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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Most portfolios are built for nobody in particular. Peter Lazaroff, chief investment officer at PlanCorp and author of The Perfect Portfolio, tells Joe Saul-Sehy and OG why the right mix starts with your goals, not a list of funds. He also shares a four-question filter for deciding what earns a spot in your portfolio. Then a listener asks who to name on life insurance for his kids, and the panel disagrees sharply with the advice he got from his agent.

Veterans Day Giveaway

Enter by Friday, Nov 6 at stackingbenjamins.com/veterans for a chance to win a Solo Stove, drawn 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 “perfect” is personal, and what a steak dinner on paper plates has to do with it
• The sign that a portfolio was built for nobody in particular
• Why your first stated goal is rarely your real one
• How to tell discomfort from danger when markets drop
• Why owning a loser in your portfolio means you are diversified
• The four questions that decide whether an investment earns a seat
• A quick round of “Does It Earn a Seat?” with international stocks, AI stocks, and bonds
• What belongs on a one-page investment policy statement, and why rules matter most when everything looks broken
• Why naming a guardian on life insurance and hoping the money reaches the kids can go wrong
• What a court does with money left to a minor, and how a trust changes that

Why This Matters Now

Financial news is built to make you react, and most investing success comes from avoiding mistakes. Year-end is a natural time to write the one-page plan you will follow when markets get loud. If you have kids, it is also a good time to check who is named on your beneficiary forms. The estate discussion is general education, and an estate attorney can set up the specifics for your situation.

From the Basement

Doug’s trivia asks what “alpha” means in finance, after he makes his case for being the alpha of the basement because he controls the trivia microphone and the thermostat. Joe Saul-Sehy and OG compare notes on how warm mom likes the house. Doug also gives the Bay Area another reason to write in with “San Fran.”

Resources Mentioned

• Veterans Day giveaway: enter to win a Solo Stove
• The Perfect Portfolio: A Proven Guide to Smart Investing for Long-Term Success: Peter Lazaroff’s book from Harriman House
• The Long Term Investor podcast: Peter’s show
• Peter Lazaroff at PlanCorp: his bio and firm
• Mind the Gap US 2025: Morningstar’s research on the gap between investor and fund returns

See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

Every money decision comes with a basement door. Sometimes you go down and find a great deal, and sometimes you should run. Joe Saul-Sehy and OG run a Halloween game show in which the panel rules on eight real-life dilemmas, including a stock that has tripled, a dream house that leaves almost no cash, and a car loan a parent is asked to cosign. The panel disagrees, and the reasoning behind each answer is the useful part.

Veterans Day Giveaway

Enter for a chance to win a Solo Stove at stackingbenjamins.com/veterans. Veterans and active duty service members get three entries, and everyone else gets one. If you’re already in the 201 email series, you get an entry too, and you can earn more by referring friends.

What You’ll Walk Away With

• What to do when your company stock has grown into a huge slice of your portfolio, and why a gains budget beats waiting for the perfect moment
• Why optimism about your employer is not the same as a good price on its stock
• How much house is too much, and why the bank’s limit is not your limit
• What a thin cash cushion after closing really risks, and when a plan to rebuild it changes the answer
• How to weigh a bigger paycheck against a boss who keeps losing people, and the airport layover test for judging a future manager
• Why a tax bracket jump does not cost you more than you earn
• How to say yes to helping an adult child with a car while keeping the title, insurance, and risk in your own hands
• Why many people treat family loans as gifts
• Emergency fund or great credit? Low fixed expenses or great insurance? High savings rate or diversification? High income or financial knowledge? The panel picks sides

Why This Matters Now

Big decisions rarely arrive with a clean right answer, and the fear of making an irreversible mistake can stall good choices. Hearing smart people disagree, and explain why, builds your own judgment faster than a rule of thumb does. Year-end is a natural time to look at your concentrated holdings, your housing costs, and your cushion.

From the Basement

Doug arrives in a tin foil hat to resist Federal Reserve brainwaves, the panel shows up as a genie villain, a wreath-wearing leaf pile, and an Oktoberfest regular, and Doug’s trivia asks where “I’ll be back” ranks among the greatest movie quotes ever. He also reports that the Terminator spoke very few words in the whole film and that he once lost an argument at The Sizzler over the senior discount on shrimp cocktail. OG explains his Halloween yogurt policy, and a new traveling trophy with an honest inscription makes its debut.

Resources Mentioned

• Veterans Day giveaway: enter to win a Solo Stove
• AFI’s 100 Years...100 Movie Quotes: the list behind Doug’s trivia
• Afford Anything: a podcast from one of the panelists
• Personal Finance for Long-Term Investors: a podcast from another panelist

See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.