In this solo episode of This Old Marketing, Robert dives headfirst into the uncomfortable - and increasingly urgent - tension at the heart of modern content strategy:

Can we still create truly human content, full of nuance, voice, and emotional honesty… while also making sure the machines don’t misinterpret (or mangle) what we mean?

Inspired by the announced end of The Late Show with Stephen Colbert, Robert explores how the final stretch of a show - or a career, or even a blog archive - can shape both public perception and machine learning for years to come.

This week Robert covers:

Why “good” content now means craft, not just output.

The shift from writing for search engines to teaching AI what to say about you.

The danger (and opportunity) of legacy content becoming training data.

A new strategy for structuring content that serves both people and machines.

Four practical steps you can take right now to future-proof your brand’s voice.

Oh - and Joe’s out this week, off pitching new names for the Guardians and Commanders to the Trump administration. Don’t worry. Robert’s got it handled.

Tune in, laugh a little, squirm a little, and leave with a renewed sense of purpose—and a checklist.

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This week's sponsor:

You don't become the world’s most valuable women's sports franchise by accident.

Angel City Football Club did it with a little help from HubSpot.

When they started, data was housed across multiple systems.

HubSpot unified their website, email marketing, and fan experience in one platform.

This allowed their small team of three to build an entire website in just three days.

The results? Nearly 350 new sign-ups a week and 300% database growth in just two years.

Visit https://www.hubspot.com/ to hear how HubSpot can help you grow better.

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Liked this show? SUBSCRIBE to this podcast on Spotify, Apple, Google and more. Catch past episodes and show notes at ThisOldMarketing.com.

Catch and subscribe to our NEW show on YouTube. NOTE: You can get captions there.

Subscribe to Joe Pulizzi's Orangeletter and get two free downloads direct from Joe.

Subscribe to Robert Rose's newsletter at Seventh Bear.

Get ready for this special episode that you needed to hear years ago.

Let me say this plainly: Working for someone else is the riskiest thing you can do right now.

For decades, we believed that a "good job" was the ultimate security.
A steady paycheck.
Healthcare.
Maybe a 401(k) with a match.

But that model is falling apart in real time.

I’ve seen this from the inside. I’ve been the employee. I’ve been the boss. I’ve been the guy who signed the layoff papers. When I was at Penton we went through three rounds of layoffs in 18 months and it was devastating for everyone involved. And this continues today but at breakneck speed. Here’s the truth: no job is safe anymore...especially in marketing.

AI is replacing entry-level marketers faster than we can track. Some agencies I know are in desperation mode. The only advice brand marketing teams get is to lean more into AI. Is that even the right strategy? And executive teams still don’t understand what content actually does...until they decide it’s too expensive (even thought it’s not) and cut it.

Here’s the harsh truth: Most people following the “good job, good life” blueprint are broke, stressed, unfulfilled, and trapped.

The old dream isn’t dead because people stopped working hard. It’s dead because the game changed and nobody updated the playbook.

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This week's links:

Dallas Cowboys NOT America's Team

Joe Pulizzi's New Book "Burn the Playbook" Pre-Order

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This week's sponsor:

You don't become the world’s most valuable women's sports franchise by accident.

Angel City Football Club did it with a little help from HubSpot.

When they started, data was housed across multiple systems.

HubSpot unified their website, email marketing, and fan experience in one platform.

This allowed their small team of three to build an entire website in just three days.

The results? Nearly 350 new sign-ups a week and 300% database growth in just two years.

Visit https://www.hubspot.com/ to hear how HubSpot can help you grow better.

-------

Liked this show? SUBSCRIBE to this podcast on Spotify, Apple, Google and more. Catch past episodes and show notes at ThisOldMarketing.com.

Catch and subscribe to our NEW show on YouTube. NOTE: You can get captions there.

Subscribe to Joe Pulizzi's Orangeletter and get two free downloads direct from Joe.

Subscribe to Robert Rose's newsletter at Seventh Bear.

This week Robert flies solo (Joe’s busy revolutionizing dairy on the blockchain) to ask a question: 

What if slower is the new smarter?

After riffing on OpenAI’s burnout‑induced shutdown, he unveils a sneak peek of his upcoming book, Valuable Friction. From Netflix’s “Skip Intro” button to AI‑generated sameness, Robert shows how our obsession with frictionless everything is draining the meaning out of marketing...and life.

Tune in for the four kinds of friction that sharpen ideas, deepen relationships, steady operations, and save you from knee‑jerk strategy. No co‑host, no fast‑forward, just 100 percent Robert. Press play, don’t skip the intro, and discover why a little resistance might be your brand’s unfair advantage.

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This week's sponsor:

You don't become the world’s most valuable women's sports franchise by accident.

Angel City Football Club did it with a little help from HubSpot.

When they started, data was housed across multiple systems.

HubSpot unified their website, email marketing, and fan experience in one platform.

This allowed their small team of three to build an entire website in just three days.

The results? Nearly 350 new sign-ups a week and 300% database growth in just two years.

Visit https://www.hubspot.com/ to hear how HubSpot can help you grow better.

-------

Liked this show? SUBSCRIBE to this podcast on Spotify, Apple, Google and more. Catch past episodes and show notes at ThisOldMarketing.com.

Catch and subscribe to our NEW show on YouTube. NOTE: You can get captions there.

Subscribe to Joe Pulizzi's Orangeletter and get two free downloads direct from Joe.

Subscribe to Robert Rose's newsletter at Seventh Bear.

After a quick cover of the Cloudflare news where it will be possible to select and make money from AI companies crawling your site, Joe and Robert dive into marketing plan B.

Specifically - 

The New Normal: Why Everyone Needs a Personal Brand (Even If You’re Not Selling Anything)

The collapse of the idea that a job = stability.
From creators to CMOs: why everyone needs visibility.
The difference between self-promotion and self-preservation.
Hot take: You’re always in stealth mode for your next job (even if you don’t know it yet).

And...Content as Career Insurance: Best Practices for Building Your Brand
What platforms actually matter (and which ones are dead weight)?

Where to start?

We have the answers in this episode.

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This week's links:

Cloudflare Launches AI Marketplace

Paramount Settles Trump Case

Joe's Newsletter Post on Freedom

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This week's sponsor:

You don't become the world’s most valuable women's sports franchise by accident.

Angel City Football Club did it with a little help from HubSpot.

When they started, data was housed across multiple systems.

HubSpot unified their website, email marketing, and fan experience in one platform.

This allowed their small team of three to build an entire website in just three days.

The results? Nearly 350 new sign-ups a week and 300% database growth in just two years.

Visit https://www.hubspot.com/ to hear how HubSpot can help you grow better.

-------

Liked this show? SUBSCRIBE to this podcast on Spotify, Apple, Google and more. Catch past episodes and show notes at ThisOldMarketing.com.

Catch and subscribe to our NEW show on YouTube. NOTE: You can get captions there.

Subscribe to Joe Pulizzi's Orangeletter and get two free downloads direct from Joe.

Subscribe to Robert Rose's newsletter at Seventh Bear.