He knows youYour business, your team, your goals, your relationships — held in memory and recalled the moment it matters.
⚡
He acts before you askMorning briefing. Meeting prep. Urgent emails escalated. Everything else handled quietly so you're not monitoring anything.
✅
He finishes what he startsNot a task logger. Emails drafted. Events scheduled. Follow-ups sent. Done means done.
Always On
Voice
Text
Phone
Every Device
12 AI Agents
Mac Mini M4
Explore
He Knows You
Not a chat window you re-explain yourself to every time. A persistent knowledge system built around one person — your business, your team, your goals, and the relationships that matter most.
Business & Goals
Company strategy, active priorities, fundraising stage, what winning looks like this quarter
Your Team
Who does what, working styles, strengths, history together, active projects
Relationships
Every contact, what you've discussed, what you promised, personal details that matter, when you last connected
Your Life
Family context, personal goals, preferences, patterns, things that matter outside work
Memory Browser — browsable and searchable at any time
How memory actually works ›
Under the Hood
Facts
Extracted from every conversation, deduplicated and conflict-detected automatically
Goals
Tracked separately from facts — marked done when completed, archived when stale
Patterns
Inferred from observed behavior over time, not self-report
Context injection
Woodhouse never starts from scratch; your knowledge is part of every conversation
Nightly governance
Removes stale facts, resolves contradictions, keeps the knowledge system clean without manual curation
Your Day Starts Before You Do
Before you pick up your phone, Woodhouse has already scanned your inbox, prepped your meetings, reviewed your pipeline, and decided what the day should look like. You get the output — not the work.
☀️
Morning Briefing
Top 3 prioritized focus items scored by deadline, revenue impact, and goal alignment. Delivered to Telegram before your day starts.
📧
Email Triage
Inbox scanned 4× daily. Categories auto-applied and organized. You're only pinged when something genuinely needs your attention.
📅
Meeting Prep
Full dossier prepared before every qualifying meeting: the people, your history, what you committed to, talking points.
📈
Investor Pipeline
Stale deals flagged every morning. Days-to-deadline tracked. Priority actions surfaced automatically.
What's running in the background ›
Under the Hood
14+ scheduled jobs
Covering email, relationships, content, pipeline, meeting prep, and self-improvement — running on cron schedules around the clock
Two-phase morning brief
Researcher agent gathers raw intel, then Chief of Staff synthesizes it into a prioritized Top 3 — two perspectives, one output
Notification discipline
Max 2 Telegram pushes per day. Only urgent or time-sensitive items ping you. Everything else waits for the morning brief or on-demand review.
Full stack
Each job routes through the agent + MCP stack, not canned scripts — they reason, take action, and report back
Individually controlled
Every proactive job can be enabled or disabled independently, with per-job budget caps and cost tracking
With You Everywhere
No apps to learn. No mode to switch into. Woodhouse is wherever you already are.
Phone
Apple Watch
Telegram
CarPlay
Desktop
Voice Notes
AirDrop
Call him. Text him. He picks up.
"Voice note from your car — event scheduled before you park."
"Text from your watch — full research back before you sit down."
"Drop a PDF from your Mac — summarized, filed, actioned."
More Relationships. Deeper Ones. Less Effort.
There's a limit to how many relationships a person can genuinely maintain. Woodhouse pushes that limit — not by doing the relationship for you, but by making sure you never show up empty-handed.
"You're seeing Paul tomorrow — last time you talked, his daughter had just started college. He mentioned she was interested in finance."
"You haven't spoken with Jill at CW Wealth in three weeks. Here's a message — want me to send it?"
"Just met Sarah at Future Proof — contact created, company researched, follow-up scheduled. Walk away."
He captures it from your calls and meetings automatically — and surfaces it at the moment it's useful. Not in a database you have to search. Proactively, in context.
How relationship intel flows ›
Under the Hood
Meeting transcripts
Meeting transcripts scanned automatically after every call; personal details, commitments, and key moments extracted
CRM sync
Relationship intel written directly to your CRM contact notes — no manual entry
Daily touchpoints
Two people to reach out to surfaced each morning with ready-to-send message drafts
On-demand dossier
Full relationship history, shared connections, personal details, and past commitments available instantly
Your Second Brain
Woodhouse holds more than your calendar and inbox. Side projects, conference notes, ideas, voice memos, research — all captured, organized, and written into your Obsidian vault. Everything you care about, in one place, always current.
