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Gentleman Speculator

Andrew Flattery

Insights on investing, legacy, and the life well-lived from Andrew Flattery and Flattery Wealth Management, LLC.

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Substack
PricingOnly free issuesPublishesWeekly
Issues85Founded2 years agoLast Issue4 months ago
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Latest Issues

Flattery Wealth 2025 Annual Letter

Friends,

My Flattery Wealth Management Annual Letter is available to download in PDF form here:

2025 Annual Letter

This year’s letter explores the balance between staying true to the investment philosophy and adapting to changing market...

4 months ago
3

Have Yourself a Home Alone Family

I dive into what I’m calling peak America, that is the Peter McAllister (Dad) character from Home Alone. Watching this at age 41 and the movie is now a meditation on what’s worth fighting for. I get into how the McAllister house functions a...

5 months ago
7

Johann Kurtz (Becoming Noble) - Leaving a Legacy

I speak with with the semi-pseudonymous on his terrific new book Leaving a Legacy: Inheritance, Charity, & Thousand-Year Families. Johann lays out the foundation for why it can be moral to leave an inheritance when pared with virtue. We ta...

6 months ago
7

The Casey's Pizza Inflation Index (CPI)

Around four years ago, I posted a joke on Twitter about Casey’s gas station pizza getting more expensive. I called it the “Casey’s Pizza Inflation Index (CPI)” and framed it as a quasi-earnest effort to track inflation, with a subtle jab at...

6 months ago
3
3

Zack Grafman & Frank Theodat on The Boys Book of Adventure

I chat with editors Zack Grafman and Frank Theodat about the need for aspirational books for boys. Many recommendations from the Dads here, including classics like The Hardy Boys, Treasure Island, Jules Verne but also some new stuff (Redwal...

8 months ago
11
3

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