Investing in a Destabilized World

They've been better than virtually all managed funds for decades -- has the index fund's moment passed, or are they still the best option for most investors?

Keith talks about the logic of constructing his cash-heavy defensive portfolio, how it is designed around his life goals, and the tradeoffs versus traditional investing advice.

What does the SpaceX IPO mean, considering the many ways in which market norms, regulations, and corporate governance standards are being violated?

We're now tracking four portfolios as we invest in a destabilized world. Today, Ethan presents the case for one of his high-conviction stocks -- the New York Times -- while Keith plays the role of the skeptical doubter.

Keith and Ethan tackle an investing landscape that is as confusing and ever. Plus two announcements: Different This Time? is becoming Investing in a Destabilized World, and we're adding an exciting addition to our format for episodes going forward.

Keith and Ethan discuss the investing dynamics of war: oil prices, defense contractors, and the larger global economic picture.

Keith interviews Ethan about the ways climate impacts will transform the housing market, especially the bifurcation of home values based on climate vulnerability. They also discuss how to assess the resilience of a prospective home and Ethan's path to his new career as a real estate agent helping clients evaluate and buy climate resilient homes ( https://climateresilienthomes.com/ ).  Related...

Recent developments at Waymo have Keith and Ethan convinced that autonomous vehicles are about to start scaling worldwide. Where is this tech going, why is it shockingly under-reported compared to to AI LLMs, and is it possible to invest in this emerging tech?

Do the large and geographically widespread Democratic wins in the 2025 elections have implications for investing? Keith and Ethan discuss whether a weaker Trump necessarily means anything will change -- at least with respect to investing strategy.

With more financial turbulence ahead, Keith wonders if his longtime choice to rent should change, in order to gain portfolio diversification through ownership of a physical asset.

Inspired by Eli Kasargod-Staub's description of the Jenga Tower Economy in his recent Substack , Keith and Ethan discuss the growing brittleness of different elements of our economy, and how the AI bubble popping would make these weaknesses hit hard.

Keith and Ethan unpack the volatile state of cryptocurrency: Is it finally going mainstream, or are we witnessing the setup for the next financial crisis? Maybe both. Tune in for a candid, nuanced take on what recent developments might mean for the future of money.

Keith and Ethan get philosophical about saving and spending, understanding that without getting it right there is no money to invest.

One reason market valuations are so high is optimism about the transofrmative power of AI -- but the tide seems to be turning. From ChatGPT's recent stumbles to theoretical limitations for LLMs in general, what does the deterioration in prospects for AI mean for stocks? The Buffet Indicator: https://www.longtermtrends.net/market-cap-to-gdp-the-buffett-indicator/

Keith and Ethan discuss the US government's declining ability to understand what is happening with the economy as a result of the firing of the head of the Bureau of Labor Statistics. They also discuss whether an entire generation has been trained to "buy the dip" -- and what the implications for investors might be.

With increased inflation just over the horizon, Keith and Ethan discuss and rate the growing number of drivers of price increases.

With Ethan on break, Keith does a special video episode to take a look at economic data, finding that Trump's decisions have barely registered yet in several key economic indicators. But a quick review of pandemic era inflation data suggests it could take up to a year to really see policy impacts in the data. Some useful links: BLS interactive consumer prices graph St. Louis Fed breakeven employme...

With the US formally entering the war in Iran, there is yet one more reason to feel the world is on fire. How do we think about markets and war -- and the specter of nuclear proliferation?

With market enthusiasm for AI contributing to the recent run up in stocks, Keith and Ethan question whether investors have become irrationally exuberant, with a bubble in the making.

It's clear that consumer debt -- mortgages, credit cards, student loans, and car loans -- is rising. But are consumer debts approaching levels that could tip the US into recession? Or are consumers in ok shape, historically speaking? Keith and Ethan argue both sides to tease apart what's really going on.

The ongoing uncertainty in Trump's tariff policies create a confusing landscape for investors and consumers wondering where things will land. Keith and Ethan discuss the possibilities and discuss whether the market's resiliency has everything to do with Wall Street's TACO beliefs.

With the US in clear economic decline during Trump's second term, should we be rethinking traditional recommendations and increasing our investments overseas? What does history tell us about market performance -- has the US always outperformed, or is there a cyclical pattern to watch for? With growing inflation and a falling dollar strong possibilities, Keith and Ethan discuss the opportunitie...

After weeks of stock market gains and a 90 day tariff agreement with China, Keith and Ethan confront the possibility that maybe this time isn't actually that different. But as they talk through continued tariff uncertainty, the economic effects of the destruction of the country's publicly funded medical research apparatus and more, the red flags mount. By the the end of this episode, at le...

Keith and Ethan update Nassim Taleb's 2007 metaphor on market risk and discuss the challenge of pursuing incremental market gains without exposing oneself to the risk of catastrophic losses. They discuss their own humbling examples of getting it wrong, and how investing well requires accounting for your own fallibility. A brief examination of Japan's 35-year stock market nightmare provides fodder...

Keith and Ethan react to the disastrous tariff rollout, explore how investors should think about Trump's self-own for the ages, and debate the political consequences ahead.