Investing & Portfolio

Asset allocation, factor investing, global diversification, and the research behind how to actually build a portfolio that works over decades.

70 guides in this topic

Strategy18 min readCalculator
Stock Valuation for DIY Investors: Useful Tool or Expensive Illusion?
Damodaran's SpaceX valuation, the DCF method, and an interactive 'what has to be true?' explorer. Why valuation is worth learning but stock-picking rarely beats indexing.
Strategy18 min readCalculator
The Hungry Caterpillar Portfolio: A Silly Name for a Serious All-Weather Idea
A bedtime-story joke portfolio that eats small-cap value, bonds, gold, T-bills, and trend. Over 10 years it earned less than 60/40, with half the drawdown.
Concept17 min readCalculator
The Risk Parity Reality Check: What DIY Investors Should Know Before Levering Bonds
A 60/40 looks diversified, but equities can drive 90% of its risk. What risk parity really is, whether to lever it, and when it beats a simple Bogleheads portfolio.
Concept15 min read
The S&P 500 Is Passive for You, But Not Passive Under the Hood
The S&P 500 is not the 500 biggest stocks or the whole market. It is a committee-governed large-cap index. Why it became the baseline, and how VOO, IVV, SPY, VTI, and VT differ.
Strategy16 min readCalculator
The Simplified Engineer Investor Portfolio: A 3-Fund All-Equity Portfolio With a Global Value Tilt
36% VTI, 24% VXUS, 40% AVGV: a Boglehead core with a global value tilt. The X-Ray, the equity style box, the evidence, and an interactive tilt explorer. Who it fits and who it does not.
Strategy17 min readCalculator
How to Sell Stocks, Mutual Funds, and ETFs Tax-Efficiently: SpecID and Tax Lots
Your broker's default cost-basis method silently picks your taxable gain. Learn SpecID, FIFO vs HIFO vs average cost vs MinTax, and how lot selection cuts the tax when you sell or rebalance.
Strategy15 min readCalculator
If Dimensional Gets Sold, Should Factor Investors Care? The Hidden Risk of Bespoke ETFs in Taxable Accounts
A rumored DFA sale is no reason to panic-sell, but it exposes a risk DIY investors miss: fund-sponsor and strategy-drift risk, plus the tax lock-in of bespoke factor ETFs in taxable accounts.
Strategy18 min readCalculator
How Financial Sales Pitches Hide the Real Cost of Investing: A Red-Flag Guide
The most heavily marketed financial products are often the most profitable for the seller. Learn the five marketing tactics, six risk lenses, and a hurdle calculator to evaluate any product.
Strategy16 min readCalculator
Robinhood's Agentic Trading: Should You Let an AI Agent Trade Your Account?
Robinhood now lets an AI agent trade a dedicated account. The investing evidence on agentic trading, the conflict of interest, and who it actually fits.
Strategy17 min readCalculator
Cash-Secured Puts: Getting Paid to Buy a Stock, or to Take Its Downside?
A cash-secured put is a conditional buy commitment, not free yield. The Micron case, the index put-writing evidence, the tax math, and who it actually fits.
Strategy17 min readCalculator
Portfolio Risk Is More Than Volatility: Drawdowns, Pain Index, and Ulcer Index for DIY Investors
Volatility describes how returns vary. Pain describes how it feels to live through them. Learn when each risk metric matters: standard deviation, max drawdown, time underwater, Pain Index, and Ulcer Index, with a side-by-side calculator using 98 years of Damodaran return data.
Strategy14 min read
Bengen vs. Bengen: Should Retirees Outsource Equity Risk to a Third-Party Signal?
Bengen's 1994 paper warned against pulling back from stocks after a bad early market. His 2026 recommendation moves toward doing exactly that, via third-party perceived-risk services. What the evidence supports, and what it doesn't.
Strategy14 min readCalculator
Should Long-Term Index Investors Use Stop-Loss Orders? Usually No, and Here's the Math
Stop-loss orders feel like portfolio insurance. The evidence says they usually aren't. What stops do, what they don't, and when they actually help.
Strategy15 min readCalculator
When to Sell a Winning Stock: The Question Without a Good Answer
Buying is the easy half. Selling a lucky winner means navigating taxes, anchoring, regret, and concentration. What the evidence supports.
