Steven M. Cheshire, CFA
cheshireSteven@gmail.com·Miami Beach, FL
Professional Background
Held Quantitative Equity Analyst and Equity Portfolio Manager positions at Wellington Management Company, Putnam Investments, State Street Global Advisors, and United Alpha. Consulted at Gartmore Investments, Affinity Wealth Advisors, and Hoover Financial Advisors. B.S. in Finance, Virginia Tech. MBA, Boston University. CFA charterholder.
Why this research exists
This research began a few years into my own Roth conversions. I intuited I was converting correctly, but wanted to quantifyexactly what I was getting in return for the annual tax payments. The published literature didn't answer that question cleanly. Commercial calculators answered it wrongly — often by collapsing path-dependent quantities into a single average.
Several years of testing scenarios in a working calculator (now RothGPT.com) surfaced phenomena that didn't fit the standard framing — most notably that how you pay the conversion tax (from inside the Traditional account vs. from outside funds) produces a separable economic effect that the literature had either folded into a black-box term or missed. The papers on this site are the attempt to write down those findings rigorously.
I encourage readers to try and disprove anything I present. My goal is for the truth to prevail and for Roth-conversion knowledge to improve, disseminate, and be widely understood.
Published work
Roth Conversion Valuation & Mechanics
Introduces the Synthetic Roth Contribution concept and the conversion-tax-payback decomposition. The framework has been substantially extended in subsequent working drafts — see the current Synthetic Roth Contribution and Tax-Drag Shelter papers for the formal treatment as it stands today.
Read on SSRN ↗The calculator
The frameworks developed on this site are implemented end-to-end in a working tool at RothGPT.com. Enter your own numbers and see the components in your case.