Insights

Notes from the practice.

Clear thinking on concentrated equity, tax strategy, and building a work-optional life. New writing published regularly.

Featured · Concentrated Equity

The first 90 days after lockup: a decision framework

The window after your shares unlock is one of the most consequential periods in a tech employee's financial life. Here's how to approach it deliberately.

Read the article →
Tax Strategy

Exchange funds vs. direct indexing

Two routes out of a concentrated position, with very different tax and liquidity profiles.

8 min read
Planning

What 'work-optional' actually requires

Turning a one-time liquidity event into durable, lasting financial freedom.

6 min read
Equity Comp

Reading your 10b5-1 plan like an advisor

The mechanics of pre-planned selling — and the mistakes that quietly cost the most.

7 min read
Markets

Single-stock risk, in plain numbers

Why concentration feels safe right up until it isn't, illustrated with real scenarios.

5 min read
Tax Strategy

Charitable giving as a tax lever

Donor-advised funds and appreciated stock — coordinating generosity with strategy.

6 min read
Retirement

The bridge years before 59½

Funding an early, flexible retirement without tripping over penalties and brackets.

9 min read
Stay in the loop

Notes from the Long View

Every two weeks. Equity strategy and planning, written plainly. No noise, no spam — unsubscribe anytime.

Subscribe →Every two weeks. Unsubscribe anytime.
Three ways to go deeper
Free guide

The Concentrated Equity Unwind

The framework behind our Diagnostic — concentration math, tax maps, and the 90-day plan.

Notes from the Long View

Substantive, occasional, no noise

Equity strategy and planning worth your inbox. Unsubscribe anytime.

Subscribe →Every two weeks. Unsubscribe anytime.
Talk it through

A free, 25-minute conversation

No pitch, no obligation — your situation, and whether we can genuinely help.