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Money, Examined

№3 in the series

The Yield Illusion / Chapter

Dividends and equivalent withdrawals

Compare a cash dividend with an equivalent share sale, then isolate the tax-timing difference.

a working paper on distributions, total return, and friction · drewbreyer.com

№ I — MEASURED + MODELED

Dividends and equivalent withdrawals

A cash dividend transfers value from the company to the shareholder, and the share price adjusts on the ex-dividend date. The model compares that payment with an equivalent investor-directed sale, then isolates the tax-timing difference under the displayed assumptions.

Market world — governs every modeled figure
Preset

Nominal units only. Every instrument here compares a strategy against the index under identical draws, so the deflator cancels — there is no real/nominal toggle.

Fig. 1
SellerPayer

Same company, same growth, same spending money. The only thing the dividend changes is the tax bill.

The costume. Wealth panel: the payer and the seller trace the same pre-tax wealth line, twice. Tax panel: cumulative nominal tax per initial $1 — payer 0.261 vs seller 0.171. MODELED
…given a firm’s investment policy, the dividend payout policy it chooses to follow will affect neither the current price of its shares nor the total return to its shareholders.
— Miller & Modigliani, “Dividend Policy, Growth, and the Valuation of Shares,” Journal of Business (1961)1
Annual drag δ·τ_d
0.45%
per year — a fee you can’t waive (compare №1)
Bequest-case gap
12.7%
reinvesting, never selling (step-up at death)
≈ 24 years of your spending
Sell-everything gap
7.0%
after capital-gains tax on liquidation
≈ 12 years of your spending
Fig. 2

Under the displayed taxable-account assumptions, recurring dividend tax reduces reinvested wealth each year.

The tax meter. Pre-liquidation (filled) and post-liquidation (open) terminal wealth per $1, for the reinvesting non-payer and dividend payer. MODELED
It puzzles them that we relish the dividends we receive from most of the stocks that Berkshire owns, but pay out nothing ourselves.
— Warren Buffett, 2012 Berkshire Hathaway letter, p. 1914
Notes on method— formulas, RNG, closed-form cross-checks

Units. Nominal only. Every instrument here compares a strategy against the index under identical draws, so the inflation deflator cancels exactly; there is no real/nominal toggle. Returns are lognormal in log space; geometric inputs convert with ln(1+g).

Y1 — the relabeling machine. Deterministic, annual, per $1. The payer’s share price grows (1+g) then pays a δ dividend; the seller sells the same fraction δ of shares (basis $1/share, never repurchased). Pre-tax terminal wealth is identical to machine precision. Tax: payer τ_d·dividend; seller τ_g·proceeds·(1 − 1/Q). DRIP leg: W ← W·(1+g)·(1 − δ·τ_d); the annual drag is δ·τ_d. Withdrawals and taxes are applied at year end, so the model does not represent intra-year tax timing.

Y2 — covered calls. Monthly. m_mo = ln(1+g_m)/12, s_mo = σ_m/√12. Premium from Black–Scholes with σ_iv = σ_m + vrp, r = g_cash, T = 1/12. Per month the covered factor is (min(G,k) + c)·(1−fee)^(1/12) under the same draw as the index. Live cross-check: E[G] = 1.00673, E[min(G,k)] = 0.98468, P(capped) = 54.9%, premium = 2.08%/mo. MC: 4,000 base → 8,000 effective (antithetic), CRN with the index.

Y3 — leverage. Continuous frontier growth(L) = L·m + (L − L²)σ²/2 − fee(L) − max(0, L−1)·(g_cash + 0.5%), fee(L) = 3bp at 1× else 0.95%. Growth-maximizing L in this continuous approximation: frictionless 3.14, with the stated frictions 1.78. This is an objective-specific model result, not a recommended allocation. Live cross-check: 1× 6.97%, 2× 6.74%, 3× 4.78% per year. The daily-reset truth simulation uses 252 steps/yr, w ← max(0, w·(1 + L·(e^{r_d} − 1) − cost_d)), seed 42, antithetic. Growth-rate: 0.0467 log/yr at 3×.

Gap-risk caveat. Overnight gaps beyond −1/L are not modeled; real leveraged funds can and do terminate. The two-day reset exhibit is exact: +10% then −1/11 returns the underlying to 1.0000 while the 2× fund lands at 0.9818.

