Case Studies
The most useful thing a 60 year old former operator can read is the unvarnished story of what another 60 year old former operator actually did, what it cost, and what it returned. The LinkedIn version of these stories is useless. The honest version is rare.
Board Work
A board seat is a job. The people who treat it as an honor end up doing the work of the people who treat it as a job, for less money and less credit. This is the single most useful sentence in the entire category, and most senior operators learn it the expensive way.
AI and Staying Current
The reader of this newsletter has already used ChatGPT and Claude. The question is no longer whether to engage with
The Portfolio Career Is a Job, Not Retirement
A serious portfolio career is more demanding than a single executive role, not less. The operators who treat it as semi-retirement end up applying for full time jobs again at 60. The ones who treat it as a practice compound.