Strategy15 min readCalculator
Donate Appreciated Stock or Use a DAF? The Tax Math and Where the Strategy Is Oversold
Donating appreciated stock is tax-efficient. A DAF can be a useful wrapper. Neither makes charity free. The mechanics, the 2026 OBBB changes (0.5% AGI floor, 35% deduction cap, $1k/$2k non-itemizer cash), and an after-tax cost calculator.
Strategy16 min readCalculator
The Treasury Bond Fantasy: Can You Actually Live Off U.S. Government Interest Forever?
A viral tweet imagines putting your entire net worth into Treasury bonds and living off the coupons. The math is seductive and the implementation is mostly wrong. After-tax-real income, TIPS, I-bonds, and an interactive calculator that shows what the coupon actually buys.
Strategy14 min readCalculator
AVGV Review: A One-Ticker Global Value Tilt for DIY Investors
AVGV bundles a global value, profitability, and smaller-cap tilt into one ETF that rebalances itself. A deep-dive review and a calculator comparing AVGV to a DIY basket of Avantis ETFs.
Concept17 min readCalculator
Mega-IPOs and Your Index Funds: How Free Float Decides What SpaceX, OpenAI, and Anthropic Mean for VTI, VOO, and QQQ
A trillion-dollar IPO with a 5% public float is not the same as a trillion-dollar IPO with 90%. Free-float adjustment, seasoning rules, and the methodology differences between CRSP, S&P 500, and Nasdaq-100 decide how much exposure your index fund actually takes. Includes a Mega-IPO Index Impact Calculator.
Strategy16 min readCalculator
Do You Actually Need Direct Indexing?
Direct indexing is heavily marketed to high earners, but ETF tax-loss harvesting already captures most of the value for many. A skeptical primer comparing ETF TLH, long-only DI, and long/short TALS, with an interactive decay visualizer.
Concept15 min readCalculator
The Risk-Free Rate Is Your Hurdle Rate: How to Use Treasuries and TIPS as the Starting Point for Every Investment
At 5.03% nominal and 2.74% real on May 12 2026, Treasury and TIPS yields set the hurdle every risky asset has to clear. The framework, the common mistakes, and a Hurdle Rate Check calculator.
Concept16 min readCalculator
Fama-French HML Explained: What the Value Factor Means for DIY Investors
HML is the academic version of value investing: a transparent, rules-based long-short factor that asks whether cheap stocks outperform expensive ones. What the evidence says, how it differs from AQR and Avantis, and a Value Tilt Pain Test calculator.
Concept14 min readCalculator
The Stock Market Rewards Optimists, But Not the Naïve Ones
Elroy Dimson's Rational Reminder interview, distilled. Easy data bias, U.S. exceptionalism, the GDP-vs-returns gap, and a stress tester that shows how much your plan depends on the equity risk premium.
Concept15 min readCalculator
The Engineer's Guide to Systematic Investing
Most people expect investing to be about having an opinion. Systematic investing is about having a process. The evidence, the levels ladder, and the friction calculator that quantifies how small mistakes compound.
Strategy13 min readCalculator
How Often Should You Rebalance Your Portfolio? An Evidence-Based Answer
Vanguard's 1926-2009 data shows monthly, quarterly, and annual rebalancing produce near-identical risk-adjusted returns. The real questions are bands, cash flow, and taxes. With an interactive checker.
Strategy14 min readCalculator
Futures Yield Explained: What RSSY Actually Owns
RSSY is not a high-yield ETF. It stacks U.S. equity exposure with a systematic futures carry strategy. Here is what futures yield actually is, what the prospectus discloses, and how the live track record compares to the S&P 500.
Strategy17 min readCalculator
Farmland and Timberland Investing: Real Diversifiers or Expensive Illiquidity?
Farmland and timber are real asset classes, but the wrapper is the catch. See what platform fees, lockups, and taxes do to your net return vs. public REITs.
Concept10 min readCalculator
Shareholder Yield: Why Dividend Yield Alone Is Incomplete
Dividend yield misses most of how US companies actually return cash. Boudoukh-Michaely-Richardson-Roberts (2007) showed net payout yield (dividends + buybacks - issuance) has stronger predictive power. With a Net Payout Yield Decomposer.
