January 28, 2025

From Nassim to Niall

As I march toward 40, the opportunity cost of my free time is reaching all-time highs. But in past eras — when it didn’t take an act of God to just lie on the couch — I was known for reading a book or two, especially a finance book. Don’t get me wrong, I still read more than the average bear, but not nearly at the same rate.

If you, Dear Reader, are like me and have neither the time nor the patience to read a 300-page tome, no need to worry. I’ve got you covered. What follows are quick two-sentence summaries of my personal Top 10 Most Enlightening finance books. In lieu of a full read (which I would highly recommend, by the way), these pithy notes will provide a decade-and-a-half’s worth of insights in three minutes. Talk about a high ROI.

1) The Black Swan by Nassim Nicholas Taleb

Life’s biggest moments are unpredictable, yet we constantly fool ourselves into thinking we can forecast the future. Embrace uncertainty, build resilience.

2) Die with Zero by Bill Perkins

Stop hoarding for a future you might not see. The biggest flex is spending your money on experiences while you’re alive and actually able to enjoy them.

3) When Genius Failed by Roger Lowenstein

The rise and fall of Long-Term Capital Management shows how even the “smartest guys in the room” can blow up when ego meets leverage.

4) The House of Morgan by Ron Chernow

A deep dive into how John Pierpont Morgan shaped the global banking system and built an empire that made Wall Street the world’s power center.

5) The Psychology of Money by Morgan Housel

Money isn’t about spreadsheets; it’s about emotions and habits. Understanding yourself is the ultimate financial strategy.

6) Too Big to Fail by Andrew Ross Sorkin

The 2008 financial crisis was a global game of Jenga where everyone pulled blocks at the same time, and only a handful of insiders could stop the tower from falling.

7) The Intelligent Investor by Benjamin Graham

The timeless Bible of investing: stay disciplined, focus on value, and ignore the market’s mood swings if you want to win long-term.

8) House of Cards by William D. Cohan

The story of Bear Stearns’ epic collapse. Proof that hubris, bad bets, and poor leadership can turn rockstars into roadkill.

9) A Man for All Markets by Edward O. Thorp

A math nerd cracked the casinos then cracked the markets, showing that — with enough intelligence and discipline — the house doesn’t always win.

10) The Ascent of Money by Niall Ferguson

Money is the operating system of humanity. It’s powered empires, funded wars, and shaped the world even more than politics.

 

And for kicks, here are two of the most overrated “finance” books in human history. How these authors (who will, indignantly, remain nameless) became household names is beyond me.

1) Rich Dad, Poor Dad

Advice from an imaginary father wrapped in a parable that somehow convinced millions they were one real estate deal away from becoming the next Sam Zell.

2) The Richest Man in Babylon

A bunch of ancient guys in robes sharing money tips that boil down to “save more, spend less.” Groundbreaking stuff.

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