ten31-database/AGENTS.md

Ten31 Venture CRM + Agentic System — AGENTS.md

The foundation is a self-hosted venture-fund CRM — a purpose-built fundraising tool that replaced Airtable to (1) keep sensitive LP/prospect data off third-party servers, (2) drop subscription cost, and (3) fit the fund's workflow: managing ~150 existing LPs, tracking 250+ prospects, and running the capital-raise pipeline. Core CRM domain: contacts (investor/prospect/advisor), organizations, opportunities (the deal pipeline), communications, and LP profiles. The fund (Ten31, ~$200M AUM, bitcoin/energy/AI thesis) runs it on a Start9 box, accessed on the LAN or over Tailscale by a team of ~5. Schema/API tour: docs/crm-overview.md.

The agentic system is new functionality built on top of that CRM — an in-house AI layer to widen the fundraising funnel, sharpen the thesis, and automate outreach drafting. Frontier reasoning runs on Claude (Agent SDK/API); privacy-sensitive and bulk work runs on local DGX Spark models via the Spark Control gateway. Phase 0/1 — no live outward-facing agents; agents draft, humans send.

Inbox check: At session start, if ~/Projects/standards/INBOX.md exists, scan it for items tagged (CRM) and surface them before proposing next steps; triage with /triage.

Stack (versions that matter)

• Python 3.11, standard library only at runtime. The CRM is one monolith, backend/server.py (~5k lines): a stdlib http.server.ThreadingHTTPServer + hand-written CRMHandler with manual path dispatch (do_GET/do_POST). Not FastAPI. backend/requirements.txt lists FastAPI/SQLAlchemy/Alembic/Pydantic/pytest-style deps but none are imported at runtime (vestigial).
• SQLite at data/crm.db (WAL, foreign_keys=ON), opened per-request via get_db(). Schema via ordered migrations.
• Frontend: single frontend/index.html, inline-Babel React. No build step.
• Optional runtime deps, used only if present: bcrypt, PyJWT (jwt), cryptography (Gmail module).
• MCP + ingest (in the Docker image, not the bare CRM): mcp==1.2.0 (FastMCP, backend/mcp/server.py), fastembed==0.4.2, anthropic, cryptography==42.0.5.
• Packaging: StartOS 0.4, TypeScript SDK (@start9labs/start-sdk) under start9/0.4/startos/. Live target is start9/0.4/.
• Local models (bge-m3 embeddings, bge-reranker-v2-m3, /api/search, Qdrant): always via Spark Control. Contract: docs/EMBEDDINGS.md.

Commands

# Run locally (dev, port 8080; or ./start.sh <port>) — runs python3 backend/server.py
./start.sh
# Run prod-mode (Tailscale/beta) — requires CRM_SECRET_KEY
./start_beta.sh
# Sanity-check edits (there is no compiler/build for the CRM)
python3 -m py_compile backend/server.py
# Run ONE test (tests are standalone scripts with `if __name__ == "__main__"`; no pytest installed)
python3 backend/redaction/test_scrub_leak.py        # substitute any backend/**/test_*.py
# Run all tests (aggregate runner — runs each backend/**/test_*.py in its own subprocess)
python3 backend/run_tests.py                         # add substrings to filter, e.g. `... soft_delete redaction`
# Build + install the s9pk — BUMP THE VERSION FIRST. See docs/guides/packaging.md.
cd start9/0.4 && make

• Migrations apply automatically at startup (backend/core_migrations.py, schema_migrations ledger). See docs/guides/migrations.md before adding one.
• Lint: none configured.

Directory layout (day-one)

• backend/server.py — the CRM monolith: HTTP handler, route dispatch, init_db(), auth (username/password → HS256 JWT, roles admin/member).
• backend/core_migrations.py + backend/migrations/NNNN_*.sql (+ paired .down.sql) — additive schema migrations, applied at startup.
• backend/thesis_seed.py — Thesis Workshop seed + idempotent ensure_* one-time seeders, wired in server.init_db().
• backend/thesis_review.py — thesis version review/approval (human dual sign-off → canonical).
• backend/mcp/ — architect_agent.py (Claude thesis copilot), architect_tools.py, outreach_agent.py (LP draft assistant), architect_grounding.py, crm_tools.py, server.py (FastMCP).
• backend/email_integration/ — Gmail capture via domain-wide delegation + Tier-B draft creation (compose.py).
• backend/redaction/ — scrub.py + client.py: the scrub→Claude→re-hydrate privacy boundary.
• backend/ingest/ — chunk→embed→Qdrant + retrieval modes.
• backend/entity_*.py — entity resolution/merge (the two-investor-model reconciliation).
• frontend/index.html — the entire UI.
• docs/ — architecture, phase plans, contracts, runbooks (see Deeper docs). docs/guides/ — scoped subsystem rules (see below).
• start9/0.4/ — StartOS package (startos/utils.ts holds PACKAGE_VERSION).
• data/crm.db — the live DB (gitignored). .env / .env.example — config (.env gitignored).