Concept13 min readCalculator
The Stock Market Is Not the Economy: Why GDP Growth Doesn't Predict Stock Returns
The US is 26% of global GDP and 63% of MSCI ACWI. Ritter (2005) found cross-country GDP-equity correlation is negative. Five links separate GDP from per-share return, and a GDP-to-Stock-Return Bridge calculator walks every one.
Concept14 min readCalculator
Does the Fed Really Set Interest Rates? Yield Curves, Term Premium, and r-Star Explained
The Fed sets one rate (FFR target). Everything else is markets. The yield curve = expected short rates + term premium, r-star is unobservable, mortgage rates aren't Fed funds + spread. With a Bond Duration Shock + Reinvestment Risk calculator.
Methodology16 min readCalculator
The R² Trap: Why Rolling P/E vs. 10-Year Return Charts Are Less Certain Than They Look
Why the viral R² = 0.73 forward P/E vs. 10-year return chart looks more certain than it is. Rolling-window overlap, persistent regressors, and a Monte Carlo demo of spurious R²-with the BRW (2008), Stambaugh, and Goyal-Welch evidence behind it.
Strategy12 min readCalculator
You Have One Household Portfolio, Not One Per Account
Account labels are wrappers; risk and return live at the household level. Reichenstein after-tax, Viceira human capital, the asset-location 80/20, and a Household X-Ray calculator with location flags.
Concept13 min readCalculator
Modern Portfolio Theory for Real Life: Stop Judging Funds in Isolation
Markowitz's portfolio choice for individual investors. Two-asset variance with correlation, the 'correlations go to one' supplement, the marginal-fund test, and a portfolio impact calculator.
Concept14 min readCalculator
Personal Leverage: Margin, Leveraged ETFs, Lifecycle Theory, and Forced Selling
How leverage relates to MPT and Sharpe, what Ayres-Nalebuff actually argued, FINRA Reg T and 25% maintenance, the margin-call drawdown formula, daily-reset path dependency, tax wrinkles, and a Margin Stress Test calculator.
Concept12 min readCalculator
RMW Explained: The Profitability Factor, Out-of-Sample Evidence, and Avantis vs Dimensional
The Fama-French RMW factor, Novy-Marx's gross profitability, out-of-sample evidence (Wahal, Linnainmaa-Roberts, Harvey-Liu-Zhu, McLean-Pontiff), the Avantis-vs-Dimensional cash-vs-operating disagreement, and a tilt + tracking-error calculator.
Concept12 min readCalculator
The Wealth Ladder: Six Levels, the 0.01% Rule, and Why It's a Map Not a GPS
Nick Maggiulli's six wealth levels, the 0.01% rule, UBS distribution data, and the liquidity / age / geography corrections peer book reviews skip. With total-vs-liquid calculator.
Strategy13 min readCalculator
Tax-Aware Long-Short: Real Tax Alpha or Complex Marketing?
TALS for HNW taxable investors: AQR's loss-capacity research, the gain-deferral surprise, Section 1259 caveat, SMA pass-through, and a hurdle calculator that refuses to estimate alpha.
Concept10 min read
What Real Return Should You Assume for Stocks? About 5%, Not 7%
The popular 7% real figure is U.S.-only and often quoted as an arithmetic mean. The globally diversified geometric historical mean is closer to 5% real. Here is where each number comes from, why the gap matters for your planning, and what to do about it.
Concept13 min readCalculator
The Problem With Buy the Dip: Why Wasn't the Money Already Invested?
AQR tested 196 buy-the-dip rules; most lost. Vanguard, Dimensional, PWL, and Morningstar agree. The empirical case for investing today, with a cost-of-waiting calculator.
Concept12 min readCalculator
Just Keep Buying: A Strong Habit, Not a Complete Plan
Nick Maggiulli's accumulation rule, what it gets right, the savings-vs-returns crossover most peer posts miss, and which dollars it doesn't apply to. With calculator.
Concept17 min readCalculator
Do Stock Valuations Still Matter? What CAPE Tells You About the Next Decade
CAPE near 40 doesn't mean sell. It means lower your forward return assumptions. The academic evidence on valuation ratios as long-horizon return forecasts, the valid criticisms of CAPE, and an interactive calculator for your own assumptions.
