connection & community playbook
a practical, opinionated guide to building genuine connections and communities. not self-help — specific tools, formats, and systems grounded in real experience.
the operating principle: intentionality compounds. small, consistent investments in relationships and community create disproportionate returns over time. the people who seem effortlessly connected aren't effortless — they're systematic.
the playbook
icebreakers & conversation starters
curated collection of the best icebreakers — the nick gray format, 36 questions for increasing closeness, we're not really strangers, authentic relating games, askhole, and more. includes a context guide for which icebreaker fits which setting, and anti-patterns to avoid.
books & resources
the best books and articles on connection and community, tiered by priority. supercommunicators, the 2-hour cocktail party, the mom test, never eat alone, the art of gathering, neel nanda's making friends guide, and more. includes what not to read.
building a community from scratch
practical guide based on running socratica, build chain, and observing SF builder communities. covers the socratica format, lessons from failure, what makes communities stick vs. die, the minimum viable community, how to get the first 10 people, and scaling to 50.
relationship maintenance systems
how to maintain relationships at scale. the tiered system (weekly/monthly/quarterly/annual), what touchpoints look like at each tier, CRM tools (dex, monica, notion), deliberate relationship repair, and common failure modes.
event formats that work
specific event formats that create connection: co-working + demo (socratica), dinner parties, hackathons, demo days, unconferences, salons, and the walk-and-talk. each with format details, group sizes, and failure modes.
the art of the introduction
how to introduce people well: the double opt-in intro, anatomy of a good introduction, when not to introduce, the pre-conversation questionnaire, and how to be introduced well.
online community building
building community in digital spaces: discord server design, slack dynamics, twitter/X community building, what makes online communities die, the hybrid model, and the 1% rule.
sources and influences
this playbook draws from:
- running socratica at my school
- organizing build chain (16-person relay-build project)
- co-organizing startup pitch hackathons
- maintaining 124+ contacts in a tiered CRM
- the SF builder community (AGI house, SVFounders, sunday dinners, a builder house, dorm lectures at a university)
- neel nanda's making friends guide
- nick gray's the 2-hour cocktail party
- charles duhigg's supercommunicators
- priya parker's the art of gathering
- build irl and the IRL community building movement