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Board prep, investor updates, team comms. You write 60% of them yourself because generic AI doesn't know your business. This one does.
95+ founders & leaders deployed • 58% non-technical • Your database, your rules
Same AI model. Same prompt. The only difference: context. Examples use illustrative data to show the format.
"Prepare my board deck for next week."
"Sure! I can help with a board presentation. What metrics should I include? What format do you prefer? What time period should I cover?"
"Prepare my board deck for next week."
"Based on your Q1 financials (pulled from Stripe + Supabase), ARR grew 34% to $2.1M. Churn dropped to 3.2% after the onboarding changes you shipped in February. I've drafted 12 slides using your board template with the narrative structure Sarah liked last quarter."Pulls real data, uses your template, references past board feedback.
"Write my monthly investor update."
"I'd be happy to help with your investor update. Could you share your recent metrics, key wins, and any challenges you'd like to highlight?"
"Write my monthly investor update."
"Draft ready. March highlights: closed Series A extension ($2.4M, led by Sequoia scout). Product: shipped v2.0 migration tool, 47 customers onboarded this month. Challenge: engineering bandwidth, considering a contractor for Q2. Tone matches your previous 8 updates."Pulls from your actual data sources. Written in your voice.
"What should I focus on today?"
"I can help you prioritize! What tasks do you have today? Any deadlines or meetings coming up?"
"What should I focus on today?"
"You have 3 meetings today. The 2pm with DataCorp is the priority. They asked for a revised proposal last week and you haven't sent it. Your CTO flagged a production issue overnight (P2, not urgent). Two investors replied to your fundraise update, one wants a follow-up call."
Every Claude session starts from zero — unless you engineer the context it receives. A Second Brain is the system that ships with your metrics, your board history, your decision log, and your voice already loaded.
Your metrics, board history, investor asks, past decisions, and team org — stored in a local SQL database so AI can brief you before you ask.
Pre-configured agents for board prep, investor updates, team comms, and strategic memos. Trained on your voice and standards.
Commands like /board-prep, /investor-update, /strategy-memo, /daily-priorities — one prompt, complete output in your voice.
Slack, Linear, Notion, Stripe, Gmail, Calendar — AI reads real business data so outputs reflect your actual state, not generic templates.
Plus: Your Own Operating Layer
ARR, burn, runway, churn, NPS — queried from Stripe + Supabase on demand. Ask your AI, get the number.
Every strategic call, the options considered, the rationale — searchable. The company memory lives outside your head.
Board decks, monthly updates, fundraise emails — drafted in your voice with real metrics. Validated before you send.
All-hands, standups, announcements — AI writes from your actual week, not what it assumes happened.
How it fits together
You
talk to Claude
Second Brain
structures your context
Claude
works with full context
Decisions
not documents
Better Output
every time
The result: Instead of re-explaining your business every session, Claude already knows. It has last week's metrics, your board's last questions, your investor thesis, and your voice — across every session. Plus a decision log that compounds every call you make.
Static Context
Engineered Context
Setup
You copy-paste your company context every chat
AI loads metrics, board history, and voice from day one
Memory
Forgets last quarter's strategy decisions
Decision log compounds — the company memory lives outside your head
Tools
Copy-paste between Stripe, Slack, Notion, CRM
AI reads real business data directly via MCP
Quality
Hope the investor email sounds like you
Voice + standards rubric blocks sends that miss the bar
Speed
60% of your week writing updates
Draft in 2 minutes, edit in 5, focus on decisions
Ownership
Company knowledge trapped in a vendor's DB
Your Supabase. Your decisions. Cancel us, keep everything
This is why ChatGPT Memory, Notion AI, Cowork, and DIY setups all hit the same wall.
Personalized
not templated
Connected
not isolated
Measured
not guessed
Compounding
not static
Owned
not rented
Five patterns we see in every founder setup. Which one is you?
Every decision, every review, every piece of quality communication runs through you. Your team waits while you context-switch between fires.
"I need to clone myself. Or at least my judgment."
— Series A founder, SaaS
Investor updates, board decks, customer emails, team standups. You spend 60% of your time writing instead of building.
"If there was a reseller model, I would be all in."
— Andreia
Your standards, voice, and strategy are the company's moat. But they only exist in your head.
"I don't want to give them my brain."
— Celine
You're already in Claude Code building your product. Now you want AI to handle the CEO stuff too.
"I'm mostly curious on how you do things differently."
— Wouter
No exec team yet. You run product, sales, ops, and fundraising yourself. You need a system that acts like a chief of staff.
"My biggest worry is that I do things half."
