Part 1
How Markets Actually Work
What a market is and what it is not. Who is on the other side of your trade -- the Goldman analyst who met with the CFO last Tuesday. Price discovery and why it means current prices already reflect everything publicly known. The information hierarchy -- four levels, retail investors at the bottom. Market efficiency and what it actually means. Why most people lose to the market.
Part 2
The Asset Class Map
What each asset class is, how it generates returns, and what role it plays in a portfolio. Equities, bonds, real estate, commodities, cash, private equity and venture capital, cryptocurrency honest assessment, collectibles. The reason to hold multiple asset classes is correlation -- not being in everything.
Part 3
Building a Portfolio That Works
What a portfolio actually is -- one integrated system, not a pile of accounts. Asset allocation explains 90% of returns. The primary factors: time horizon, risk tolerance, income stability, existing assets. The risk tolerance reality -- most people discover their true tolerance during the first bear market. Diversification done correctly. Correlation and why it matters. Rebalancing. The evidence on what works.
Part 4
The Index Fund Truth
The SPIVA scorecard -- 55% of active funds underperform year one, 90-95% underperform over 20 years. The zero-sum problem. The fee drag in real numbers -- $175,000 difference on a $100,000 investment over 30 years between 0.05% and 1.00%. The tax drag. The best index funds available: Fidelity zero-fee, Vanguard, Schwab. How to implement a three-fund portfolio. Total annual cost: 0.05%.
Part 5
The Stock Market Deep Game
How to read what markets are doing without predicting them. The CAPE ratio as a calibration tool. Credit conditions. Market breadth. Investor sentiment. Valuations and what they tell you over 7-10 year horizons. Market cycles and sector rotation -- real in broad strokes, nearly useless for timing. The Dividend Aristocrats. The market timing trap and the missing best days problem.
Why private markets exist and why passive index investors are increasingly missing the most dynamic growth. Private equity buyout mechanics -- 30-40% equity, 60-70% leverage, operational improvement, multiple expansion. Venture capital power law -- one 100x return covers the fund. Angel investing via AngelList and syndicates. How to access private markets at different asset levels. The real return numbers and the IRR measurement problem.
Part 7
Alternative Assets
Why alternatives exist in a portfolio. Gold -- near-zero correlation with stocks, crisis hedge function more reliable than pure inflation hedge. Commodities as an inflation hedge and the contango drag problem. Cryptocurrency honest assessment -- store of value thesis, network effect thesis, correlation problem, 1-5% defensible allocation. Collectibles as passion investment. Real assets and infrastructure.
Part 8
The Behavioral Investor
The DALBAR study -- S&P 500 returned 9.8% over 20 years, average investor earned 6.0%. The $316,000 behavioral penalty on a $100,000 investment. The specific mistakes: recency bias, overconfidence, loss aversion, narrative fallacy, herding, anchoring. Building systems against yourself -- written investment policy, automation, limiting information, predetermined response rules. The investor checklist.
Part 9
Advanced Strategies
Factor investing -- value, size, momentum, profitability, quality. Eugene Fama won a Nobel Prize for this work. Dimensional Fund Advisors and Avantis for retail access. Tax-loss harvesting at scale with direct indexing -- 0.5-1.5% annual after-tax alpha. Options: covered calls, protective puts, cash-secured puts -- when they make sense and when they do not. Dividend investing. Why the 60/40 portfolio is not dead. Direct indexing.
Part 10
The Investing Toolkit
Account types and their tax treatment -- 401k, Roth, IRA, SEP, Solo 401k, HSA, 529, taxable brokerage. The right brokerage for your situation: Fidelity, Vanguard, Schwab, Interactive Brokers, M1, Wealthfront. Asset location -- which accounts hold which assets to minimize total tax drag. The investing calendar. Who you actually need. Red flags in investment advisors -- the AUM conflict, commission-based recommendations, guaranteed returns.