Framework · All Stages
After-Tax Investment Decision Engine
Rate any investment, strategy, or tax position on 7 factors. Get a weighted score and recommendation. Use this before committing capital to anything — real estate, private funds, concentrated stock, complex tax strategies.
Pre-Tax Economics
Does this investment make sense before taxes?
Would you do this if there were no tax benefit? If the answer is no, taxes are carrying a bad investment.
After-Tax Return
What is the actual after-tax return vs the index benchmark?
After-tax return must beat VTI/VXUS after fees, drag, and exit taxes — at the same risk level.
Liquidity
Can you exit? How long is capital locked? What is the cost?
Capital locked for 7 years has a real opportunity cost. Demand a meaningful illiquidity premium.
Complexity Cost
What is the admin, accounting, and time burden?
K-1s, 1031 timelines, STR logs, entity maintenance — these are real costs that reduce after-tax return.
Audit / Legal Risk
Is this position defensible? What is the compliance exposure?
An aggressive deduction that gets challenged in audit often costs more than it saved.
Concentration Risk
Does this create single-asset, single-market, or single-employer exposure?
Concentrated positions require higher expected returns to justify the undiversified risk.
Opportunity Cost
Is this better than low-cost index investing in a tax-advantaged account?
Every dollar here is a dollar not in a Roth IRA or 401k. That benchmark is hard to beat.
How the scoring works
Scoring scale
1 = Poor / very risky
2 = Below average
3 = Acceptable / neutral
4 = Good
5 = Excellent / very low risk
Weighted factors
Pre-tax economics: 3x (if bad, nothing else matters)
After-tax return: 3x (the whole point)
Opportunity cost: 3x (the benchmark is always VTI)
Liquidity, complexity, audit: 2x
Concentration: 1x
Recommendation thresholds
Proceed
Score ≥ 80
Investigate
Score 60–79
Pass
Score < 60