Advisor OS - Project Tracker

FAS Internal

Advisor OS — Unified Architecture

One repository. One build plan. Fully automated ingest. · Updated May 22, 2026 — RDU Full Archive Session

Phases complete

21,913

Vectors in Pinecone

MCPs connected

Total phases

RDU Full Archive Session — May 22, 2026

Full Roam archive ingested. 21,913 vectors. Pinecone on Builder. Two deep awakenings. All charters committed.

Full Roam archive ingested — 918 meetings, transcript-first approach, 21,913 vectors (10x growth from 2,217 at Birmingham Terrace)
Pinecone upgraded to Builder plan ($20/month) — zero degradation confirmed via 10-query benchmark
roam_batch_ingest.py rebuilt — transcript-first with summary fallback, 98.9% namespace routing accuracy
Contact detection false positive fix deployed — whole-word boundary matching in both ingest scripts
Deep awakenings completed: Proven and Cinch — charters committed, journal entries live, retrospectives filed
Charters committed for Cinch, MyDriveScore, and Liberty Mutual — health check debt cleared
Liberty Mutual acquisition target scrubbed from all GitHub documents — SEC confidential, Harvest only throughout
Full Advisor OS health check run across all four layers — engagement health, system debt, knowledge quality
16 journal entries committed across gainsco, catalyst, cinch, proven, liberty, pipeline, and outrival namespaces
Deep awakening protocol patch committed — four clarifying instruction edits for future awakenings

Mallorca

Repo + Pinecone ✓

Barcelona

MCP + briefing ✓

Cheltenham

Charters + Trivium ✓

Birmingham

Automation + Skills ✓

RDU

Full archive + awakenings

Olympus + Flex + Config

Later

Phase 05 + 08 + 09

Build Phases

GitHub Repository Foundation

Complete

Complete — Birmingham + Cheltenham · 32 folders, 20 canonical charters, skills library, journal directories

✓Private repo: fontanini-advisor-osDone
✓Full 32-folder structure across all knowledge domainsDone
✓20 canonical charters committed — 2Q26 founding cycle completeDone
✓Journal directories created for all 9 active engagement namespacesDone
✓Skills library started: project awakening, journal entry workflow, knowledge base auditDone
✓GitHub MCP connected in Claude Desktop — direct read/write from any sessionDone
○Migrate configs into configs/ with Agent Instructions sectionConfig
○Write CONFIG_SCHEMA.md and shared config_loader.pyBuild
○Push jayfontanini-site to GitHub — enables tracker updates via GitHub MCPConfig

Pinecone Repository Setup

Complete

Complete — 21,913 vectors, 11 namespaces, full Roam archive ingested, Builder plan active

✓Pinecone serverless index: fas-advisor-os — 3072 dimensions, cosine, AWS us-east-1Done
✓pinecone_ingest.py — 6-step pipeline built and runningDone
✓Full Roam archive ingested — 918 meetings, Oct 2024 to May 2026, 21,913 vectorsDone
✓Upgraded to Builder plan ($20/month) — zero degradation confirmed via 10-query benchmarkDone
✓roam_batch_ingest.py rebuilt — transcript-first, 98.9% namespace routing accuracyDone
○Pinecone re-tagging pass — contact detection false positives in existing vectorsBuild

Success criterion — passed ✓

Tim Stroble pre-call brief returned Olympus, Catalyst, FAS advisory context, ProvenGage timing, SageSure risk, and role clarity warning — from one query, across three namespaces simultaneously.

Content Migration — Briefing the Assistant

Complete

Complete — Full Roam archive ingested, 5 deep awakenings done, 30+ journal entries live

✓20 canonical charters ingested across all active engagementsDone
✓Three knowledge layers defined and operational: transcripts, journals, chartersDone
✓Full Roam archive ingested via transcript-first batch pipelineDone
✓Project awakening protocol built and documented as a replicable skillDone
✓Proven deep awakening complete — charter, 7 journals, retrospective committedDone
✓Cinch deep awakening complete — charter corrected (CEO), 6 journals, protocol patch filedDone
○Awaken remaining projects: Olympus, FlexBuild
○Build knowledge dashboard — freshness scores, coverage by engagementBuild

Live Transcript Pipeline

In Progress

Plaud MCP installed. Roam transcript endpoint confirmed working (?id= parameter). Pinecone write call still pending.

