We have spent the last 15 years building and participating in communities and found tremendous joy in them. Based on our own experience and with the generous help of leading community builders, we have developed a framework that helps build stronger communities and make our society a bit more connected: the Community Canvas.
There was a time when I said “I am a community builder.” I am currently the steward of the Podcaster Community—because the people there and podcasting itself are near and dear to me. But, I’m no longer interested in communities generally. I no longer go around seeing everything as a nail that should be fixed with the community hammer. That said, I wish I had seen that work above, about 20 years ago.
What does it take to use your voice with intention and create meaningful connection through audio?
This conversation reveals how intentional voice, genuine connection, and thoughtful preparation shape meaningful podcast experiences.
It’s not about good or bad. Loud is good. Projecting is good. Soft is bad. It’s having that variety in your voice and knowing when to use it. That knowing piece just comes from daily practice and listening back. That comes from my radio school days. I mean, most people are like, ‘Oh, I published the episode. I don’t want to listen to it anymore.’ But if you want to learn and grow, you need to listen. Subscribe to your own show. Listen to it.
~ Mary Chan (36:30)
Craig and Mary explore the tension between creative ambition and strategic clarity in podcasting, focusing on the decision to adopt video. Mary cautions against following trends without first understanding one’s audience, arguing that the additional effort required for quality video production is often unjustified. Craig reflects on his own temptation to “just hit record” and appreciates the freedom that comes with embracing audio-only formats. Together, they highlight the importance of intentionality—knowing where listeners actually engage and tailoring production efforts accordingly.
Beyond format choices, the conversation centers on voice as a tool for authentic connection. Mary explains how vocal tone, pacing, and emotional presence create intimacy with listeners, especially in solo episodes. Craig notes how podcasting builds lasting relationships, both with guests and unseen listeners, and how even small gestures of feedback can be deeply rewarding. They agree that successful podcasting requires self-awareness, clear purpose, and a commitment to serving the listener’s experience above all.
Takeaways
The pressure to add video — Many podcasters feel compelled to incorporate video due to platform trends, but this may not serve their actual audience.
The complexity of video production — Creating video content requires more than just hitting record; elements like lighting, editing, and set design significantly impact quality.
Knowing the audience — Understanding where listeners consume content is crucial before adopting new formats like video or written newsletters.
The power of voice — Voice carries meaning beyond words, and thoughtful delivery can make content more engaging and memorable.
Podcasting as an intimate medium — Listeners form deep connections with hosts, often feeling like they personally know them.
Self-doubt in content creation — Many podcasters second-guess themselves, wondering if they should be doing more or following new trends.
Authenticity in podcasting — A podcast host should sound like themselves, not an artificial version, to build a genuine connection with the audience.
The importance of show preparation — Planning a conversation’s direction helps create a natural flow while allowing for spontaneous moments.
Building relationships in podcasting — Long-term connections with other podcasters can lead to opportunities, collaborations, and shared growth.
Podcast listener engagement — Many hosts wish for more feedback from their audience, but this requires encouraging interaction and setting the expectation.
The difference between podcasting and cinematographic content — High-production video podcasts differ significantly from casual video recordings of audio-based shows.
The hidden work in podcasting — Even for audio-only podcasts, preparation, editing, and audience engagement require significant effort.
Off Camera with Sam Jones — A documentary-style interview series mentioned, which features long-form conversations with creatives and includes high production-value video.
The final challenge isn’t just to do the work but to exceed expectations. My approach at Borland and whenever a helpful someone gives me constructive feedback is to hear it, address it, and act on it in a fashion that demonstrates that I am the expert.
Exceeding expectations is a slippery slope. By definition, that’s moving beyond the point of success. (Assuming those expectations are reasonably set.) A little bit of better, is better. But how much of myself do I want to sacrifice as I push farther? A key part of the dance of being professional is learning how to set my own goals and expectations which are beyond those of others and still reasonable.
Nature and artificial, entirety and piece, universality and uniqueness, the past and the present. Architects are tormented by the constant conflict of these dualistic propositions! The deeper and more intense the tension is, the more dynamic the creation becomes. That is why architects must continue thinking.
Of course, not just architects must continue thinking. I find so much more value within things (for example, a conversation) when I hold up pairs of opposites as Ando suggests. Each pair suggests a dimension for consideration, and it’s easier than just staring into the original thing looking for the interesting parts.
There’s no correct answer to this question. The only important thing is that each of us takes the time to find our own answer. This is not a “set it and forget it” situation: You have to reconsider this question periodically too.
Yesterday I was talking with a podcaster who is in the middle of a significant pivot of their show. Why the pivot? It wasn’t working for them any more.
I’ve pivoted shows, started new shows, intentionally stopped publishing episodes of a show, and completely deleted shows from existence. Each time because there was a clear sign (often a sign I’d been in denial about) that the show was no longer working for me.
