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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.

Platform
Substack
PricingOnly free issuesPublishesWeekly
Issues88Founded2 years agoLast Issue21 days ago
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Latest Issues

Dad Books: The Compiled List

This thread started right after that WSJ piece on how ‘Dad Books’ are a dying breed. It’s a pretty good moniker and we know the vibe. These are the nonfiction business traveler airport books. It’s grandpas listening to audiobooks while mowi...

21 days ago
128
18

Some Thoughts On The Modern “Family Seat”

Gregory Treat, writing at his Avalon Circle Substack, recently published a piece called “Where is the Modern Family Seat?” It is one of the more interesting things I’ve read on wealth planning lately. I had learned of this author by way of...

a month ago
16
2

The Book of Elon

Eric Jorgenson is back on the pod to talk about his new book, The Book of Elon, a five-year project distilling Elon Musk’s most useful ideas in his own words. Eric and I talk about why Musk is the greatest living entrepreneur, the recursive...

2 months ago
5
1

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...

5 months ago
4

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...

6 months ago
7

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