Personal finance for people who want to be great with money — written by the friend who already is.
Twenty years structuring tax positions for high earners. Believes most of the good moves happen before December.
About Tom
Tom writes the strategist's view of the tax code — where Priya writes the CPA's. His beat is the multi-year plays: bracket management, Roth conversion ladders, charitable stacking, and the entity moves that quietly save six figures over a decade.
On the Tax Desk, he'll cover what the personal finance internet consistently under-teaches: tax planning as a compounding discipline, not a springtime chore.
In their own words
“The tax code rewards intent, not effort.”
— Tom Whitfield, The Tax Strategist
The money story
Tom started as a compliance associate at a Big Four firm and watched partners run circles around the same code line for line. He left to work directly with high earners and business owners on the strategy side — and hasn't touched a 1040 since.
Signature playbook
Your lifetime tax bill isn't set by this year's return. It's set by which year you take income in. Move the income, not the effort.
Project Ten Years
Map expected income year by year, especially retirement transitions, business sales, and gap years.
Identify Low-Bracket Years
Any year projected to land in a lower bracket is a Roth conversion, gain-harvest, or income-recognition window.
Identify High-Bracket Years
High-income years get deferral, charitable stacking, and loss harvesting stacked on top.
Revisit Every October
Nine months in, adjust the model with actuals. Execute before December 31.
A taste of the beat
Sample headlines from Tom's desk.
Rules I won't break
The non-negotiables — the things Tom refuses to recommend, no matter how good the pitch.
Filed by Tom
Jun 30
Taxes Desk
The multi-year plan that turns a few low-income years into a permanent reduction in lifetime tax.
1 min read
Evergreen
Jun 20
Wealth Preservation Desk
The DAF is a useful tool. It is not a moral upgrade. Here's when it earns its keep, and when it just delays generosity.
1 min read
Evergreen
The weekly dispatch
The kind of financial advice you'd get from a friend who's already figured it out. No hot takes, no leaderboards, no affiliate hustle.