That’s what you have to figure out for yourself.
I did 1,400 episodes of Little Box of Quotes as a daily show. I had specific things I was practicing. When creating new episodes became a thing I started avoiding, I stopped. A year later, I’m thinking of resuming publishing the show, but my reasons for publishing it are now completely different.
I’ve tried two different show-formats for the Open + Curious podcast. Now in 2025, I’m scheduling guests for its 3rd season which will be in my signature style of conversation.
The Movers Mindset podcast hasn’t been the same format since day one. There’s been a bunch of experiments within that show. As I have new ideas, and new questions about what can a recorded conversation be, that’s where I’ve done most of my experimentation.
Even Podtalk has changed over time. What began as “the companion podcast to the Podcaster Community” (conversations with the community’s members) expanded to conversations with any independent podcast creator.
As I said: There’s no one, correct answer for everyone. There isn’t even one, correct answer for each of us!
No one gets everything right in their first few episodes (or even after 100 episodes). Looking back, what’s something you used to do—or believe—that you’ve completely changed your mind about?
~ Asked by the LLM(1)
By far my biggest mistake was chasing perfection.
It’s subtle when simply improving as one does more work, tips over into chasing perfection. Improvement is fine, but it’s not the reason why I’m making podcasts. I first had to figure out my reasons for podcasting, then it became easier to see when an improvement was fine, and when an improvement was an unnecessary detour. (Perfection, after all, can be hiding from the actual work.)
For me, an example of chasing perfection went like this…
In my initial recorded conversations, I first paid-per-minute for a human-done transcription. (It was 2017.) Then I printed the entire transcript. Then I reviewed the audio with the transcript as a guide, enabling me to keep track of the larger themes and story-arc in each conversation. Then I was annotating the transcript for various editing possibilities. Finally, I passed the editing off to another person (a paid, team member) that I was working with to create the show. Today, of course, this can all be done much quicker and with little (if any) actual cost.
Eventually, I realized that for what I’m trying to accomplish there’s no need to edit. So all that getting better editing, or doing it for less cost, turns out to be the wrong thing for me to be doing. Chasing improvement was hiding. Chasing perfection was an error.
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(1) I’m working with an LLM instance which has access to everything I’ve written about podcasting, and all the episodes I’ve published. It prompts me by asking me these questions.
In summary – I believe you should be publishing something to the web, maybe an esoteric spreadsheet, perhaps an open source javascript library, a deep dive into semantic analysis of your favorite author? Who knows? Publish, but keep it weird and humble.
It’s probably confirmation bias, but I definitely agree with this sentiment. The internet enables an endless array of things. For me it’s mostly about me being enabled to share what I’m creating. Weird? Definitely. Humble? …uh, okay okay still working on that.
This point about presence is one I’ve not seen made before about ‘mise en place.’ I’ve always focused on the preparation part, and how that then makes it possible to do great work (under press, amidst chaos, etc.) The idea that you can set yourself up for being present is quite enticing.
There’s a lot of conventional wisdom in podcasting—things like “You have to publish weekly” or “Shorter episodes are better.” But not all common advice applies to everyone. What’s something you’ve found doesn’t actually work or that people should rethink?
~ Asked by the LLM(1)
Don’t go alone.
I don’t think people do well trying to do their podcast entirely by themselves. I think this is really a point about creating art in general.
Yes, one definitely should do the work for the work’s sake. (What is referred to as autotelic.) Yes, don’t depend on external motivation and reward. But it is not easy to do that entirely alone.
The easy way is to find others who share your passion. You don’t need to directly collaborate on your work. But you absolutely will be happier if you have others who speak your jargon, do the thing, and face the same struggles.
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(1) I’m working with an LLM instance which has access to everything I’ve written about podcasting, and all the episodes I’ve published. It prompts me by asking me these questions.
Being quiet and slowly building mastery and expertise doesn’t pay off much at first. So many creatives must make a calculation: Do I want the short term, could-go-viral-at-any-second thrill of being a vocal expert in my field? Or am I more content playing the long game? More people are incentivized to choose the former — and it’s getting crowded in here.
This is closely related to the bit the other day from Offerman. In fact, it’s closely related to anyone’s journey of self-discovery. It is directly related, and critically important, for creatives to understand the trap of the idea of there being a possible short-term payoff. There is no short-term payoff. It exists, in the same sense that car accidents exist: Yes, but we don’t hope for that. We don’t set out trying for that.
But if you only paid attention to television and social media, you would think that all we’re supposed to do is make as much money as possible, and buy as many retail goods as possible. I’ve found that making a life with one’s hands and spending your time with loved ones pays less dollars but makes your life much more rich. I feel like the American Dream has been a bit hijacked by consumerism… And I learned the hard way that that’s actually quite empty and depressing as a lifestyle.
