In honor of 25 episodes, I thought it would be good to reflect. As always, you can listen to Dialectic here on Substack, Spotify, Apple, YouTube, and access all links and transcripts on my site.
While some of this is specific to hosting a conversational interview podcast, I hope it is broadly helpful for anyone seeking to have deeper, richer conversations or creating new things.
Plant the seed. I've spent much of my life evaluating seeds in my hands without any of them making contact with soil. I considered variations of an interview show for a long time, but always had too many ideas for what shape was needed before I could start. With Dialectic, I finally relented (thanks to some strong encouragement from friends) and put a seed in soil. The sprout isn't exactly what I had in mind, and that's the best part.
There's still room. I remember watching YouTube vloggers in the summer of 2013 and thinking, "this would be cool to try, but I'm surely too late. YouTube is mature." Casey Neistat, David Dobrik, and Emma Chamberlain had not started creating videos. MrBeast probably had a few hundred viewers. I felt the same about interview podcasts. One listener said this about the show: "Dialectic has reminded me that it’s still possible to build something strange & exciting in crowded places."
You know what you need to do. Strangely, a few people told me variations of this over the course of an extended period of exploration. It was frustrating to hear but directionally true. Put another way: when you (1) have a running list of people you'd like to interview some day in your notes app for the better part of a decade, and (2) the most recurring pattern in your life is a compulsive desire to meet interesting people and ask them questions—well, perhaps you know what you need to do.
It's about the guests. No matter how much I might try to convince myself otherwise, Dialectic's success is because of the guests I choose to talk to. 75% of episode quality is the guest selection, at least. That means all my other effort is contributing to at most 25%!
Follow the rabbit, socially. Speaking of guests: many of them have come out of my research or conversations in prior episodes. Shockingly, authentic, inspiring, and original people tend to know and admire each other.
The well is infinite. Again--the world (and internet) is full of so many original people with all kinds of loose threads that can be pulled. Matt Mullenweg once told me: Everyone's interesting. If you're bored, you're not asking the right questions."
Illegibility can be a feature. Mackenzie told me early on that there are benefits to illegibility, at least for a time. There will be a time to be legible, but in the formative period of a project, let things be illegible and focus on your own curiosity, energy, and exploration.
Let the dots connect. Despite Dialectic's illegibility and inconsistency of theme, patterns have emerged! As Steve Jobs used to say, the dots connect in reverse. It's been fun to realize various "tracks" of ideas (tools, agency, slop and intention, culture and taste, authenticity, etc) in hindsight.
Lead with curiosity. Some people have asked about my preparation process. For most guests, I just read and listen to as much of their content as I can and write down the quotes and ideas that stand out. I don't think about through lines or questions or themes. I just collect. Benjamin Labatut compares fiction writing to picking flowers up off the ground. After I've collected a bunch of scraps, I synthesize and plenty of patterns emerge. But it starts with the inputs.
"Plans are worthless, planning is priceless." All great craft combines rigorous preparation and skill with a certain looseness, almost a playfulness. Masters (like the Coen Brothers) seem completely at ease, but that is built on a foundation of having "done the work." I've found myself in a paradox, where the more preparation I do, the more tempted I am to cling to the plan. My best conversations are those when I let go a bit and trust myself to really be there. To listen.
Am I really listening? Speaking of listening, as I have spent most of my life continuing to more deeply learn, true listening is a sacred and remarkably difficult act. Most of my "listening" is in fact LARP, holding space for another until I can say the next thing or--more insidiously--waiting for the first interesting bit I can launch off of. Kevin Kelly's rule of 3 has it closer to right: asking "is there more?" two times shows how much more people have to say.
Presence creates magic. There are lots of great podcasts that happen over video call, but for me, it has to happen in a room with the person. Some of this is because of the length, and if I don't know someone well, meeting them where they are helps ease us in. But more than that, there's just too many invisible parts of connection that happen in the real world that you can't get when conversations are intermediated by bits.