Concept18 min readCalculator
Do 200 Years of Stock Returns Still Matter? Yes, but Not as a Forecast
Long-run stock history is relevant because it shows returns are regime-dependent, not because it produces a clean 6-7% real constant. McQuarrie's data corrections, the international evidence, the railroad case, and a calculator that compares terminal wealth across five historical regimes.
Concept13 min readCalculator
Stocks Usually Win. "Usually" Is Not a Financial Plan.
Stocks lost to bonds for 20, 41, and even 68 years in a row. Your retirement plan needs to survive that scenario. Here's what 220 years of data show.
Strategy16 min readCalculator
Do You Need Managed Futures? An Evidence-Based Look at Trend Following, Return Stacking, and the Cockroach Portfolio
Trend-following managed futures can diversify across regimes, but they're not magic. Here's the evidence, the tradeoffs, and who should and shouldn't use them.
Strategy17 min readCalculator
Covered Calls Are Not Free Income: What XYLD, QYLD, JEPI, and JEPQ Actually Cost You
Covered-call ETFs distribute 8-12% per year while the underlying strategy earns far less. Here's the academic evidence, the tax drag, and who they actually fit.
Strategy16 min readCalculator
Do You Need Return Stacking? A Hurdle-Rate Framework for Portable Alpha
Return-stacked ETFs (NTSX, RSSB, RSST, SPLS) promise diversification without sacrificing equity. Here's the hurdle-rate framework for evaluating any of them.
Concept18 min readCalculator
Should You Buy IPO Stocks? Why the "Ground Floor" Is Often the Exit
Mega-IPOs from SpaceX to OpenAI are coming. Here's the academic evidence on IPO returns, the first-day-pop trap, and what indexers actually own.
Concept14 min readCalculator
Most Stocks Lose to T-Bills. The Market Still Wins.
58% of U.S. stocks since 1926 lost to Treasury bills lifetime. Just 4% account for all stock-market wealth. Here's why broad diversification wins mathematically.
Concept17 min read
Stocks Are Always Risky: The Equity Premium Exists for a Reason
Long horizons do not repeal risk. Russia 1917, China 1949, and Japan's 51-year climb to guaranteed non-negative real returns show that time alone does not make stocks safe. Bernstein's four deep risks, DMS global evidence, and why global diversification still matters.
Concept12 min readCalculator
VTI vs. VOO: The Most Overrated Decision in Investing
VTI and VOO are 99% correlated with 87% overlap. VTI is the more principled choice. VOO is perfectly fine. The bigger mistake is obsessing over this decision instead of the ones that actually matter.
Strategy16 min read
Your Portfolio Is Not Just Your Brokerage Account: Human Capital Risk for Tech Workers
RSU-heavy tech workers are already concentrated in U.S. mega-cap growth before buying a single ETF. Here is why the standard index fund portfolio has gaps, and what to do about it.
Concept16 min read
60/40, Target-Date Funds, or 100% Stocks Forever? They're Solving Different Problems.
The 60/40 portfolio, Vanguard's target-date glide path, and Cederburg's all-equity research are not competing answers to the same question. Here is what each approach actually solves, who it is for, and who it is not for.
Concept14 min read
The Four Deep Risks of Investing: What Bernstein Got Right About Real Danger
Volatility is not the real enemy. Inflation, deflation, confiscation, and devastation are. Here is Bernstein's framework for understanding what can permanently impair your purchasing power, and what you can actually do about each.
Concept14 min read
JL Collins Is Right About Simplicity. He's Wrong That VTSAX Is All You Need.
VTSAX is an excellent U.S. stock fund. But treating it as a complete global equity portfolio confuses simplicity with concentration and mistakes foreign revenue for true international diversification.
Concept14 min read
The Tech Bro Portfolio: Why VOO + QQQ + NVDA Is Not Diversified
A portfolio split across VOO, QQQ, VGT, and a few tech stocks can still put 26% of your money in three companies. Ticker count is not diversification. Here is the evidence.