Tax constants. Qualified-dividend and long-term capital-gains rates share brackets (0/15/20%, 2025 IRS thresholds); both sliders default to 15%. The model does not select a filing status, account type, state tax, NIIT status, or holding-period qualification. Basis step-up at death per IRC §1014 is relevant only to the no-liquidation comparison. This is a simplified federal-tax illustration, not tax advice.13

Market-data methodology. Product-table figures are computed from dividend/split-adjusted price series and corroborated against totalrealreturns.com and financecharts.com, pinned to their as-of dates.38

References

  1. 1.Miller, M. H. & Modigliani, F. (1961). “Dividend Policy, Growth, and the Valuation of Shares.” Journal of Business 34(4), 411–433. www.jstor.org/stable/2351143
  2. 2.Black, F. (1976). “The Dividend Puzzle.” Journal of Portfolio Management 2(2), 5–8.
  3. 3.Williams, J. B. (1938). The Theory of Investment Value. Harvard University Press.
  4. 4.Elton, E. J. & Gruber, M. J. (1970). “Marginal Stockholder Tax Rates and the Clientele Effect.” Review of Economics and Statistics 52(1), 68–74.
  5. 5.Elton, Gruber & Blake (2005). “Marginal Stockholder Tax Effects and Ex-Dividend Day Behavior — Thirty-Two Years Later.” Review of Economics and Statistics 87(3), 579–586.
  6. 6.Fama, E. F. & French, K. R. (2001). “Disappearing Dividends.” Journal of Financial Economics 60(1), 3–43.
  7. 7.Michaely, R. & Moin, A. (2022). “Disappearing and reappearing dividends.” Journal of Financial Economics 143(1), 207–226.
  8. 8.Hartzmark, S. M. & Solomon, D. H. (2019). “The Dividend Disconnect.” Journal of Finance 74(5), 2153–2199. papers.ssrn.com/sol3/papers.cfm?abstract_id=2876373
  9. 9.Harris, Hartzmark & Solomon (2015). “Juicing the Dividend Yield: Mutual Funds and the Demand for Dividends.” Journal of Financial Economics 116(3), 433–451.
  10. 10.Chen, Y. & Israelov, R. (2024). “Income illusions: Challenging the high yield stock narrative.” Journal of Asset Management 25(2), 190–202.
  11. 11.Schlanger, T. & Kesidis, S. (2017). “An analysis of dividend-oriented equity strategies.” Vanguard Research.
  12. 12.Padmawar, S. & Jacobs, V. (2023). “Asset location for equity.” Vanguard Research. corporate.vanguard.com/content/dam/corp/research/pdf/asset_location_for_equity.pdf
  13. 13.IRS Topic No. 404 (Dividends), Topic No. 409 (Capital Gains and Losses); IRC §1014 (basis of inherited property). www.irs.gov/taxtopics/tc409
  14. 14.Buffett, W. E. (2013). Berkshire Hathaway 2012 Shareholder Letter, “Dividends,” pp. 19–21. www.berkshirehathaway.com/letters/2012ltr.pdf
  15. 15.S&P / Silverblatt, via Bloomberg (Dec 2009): 2009 S&P 500 dividend decline, worst since 1938; CNNMoney (Nov 2009).
  16. 16.S&P Dow Jones Indices (July 2020). $42.5B decrease in Q2 2020 US indicated dividends — worst quarter since Q1 2009.
  17. 17.CNBC (Oct 28, 2020). 42 S&P 500 suspensions + 25 cuts in 2020 (Silverblatt).
  18. 18.Janus Henderson Global Dividend Index (Feb 2021): global 2020 dividends −12.2%; one company in eight cancelled; UK −41.6% (Q3); US total +2.6% to a record.
  19. 19.Israelov, R. & Nielsen, L. N. (2015). “Covered Calls Uncovered.” Financial Analysts Journal 71(6), 44–57. images.aqr.com/-/media/AQR/Documents/Insights/Journal-Article/Covered-Calls-Uncovered.pdf
