Notes on building, selling, and keeping a fortune.

Most founders start tax planning after they sign the LOI. By then the most valuable moves are already off the table. Here is what gets locked in earlier than you think, and why dynasty trusts and insurance wrappers belong in the conversation years before a sale.

Featured · Pre-Exit Planning

The work that has to happen before the wire clears

The work that has to happen before the wire clears - featured article mobile

Post-Exit Strategy

June 11, 2026

Living on the portfolio without feeding the IRS every April

After the sale, the goal flips from growth to income. But income is where the tax code is most punishing. A private placement life insurance structure can turn a taxable portfolio into a stream of tax free cash flow, if it is buil…

Post-Exit Strategy

Living on the portfolio without feeding the IRS every April

June 11, 2026

Living on the portfolio without feeding the IRS every April - article image mobile

After the sale, the goal flips from growth to income. But income is where the tax code is most punishing. A private placement life insurance structure can turn a taxable portfolio …

Investment Philosophy

June 4, 2026

Risk is the chance of losing money, weighted by how much

The industry measures risk with a Greek letter and calls it a day. But the number on the statement is not the thing that hurts you. Real risk is the permanent loss of capital, and you only find out who took too much of it when the…

Investment Philosophy

Risk is the chance of losing money, weighted by how much

June 4, 2026

Risk is the chance of losing money, weighted by how much - article image mobile

The industry measures risk with a Greek letter and calls it a day. But the number on the statement is not the thing that hurts you. Real risk is the permanent loss of capital, and …

Pre-Exit Planning

May 28, 2026

The exemption that can make millions of your gain disappear

Section 1202 lets qualifying founders exclude a large slice of their gain from federal tax entirely. Most learn about it too late to use it well, or never learn that the same exemption can be multiplied across more than one taxpay…

Pre-Exit Planning

The exemption that can make millions of your gain disappear

May 28, 2026

The exemption that can make millions of your gain disappear - article image mobile

Section 1202 lets qualifying founders exclude a large slice of their gain from federal tax entirely. Most learn about it too late to use it well, or never learn that the same exemp…

Liquidity Events

May 21, 2026

The price on the term sheet is not the money you keep

Founders fixate on the headline number. Buyers know that the real negotiation is in the structure underneath it, where earnouts, equity rollovers, and the form of the deal quietly decide what actually lands in your account and whe…

Liquidity Events

The price on the term sheet is not the money you keep

May 21, 2026

The price on the term sheet is not the money you keep - article image mobile

Founders fixate on the headline number. Buyers know that the real negotiation is in the structure underneath it, where earnouts, equity rollovers, and the form of the deal quietly …