
Covering the intersection of psychology, investing, and the consumer and technology sectors. Written by investor and mental health tech entrepreneur Benjamin Tan, who holds a master’s degree in clinical mental health counseling.
| Platform | Pricing | Only free issues | Publishes | Weekly | |
|---|---|---|---|---|---|
| Issues | 93 | Founded | 4 years ago | Last Issue | 15 days ago |
| Active | |||||

Trupanion’s () latest quarter (Q1 2026) did not change the story so much as clarify it. This is no longer the old hypergrowth pet insurance darling that could do no wrong. It is a more mature, more disciplined business rebuilding credibilit...
Over time, I have come to realize that many of the biggest mistakes investors make—myself included—are not analytical. They are behavioral. They come from misalignment between who we are and how we invest.
The pet insurance category is underpenetrated; Trupanion’s margins are normalizing. Yet, the current valuation reflects neither.
If you have read my book Suit Yourself, you will know that Enneagram Type Fives gravitate toward the complex a...
Project 350K: A mid-year review was posted in June 2025
At the beginning of 2025, I set a goal for my Traditional IRA: to grow it to $350,000 over a 10-year period, as outlined in parts 1, 2, and 3. Since I already have most of my net wort...
The Trade Desk ( ) has long been the open internet’s counterweight to the walled gardens — an advertising platform built on transparency, neutrality, and scale. For years, that narrative justified a premium valuation. But in the wake of Ju...
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The writers behind this newsletter.
Author of Suit Yourself, Benjamin Tan combines his growing expertise in clinical psychology, portfolio management, and years of experience in banking/buy-side (Credit Suisse, UBS, Oaktree) to write about investing behaviors.
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