Playbook · operator how-to
How to build a Dream-100 of GitHub orgs (community-led VC sourcing)
A community-led playbook for building a 100-org watchlist that produces compounding deal flow — modeled on the Dream-100 distribution discipline but applied to GitHub.
The Dream-100 discipline — pick a hundred high-leverage relationships and compound them quarterly — is one of the most underrated sales mechanics in software. It maps cleanly to GitHub because GitHub orgs are public, persistent, and have built-in surface area for engagement (issues, PRs, discussions, contributors).
This playbook gives you the exact mechanic for building, tracking, and compounding a GitHub-flavored Dream-100. The output is not a marketing list — it's a relationship watchlist where every entry is one you'd want a deeper relationship with regardless of whether they ever take a meeting.
It works in 18-month chunks. The first six months feel like nothing. The second six months produce occasional warm intros. By month 18, the list is producing 8–12 active deal-flow conversations a quarter, almost entirely inbound.
Before you start
Prerequisites
- · Long-term mindset — this is an 18-month commitment, not a quarter
- · A spreadsheet or simple CRM
- · Willingness to publish in public consistently
Tools
- · GitHub web UI
- · GitDealFlow signals feed
- · Spreadsheet / CRM / Notion
- · Twitter / LinkedIn / your newsletter
Steps
- 01
Pick 100 orgs you'd be proud to have in your portfolio in 5 years
60mNot 100 hot orgs. Not 100 funded orgs. 100 orgs where, if you were sitting on a cap table with them in 2031, you'd be quietly proud. Mix of well-known (PostHog-style) and lesser-known (single-maintainer indie projects you respect). Bias toward orgs whose values you understand, not orgs whose valuations you envy.
- 02
Set up the watchlist spreadsheet
30mOne row per org. Columns: org URL, primary contact (maintainer name + handle), what they do in one line, current relationship state (cold / aware / acquainted / warm / friend), last meaningful interaction date, next planned touch.
- 03
Tier the list by relationship state
30mTier 1 (warm/friend) = 5–15 orgs. Tier 2 (acquainted/aware) = 25–40 orgs. Tier 3 (cold) = 50–70 orgs. Each tier has a different cadence — Tier 1 = monthly touch, Tier 2 = quarterly touch, Tier 3 = semi-annual touch. Yes, this is intentionally slow.
- 04
Set the weekly tracking pass
30mOnce a week (Tuesday afternoon, 30 min) — open the signals feed for the orgs on your list and note anything new. New repo, new committer, accelerating velocity, major release. Save the notes to your watchlist row — you'll mine them for touches later.
- 05
Run the monthly touch pass on Tier 1
60mFirst Monday of every month, send 5–15 personal notes — one per Tier 1 org. The note references something you noticed in the weekly tracking. Examples: 'Saw you shipped v0.4 last week — the breaking change on [X] looks like it solves what we talked about at [conf]. How's adoption looking?' Never asking for anything. Never selling.
- 06
Run the quarterly public engagement pass on Tier 2
60mOnce a quarter, write one piece of public content that elevates 5–10 Tier 2 orgs. A newsletter issue, a Twitter thread, a podcast episode if you have one. The point is that each Tier 2 org gets a tag or mention, not a DM. Public elevation builds Tier 2 → Tier 1 over time more reliably than 1:1 DM does.
- 07
Resort the list every 6 months
30mTwice a year, move orgs between tiers based on relationship state. Orgs that have moved cold → warm graduate to Tier 1. Orgs that have moved warm → cold get demoted to Tier 2 or 3. The list itself can grow — but only by removing one org for each one you add. The 100 constraint is what makes it work.
Run the play
Read the Dream-100 chapter in the free book →Frequently asked questions
Can I start smaller than 100?
Yes — start with 20, get the cadence working, then grow. The fail mode is starting with 100 and dropping the cadence in month 3; better to start at 20, hold the cadence for a year, then expand.
What if an org I picked turns out to be a bad culture fit?
Drop them and add a new one in the semi-annual resort. The list is a working roster, not a museum. The bar is 'still proud to be associated' — if that breaks, the relationship doesn't compound, no matter how hot the org gets.
How public should this be?
The list itself stays private (it's your working board). The engagement is fully public — your monthly touches, your quarterly public-elevation pieces, your weekly tracking are all visible. Privacy of the list, publicness of the engagement.