September 2025 – CGW's Blog

How not to invest

Public stock markets are exchanges to buy and sell shares in big companies. Most days most people involved are trying to solve some problem. Share prices go up when there is more demand, reflecting market conditions, innovations and/or a story about the future, and they go down when there is less demand.

Shorter-term business cycles (a few years) rotate longer-term secular trends (decades). Investors try to make money by putting this all together into a theory about the world. Different eras call for different strategies. For example, more than three-quarters of the gains in the American stock market between 1982 and 2000 were from rising price-to-earnings multiples (how much more expensive stocks got), rather than rising corporate profit (how much more efficient companies got). Over those 20 years, one could have called stocks “too expensive” and been wrong, until the very end, when a correction brought a big reset. “Fair value” is just just a mark in a continuum on the path from the start to the end of a bull market. Gotta pick your bets.

That’s from How Not to Invest, a book out this year from the investor Barry Ritholtz, who is a frequent writer and speaker.

The reason his book as a negative title? His big idea? A tiny sliver of any competitive field, including wealth accumulation, play the “winner’s game,” in which they’re competing on expertise. The rest of us play the “loser’s game,” as an analyst called it, in which we just try to avoid unforced errors. It’s true in tennis, and in money management. Just be smart, cautious and consistent and you’ll outperform most of the rest.

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The book’s foreward was written by Morgan Housel, another wealth manager who is active online and whose Psychology of Money was a bestseller in this tradition of the approachable personal finance books. Ritholtz’s book is longer and more tactical, but continues the tradition of introducing broader strategy and worldview.

He brings up lots of familiar, but effective, truths from psychology and other social sciences.

For one, he brings up the evolutionary mismatch hypothesis, which suggests that traits beneficial in our ancestral past, like craving sugar or storing fat, become detrimental in the rapid, modern world, leading to modern diseases like diabetes, obesity, and inflammation, because our ancient biology hasn’t caught up to today’s vastly different environments (e.g., sedentary lifestyles, abundant processed foods, constant stress). It’s also why basic personal finance strategies are so hard, even if the research has been so dependably clear for decades: put little bits into a diversified portfolio with the lowest fees possible.

Then again, when it goes wrong, as investor Howard Marks wrote: “Experience is what you got when you didn’t get what you wanted.”

Below I share my notes from the book for future reference.

The Gulf War Did Not Take Place

The Gulf War was a seemingly decisive military action led by the United States against Iraq in 1991.

Over a series of essays, French philosopher Jean Baudrillard argued the war was an expression of his concept of “hyperreality,” in which emerging visual media could be used to create something false that appears even realer than reality itself.

By 1995, he assembled these essays into a final, short book called The Gulf War Did Not Take Place.

My storytelling keynote to Tech Hubs leaders in Montana

Meaningful commercialized science and intentional local economic coalition building does not correlate to high-quality storytelling about it. Economic development leaders should take storytelling seriously.

The kind folks at Montana’s Headwaters Tech Hub gave me the chance to address their summit of Montana ecosystem members and other tech hub leaders from around the country. I gave a storytelling presentation informed by this research — and led with the impressive tale of how Jeanette Rankin became the country’s first female Senator.

The “housing affordability crisis” is really a mobility crisis

What Americans call a “housing affordability crisis” is really a mobility crisis — economic, geographic and social. Housing is where that immobility becomes most visible, and so expensive housing is more a symptom than the disease.

That’s from a new book by historian and Atlantic journalist Yoni Appelbaum called “Stuck: How the Privileged and the Propertied Broke the Engine of American Opportunity.“

In healthy economies, including for much of the American golden age, people move to better jobs, cheaper places, growing regions. In the US today, people are increasingly trapped in place. When people can’t move, demand piles up in a small number of “winning” metros. Prices explode there, while other places stagnate or hollow out. I’ve written on the topic this year myself here and here.

Appelbaum’s book recounts the long trends that are piling up today. He recounts how American zoning regulations were introduced for race and class control, not for genuine health or safety concern. Early 20th century leaders, including eventual-US President Herbert Hoover, misunderstood crowded tenements and single-family homes as the obstacle and the accelerant, rather than what they really were: the launching pad and the eventual destination for those who made it out.

That history has persisted to today, where regulation and competing priorities strangle what might naturally occur. As famed mid-century urbanist Jane Jacobs said, over-planning a community is “attempting to substitute art for life”

Below I have notes for my future reference from Greenbaum’s detailed book. It’s wonky, and less colorful than I expected, but for anyone invested in the topic, it’s worth it.

Of Boys and Men

A very small number of men dominate the most powerful and wealthiest positions, and are among the most aggressive humans alive.

But though this tiny number accounts for many disparities, and men have not taken enough domestic imbalances, their trend lines are worrying. Boys and men are going the wrong direction fast.

That’s from the 2024 book by Richard V. Reeves: “Of Boys and Men Why the Modern Male Is Struggling, Why It Matters, and What to Do about It.” It’s one of a growing collection of research and literature.

As Reeves writes: “We have an education system favoring girls and a labor market favoring men. Two wrongs don’t make a right.”

Below I share my notes for future reference.