Get Together

The episode contains meaningful observations about community building methodology (the three types of communities on Substack, the importance of consistency, the 'build with' philosophy) and some concrete frameworks from the Get Together book, but much of the runtime is spent on generalized storytelling about Substack's evolution and personal anecdotes rather than novel, non-obvious insights. The core ideas about community - knowing your 'who' and 'why,' doing something together repeatedly - are presented clearly but are not particularly surprising to experienced community builders.

“I feel like there's a couple of things that really stood out to me... the things where you actually get to meet these writers in person, especially coming out of the pandemic.”

“when you're trying to build a community, which means you're trying to grow relationships and connections within a group of people... you're almost like a barista at the local cafe. Your job is to show up consistently”

The episode rehashes the Get Together framework (spark/stoke/pass the torch) and largely confirms it works rather than challenging or substantially extending it. Bailey's framing of Substack as 'blogging is back' is catchy but not deeply original. The 'build with writers' philosophy is well-articulated but represents standard contemporary practice at creator-focused companies rather than a contrarian insight. There is limited counterintuitive thinking or fresh first-principles reasoning.

“the spirit of blogging came back with Substack”

“Build with. And now one of my secret joys... is that the whole company uses that phrase. We build with writers. Sometimes we build for them, but we also build with them.”

Bailey Richardson is a genuine practitioner with real tenure - she spent 4.5 years at People and Company researching community, co-authored the Get Together book, and spent 3 years in an operational leadership role at Substack directly building writer community. She has hands-on experience at scale (103 office hours, thousands of writers, real product decisions). However, she is no longer at the company and the episode is somewhat retrospective rather than current operational work, which limits immediate relevance.

“after four years of researching extraordinary community leaders, coaching organizations at People and Company, and writing their book Get Together”

“we did 103 office hours, which was basically every Thursday almost”

While the episode includes specific numbers (103 office hours, 35 million subscriptions, 3 million paid subscriptions, 3,000 Art Dogs subscribers, 10% Substack take, 90% to writers, 50,000-100,000 questions answered), it lacks concrete data on outcomes. Claims about office hours being 'generative' or about the methodology 'working' are asserted but not backed with metrics on adoption, retention, revenue impact, or retention. Anecdotes about Patti Smith or Elizabeth Gilbert reading Art Dogs are memorable but illustrative rather than evidential.

“we did 103 office hours”

“Substack Subscription Network encompasses more than 35 million active subscriptions, including more than 3 million paid subscriptions”

Katie and Kevin (hosts/co-creators) ask thoughtful structuring questions and show genuine knowledge of the work, but the conversation lacks sharp pushback or productive disagreement. When Bailey makes claims (e.g., 'our methodology works'), they accept and affirm rather than challenge or probe deeper. The conversation is warm and collaborative but feels more like a retrospective celebration than a rigorous interrogation. There are few moments where the hosts push back on assumptions or request evidence.

“Can you tell us about that moment of joining Substack and what was on your mind, what you were most excited about?”

“I'm curious if you could tell us a little bit about that and how you think about community on Substack.”