Concept14 min read
VOO + QQQ + SCHD: The Reddit Portfolio That Isn't Diversified
Equal thirds in VOO, QQQ, and SCHD looks like three different bets. It is actually one: U.S. large-cap stocks with a growth/dividend barbell and zero international exposure. Here is what the data shows.
Methodology14 min read
Passive Investing Is a Label, Not a Literal Description
Index investing is better understood as delegated management. Someone chose the rules, the screens, and the reconstitution schedule. Here is where the discretion actually lives, and why broad indexing is still a good idea.
Concept14 min readCalculator
Zero Fee, Non-Zero Benchmark Risk: Why Fidelity's ZERO Funds Optimize the Wrong Variable
Fidelity's ZERO funds are fine investments. But '0.00% expense ratio' draws attention to the least important basis points while hiding proprietary benchmark risk and narrower market coverage.
Strategy14 min readCalculator
Lump Sum vs. Dollar-Cost Averaging: 98 Years of Evidence
Lump sum investing beats DCA 67% of the time. But the real question is when it doesn't. Explore 98 years of S&P 500 data with an interactive calculator and see which strategy won in every starting year since 1928.
Methodology12 min read
Growth Stocks vs. Systematic Momentum: They're Not the Same Thing
Growth investing buys expensive companies with strong fundamentals. Momentum investing buys whatever is going up. They hold the same stocks for completely different reasons, and the academic evidence favors one over the other.
Concept14 min read
Dividends Are Not Free Money: What Every Investor Should Know
When a company pays a dividend, its stock price drops by the dividend amount. You are not richer. This guide walks through the mechanics, the tax trap, why dividend capture fails, and why dividends still exist if they are not free money.
Concept14 min read
Why U.S. Companies with Global Revenue Don't Give You Global Diversification
Apple earns 60% of revenue outside the U.S., but its stock still moves with the S&P 500. Domicile matters more than revenue. See the correlation data, the CAPE valuation gap, and what the lost decade taught us.
Concept14 min read
The Case for Global Equity Diversification: Why VTI Alone Is Not Enough
U.S. market dominance over the past 15 years is the exception, not the rule. Global markets trade at significantly lower valuations. Here is the evidence for owning the world, not just America.
Concept18 min readCalculator
How to Start Investing: A Beginner's Guide to Personal Finance and Index Funds
Your first 90 days as an investor. Prioritize spending, open the right account, pick two index funds, and let compounding do the heavy lifting. Evidence-based, no jargon, with an interactive compound interest calculator.
Methodology14 min read
The Case for Small-Cap Value: Decades of Evidence, Years of Pain
Small-cap value has outperformed the S&P 500 by 3% annually since 1927. The catch: you have to survive decade-long droughts. Here is the academic evidence, the risk, and why the premium probably persists.
Strategy14 min read
Why I Like AVUV, AVDV, and AVGV: Turning Factor Research into a Portfolio
AVUV, AVDV, and AVGV turn decades of academic research on size, value, and profitability into investable portfolios. Here is what each fund does, how they compare to Dimensional alternatives, and who they are not for.
Methodology12 min read
Asset-Liability Matching: Align Your Bonds to Your Goals
Learn how to match your bond portfolio duration to your liability timeline, reducing interest rate risk and ensuring your assets are there when you need them.
Strategy14 min read
Concentration Risk: When to Sell Your Company Stock and How to Diversify
Single-stock concentration increases volatility without increasing expected returns. Learn how to measure concentration with HHI, run the sell-vs-hold math, and use multi-year projections to build a diversification plan.
Strategy14 min readCalculator
Tax-Loss Harvesting: How to Turn Portfolio Losses Into Tax Savings
Learn how tax-loss harvesting works, from wash sale rules and capital loss netting to replacement fund strategies. See a worked example of the tax benefit calculation and understand when TLH is worth the effort.
Concept15 min read
Lifecycle Asset Allocation: Why Young Investors Should Hold More Stocks
Your biggest asset in your 20s is future earnings, not your portfolio. Learn why "100 minus your age" is too conservative and how lifecycle theory, human capital, and glide paths shape smarter asset allocation by age.
Methodology14 min read
Fama-French Factor Analysis: What Your Portfolio Is Really Doing
Go beyond simple returns. Factor models decompose your portfolio performance into systematic risk exposures like market, size, value, and momentum.

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