My First Million
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Tax Alpha Over Investment Alpha Framework
Focus optimization efforts on tax reduction strategies rather than trying to beat market returns through security selection
How It Works
Tax savings are guaranteed and immediate, while investment alpha is uncertain and rare. Tax optimization provides reliable outperformance.
Components
Maximize tax-advantaged accounts first
Implement tax-loss harvesting strategies
Use municipal bonds for cash positions
Consider direct indexing for additional losses
Structure investments for long-term capital gains
Time realizations for optimal tax treatment
When to Use
When you're in high tax brackets (35%+ marginal rate) with significant investable assets
When Not to Use
When in low tax brackets or with minimal assets where tax optimization complexity isn't worthwhile
Anti-Patterns to Avoid
Example
“Instead of trying to beat S&P 500 returns, focus on direct indexing to harvest 30-40% in tax losses while matching market performance, creating guaranteed alpha through tax savings.”
Related Knowledge
Build $30M+ tax-free retirement account through legal Roth IRA contribution loopholes
Accumulate $30M+ in tax-free Roth IRA by retirement age, paying zero taxes on withdrawals
post_exit_angel_investing
Wealth Management A/B Test Framework
Split significant capital between professional wealth management and self-directed investing to empirically compare perf
Percentage-Based Fee Invisibility Model
People underestimate the long-term cost of percentage-based fees because they don't feel the pain of the payment, unlike
Tax optimization provides more reliable alpha than investment selection
Focus optimization efforts on tax reduction rather than trying to beat market returns
Zero to something is always more life-changing
The psychological and practical impact of first wealth creation far exceeds subsequent wealth increases