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🧠 When Is It Ok to Speculate?

June 18, 2025
🧠  When Is It Ok to Speculate?
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Welcome to Long-Term Mindset, the Wednesday newsletter that helps you invest better.

Today's Issue Read Time: <2 minutes

  • Lesson: America's greatest author
  • Timeless Content: The state of the housing market
  • Thread: Key SEC Statements for Investors
  • Resource: Ray Dalio's All-Weather Portfolio
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Friends,

If historians put together a list of America's greatest authors, few names would rise to the top quicker than Mark Twain (Samuel Clemens). By the time of his death in 1910, the author of The Adventures of Huckelberry Finn was one of the most popular figures in the country.

His creativity was unmatched. His lifetime earnings were prodigious (Grok estimates it to be at least an inflation-adjusted $40 million). His investing acumen, however, was horrendous.

During his lifetime, he invested huge sums in a failed typesetting machine, an independent publishing company, speculative mining ventures in Nevada, and even a milk-derived protein supplement.

It's no surprise that by 1894, he was forced to declare bankruptcy. If not for his close friendship with Standard Oil's Henry Rogers, it could have been even worse. Rogers saved his royalties from being included in the bankruptcy proceedings, and handled many of his finances following the episode.

By the end of his life, Twain had learned his lesson, saying:

"There are two times in a man's life when he should not speculate: when he can't afford it, and when he can."

This underscores an important point: Twain was brilliant beyond belief. But that brilliance -- and his endless search for dopamine hits -- was just as much a liability in investing as it was an asset in writing.

At the end of the day, there are zero points for style in investing. Your balance in your brokerage account doesn't care how it got there -- it just tells you where things stand.

That's not to say creativity itself is bad -- it's just better left applied to endeavours outside of investing. Over the long run, that's where it creates the most value.

Wishing you investing success,

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Brian Feroldi, Brian Stoffel, & Brian Withers

Long Term Mindset

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It seems like every week, there are new advances in A.I. capability announced in the media. But for investors, What AI can - and can't - do for investors right now? is the question many savvy stock nerds are asking.

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1/ For most of us, the path to financial freedom consists of: (a) SAVING our money diligently, and (b) INVESTING these savings intelligently. Here are 4 key ideas to help you understand the interplay between SAVING and INVESTING.
7:2 AM β€’ Aug 14, 2022
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Don't have a Twitter/X account? Click here to view the thread.

One resource

The market took a big step back last Friday after Israel attacked Iran. These disruptive events on the world's stage can be stressful for investors. But, it's helpful to keep these events in perspective. Check out the history on How Stocks React to Geopolitical Shocks.

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Brian Feroldi

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Brian Stoffel

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Brian Withers

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