The following is taken from one of Bo Sacks’ recent emails. The image above is not real — it’s from ChatGPT.

BoSacks Speaks Out: Greg Krehbiel is one of those media professionals who always makes you think, whether you agree with him or not. On his LinkedIn page, he describes his work this way: “I help growth-minded businesses align their technology and operations with their long-term strategy so they invest in the right tools, fix what’s holding them back, and build a foundation for sustainable growth.” It’s a solid mission, and more often than not, I find myself nodding along with Greg’s insights.

Except, of course, when I don’t.

What follows is the result of one such moment of divergence.

Sometimes disagreement is the best kind of dialogue. This was one of those times.

BoSacks Interview with Greg Krehbiel Media Mastermid

Bo Sacks: Greg, in your recent piece you described both our culture and the publishing industry as being stuck in the “ugly part” of a cycle, decline, collapse, exhaustion. That’s quite a stark framing. I’m curious: when you step back, do you see yourself more as a pessimist in this moment, or more of a realist just calling things as you see them?

Greg: First, thanks for this opportunity. I always enjoy our conversations, and I want you to feel complete liberty to disagree with me whenever you like. I disagree with me about half the time too.

The article that sparked this conversation started with some commentary on cultural cycles – to put it simply, vitality, excess, decline, revival. There are some analogies between what goes on in the culture and what goes on in publishing. For example, consider newspapers.

Vitality in the late 19th and early 20th centuries.

Excess as they consolidated in huge chains and created bloated organizations.

Decline as the internet stripped away classified ads and such.

Revival with niche, local papers.

Similar patterns can be seen with magazines, digital publishing, academic publishing, etc.

A big difference is that reviving a culture often means returning to things that have been lost. In publishing, although there are important lessons to be learned from the past, the future is going to involve more new ideas.

Bo Sacks: Related to that, how much of this sense of malaise is, in your opinion, about actual industry decline versus just perception? Because when you wrote that first version of The Krehbiel Letter and found it too depressing to send, it struck me: what shifted for you between tearing that one up and deciding to write a more hopeful second draft?

Greg: The numbers are pretty clear, as you’ve highlighted in several of the pieces you’ve distributed. Here’s something you said recently.

“Let’s abandon the diplomatic nonsense. The last decade didn’t gently ‘transform’ magazine publishing. It took a sledgehammer to the entire industry, then handed survivors a box of mismatched tools and said, ‘figure it out.’”

Right. If we look at the metrics, circulation, ad and subscription revenue, traffic, and profits are all down.

Back in the heady days of newsletter publishing, entrepreneurs handed off profitable businesses to their children. I don’t know a single person in publishing who would recommend a career in publishing to their children. I’m sure there are some out there, but I think they’re the minority.

So why did I tear up the depressing draft? Because (1) being depressed doesn’t help anybody, (2) there’s often a silver lining, and (3) there are genuine signs of hope and optimism.

Bo Sacks: You outlined a cultural cycle of vitality, optimism, excess, decline, collapse, and then, eventually, renewal. Do you think that’s a universal inevitability every industry faces, or is publishing especially vulnerable to those swings? I wonder, too, how this model aligns, or maybe clashes, with technology, which doesn’t move in a cyclical pattern but more in an exponential one. How do you bring those forces together when you apply your framework to today’s publishing landscape?

Greg: “History doesn’t repeat, but it rhymes.” I don’t think any pattern like this is etched in stone, and I think cultures tend to revive more frequently than industries. The whale oil and buggy whip industries didn’t really revive.

Some industries do revive. Oil goes up and down. Brewing and distilling go through cycles, as do movie theaters. Electric cars have been on a bit of a roller coaster.

You can’t count on a revival, but you should keep your eyes peeled for signs of hope – as you’ve done in several of your recent articles.

These two things can be true at the same time: publishing is on a downward trend, and there are some innovative and profitable things happening in publishing.

Technology is an interesting case. The tech industry goes through boom-and-bust cycles while the underlying tech continues to get better. E.g., the dot com bust didn’t change Moore’s Law.

I think we’ll see this with AI. A lot of these companies are going to fail, but the underlying tech will continue to improve.

You ask how the exponential increase in technology maps on to this cyclical nature of publishing. The obvious example is the shift in staff. We don’t need typesetters, and we don’t need as many people manning the presses, but we do need more people digging into data. Another example is the increased ability to target and personalize. Successful publishers will lean into these changes.

Bo Sacks: If you’re right and we are near the “collapse of trust” stage, what kinds of early sparks do you see now that could signal a coming rebound?

Greg: Hey, it’s not me saying there’s a lack of trust. Every survey shows that media ranks down there with poisonous snakes and Cylons.

Niche publishers will avoid some of this. There’s a lot less reason to lie and misrepresent when you’re talking about natural gas regulations than when you’re talking about politics.

Attention is shifting away from brands and towards personalities. People trust Megyn Kelly or Rachel Maddow more than they trust Fox News or MSNBC. I think that will hold for the near term and will keep a lot of attention on podcasts and videos, but eventually these personality-led efforts will coalesce into broader networks. We’re already seeing that to some extent with things like The Blaze and the Daily show. Those networks will then become bloated, sell their souls to advertisers, become untrustworthy, and the cycle will continue.