Scoped guides

Subsystem rules live in docs/guides/ and lazy-load in Claude Code via .claude/rules/ symlinks (scoped by paths: frontmatter). Read the guide before editing that area:

• Migrations or seeders (backend/migrations/, core_migrations.py, thesis_seed.py) → docs/guides/migrations.md
• Thesis logic (backend/thesis_*.py, backend/mcp/architect_*.py) → docs/guides/thesis.md
• Redaction or any MCP/Claude path (backend/redaction/, backend/mcp/) → docs/guides/redaction.md
• Ingest / retrieval (backend/ingest/) → docs/guides/spark-ingest.md
• Email capture / drafts + digest send (backend/email_integration/, backend/digest_mailer.py, backend/smtp_send.py) → docs/guides/email.md
• Building or deploying the s9pk (start9/) → docs/guides/packaging.md

Conventions

• Two coexisting investor models (classic contacts/lp_profiles + the fundraising_* grid). Reconciling them to canonical IDs is the core entity-resolution task — see docs/crm-overview.md.
• Soft-delete only: deleted_at and/or status='retired'; never hard-delete. Every READ path must filter deleted_at IS NULL — list handlers, get-by-id, nested related-data sub-selects, and aggregate sub-selects (COUNT/SUM/MAX). Audits found leaks in all of these (2026-06-12 detail + nested; 2026-06-13 list-view contact_count/total_funded/comm_count); the reports subsystem aggregates still leak (see Current state). Regression-guarded by backend/test_soft_delete_reads.py. (Thesis has a subtlety here — see the thesis guide.)
• Env: secrets in .env (gitignored); names in .env.example. Verified names: ANTHROPIC_API_KEY, SPARK_CONTROL_URL, SPARK_CONTROL_VERIFY_TLS, QDRANT_URL, X_API_KEY, CRM_DB_PATH, CRM_DEV_DB_PATH. Also used: CRM_SECRET_KEY (beta/prod), CRM_HOST/CRM_PORT, CRM_DATA_DIR; digest mailer: CRM_DIGEST_SENDER (DWD impersonation sender) + SMTP_HOST/SMTP_PORT/SMTP_SECURITY/SMTP_FROM/SMTP_USERNAME/SMTP_PASSWORD (SMTP fallback).
• Commit style: imperative subject, concise body explaining the why; put the package version in the subject (… (v0.1.0:NN)) for shippable changes. No AI co-author / attribution trailers — commits are authored by the user.

Always

• Verify before shipping: python3 -m py_compile the edited files; for DB logic, run the change against a copy of data/crm.db, never production.
• Keep real LP data out of Claude: develop only on code/schema/synthetic-or-locally-redacted data; route any real record substance through backend/redaction first.
• Get explicit user authorization before any production deploy/install to $START9_BOX_HOST.

Never

• Never treat Qdrant (or any derived index) as source of truth — the CRM/SQLite is canonical and rebuildable-from.
• Never hard-delete CRM records or thesis history — soft-delete/archive only.
• Never let an agent send email, post, or contact an LP autonomously — agents draft; a human approves and sends.
• Never set a thesis_version canonical from code/seeds — that is human dual sign-off.
• Never call a Spark directly — go through Spark Control (SPARK_CONTROL_URL).
• Never commit secrets, data/crm.db, .env, or data/backups/ (all gitignored). Scan staged files before committing. (.claude/ is tracked — launch.json and rules/ symlinks ship with the repo; keep local-only settings in .claude/settings.local.json.)
• Never bulk-export the LP list to any third party; send only minimal non-sensitive context to Claude.
• Never assume FastAPI / SQLAlchemy / pytest are in play — they sit in requirements.txt unused; runtime is stdlib + SQLite.
• Never add a Co-Authored-By / "Generated with" trailer to commits or PRs — commits are the user's.

