (I even met my wife, Kelly) in an online forum).

As someone as immersed in online culture as I am, my gut says that my feelings toward (and my pull back from) the internet, AI, and its current direction are a harbinger of where sentiment will head more broadly.

  • We can see this with teens and 20-somethings opting for flip phones instead of smartphones.
  • In the bevy of new low-tech hardware (Exhibit A, Exhibit B, Exhibit C) designed to help us distance ourselves from the omnipresence of the internet in our lives.
  • We can see it in the increasing discussion of Dead Internet Theory which posits that it’s only a matter of time before the current incentives of the internet—algorithms, pay-per-click advertising, etc—turn it into a by-robots-for-robots ghost town devoid of any real human content, interaction, or connection.

Hmmm.

So where does this all leave us as the people who rely on (and create for) the internet to run our businesses?

The Bets I'm Making Going Forward

As a creator who has often felt the need to sacrifice the craft of the work I make in order to produce at a consistent volume, I actually think this is actually an incredibly exciting time to be making stuff.

Because in a world inundated with cheap, fast, high-volume slop—both directly created by AI as well as humans using AI to increase the volume of their production, true, genuine Craft becomes a rarity.

So too does having a unique, particular, well-defined sense of Taste & Style.

Rarer still is:

  1. The application of Taste & Craft in...
  2. Creating work of Depth, Nuance, and Earned Insight that...
  3. Connects with people on a deep, human, emotionally resonant level that...
  4. Makes them feel seen...
  5. Provides a shared sense of reality, and...
  6. Helps them understand themselves and their place in that reality and their world more clearly than before.

This is the opportunity for us as creators.

In a world where the cost of producing an infinite amount of content approaches zero, none of us can win playing the volume of production game.

But there are other games we can play.

The slow, quiet, confidence of the depth of production game.

The meaning of production game.

The transformative potential of production game.

As thoughtful creators who care deeply about the quality and craft of our work, these are games we can win.

What's more, these are the games that podcasting as a medium—and the creators and consumers who make it up—is already most aligned with.

Going forward, these are the folks I'm most excited to work with.

  • Folks who love the work. Who don't want to outsource it to AI but spend more time doing more of it.
  • Folks with discerning customers, clients, and audience members with high-standards for what they consume and engage with.
  • Folks who want want to create singular shows, marketing, and offers that ooze care, thoughtfulness, and intention

Not average stuff for average people.

But exceptional work for an exceptional few.

All while getting paid handsomely and consistently to do this work they love.

That's where I'm heading.

Come along?

Stay Scrappy,

If you're a Founder, Solo Biz Owner, or Professional Creator looking to double down on the Craft of your work while getting paid handsomely by clients you love to work with, I have 3 slots left for 2025 in my 1:1 Podcast Growth Engine Program.

In the program, we'll do a full assessment of your show, marketing, sales system, and offer, and then design a strategy and system to bring them into alignment, to help you sell more and grow faster while making better, more rewarding, more resonant work.

It's not an overnight process, but if you've already got the pieces in place, it wouldn't be unreasonable to expect to add $100k in revenue over the next year.

Here's who nails the bull's eye:

  • You're a coach, consultant, service provider, or online educator with a high-ticket offer ($5k+) that already sells consistently.
  • You have a stable business that pays you a solid, predictable salary (ie. you're not in "need cash now mode") and are in mid-to-long-term planning mode, looking to build out the systems and strategy to take your business to the next level over the next 2-5 years.
  • You've got your core business assets already established—offer, sales process, email marketing, podcast, operations—but while all of them are performing OK, none of them are really optimized... and you know you're leaving money on the table and working harder than you need to to generate revenue.
  • You can see all the pieces and know you've built something of real value... but don't know how to connect them all in a cohesive way.
  • You understand business and marketing, but could really use some outside perspective from someone who deeply understands their work (creatively, strategically, and tactically) and what they're trying to do to bounce ideas off of, challenge their assumptions, and guide them.

If that's you (or close enough), reply with the words "Growth Engine" and I'll send over all the info on how the process works.

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