Maybe don’t follow Offerman’s path. But I think it’s worth following his advice. Yes, it’s difficult to balance exploring what makes me unique, with simply doing what everyone is doing. The balance you choose is part of the journey of self-creation. That’s a feature, not a flaw.
What makes parkour jam spaces unique, and how do they shape the experience of movement, community, and accessibility?
A church, a jam space, and a parkour gym—what do they have in common, and why does it matter?
The empowerment, and the kind of liberation to not care what other people think, does have a limit for some folk, I guess. I love it. I think for me, it’s been great and really powerful. I really like not caring anymore about being bad at stuff in particular— that’s so freeing.
~ Nina Ballantyne (14:00)
The conversation explores the concept of parkour jam spaces, emphasizing how they lack defined boundaries, making them more accessible in theory but sometimes intimidating in practice. The discussion touches on the contrast between structured athletic environments and the open, fluid nature of parkour, where new participants must navigate unspoken social norms rather than physical barriers. The conversation also highlights the paradox of accessibility—while jam spaces remove formal entry requirements, social and cultural factors can still create obstacles, especially for marginalized individuals.
The discussion transitions into broader themes of public space, inclusivity, and the intersection of parkour with community projects. A significant portion focuses on an initiative to purchase a historic church in Edinburgh and transform it into a community space. The conversation reflects on how physical spaces carry different meanings based on personal and cultural perspectives. The comparison between parkour jam spaces and community-driven spaces like the church highlights the broader theme of reclaiming and redefining public areas for collective benefit.
Takeaways
Jam spaces and accessibility — The absence of a physical boundary in a jam space doesn’t mean it’s truly open to everyone, as social and psychological barriers still exist.
The role of unstructured environments — Unlike traditional sports with defined spaces and rules, parkour operates in public spaces, leading to unique challenges in inclusivity and belonging.
Marginalized groups in public spaces — Individuals who are already scrutinized in society, whether due to gender, race, or body type, may experience additional barriers when engaging in parkour.
The impact of early experiences — Many practitioners come into parkour without formal athletic backgrounds, which shapes their approach to movement and learning.
Cultural norms within parkour — Different communities have their own customs, such as specific greetings or approaches to training, which can be both welcoming and exclusionary.
Reclaiming public space — Parkour’s ability to redefine urban spaces extends beyond movement, influencing broader discussions about who has access to and control over public areas.
Indoor vs. outdoor training — While some practitioners prefer the spontaneity of outdoor training, indoor spaces provide a structured environment that can be more accessible to beginners or marginalized groups.
The intersection of parkour and community work — The discussion about repurposing a church into a community space parallels parkour’s ethos of adapting and reclaiming environments.
The perception of churches as public spaces — Depending on cultural background, a church can be seen as either a welcoming community hub or an exclusive, imposing institution.
The role of storytelling in community building — Sharing experiences and narratives within parkour fosters a sense of shared culture and belonging.
The importance of understanding different motivations — Some practitioners seek challenge, while others prioritize playfulness, relaxation, or self-expression.
The limits of parkour’s inclusivity — While parkour prides itself on being an open and adaptable discipline, social realities can still make participation difficult for some individuals.
Resources
Access Parkour — A parkour organization in Scotland that provides training opportunities and works on community-focused projects.
Leith St Andrews Trust — The charitable organization working to purchase and repurpose a church in Edinburgh as a community space.
Coach Europe — A parkour coaching conference that brings together practitioners to discuss teaching methodologies and movement philosophy.
Richard Marshall — A parkour practitioner and speaker who discusses the importance of play in movement training.
Many podcasters start out assuming success looks like big audience numbers, sponsorships, or industry recognition. But in your experience, what’s something that actually matters way more than people think—or something people chase that turns out to be irrelevant?
~ Asked by the LLM(1)
All advice is useless until you first figure out why you are creating your podcast. There, that’s counterintuitive and contentious.
I’m not saying you must have a deeply considered, philosophical reason. But you must start with some reason for your podcasting. It can be any reason at all that you can imagine.
Because any useful advice must take your reason for podcasting into consideration. What’s the best mic? Should I publish on a schedule? Does the quality of the audio matter? What about show-length? …format? …social media? Even, what’s something that actually matters way more than people think? It depends.
All advice is going to be wrong if it doesn’t take your reasons into consideration. This applies to everything in life. Get up early? Stay up late? Avoid gluten? Read more? It depends.
Certainly you can change and refine your reasons. When you do that you can get real power from all that advice. If you get advice towards one course of action, but you don’t want to do that, then you need to dig into your reason, or you need to dig into that advice. One of them needs to be updated.
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(1) I’m working with an LLM instance which has access to everything I’ve written about podcasting, and all the episodes I’ve published. It prompts me by asking me these questions.