Deeper docs

• Full constitution + guardrails: docs/ten31-constitution.md
• Architecture & rationale: docs/Ten31_Agentic_Build_Plan.md
• Retrieval/embeddings contract: docs/EMBEDDINGS.md
• CRM schema/API tour: docs/crm-overview.md
• Current thesis handoff: docs/thesis-handoff.md
• Operations & runbooks: docs/OPERATIONS.md, docs/go-live-runbook.md, docs/gmail-enablement-runbook.md

Current state

Phase 0 substrate + Phase 1 thesis/outreach are built; box and repo at v0.1.0:76 (Gmail-DWD digest send; deployed & verified live 2026-06-16). Repo carries minor post-76 review polish (committed, rides the next build). Longer-term backlog: ROADMAP.md.

• Working (all draft-only): CRM + ingest (chunk→embed→Qdrant + retrieval) + redaction boundary; Gmail capture (DWD) + email-activity propose→approve; Thesis Workshop + Architect (Claude) with dual-approval gate; Outreach Draft Assistant + follow-up radar + per-user voice + Tier-B in-thread Gmail draft creation.
• Deployed & verified live: v0.1.0:76 (box $START9_BOX_HOST/immense-voyage.local; installed-version→0.1.0:76, healthy on :8080). Daily-digest send is live: backend/digest_mailer.py routes Gmail-DWD (primary) → SMTP (fallback). DWD path (backend/email_integration/gmail_send.py, gmail.compose→users.messages.send, sender=CRM_DIGEST_SENDER else first admin) needs no app password and is proven by a live send to grant; the box's DWD grant has gmail.compose but not the narrow gmail.send. v75 added the SMTP fallback (Configure Digest SMTP action → /data/secrets/smtp/*, entrypoint exports SMTP_*), a Settings→Admin Send Test Digest Email button (admin-only, recipients restricted to the admin set), and the list-view soft-delete aggregate fix. Subsystem detail: docs/guides/email.md.
• Live since v74 (2026-06-13): login works; /assets/ traversal 404s (plain + URL-encoded), root health 200. On boot, ensure_thesis_v2_promoted makes the v2.0 reserve-asset spine the working approved spine (node-level, reversible). Security/privacy hardening (path-traversal close, outreach NER backstop, get-by-id soft-delete) shipped in v74 — detail in EVALUATION.md.
• Tests (2026-06-16): 19/19 backend tests green via python3 backend/run_tests.py (+test_smtp_send.py/test_smtp_endpoint.py/test_gmail_send.py this session). py_compile clean; the s9pk TypeScript typechecks (cd start9/0.4 && npm run check, deps installed); docker_entrypoint.sh passes sh -n. The 2 stale thesis tests stay fixed (seed structure in docs/guides/thesis.md).
• Decided, not yet built: CRM as canonical thesis backbone with the signal-engine reading from it (reconciliation unwired); reply-all for Tier-B drafts (drafts currently reply to the LP only).
• Known debt (P2, not deploy-blocking): the reports subsystem (handle_dashboard_report/handle_pipeline_report/handle_lp_breakdown_report, ~16 aggregate queries over contacts/opportunities/communications/lp_profiles) still counts soft-deleted rows — the list/detail aggregates were fixed (v74 + the org/contacts list-view follow-up) but the reports were not; needs its own pass + report-endpoint tests; ?limit=abc crashes the request thread (authenticated list path); scrub-gateway TLS verify off; cryptography==42.0.5; unpkg/no-SRI frontend; stale user-visible start9/0.4/assets/ABOUT.md; hardcoded Spark/Qdrant IPs in the s9pk; the 5.4k-line server.py monolith. P3 batch + full list in EVALUATION.md.
• Other gaps: the v2.0 spine is the working spine but not a canonical thesis_version (needs Grant + Jonathan dual sign-off); Appendix-A conviction/exposure (incl. ~40% Strike) stay Grant's working read, not canonical, not fed to the engine; live features (Claude/Qdrant/Gmail) unverified on the box.
• Next: 1) Grant clicks Settings→Admin Send Test Digest Email (the app-path confirmation; raw DWD send already proven); 2) digest Phase B — daily scheduler + per-user→per-investor activity query (deleted_at IS NULL) + Spark-narrative summary (never Claude) → email all admins (decisions locked in ROADMAP.md); 3) reports-subsystem soft-delete sweep (~16 aggregates still leak; fix + tests); 4) ?limit=abc crash (P2); 5) Grant + Jonathan freeze v2.0 canonical; 6) build reply-all; 7) confirm Appendix-A + Maple/OpenSecret/Primal, then promote.