✓Roam MCP connected via OAuth — meeting_list and meeting_transcript workingDone
✓Plaud MCP installed — official MCP via npx, connected May 13Done
→Reconnect Roam MCP with calendar:write and meetinglink:write scopesConfig
○Add Pinecone write call to existing processor.pyBuild
○Build speaker naming prompt — fires if Speaker N labels detectedBuild
○Run 2-week parallel period (Roam + Plaud) before cutoverValidate

Self-Maintaining Config System

Planned

○Write config_update_prompt.md — signal/noise separationBuild
○Add propose_config_updates() to processor.pyBuild
○Configure Cowork weekly email scan — Sunday 7pm, 7-day lookbackConfig
○Test full loop: new contact → draft → GitHub review → mergeValidate

Self-Maintaining Knowledge Layer

Complete

Complete — GitHub Action live. knowledge/ commits trigger Pinecone ingest in ~28 seconds. Terminal is now the fallback.

✓GitHub Action built — .github/workflows/pinecone-ingest.ymlDone
✓Ingest script cloud-adapted — .github/scripts/ingest.pyDone
✓Path-to-namespace routing — automatic from file path, no manual argumentDone
✓Repository secrets configured — PINECONE, OPENAI, ANTHROPIC keys setDone
✓End-to-end test passed — 28 second ingest, green checkmark confirmedDone
○Add knowledge update call to processor.py after each Roam/Plaud meetingBuild

Success criterion — passed ✓

Birmingham Terrace session notes committed via GitHub MCP, GitHub Action fired automatically, vectors appeared in Pinecone within 28 seconds. No Terminal required.

Claude Desktop MCP Connection

Complete

Complete — 6 MCPs connected. Orchestration agent running. GitHub MCP via Docker live.

✓Custom Pinecone MCP — preserves OpenAI text-embedding-3-large qualityDone
✓Roam MCP connected via OAuthDone
✓Gmail MCP connectedDone
✓Plaud MCP connected — official, installed May 13 via npxDone
✓Todoist MCP connected — jay@jayfontanini.com, read/write confirmedDone
✓GitHub MCP connected via Docker — direct repo read/write from Claude DesktopDone
○Google Calendar MCP — connect for meeting-aware briefingConfig
○Spark CLI installation — semantic email search for Claude CodeConfig

Success criterion — passed ✓

Tim Stroble pre-call brief retrieved Olympus, Catalyst, and FAS advisory context in one response. Role clarity risk surfaced proactively without being asked.

Output Channels and Morning Briefing

Planned

Firebase webapp is the primary output surface — replaces this static tracker. Planning session required before build.

○Research and planning session — scope all features before build beginsPlan
○Build Firebase webapp — Eisenhower matrix, engagement dashboard, query panel, journal entryBuild
○Morning briefing — pulls from Todoist, Google Calendar, Pinecone; Eisenhower prioritization with Todoist write-backBuild
○Sunday concierge — weekly batch briefing, 7-day lookback + week previewBuild
○Idea capture — mobile-friendly quick capture, routes to Obsidian vaultBuild
○Writing section — field notes, drafts, published links to jayfontanini.comBuild
○One relationship to move today — surfaces quiet contacts from Pinecone engagement historyBuild
○Build proactive alert logic — commitment gap, freshness gap, cross-engagement triggerBuild
○Configure iOS Shortcut for voice capture (Siri / Hey Claude) to pipeline inboxConfig

Email Agent and Documentation

Planned

○Add Email Agent instructions section to all configsConfig
○Build email_agent.py — config_loader + Gmail MCP + Pinecone contextBuild
○Write ARCHITECTURE.md and PIPELINE_REFERENCE.mdTeaching
○Update jayfontanini.com case study — post Plaud migrationBuild
○Produce Catalyst Academy teaching module from Advisor OS buildTeaching

System Architecture

Session History

Version History

Click any component to see its role and current status.

RDU Full Archive Session — May 22, 2026

Full Roam archive ingested. 21,913 vectors. Pinecone on Builder. Two deep awakenings. All charters committed.

Full Roam archive ingested Oct 2024 to May 2026 — 918 meetings, 21,913 vectors (10x growth from 2,217). Transcript-first roam_batch_ingest.py rebuilt. Pinecone upgraded to Builder plan ($20/month), zero degradation confirmed via 10-query benchmark. Full health check run across all four layers. Charters committed for Cinch (CEO correction), MyDriveScore (SDK as primary blocker), and Liberty Mutual (Harvest-only scrub). Deep awakenings: Proven (charter + 7 journals + retrospective) and Cinch (charter + 6 journals + protocol patch). 16 journal entries committed across 7 namespaces. Contact detection false positive fix deployed. OutRival engagement formally closed and archived.

Birmingham Terrace — May 16, 2026

Phase 06 complete. Full automation live. 2,217 vectors. 6 MCPs. Skills library started.