— Lucas
54%
Never opened a terminal
58%
Non-technical roles
87%
Disorganized files
8/8
Setup friction = #1 blocker

I'm Iwo Szapar. For the past 14 weeks, I sat down with 95 professionals — one at a time, 1-2 hours each — and manually built their Second Brains. What I was really doing was context engineering. That's also what made it impossible to scale.
I was the bottleneck. So I built Second Brain 2.0.
Deliverables that took 3 hours now ship in 15 minutes. Not because AI remembers more. Because AI validates before you review.
Co-founded the AI Maturity Index with Harvard researchers (420,000 data points, acquired by ISG in 2026). Helped 3,000+ companies and 25,000+ professionals at Microsoft, Walmart, and governments worldwide.
Trusted By




Self-paced. No call needed. No technical knowledge required.
A conversational questionnaire maps your role, expertise, writing style, and current tools.
Answer questions about your work, clients, and preferences
AI analyzes patterns — writing style, decision frameworks, domain expertise
Generates a personal profile that becomes your AI's foundation
No technical knowledge required — like a structured onboarding call
After setup
New clients, new projects, new preferences — if AI doesn't learn about them, it falls behind. MemoryOS runs decay detection on your SQL database, flagging knowledge items not accessed in 30+ days, tracking confidence scores, and monitoring context pressure across 38 dimensions.
Beyond chat — CEO-level outputs
Every founder command combines real business data, your voice, and your quality bar into one action. Type one slash command — get a board deck, not a brainstorm.
/strategy-memoFrame a decision, lay out options, pull relevant prior context, recommend a path. Uses your writing structure. Logged to decision journal automatically.
→ memos/pricing-tier-strategy.md + decision logged
/decision-logSearches every strategic call you've made, rationale, and outcome. Resurfaces patterns before you repeat a mistake.
→ 4 similar decisions found, 2 worked, 2 reversed
/daily-prioritiesCalendar, inbox highlights, open threads, yesterday's metrics, and the three things only you can do today. 30 seconds to focus.
→ Morning brief: 3 focus items, 2 threads needing reply
/board-prepDrafts a 12-slide deck using last quarter's template, real Stripe metrics, and narrative structure from past board feedback. Ready for your edits.
→ decks/board-q2-draft.html (12 slides)
/investor-updatePulls this month's wins, misses, metrics, and asks. Matches your voice from past updates. One-tap send after review.
→ Draft ready, voice score 94/100
/team-updateWeekly team update: what shipped, what's next, team wins. Reads Linear + Slack, writes in your all-hands tone.
→ all-hands-week-16.md + speaker notes
/metrics-checkARR, burn, churn, runway, cohort LTV — pulled from Stripe + Supabase on demand. Ask in plain English.
→ ARR $2.1M (+34% QoQ), churn 3.2%, runway 18mo
/review-readyReads the inbox, flags what only you can decide, drafts responses for the rest. WhatsApp ping when drafts are ready.
→ 3 decisions needed, 7 drafts ready for approval
10 founder skills. Build your own in minutes.
Every skill is a markdown file. Edit it, duplicate it, or chain it into your own /ceo-morning variant.
The Guide is a remote plugin that reads your local brain structure to give guidance. Your actual content, client data, and personal information never leave your computer. We only see which tools you call and how often — for product improvement.
Context engineering isn't one thing — it's a stack. Each layer makes AI smarter about you and your work.
A file at the root of your workspace that Claude reads on every conversation. Your preferences, rules, writing style, tool conventions — loaded automatically, every time.
# CLAUDE.md ## Voice: Direct, no fluff. Never use "leverage" or "synergy." ## Clients: Enterprise SaaS, 50-200 employees ## When writing proposals: Use the 3-part framework from /templates
AI learns from every conversation and stores patterns, client details, and decisions in a local SQL database with 12 queryable collections and confidence scoring. Month 1: knows your name. Month 6: knows your client's pricing objections, when the last interaction was, and which proposals need updating.
The Model Context Protocol lets Claude read and act on your real operating stack — Stripe (ARR, churn, cohorts), Linear (what the team shipped), Slack (team sentiment, open threads), Notion (your strategy docs). Instead of describing your business, Claude queries it directly.
Reusable commands like /daily-briefing or /draft-proposal that combine multiple tools and context sources into one action. Type one command, get a complete output that would've taken 30 minutes manually.
This is where context engineering gets powerful. Hooks are shell commands that fire automatically at specific points — before a tool runs, after a file is saved, when a session starts. They don't rely on AI judgment. They always execute.