Before the Conference
He did the homework
For Future Proof — a 3,000-person advisor and fintech conference — Woodhouse analyzed the attendee list against goals, investment thesis, and relationship history. Recommended who to request meetings with and why. Then built a full research dossier for every scheduled meeting: the firm, the person, shared connections, relevant context, and exactly what to focus the conversation on.
At the Conference
Quick notes in. Everything out.
After each meeting, a quick voice note or typed summary — who, what was discussed, what was promised. Before the next meeting started, Woodhouse had already drafted the follow-up email, scheduled the next touch, logged the CRM notes, and was working through the action items. No mental stack to carry. No list to process later.
Before Leaving the Venue
Essentially done.
Nearly 100 meetings. 55 people to follow up with. All handled — from a phone, in context, in real time, in my sandals, while on the beach. What used to require two days of mental downloading and manual debriefing was done before the closing keynote.
~100 meetings. 55 follow-ups. All drafted, scheduled, and logged — in my sandals, on the beach, before the closing keynote.
How conference intelligence works ›
Under the Hood
Pre-event research
Attendee list + your goals + relationship history → ranked meeting recommendations with reasoning
Meeting dossiers
Deep research on each scheduled meeting: firm, person, shared connections, past interactions, talking point recommendations
In-field capture
Voice note or text → full transcript → action items extracted → email drafted, event created, CRM updated
Knowledge capture
Conference notes, ideas, and follow-through written into your knowledge vault — organized by project, person, or topic
Side projects & ideas
Independent projects (Conference File Up, new ideas, research threads) tracked separately with their own context and next steps
Not Added to Your List. Done.
Most AI tools create more things to manage. Woodhouse tries to eliminate them. When something needs doing, he does it — and tells you what he did.
📧
Email drafted
Written and saved as a draft. Never sends without your approval.
📅
Calendar managed
Checks for conflicts, creates the event with full context.
Tasks extracted, categorized, and acted on before you leave the call.
What runs automatically vs. what asks first ›
Under the Hood
Read actions
Run instantly with no confirmation: checking calendar, reading email, looking up contacts
Write actions
Execute and notify: creating events, drafting emails, logging CRM notes
Send / delete actions
Always confirm first via Telegram: sending messages, deleting files, external communications
Audit trail
Every autonomous action logged with timestamp, agent, and outcome
His Principles
Autonomy without accountability is just a liability. Woodhouse earns authority through a tiered trust system, a deeply personal profile, and domain expertise injected at the right moment.
🔐
Trust Through Transparency
Every action classified. Every high-stakes decision confirmed. Every execution logged.
Tier 0
Read
Check calendar, read email, look up contacts — instant, no confirmation
Send messages, delete files — always confirm via Telegram first
Tier 3
System
Service restarts, system commands — confirm first, logged permanently
🧬
Configured Around One Person
Not a generic assistant. Shaped by a profile that defines personality, boundaries, and deep context.
Personality
Tone, proactiveness, anti-patterns — no sycophancy, no corporate speak, no filler
Communication
Brevity rules, voice response limits, how to deliver bad news
Boundaries
What requires confirmation, what's off-limits, scheduling constraints
Deep Context
Family, work schedule, business entities, team members, personal goals
Domain Skills
12 skill modules — CRM, email, calendar, content, sales, investor pipeline, podcast — injected when the context demands it
The security model ›
Under the Hood
Local-first
No public-facing ports. Remote access only through Tailscale. Everything runs on trusted local hardware.
Allowlist-only
Shell commands restricted to a pre-approved list. Adding new commands requires a code change, not a prompt.
Progressive capability
Started as a chatbot. Added local system control, then file intelligence, then browser automation — each phase earned through safe operation.
Full audit trail
Every autonomous action logged with timestamp, agent, tier, and outcome. Searchable and reviewable at any time.