You just have to use what you have, and have great cohorts. I have people that I’ve played with a very long time. We are connected by our common understanding of what we’re doing, all the experiences we’ve had over the years… And most of all, there’s a friendship between us which allows us to do it without having to explain everything with a huge long manifesto. It has a lot to do with the trust I’m able to place in them to do our work.
Time after time I hear creatives talk about that. How they have an inside circle of peers. Of people who are also friends. Creatives need to have a group of people which somehow form a scene; They have access to a place where others like them freely associate.
When it comes, this will be the fourth message received from Alsafi in my lifetime. Few have timed their career so fortuitously. The first came when I was a child. The second came just weeks after I joined the Intercivilizational Observatory’s San Francisco office, and I wormed my way onto the analysis team. The third came the year I met Cassio, and I was doubly lovestruck. Still, I was reading responses to questions another generation had asked. But now, a full 39-year round-trip after I began, I’ll finally get answers to my questions. Ones from my youth, maybe, but they’ll be mine. After all this time, I’ll finally be In Conversation.
This piece of fiction is one of those things I start skimming, thinking “should I mark this for later reading?” and then read it all the way through. So of course I recommend you do too.
I find tremendous value in considered conversation. Usually, a conversation about the weather isn’t such a valuable opportunity. But this conversation about “weather” is really about what are the limits of what can be considered a conversation… is understanding required for it to be a conversation? Or is simply trying to understand, enough?
Writing issues of 7 for Sunday has become familiar (not to be confused with “easy”). I have a checklist which I use when I’m writing each issue. It’s as much for scratch-paper thinking, as it is for ticking off completed steps. Originally, the checklist had a lot of notes about formatting, what goes where, how to typeset the specific parts, image sizing, etc. all nuts-and-bolts stuff. As I’ve modified it, it’s now mostly signposts and I use it to celebrate each phase of the issue’s development.
Today, I was down to just a couple of these checklists and I hit print. How many copies? Without hesitation I printed 20—because that would be checklists through issue 150. It simply struck me as interesting that I’ve moved beyond “should I continue” and even beyond “can I continue” for this neat little weekly missive that I enjoy putting together.
With everything you’ve learned from running multiple shows, what are the biggest mistakes or inefficiencies you’d avoid if you were launching a new podcast from scratch? Would you approach production, audience growth, or personal mindset differently?
~ Asked by the LLM(1)
Picture me smiling and chuckling nervously because, for more than a year, I have been trying to restart one of my shows. Certainly a big part of my 2024 was reallocated for health reasons, but my attempted restart of the Open + Curious podcast has had many months available to me before, and since. Still, there’s no new show. It’s all about the mindset, for me. I have a too-grand vision of what it should be. I can’t stop seeing all the things it could possibly become, and fixating on getting everything right (my vision of what it should be) from launch day.
However, the best wisdom that I have here for others, is just a repackaging of Heraclitus’s “no one steps in the same river twice” (the flowing water implies the river is different, and the person is also different.)
If someone is actually starting their first show: Once you understand how to do a podcast (it takes perhaps 10 minutes to learn that?) then do not spend more time asking people about starting. That’s hiding from the work. Rather, start. The experience of the doing is what you are actually seeking.
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(1) I’m working with an LLM instance which has access to everything I’ve written about podcasting, and all the episodes I’ve published. It prompts me by asking me these questions.
[Don’t you need a certain kind of passion during those dry spells, to keep going?] Not at all. What keeps you going is stubbornness, economic necessity, or simply endurance. Passion will, at most, lead to frustration, but not to perseverance. For that, you don’t need passion, you need persistence.
It’s an interesting interview just for his views on passion. I agree with him: Passion will get you out the door on days 1 and 2. But by day 3 you need a routine, an understanding of the effort your undertaking, a clear perspective on what it’s going to be in the long haul, and more. But if you really want to get wowed by Waltz, go find Quentin Tarantino’s conversation on The Moment podcast with Brian Koppelman… the part where Tarantino talks about bringing Waltz onto the project…
Postrel’s argument about dynamism, evolutionary processes, and dispersed knowledge has direct relevance to technological change. She suggests that technological progress, much like biological evolution, is unpredictable and emerges through decentralized innovation rather than central planning, mirroring Hayek’s insight that no single entity can have enough knowledge to foresee or control all the variables involved in invention and innovation.
For a long time—perhaps all of my life until just a few years ago—I would have said I was completely on team Continuous Forward Progress; I would have said that change is good simply because it implies forward progress. But now I’m really seeing the value of “if this isn’t nice, I don’t know what is.” In most situations, I’m now feeling that leaving something just as it is would be great. The article is making a point about people who are against change on principle (although I’d wager most such people haven’t thought of it as a principle) and that’s not me either. I’m perfectly fine with change. But this is nice too.