PreToolUse
Block investor-update send without metrics
Every external comm must quote real Stripe/Supabase numbers, not hallucinated ones
PostToolUse
Log every decision to the decision journal
After a /strategy-memo, auto-append to memory/decisions with rationale
SessionStart
Load this week's top 3 priorities
When you open Claude, inject the week's focus + open investor/board threads
Stop
Check draft against voice standards
Before finishing, run the voice rubric on any outbound email or doc
# Example: Block investor update from sending without real metrics attached
{
"hooks": {
"PreToolUse": [{
"matcher": "Gmail.*send",
"hooks": [{
"type": "command",
"command": "$CLAUDE_PROJECT_DIR/.claude/hooks/require-metrics.sh"
}]
}]
}
}The system configures your hooks automatically. You don't write JSON — you tell it what you want enforced.
Most "AI setups" only use Layer 1.
A Second Brain uses all 5 layers working together. That's why the output quality is fundamentally different.
What no other AI tool gives you
Every AI wrapper stores your data on their servers. Cancel and it's gone. Your Second Brain deploys on infrastructure you own — Supabase + Vercel, both free tier. Cancel us and keep everything.
A local database on your laptop or your own Supabase instance. Your metrics, board history, investor list, decision log — all in tables you control. Not trapped in a vendor's API.
Vercel runs your dashboards, cron jobs, and data pulls. Nightly metric snapshots. Weekly decision digests. All on your account.
Claude Code agents run locally with full business context. Your board prep, investor drafts, and strategic memos never leave your device.
Templates and workflows live in the database, not code. When we improve a board-prep flow, you get it by updating one row — no git pull, no deploy.
SaaS expires. Infrastructure compounds.
Richard Wilson
3-4 months saved on setup
Transformation Partners
"I was building my own system from scratch. Cobbling together prompts, trying to get Claude to remember context between sessions. The Second Brain saved me three to four months of hacking my way through it. Now I have a system that actually knows my business."
3-4 mo
Setup time saved
$597
Kickstart investment
100%
Worth it (his words)
Wouter van den Bijgaart
AI Developer / Founder
Replaced DIY setup
"I built my own system and spent 3 hours a week maintaining it. The Second Brain does the maintenance automatically. The propagation alone saved me from constantly updating my assistants manually."
Damian
Professional
Profoundly changed
"The regular AI tools now just seem like child's play. This has profoundly changed how I work."
Dominic Albrecht
Non-technical founder
Zero code needed
"I'm not a coder. I don't write code. So it's incredible that this type of stuff is available and can happen."
Gabe Marusca
Consultant / Founder
93% faster prep
"Now I type /prep and get a complete brief with their history, concerns, and my recommended approach."
"This replaces my entire SaaS stack." — Mark & Stas
Pay once. Own it forever.
Quick math
97 professionals are running their Second Brain right now. If it saves you 5 hours per week at $200/hr, that's $4,000/month in recovered time. The Kickstart pays for itself in the first week. One purchase. No subscriptions.
For technical users who want full control
The full system. You set it up.
Full repo: 55 skills, 21 agents, 7 integrations
Setup guide + Health Check MCP
Community access
Self-serve — you configure at your pace
MemoryOS available separately ($199/yr)
No support included
7-day money-back guarantee.
For professionals who want it working today
AI configures it. You're running in minutes.
Everything in DIY
AI agent builds your system from your answers
48-hour priority async support
First year of MemoryOS Pro included ($349 value)
Async support — no calls needed
7-day money-back guarantee.
For leaders who want it built for them
2-hour onboarding call + full setup.
Everything in Kickstart
2-hour onboarding call with Iwo
I deploy your infrastructure (Vercel + Supabase)
Monthly Second Brain updates (new agents, skills, tools)
12 months MemoryOS included
2-hour call + direct access to Iwo
7-day money-back guarantee.
New tools and skills ship through MemoryOS. Updates arrive without you doing anything. Health monitoring spots what needs attention. Weekly recommendations tell you what to fix. Included in Kickstart and Done-With-You.
Get Repo
5 min
Instant email with GitHub repo
Questionnaire
15 min
Answer about role and workflows
Build
~60 min
System generates, configured for you
First Win
7 min
Run /overview, priorities are there
Deploy Infra
30 min
One-click Vercel + Supabase (optional)
Learn more about context engineering, MCP, and building better AI systems.
Deep dive into the Model Context Protocol — what it is, how it works, and why it matters for building AI systems that actually know about your work.
How the Model Context Protocol turns AI memory into AI action. Connecting your Second Brain to Gmail, Calendar, CRM, and more.
The emerging role nobody trained you for. Why context engineering is the new high-leverage skill for knowledge workers in 2026.
Production patterns, hook configurations, and context engineering workflows from 6 months of hardcore use building real systems.
Not ready to buy? Watch how it works or try a free resource.
Stop fighting generic AI. Start with a system that knows you.
DIY
Kickstart — Most Popular
Done-With-You