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What Mark Twain Can Teach You About Investing (Besides Not Putting All Your Eggs in One Steamboat)
Meet Your New Investing Coach: Samuel Clemens (a.k.a. Mark Twain)
He may have died in 1910, but Mark Twain could probably outmaneuver half of Wall Street today—with a cigar in one hand and a sharp jab at human greed in the other.
Twain lost money in silver mines, publishing ventures, and speculative gadgets. He went bankrupt once. But the guy also understood risk, emotion, and the madness of crowds better than most MBA textbooks ever will.
Twain’s Best Investing Lessons—In His Own Words
1. “History doesn’t repeat itself, but it often rhymes.”
This is practically the motto of every macro manager ever.
- 2000: Tech bubble
- 2008: Housing bubble
- 2021: Meme stocks + SPACs + NFTs in one big frothy smoothie
Investor takeaway: Be alert for the pattern, not the copy and the signs. Bubbles don’t clone—they remix.
2. “October. This is one of the peculiarly dangerous months to speculate in stocks… The others are July, January, September, April, November, May, March, June, December, August, and February.”
In other words:
Markets are always dangerous when you’re gambling instead of investing.
Twain was being sarcastic—but he wasn’t wrong. The market doesn’t care what month it is. The danger lies in how you play the game.
3. “Whenever you find yourself on the side of the majority, it is time to pause and reflect.”
If everyone is bullish, maybe you should be bearish. If everyone is piling into AI stocks, maybe look at trash hauling or boring defense companies.
Contrarian investing = classic Twain logic. Crowds are often wrong at the top.
4. “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 is Twain’s version of Buffett’s “Don’t lose money.”
Whether you’re broke or ballin’, speculative fever has a way of frying your brain.
Twain Was a Great Writer—But Not Always a Great Investor
He made big bets on:
- Typesetting machines that never worked
- Silver mines in Nevada that fizzled
- His own publishing firm, which tanked despite publishing Ulysses S. Grant’s memoirs
But guess what? He owned it. He joked about his mistakes, and then learned from them.
The ultimate Twain lesson?
“It ain’t what you don’t know that gets you into trouble. It’s what you know for sure that just ain’t so.”
For Investors
Apply Twain’s truths to modern investing:
| Twainism | Modern Translation |
| Don’t follow the crowd | Question overhyped trends |
| Watch your confidence | Be humble about what you know |
| Speculation is risky | Invest, don’t gamble |
| History rhymes | Study patterns, not predictions |
Final Thought: Twain Wasn’t a Great Investor—But He Was a Genius About Why We Fail
You can’t always avoid bad markets. But you can avoid being the sucker at the poker table.
And as Twain might say, “It’s easier to fool yourself than to admit you were the fool.”
So… diversify, question consensus, and maybe don’t buy that talking toaster NFT.
DISCLAIMER: This analysis of the aforementioned stock security is in no way to be construed, understood, or seen as formal, professional, or any other form of investment advice. We are simply expressing our opinions regarding a publicly traded entity.
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