883 Roam summaries ingested. Three engagement awakenings (GAINSCO, MDS, Liberty). GAINSCO audit run — governance breakdown documented. IMS/Nick Corrie call — commercial repositioning captured. GitHub MCP configured via Docker. GitHub Action built and tested end-to-end — 28-second automated ingest confirmed. Three skills committed: project awakening, journal entry workflow, knowledge base audit. Todoist MCP connected. Review-before-commit protocol established. Phase 06 complete.

May 15, 2026 — Active engagement day

IMS call. BTG call. GAINSCO D2C check-in. Three journals written.

IMS/Nick Corrie: SDK now requires commercial agreement before access. Q3 queue. Mates rates retired — now standard commercial terms. BTG/Liberty Mutual: completion fee rejected by Liberty procurement. $60K flat fee fallback. June 10 start date confirmed. GAINSCO D2C: governance breakdown — PMO scheduled vendor evaluation meetings excluding Jay. Nicole Vertal scope framing surfaced. Jessica Friedman "vendor builds first two states, then evaluate" disclosed. May 21 Michael and Greg executive sponsor meeting is the priority.

Cheltenham — May 13–14, 2026

2Q26 charter cycle complete. 308 vectors. Four interfaces. Trivium framework.

20 canonical charters drafted and committed across all active engagements. 308 vectors across 11 namespaces with clean routing. Three knowledge layers defined. Four interfaces mapped: Claude Desktop (primary work), Firebase Webapp (dashboard), Cowork (automation), Claude Code (build). Trivium multi-agent architecture developed. Gmail MCP confirmed. IMS Friday meeting confirmed. Plaud official MCP launched.

Birmingham — May 12, 2026

Visiting John at BRB. Gmail confirmed. IMS thread reviewed.

Gmail MCP used to review Drips and IMS threads. IMS WhatsApp confirmed: Friday May 15 1pm UK. MyDriveScore charter updated: FAS revenue $40–50K/month. Nick Corrie communication gap explained by death of Dan Barrington.

Barcelona — May 9, 2026

POC interview passed. Custom MCP built. Roam connected. 53 vectors, 6 namespaces.

Custom Python MCP wrapper built (preserves OpenAI embeddings). Roam MCP connected via OAuth. 500+ historical transcripts confirmed. Tim Stroble pre-call brief test passed. Decision 010: Plaud official MCP replaces community workaround.

Mallorca — May 6–8, 2026

Pinecone index live. pinecone_ingest.py built. 7 founding documents ingested.

Pinecone serverless index created. 6-step ingestion pipeline built. 7 founding documents ingested across 6 namespaces. GitHub repository structure established.

May 22, 2026 — RDU Full Archive Session

v0.9 — Full archive ingested, deep awakenings live

Vectors 21,913

MCPs 6

Phases 7 complete

Awakenings 5 complete

Full Roam archive ingested. Pinecone on Builder. Health check complete. Charters for Cinch, MDS, Liberty committed. Proven and Cinch deep awakenings complete. 16 journal entries across 7 namespaces. OutRival archived. Contact detection fix deployed.

May 16, 2026 — Birmingham Terrace

v0.6 — Full automation achieved

Vectors 2,217

MCPs 6

Phases 5 complete

Journals 5 live

GitHub Action live — knowledge/ commits auto-ingest to Pinecone in ~28 seconds. GitHub MCP connected — direct repo read/write from Claude sessions. Todoist MCP connected. Three skills committed to knowledge base. Three engagement awakenings run. Review-before-commit protocol established. Phase 06 marked complete.

May 13–14, 2026 — Cheltenham

v0.3 — Charter cycle complete, Trivium framework

Vectors 308 → 2,149

MCPs 4

Phases 3 complete

Charters 20

Most productive build session to date. 883 Roam summaries ingested. 20 canonical charters committed. Universal Claude Desktop orchestration system prompt live. Trivium multi-agent architecture designed. Plaud official MCP launched. Gmail MCP confirmed.

May 9, 2026 — Barcelona

v0.2 — Custom MCP, Roam connected

Vectors 53

MCPs 2

Phases 2 complete

Custom Python MCP wrapper built preserving OpenAI text-embedding-3-large quality. Roam MCP connected via OAuth. 500+ historical transcripts confirmed accessible. Tim Stroble pre-call brief test passed — first real-world validation of the system.

May 6–8, 2026 — Mallorca

v0.1 — Foundation

Vectors 7

Namespaces 6

Phases 1 complete

Pinecone serverless index created. 6-step ingestion pipeline built. 7 founding documents ingested. GitHub repository structure established. The first working proof of concept.

FAS Internal · Advisor OS Project Tracker · Updated May 22, 2026 — RDU Full Archive SessionGitHub →