APRIL 2026
IN THIS ISSUE
AI shoes
Shiller on options
Kiyosaki never stops
Buy in May and Stick Around
Trump advisors should be more forthcoming?!!
What can Hugh Jackman teach us about Investing?
In May 2022’s Likelyhoods I featured the contrasting styles of Elon Musk and Warren Buffett, including their stance on passive indexing. (‘I’m Not His Biggest Fan’: Elon Musk Says Warren Buffett’s Way of Getting Rich Is ‘Pretty Boring’ — but Here’s Why You Should Copy the Oracle of Omaha).
Elon Musk argues that "passive has gone too far" and the market needs a shift back toward active investment. Musk said he is “not [Buffett’s] biggest fan”, and called Buffett’s approach to investing “pretting boring really” and “lame”.
Warren Buffett argues that almost every investor will be better off buying and holding a low-cost S&P 500 index fund instead of actively managed stock-picking.
George Soros has similarly said:
“If investing is entertaining, if you’re having fun, you’re probably not making any money. Good investing is boring.”
Allow me to add another star into the conversation, albeit more of a Hollywood star. Hugh Jackman has said:
“The longer it takes you to become successful, the harder it will be for somebody else to take it away from you.”
Hugh Jackman’s career can help us understand several keys to successful investing:
Compounding. By spending years in the "unseen repetition" of theater before his global breakout, Jackman allowed his professional talents to compound, ensuring his eventual success was rooted in a strong experiential foundation and not a temporary industry trend.
Preparedness. As he seized the opportunity of the Wolverine role as a replacement, we can learn the importance of being "experientially prepared" and ready to strike when high-conviction opportunities arrive.
Diversification. Jackman’s deliberate movement between action blockbusters, Broadway, and prestige drama has created a defensive moat around his career, creating a diversified career portfolio that remains resilient against the volatility of any single segment of the entertainment business.
Elon has taken many large risks and has gotten very rich very fast. But how many others can expect to replicate Elon’s successes? Plenty of investors take a similarly intensive approach to investing, although their approach is better described as speculating or even gambling. Meme Stock Mania, high-stakes options trading (taking a "billion-dollar bath"), and other such strategies can certainly be fun! But they also have a fun-damentally high risk-of-ruin.
Amid January 2021’s Meme Stock Mania I wrote about Jayden Carr, the 5th grader whose mom, in 2019, bought him 10 shares of GameStop at $6/share, and who cashed out a $3,200 gain on that $60 investment when GameStop’s stock price went “to the moon”. I wrote:
“The worst possible outcome for a new investor is to get lucky on their first trade.”
I don’t know what Jayden Carr or his mom are up to these days, but I hope they have not concluded that they are naturals at stock-picking, or that they “just knew” GameStop was a good company, or any other variation of the Fundamental Attribution Error. "Get rich slow" strategies do not carry these same high behavioral risks, which is one reason those successes cannot as readily be lost. That’s what investors can learn from Hugh Jackman.
ONE MORE THING…
AI shoes. AI compute is probably not a core competency of a shoe maker? Reminiscent of Long Island Iced Tea Corp rebranding to Long Blockchain Corp in 2017. Struggling shoe retailer Allbirds makes bizarre pivot to AI, adds $127 million in value
Shiller on options. Nice lecture, not about technical options strategies but about options and their role in markets. https://x.com/i/status/2044297226365874588
Kiyosaki never stops. The biggest crash in history is still about to hit… I prefer Peter Lynch’s "Far more money has been lost by investors preparing for corrections, or trying to anticipate corrections, than has been lost in corrections themselves." Robert Kiyosaki says the ‘biggest crash in history’ is about to hit — warns millions could lose everything.
Buy in May and Stick Around. It doesn’t rhyme, but some say this is the year to stick around. Investors usually 'sell in May and go away.' Why that may not work this year
Trump advisors should be more forthcoming?!! But when he fires the BLS Commissioner for reporting factually lower than expected jobs numbers, it’s no wonder why your advisers will tell you lies that you want to hear. Trump’s Top Aide Freaks Out About What Trump’s Being Told on Iran War | The New Republic
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