As an aside, many people forget that the idea of the independent newspaper was a relatively recent invention. Before that, newspapers were aligned with political parties. The experiment in so-called “independent” newspapers seems to be ending.

Bo Sacks: Let me push a little here. Some people in our business, including myself, don’t experience this moment as bleakness at all, but as transformation. Change for sure, but with an upside. What do you say to those who believe the opportunities for reinvention actually outweigh the decline narrative? And how do you think about counterexamples like thriving niche magazines, indie presses, and local community outlets? Are they exceptions to your cycle, or early signals of renewal?

Greg: I think you need to eat your own cooking. There’s plenty of bad news about publishing in the articles you distribute – e.g., the decline of local newspapers, disruption from AI, fraud in online advertising, and even that thing with the Kansas prisons.

Yet, as you say, there’s also good news. Transformation. Innovation. As I said in my original article, there are fortunes to be won. Sean Griffey did a fantastic job with Industry Dive.

There are lots of opportunities in publishing, but I don’t quite know what you mean about whether the opportunities “outweigh” the decline. Once again, two things can be true at once. Publishing as a whole could be on the decline – lower circulation, lower ad revenue, fewer titles, lower overall reach – while there are still bright spots and great business models.

This isn’t a rising or sinking tide scenario. You can catch a lot of fish while the tide is going out.

Bo Sacks: History shows us that so-called bleak moments in media have often been fertile ground for innovation, the rise of alt-weeklies, underground zines, even the early days of digital-first media. Is that what we’re seeing now with podcasts, newsletters, and maybe even AI-enabled publishing?

Greg: Absolutely.

Bo Sacks: On that note, in your article, you were blunt in calling ad-supported free content “a dumb idea.” For me, that depends on the circumstances. So what’s next? Do you believe subscription, memberships, or even micropayments are realistic long-term replacements? And if you were suddenly at the helm of a legacy magazine brand today, what’s the first baked-in assumption you’d throw out the window?

Greg: Ad-supported content is dumb for several reasons.

• It puts pressure on the publisher to design for ads rather than to design for the reader. This is especially true on mobile. Many sites are simply unbearable.
• Over-reliance on ads limits revenue diversification and exposes the publisher to a lot of risk when ads dry up.
• There’s tons of fraud in the ad space.
• “Free with ads” has devalued content in the mind of the public. It’s trained people to believe that content should be free.
• “Free with ads” undermines copyright. People start to believe that anything on the internet is fair game – to be used however they like. AI is the culmination of that.

Ads are a legit part of the revenue mix, we’ve just gone way too far in the ad direction. Subscriptions, sponsorships, and memberships need to make (and are making) a comeback.

Micropayments are another story. They remind me of that sign in the pub: “Free beer tomorrow.” They sound like a great idea, but somehow it never works.

If I were suddenly at the helm of a legacy magazine brand, the first “baked-in assumption” I would throw out the window is that there is such a thing as a “digital magazine.” I find the concept as absurd as a digital kiss.

A magazine is a physical thing. Digital content is simply different, and it’s counter-productive to try to smash the two concepts together.

Bo Sacks: AI is another thread you raised. Right now, it feels ambiguous, sometimes threatening, other times extremely useful. Do you lean toward seeing it as more of an economic disruptor or more of a creative tool for publishers?

Greg: There’s no question that it’s a disrupter. We’re already seeing job losses from AI, and that’s going to accelerate.

AI is a wonderful tool that I use all the time, but I’m not comfortable with calling it a “creative tool.” People are creative. AI mimics creativity. And sometimes it’s dumber than a mud fence. The other day I couldn’t convince Nano Banana that when the wolf comes down the chimney, his tail has to be inside the fireplace.

I’m skeptical that AI will get all that much smarter than it already is. The dream of “general intelligence” is fading and that side of the equation will be heading towards the “trough of disillusionment” pretty soon.

But if you abandon the sci-fi dreams and use AI as a productivity tool (with careful safeguards), you can skip all that and head straight to the “plateau of productivity.” (Of course I’m referring to the Gartner Hype Cycle.)

Bo Sacks: You ended your piece with the challenge: “Are you up for it?” So let me turn that back on you. What do you think is the biggest challenge the publishing industry must confront in the next two or three years? And conversely, where do you personally find the most optimism about publishing’s renewal right now?

Greg: Whenever I tell someone I’m in publishing, they tell me about the book they’re writing.

“Publishing” is a broad category. The challenges for magazines are very different from the challenges for niche B2B publishers.

If I were to generalize, AI is clearly the biggest challenge. Why is somebody going to consult your advice on Roth IRAs when ChatGPT can give an answer in five seconds?

Turning that on its head, I’m most optimistic about personalities. ChatGPT can’t do what Joe Rogan does.

I’m also optimistic about our ability to use AI to target professionally curated content to the user.

Bo Sacks: Finally, you framed it all with a surfer’s metaphor: when the right wave comes, we need to ride it. What does that wave look like to you? Is it backlash against social media, some new format breaking through, or something we haven’t even imagined yet?

Greg: You’re highlighting a lot of the waves in the work you do, pointing out innovative tactics, new revenue models, and clever uses of personalization. People need to study those examples.

The wave I fear is personalized AI agents, like the one in the movie “Her,” or the AI character Jane in the Ender series. Once I have every answer I could possibly need in my ear any time I want it, what’s left to publishing except to feed that monster?