Profile-driven
A single markdown file — config/profile.md — shapes every interaction. Personality, user context, integration rules, and explicit "don'ts" all defined in one place.
Your Command Center
Woodhouse doesn't just live in Telegram. He built his own command center — and keeps improving it.
Dashboard — Today, Tasks, Goals, Memory, Reports
Agent selector
Apps & controls
The dashboard tracks today's focus, tasks, goals, memory, cost, and job reports.
The Hub gives instant access to every agent, workflow, and app — directly from Telegram.
Board Room, Post-Meeting Review, Memory Browser, Investor Pipeline — all one tap away.
How the dashboard was built ›
Under the Hood
Proposed and shipped by Woodhouse
Designed via the nightly builder, built on an isolated branch, submitted for approval
Stack
Next.js frontend, full database backend, authentication — built and shipped by Woodhouse
Mini-apps
Built as Telegram Mini Apps (Vite + React + Tailwind), served from the same Mac Mini
Iterating
Woodhouse adds features and fixes bugs on an ongoing basis; the dashboard you see now is not the same one from launch
Your Organization's Brain
Most AI assistants only know what you tell them in the moment. Woodhouse has access to your complete organizational knowledge base — every meeting transcript, every proposal, every research article, every SOP — through Sirdar. A graph database and semantic search engine that the entire firm uses, now connected directly to Woodhouse's agents.
Meeting Transcripts
Fireflies recordings, automatically captured and indexed
Shared Documents
OneDrive, SharePoint libraries, and shared organizational files
Knowledge Vault
Obsidian notes, research threads, and connected ideas
Curated Research
RSS feeds, saved articles, white papers, and industry intel
Client Work
Proposals, contracts, SOPs, and engagement history
Synced Notes
iCloud, manual uploads, and everything else worth keeping
"Do we have a proposal similar to what Client X is asking for?" — finds prior proposals, extracts the playbook, and adapts it.
"What did we discuss with this prospect last quarter?" — surfaces meeting transcripts, CRM notes, and relationship history in one query.
"What's our playbook for this type of deal?" — finds SOPs, past meeting notes, and successful deal patterns across all sources.
Most tasks don't need it. But when you're doing deep research, locating a document, or modeling work after something you've done before — Sirdar makes it possible. Available to agents and the entire firm as a mobile app and desktop webapp.
How organizational search works ›
Under the Hood
Graph + RAG hybrid
Graph database for relationships and entity connections, plus vector embeddings for semantic search — surfaces what pure text search can't
Low latency
Designed for real-time agent queries, not batch processing — results come back fast enough to use mid-conversation
Source-aware
Every result includes document type, import source, firm names, topics, and relevance score — agents can cite their sources
Read-only layer
Woodhouse searches but never modifies Sirdar — organizational data stays pristine
Meeting prep integration
Before every qualifying meeting, agents search Sirdar for all prior organizational knowledge about attendees and their firms
Firm-wide product
Same knowledge base powers the Sirdar mobile (PWA) and desktop apps used by the broader team — Woodhouse is one consumer
Meet the Agents
Twelve specialized agents. Each one built for a specific domain — not with generic prompts, but with real frameworks from practitioners. Every request routes to the right one automatically, or at your direction.
🧭
Chief of Staff
Orchestration
Complex reasoning, multi-step planning, and coordination across your entire day. The one who figures out what needs to happen next.
💻
Developer
Engineering
Full-stack coding, debugging, and shipping. Builds features and fixes bugs — on isolated branches, overnight, waiting for your approval in the morning.
🔭
Strategic Advisor
Strategy
Deep synthesis for the decisions that matter. Investor strategy, architecture trade-offs, business model questions. The one you bring in when the stakes are high.
Built on Alex Hormozi's Value Equation, Bottleneck Rule, and Grand Slam Offer frameworks
📣
Marketing Strategist
Marketing
Positioning, messaging, growth strategy. Opinionated, direct, and keeps the audience front and center.
✍️
Content Creator
Content
LinkedIn posts, newsletters, blog outlines — sourced from your actual meetings and conversations. Publish-ready, in your voice.
