Most investing advice starts with what to buy. Dr. Daniel Crosby, behavioral finance expert and author of The Behavioral Investor, starts with you. He tells Joe Saul-Sehy and OG why a brain built for survival on the savanna makes a poor money manager, and how four predictable troublemakers (ego, conservatism, attention, and emotion) show up in real portfolios. Then they play a round of “Who Broke the Portfolio?” In the headline segment, Joe Saul-Sehy, OG, and Doug look at why companies that lean on AI are running into an insurance problem, and what that means for protecting your own finances.

Last Call: Veterans Day Giveaway

Enter by Friday, Nov 6 at stackingbenjamins.com/veterans for a chance to win a Solo Stove, given away next Wednesday on Veterans Day. Veterans and active duty service members get three entries, and everyone else gets one. If you already get the 201, you can still enter.

What You’ll Walk Away With

• Why the first investing question is not what to buy but how you will act when things get scary
• What a plane crash with monkeys and humans reveals about why we herd
• Why your brain is old, hungry, and impatient, and what that means over decades of investing
• The four troublemakers and how to spot each one in the wild
• Why loud financial news can switch off your critical thinking
• A game of “Who Broke the Portfolio?” with company stock, AI stock envy, and “this time feels different”
• The difference between risk tolerance, risk capacity, and risk composure
• Three simple fences: education, environment, and encouragement
• Why diversification is humility made visible
• A four-letter check to run before any money decision
• How to figure out which of the four is most likely to get you
• Why insurers are getting nervous about AI errors, and why that is a good reminder to check your own liability protection
• What an umbrella policy does on top of your auto and home coverage, and why lawsuits tend to arrive from left field

Why This Matters Now

Market noise gets louder at the end of the year, and so do tempting ideas from coworkers and group chats. Having fences in place before the next surprise is cheaper than a mistake you cannot reverse. The same goes for your safety net. Year-end is a natural time to look at how well your insurance covers what you have built. This episode helps you learn your own patterns without feeling judged for having them.

From the Basement

Doug’s trivia heads to the 1922 discovery of a long-sealed tomb and the legend of its curse, then to his metal detector and the cash he buried years ago and still hasn’t found. He also reports on his lifetime ban from the Sizzler dessert bar, as ruled by Todd, and OG and Joe Saul-Sehy compare their fast food glass collections.

Resources Mentioned

• Veterans Day giveaway: enter to win a Solo Stove
• The Behavioral Investor: Dr. Daniel Crosby’s book, with a new edition from Harriman House due Nov 10

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