Portfolio Management
Diagrams | Matrices | Thinkers
How do you balance risk vs potential reward?
Invest in systems that recognise value and sell dreams. Understand the forces shaping the future then position to thrive in that reality.
Conviction must be earned it cannot be borrowed
Operating Rhythm
The investor's operating system. Routines prevent both paralysis and impulsiveness.
Daily (15 min)
- Scan macro headlines — rates, regulation, geopolitical shifts
- Check portfolio for anomalies — unusual volume, price gaps, liquidation events
- Log one observation in your decision journal
Weekly (3 hrs)
- Deep dive 1-2 positions — re-read thesis, check on-chain metrics, review community sentiment
- Update financial models with new data
- Review watchlist — has anything changed conviction level?
Monthly (4 hrs)
- Re-examine each position against its original thesis
- Adjust position sizing based on updated conviction
- Run contrarian review — argue against your biggest position (Howard Marks)
Quarterly (6 hrs)
- Full portfolio stress test — simulate 30% drawdown, which positions survive?
- Decision post-mortem — review every buy/sell decision. What was your reasoning? What happened?
- Update investment principles based on what you learned
Annual (12 hrs)
- Strategic reset — which macro trends shifted? Which theses are stale?
- Eliminate positions held by inertia, not conviction
- Update mental models. Ray Dalio: "Pain + Reflection = Progress"
Position Sizing
Conviction-based allocation. Size matches confidence, not excitement.
| Conviction | Evidence | Allocation | Example |
|---|---|---|---|
| 5/5 | Multi-cycle proof, on-chain validation | 5-7% | Core thesis positions |
| 4/5 | Strong data, clear catalyst | 3-5% | High-conviction plays |
| 3/5 | Early product-market fit | 2-3% | Growing conviction |
| 2/5 | Hypothesis, partial validation | 1-2% | Research positions |
| 1/5 | Exploratory, learning bet | 0.5-1% | Skin-in-the-game scouts |
Rules:
- No single position above 7% unless 5/5 conviction with multi-year track record
- Rebalance when any position drifts 2x from target (eg. 3% target hits 6%)
- Cash position: maintain 10-20% for opportunities during drawdowns
Before Buying
- How many people will buy this? What drives their demand?
- What time horizon? Will there be liquidity when selling?
- Have you written your thesis? (If not, stop here)
If you have an inkling you need to pay attention to something, place a small bet so you're incentivised to evolve your thesis.
Events and Signals
Market triggers that demand attention:
- Act of War — Bitcoin breaks out 60 days afterwards (Blackrock research)
- Positive news without uptick — Signal the market is fully allocated. Consider taking profit to have cash on hand (1000x)
- VC funding cycles — Profit distribution timing drives secondary market flows
- Scheduled macro events — Federal Reserve Calendar
- On-chain anomalies — Whale movements, exchange outflows, unusual staking/unstaking
Assets and Narratives
Compelling Narratives capture attention to attract liquidity, strong fundamentals prevent it from exiting.
| Value Abstraction | Tags |
|---|---|
| AI Agents | Autonomous, Intent, Automation |
| Memecoins, Bitcoin | Meme-Culture, No-Utility, Attention |
| DeFi | Finance, DeFAI, Yield |
| DePIN | Physical Network Infrastructure |
| RWAs | Tokenization |
| Governance | Voting, Futarchy |
| Stablecoins | Payments, Settlement |
| Coins | Blockchains, Protocols |
| Proof of Identity | Critical, Privacy, Proof-of-Personhood |
Core Principles
- Truth and Trust are foundational for goodwill in just societies
- Everything of perceivable value will be tokenized and traded directly
- Culture builds loyalty, loyalty builds liquidity
- The games we love shape our culture
- Trillions of AI Beings will run the world — alignment is everything
Token Transparency
A standardized, open-source disclosure framework by Blockworks.
| Variable | Max Score | What It Measures |
|---|---|---|
| Project Team | 10 | People, governance, conflict-of-interest controls |
| Token Allocation | 18 | Supply, vesting, distribution across insiders/community/treasury |
| Market Structure | 7 | Liquidity, market-maker agreements, related-party transactions |
| Financial Disclosure | 5 | Reporting standards for financials and operations |
Dig Deeper
- Risk Management — Position-level and portfolio-level controls
- Investment Research — Where to find signal in the noise
- Capital Flows — How capital forms and where it moves
- Investing Team — AI agents as portfolio co-pilots
Context
- Investment Thesis — Develop conviction before allocating
- Crypto Trading — DeFAI, market psychology, and execution
- Capital — What you have and how to convert it
- Predictions — Score your conviction
- Decision Journal — Learn from process, not results
Links
- Creating an Investment Thesis
- Protocol Economics
- Investment Thesis Frameworks
- The AI Bottleneck is Data
- Compute is the New Primitive
- Crypto AI Mental Models
- Bittensor Subnets
- Sovereignty Game
Questions
If conviction must be earned, what's the minimum evidence threshold before a position deserves real capital?
- Does the operating rhythm (daily/weekly/monthly) actually prevent bad decisions, or does it just create the illusion of control?
- When every narrative attracts liquidity, how do you distinguish stories that compound from stories that collapse?
- What's the cost of the positions you held from inertia that you should have cut at the last quarterly review?