  20. 20.Israelov, R. & Nielsen, L. N. (2014). “Covered Call Strategies: One Fact and Eight Myths.” Financial Analysts Journal 70(6).
  21. 21.Carr, P. & Wu, L. (2009). “Variance Risk Premiums.” Review of Financial Studies 22(3), 1311–1341.
  22. 22.Bakshi, G. & Kapadia, N. (2003). “Delta-Hedged Gains and the Negative Market Volatility Risk Premium.” Review of Financial Studies 16(2).
  23. 23.Wilshire Associates (2019). “Options-Based Benchmark Indexes: Performance, Risk” (6/1986–12/2018). cdn.cboe.com/resources/spx/wilshire-options-based-benchmark-indexes-2019.pdf
  24. 24.Global X, QYLD fund page (as of 6/30/2026); totalrealreturns.com QYLD/QQQ (as of 7/7/2026). www.globalxetfs.com/funds/qyld
  25. 25.J.P. Morgan Asset Management (2026). JEPI Fact Sheet, May 31, 2026. am.jpmorgan.com/us/en/asset-management/adv/products/jpmorgan-equity-premium-income-etf-etf-shares-46641q332
  26. 26.YieldMax, TSLY fund page (6/30/2026); reverse-split announcements (Feb 2024, Dec 2025); totalrealreturns.com TSLY/TSLA. www.yieldmaxetfs.com/our-etfs/tsly/
  27. 27.Morningstar (2025). Morningstar’s Guide to ETF Trends in 2025, derivative-income section.
  28. 28.Rekenthaler, J. (2024). “Covered-Call Funds: A Mystery Wrapped in an Enigma.” Morningstar, Jan 25, 2024.
  29. 29.Natixis IM (2025), citing ISS SimFund: US derivative-income ETF AUM ~$1B (2018) → ~$100B (Nov 2024).
  30. 30.Cheng, M. & Madhavan, A. (2009). “The Dynamics of Leveraged and Inverse Exchange-Traded Funds.” Journal of Investment Management 7(4).
  31. 31.Avellaneda, M. & Zhang, S. (2010). “Path-Dependence of Leveraged ETF Returns.” SIAM Journal on Financial Mathematics 1, 586–603.
  32. 32.FINRA (2009). Regulatory Notice 09-31: Non-Traditional ETFs. www.finra.org/rules-guidance/notices/09-31
  33. 33.SEC. “Updated Investor Bulletin: Leveraged and Inverse ETFs.” www.investor.gov
  34. 34.Crenshaw, C. A. (2022). “Statement on Single-Stock ETFs.” SEC, July 11, 2022. www.sec.gov/newsroom/speeches-statements/crenshaw-single-stock-etfs-20220711
  35. 35.ProShares UltraPro QQQ (TQQQ) summary prospectuses, SEC Form 497K (Oct 2017; Sept 2024), via EDGAR.
  36. 36.Guedj, I., Li, G. & McCann, C. (2010). “Leveraged ETFs, Holding Periods and Investment Shortfalls.” Journal of Index Investing (Winter 2010).
  37. 37.Ptak, J. (2025). “Why Leveraged ETFs Are for the Birds.” Morningstar, Feb 19, 2025.
  38. 38.Market-data computations from dividend/split-adjusted price series (Yahoo Finance), corroborated by totalrealreturns.com and financecharts.com. Methodology in Notes on method. totalrealreturns.com/
  39. 39.Ayres, I. & Nalebuff, B. (2010). Lifecycle Investing. Basic Books.
  40. 40.Felix, B. — PWL Capital / Rational Reminder: the videos in §further watching, and the 2023 post quoted as QY8.
  41. 41.Morningstar (2025). “Covered-Call ETFs Are Booming. But Not All Yield Is Good.” Derivative-income category ≈$145B by mid-July 2025; ≈$31.5B of net flows in H1 2025.

Further watching

  • Ben Felix (PWL Capital): “The Irrelevance of Dividends” (Sept 14, 2019)
  • “The Relevance of Dividend Irrelevance” (June 9, 2022; Rational Reminder ep. 201)
  • “Covered Calls: A Devil’s Bargain” (Sept 14, 2025; Rational Reminder ep. 375)
  • “How Leverage Can Boost Returns (And What Can Go Wrong)” (Dec 21, 2019)

This paper’s synthesis follows the academic literature these videos popularized.

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