Dick Cavett Style

A master class in holding space - and why I'm trying to do the same

Matt Zeigler
November 21, 2025

When The Dick Cavett Show launched in the late 60s, America was going through some stuff. There was a war and protests, a civil rights movement and protests of protests, and an emerging generation gap in American culture that made community across ages feel stranger than anyone alive could imagine in the moment.

In hindsight, it was the perfect time to launch a show like his. But it's not remembered that way today. At least not with the same weight of how people talk about Johnny Carson, or David Letterman, or Conan O’Brien, or - take your pick of anyone from today's crop.

On one hand, I want to shout about "why" he was the best, and to convert you to my level of fandom. But, on the other hand, I kind of like that Cavett is still one of my modern-era secrets. I like that when I talk about him most people say, "who?" I like that my wife and I have exhausted our paid app versions of his shows, and regularly seek out his interviews on YouTube or even Tubi.

Bottom line, Cavett was onto a whole different approach. He’s magic to me. At least, to revisit, and think about how he would work if he were my age, today.

When he started, he stood out because he gave network TV platforms to the post-Woodstock voices, various political adversaries (away from a campaign stop), and regularly showcased his willingness to have a less-than-comfortable conversation because it was A. too narrow for anyone to attempt (shoutout Oscar Peterson), B. just plain awkward for anyone to attempt (shoutout the infamous Gore Vidal versus Norman Mailer episode), or C. just plain weird (i.e. "drugs" - special shoutout to Sly Stone). The audacity of what he was willing to try is what makes my brain scream.

Looking back, I know the cultural net was wider than anything else on TV. And, without the stream of jokes or (far less) solely promotional angles, he got people to behave like people. That’s the biggest accomplishment you can look back and see.

Later shows would borrow styles from it. And while he didn't invent the in-depth interview, he sure altered where and how you could capture a deep thought from a person of genuine, cultural interest. Without pandering.

These were choices. These were deliberate. Cavett wanted to challenge the system by going deeper with people inside of the system itself. Call Carson conservative for some of his guests, or who he invited onto the couch after a first pass, but recognize it was happening. Cavett carved out a whole new type of space for these guests, that no other host was making proper time and space for.

But why, really, am I opining about Cavett, now, in 2026? Because the more I think about strategy, especially around podcasts and the conversation based shows and content I want to work on, the more I think about why I love his show so much. He can’t do it today. Maybe I can?

In my notes, going from memory and impressions, I have stuff like:

The guests weren't always the biggest, but they were always interesting. Sometimes for popularity, but often because they represented something culturally astute. Buzz wasn't the only factor they booked for.

Guest combinations were almost always allowed to evolve, with Cavett's guidance. There are pairings that make no real sense on paper, but once everyone was gathered in the circle of chairs, you got real questions and new perspectives. Holding that space was a gift.

And, speaking of the chairs, there was no hierarchical “host as star” complex in the way the set or the conversation felt. Cavett was a conversationalist and that invited in all sorts of humble conversations. He was a master at lowering his own status around these people so they’d almost look after or care for him. Not out of pity, but - he pulled genuine responses out of them because he was so disarming.

Even when it wasn't working, and maybe especially when it wasn't working as good or compelling TV in any traditional sense, Cavett's personality was working overtime. The willingness to be naïve, or even dumb/silly/contrarian without being mean - that was always there. He made it look so easy to engage anyone.

I want to be more like Cavett in my work. It's a work in progress. But I see lots of rhyming issues and debates on the landscape that say even if it doesn't wildly succeed, the world could use this too.

Cavett's approach was radical for a reason: he chose his guests deliberately, which connected to the broader audience who formed around those deliberations, and then, he built the whole show concept around serving both guests and the audience as deeply as he could within the medium’s natural constraints (i.e. time, camera frames, etc.)

That's not how most TV worked then. It's not how most content works now either. The incentive is still the same - go wide, get famous, sell ads. But Cavett understood something that the most interesting conversations happen when you know who you're talking to.

In guest, AND in audience. Curious people who engage in real dialogue. People who would want to be on and talk, or watch and talk. Those are word-spreaders. Genius.

Which is exactly the shape of what I'm trying to build across Excess Returns, Epsilon Theory, and Cultish Creative. Three channels. Three distinct guest profiles and audiences. Three different ways to hold space for conversations worth talking about.

On Excess Returns, I'm holding that space for investors who want education alongside entertainment. On Epsilon Theory, for people who understand that narrative shapes how we think about money and strategy. On Cultish Creative - on Just Press Record - for people who want to eavesdrop on strangers becoming less strange to each other, however it might unfold.

Each channel has its own guests, and then respective audiences who I imagine will care about what’s happening here. Each one knows what to expect (or, I’m working really hard at that - from my guest calendar invites to how I frame it when we’re promoting episodes).

And each guest gets shown the same respect Cavett showed his guests: genuine curiosity, willingness to go awkward or weird if that's where the truth is, and the belief that holding space for real conversation is worth doing even if it doesn't win a ratings war.

I'm not trying to be Cavett. I'm trying to learn from him, by thinking what he’d do today, if he were starting fresh. And if the world could use more conversations - more channels, plural - that operate this way, then I'm doing my part to build it.

h/t to Paul F., and Madison F., who inspired this chain of posts this week. And extra special thanks to Tony G. for our sidebar Carson conversation that got me thinking deeper on Cavett, and Scotty B. for basically anticipating my entire week of posts on Monday (and thus validating I was onto something).