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Consume Your Own Tech Investing

Benjamin Tan

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.

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Substack
PricingOnly free issuesPublishesWeekly
Issues93Founded4 years agoLast Issue15 days ago
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Latest Issues

Trupanion: Recovery Is Real, and the Story Is Narrower Now

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...

15 days ago
1

Most Investing Mistakes Are Not Analytical

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.

  • Some people freeze, waiting f...
2 months ago
2

Trupanion: Mispriced Coverage

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...

3 months ago
2

Project 350K: A Review of My 2025 Traditional IRA Performance

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...

4 months ago
2

The Trade Desk’s Existential Crossroads

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...

7 months ago
3
3

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  • Benjamin Tan

    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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