Built on Nicolas Cole's 1/3/1 Framework and lean writing progression
🤝
Sales Outreach
Sales
CRM-aware outreach sequences, follow-up cadences, and prospect research. Knows who you've talked to, what was said, and what to say next.
Built on Chris Voss's tactical empathy from Never Split the Difference
🔍
Researcher
Research
Web search, deep dives, real-time intelligence. Finds what you need — a company background, a market trend, a person's history — before you need to ask twice.
💼
Relationship Manager
Relationships
Tracks your contacts, surfaces who to reach out to, writes the message, and keeps the relationship history current — automatically, from your calls and meetings.
💬
Negotiation Coach
Deals
Deal strategy, counterparty analysis, term sheet review. Helps you walk in prepared and walk out with the right outcome.
🎯
Prioritizer
Focus
Scores every open task and opportunity by deadline, revenue impact, and goal alignment. Tells you what to work on — and what to ignore.
⚡
Triage & Router
Intake
Classifies every request in milliseconds and routes it to the right agent. The one you never notice — because it just works.
📊
Finance
CFO
Conservative financial analysis with chain-of-thought math. ROI calculations, spend reviews, and budget decisions — always shows the work.
Default stance: preserve capital, quantify everything, show the math
The Board Meeting
For the problems that deserve more than one perspective. Type /board and Woodhouse convenes a full strategic session — Finance, Strategy, Marketing, Operations, and a Critic who challenges every conclusion.
Convene from Telegram
Live agent graph
Each agent works the problem from their domain. A synthesis phase combines perspectives. The Critic stress-tests the conclusions. You get a multi-dimensional answer — not a single-model response.
What's actually happening ›
Under the Hood
Full Claude Code sessions
Each agent is a complete Claude Code session with domain-specific skills and MCP access, not a prompt variant
Sequential phases
Research, analysis, cross-examination, synthesis — each phase informed by the previous
The Critic
Has explicit permission to challenge and contradict other agents' conclusions; prevents groupthink
Board Room mini-app
Full transcript of every phase available for review; results persist across sessions
He Builds Himself
Every weeknight at 10 PM, Woodhouse reviews his own logs, picks one thing to improve, builds it, and asks for your approval the next morning. He's been doing this since day one.
🔧
Nightly Builder
Reviews logs, identifies the highest-impact improvement, builds it on an isolated branch. You get Approve / Revise / Reject. Ships code while you sleep.
Isolated git branches — no risk to production
Bug fixes, new features, prompt improvements
Proposes, builds, and waits for your call
⚡
Autonomous Mode
For tasks that demand it. Full tool access, extended reasoning, all integrations unlocked. Returns to normal when done.
Activate from Telegram or the Hub mini-app
Returns to normal mode automatically
The nuclear option for complex work
🧠
Memory That Governs Itself
Nightly cleanup removes stale facts, deduplicates, resolves contradictions. The knowledge system stays accurate without manual curation.
Facts, goals, tasks — stored and governed separately
Runs silently; you're only notified when significant changes are made
Getting smarter every night
👁️
Human-in-the-Loop Review
Every nightly build goes through a formal review. Approve to merge and deploy. Revise to send back with feedback. Reject to discard. Nothing ships without your sign-off.
Budget caps per job — no runaway spending
Active goals injected into every scheduled job's context
Full cost tracking per agent, per run, per month
How the nightly builder works ›
Under the Hood
Git worktrees
Each build runs on an isolated branch; production is never touched until you approve
Full access
Claude Code + all MCP tools available during the build session
Transparent proposals
Every submission includes a summary, what changed, and why it was chosen
Approve / Revise / Reject
Ships the branch, sends it back for another pass, or discards it entirely
"Built from scratch. Running since day one. Getting better every night."
Running now — always watching, always learning, always ready
James has spent over 25 years working in and around wealth management technology — including nearly a decade at SS&C Advent, and now running WealthTech Select where they track over 1,000 wealthtech companies. He also co-hosts the AI for Advisors podcast and recently started Ascent Growth Platforms, which will launch RIA Ascent later in 2026.
Building something similar? Reach out on LinkedIn — always happy to talk shop.