Physical spaces shape us. On the note of presence: I've been fortunate to talk to many guests in their home or office. This creates an opportunity to meet them where they are and shine a light on their authenticity. I'm hopeful to explore more of how space(s) can shape the show.
Help people past their cache. I'm keen to talk about pushing people past their "cache," or the default programming they've repeated. So many of our conversations are sharing pre-articulated talking points back and forth. The best conversations happen when both parties go somewhere new, together. I aim to prompt people on domains I know they've spent a lot of time pondering within, and get them to color a bit outside the lines.
Jump into the deep end. Matt observed that I, like Patrick O'shaughnessy (an inspiration), "jump in at 90mph…" which might catch some guests a little off guard, but leads more quickly to a richer discussion and sets the tone for the level of depth. I can't say I started doing this consciously, but in trying to avoid the traditional "what's your story?" opening question, I've landed here. It's also a good way to establish quick credibility.
We all take time to settle in. In contrast to the above—and I've yet to solve this—many of the episodes are at their best in the back half. This should be obvious: great conversations take a bit of time to find their rhythm. Perhaps this simply means longer raw conversations with more editing. We'll see.
Niche at scale. Despite the temptation for infinite reach, this is what the internet is really about. Henrik calls a blog post a search query. for finding your people. Dialectic has blown me away in the ways it's found people that resonate with me and the people I talk to.
Let the world conspire to help you. From world-class podcasters to unexpected internet friends and strangers, I've been blessed by the range of people who have reached out to help Dialectic in small and huge ways. People want to help you when you're doing your thing.
There's nothing like writing. (But please listen to my podcast). In seriousness, I love interviewing writers because of how great that medium is at compressing someone's ideas. I like Alex Danco's framing of a collaboration between a writer and their readers, and how ideas are shared as output of that. When I talk to writers, I feel privileged to help them expand their ideas and articulate them for other audiences.
Structure the right accountability for yourself. Ben Thompson talked about his daily writing model and how he might never write a book because he needs the atomic constraint to publish. Willpower can be overrated, and the right constraints underrated. I know that I will do the work to prepare for an interview because I care so deeply about honoring the other person's time and generosity to do it.
Directing and editing is hard. I now know why Sean Baker is a rare breed. I struggle to materially cut content from the raw conversations, with a few exceptions. It's definitely a muscle, but similarly, writing and editing require fundamentally different approaches. It's tempting to be precious when you (co-)created the thing. Perhaps separate roles is the ideal setup.
Make the thing you want. I realize this advice has probably been overblown, but for good reason. I make a 2+ hour interview podcast with fairly esoteric, nich-internet-famous guests, no consistent pattern of guest, no set category, with no video and overly-detailed show notes and links. Many of the decisions haven't been hard because it's what I'd like to listen to.
Ideas and action. I'll leave it to listeners to be the judge, but as much as I try to understand someone by way of their ideas, I also try to ground the conversations in the implications of those ideas. My favorite thinkers are those who have a tight feedback loop between thinking and doing.
It's nice to try another mind on. It's a lovely experience to funnel your attention through another person's thoughts for a little while. Biographies can do this, but even autobiographies give you the export of someone else's (even the subject's) synthesis of their thinking. I recommend deep-diving the available inputs and seeing what threads you find in the pools of a person's mind.
Humanity shines. This is my north star. How can I get people talking about the stuff that makes their eyes light up? In a world that increasingly wants to reduce all friction and automate everything--including ourselves--humanity blazes brightly.
Bonus:
26. HAVE YOU CONSIDERED VIDEO? If you start a podcast, people (and by that, I mean literally every single person you talk to) will suggest that you do video (and short form clips from it). More on that soon.
really like Dialectic!
thank you for sharing this:)
#4 is brutal. #6 is the best secret. #17 is opportunity. #25 the most beautiful conclusion.