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

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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

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Amy Wilson and her husband did nearly everything right on the road to financial independence, and the one task they kept postponing turned out to matter most. She shares what happened when a sudden loss met an unfinished estate plan, how she rebuilt her financial life on her own, and what she’d want you to do this week. Then Joe Saul-Sehy and OG explain how a change in IRS guidance can turn marketplace premium help into a bill for early retirees and side hustlers, with a quick round of income detective to show what counts.

What You’ll Walk Away With

• Why “we’re married, so it all goes to each other” isn’t a plan
• How beneficiary designations and default rules can pull in different directions across accounts
• Why your state already has an estate plan for you, and how to find out what it says
• What mattered, and what didn’t, in the first hours after a loss
• Whether to do nothing with your money for a while or dive into the details, and how to tell which fits you
• What it’s like to go from saving to spending overnight, and why a money nerd hired an advisor
• The small clues that told her an advisor was the right one
• A simple allowance system that keeps spending steady and leaves room for big plans
• Why advance premium help is an estimate, not a price guarantee
• The change that removed the cap on repayments, the income line that can cost you the entire credit, and what to recalculate before year-end

Why This Matters Now

Plans get interrupted, and the paperwork we postpone is usually the paperwork that matters most. Year-end is when open enrollment arrives and good intentions pile up, which makes it a natural time to finish the estate documents and recheck your income estimate. If you worry about a mistake you can’t undo, this episode treats both as checklist items you can finish, not worries to carry around.

From the Basement

Doug’s trivia is about cacao beans as currency, which leads him to try paying for dinner at The Sizzler with a bag of chocolate chips. Then OG explains his Halloween policy of yogurt only, with a granola exception.

Resources Mentioned

• Repayment caps eliminated for excess advance payments of the Premium Tax Credit: IRS guidance on the change
• Questions and answers on the Premium Tax Credit: IRS answers on how reconciliation works
• HealthCare.gov: where to update your income estimate with the marketplace
• Camp FI: in-person gatherings for the financial independence community, where Amy is a regular

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How to Turn Trick-or-Treat Into a Money Lesson (and Choose a Pension Option)

One doorstep each Halloween becomes a lesson in risk, reward, and generosity, and one listener believes it helped him land a job. Chuck Jaffe walks through the cash-or-candy game he’s refined over the years, including this year’s twist, and how to run a version whether you get a hundred trick-or-treaters or six. Then Joe Saul-Sehy and OG take a question from a listener with a military pension: how to weigh the survivor benefit, why the choice can’t be changed later, and what to ask before you sign. It’s a lighthearted start and a practical finish.

What You’ll Walk Away With

• The simple cash-or-candy trade that turns a doorstep into a lesson on risk and reward
• Why kids who never think about money will happily do the math when it’s a game
• How the game changes every year, including the lottery option and a choice that lets kids give something away
• How to run a version with a handful of trick-or-treaters and a few envelopes
• Why the dollar bill is the worst deal on the table, and why plenty of kids still take it
• How a doorstep wave turned into a jump start on the way to a job interview
• What a pension survivor option actually means, in plain terms
• How to compare a reduced pension against buying your own insurance
• What a “pop-up” provision is, and which questions to ask the pension office about a spouse’s health coverage
• Why a pension choice deserves far more research than picking a fund

Why This Matters Now

Some of the best money lessons are low-stakes enough for a fourth grader, and some of the biggest decisions are high-stakes enough that you only get one try. Both reward thinking early. If you worry about making a choice you can’t undo, or you want to give the kids in your life a calm, fun way to learn about money, this episode covers both ends of that range.

From the Basement

The basement debates candy corn versus Kit Kats, while OG volunteers to hand out Greek yogurt to trick-or-treaters. Doug’s trivia introduces a mule named Kevin and an Erie Canal that paid for itself in a year.

Resources Mentioned

• Survivor Benefit Plan: Military OneSource’s overview of the military survivor benefit
• Money Life with Chuck Jaffe: Chuck’s daily podcast, wherever you listen

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You build a plan around a goal, the goal changes, and the spreadsheet keeps marching toward the old one. Joe Saul-Sehy and a roundtable of regulars, joined by Financial Bliss Coach Kelley Long, CFP, ask what happens when the house, the career, or the family you saved for stops being the life you want. They play a game of keep it, kill it, or change it, then get practical about the real invoice for changing course: cash runways, taxes, selling while markets are down, and the stubborn pull of sunk costs. You’ll also hear why staying put has a price of its own.

What You’ll Walk Away With

• A three-card game (keep it, kill it, change it) applied to a house the kids have outgrown, a plan built around children that no longer applies, and a career plan with a countdown
• Why people regret never questioning a goal far more than missing it, and what a story from base camp has to do with it
• How to tell whether you want to stop working or just want out of a job you’ve outgrown, a lot like mistaking thirst for hunger
• The “invoice” for changing course, and the fixed expenses worth covering for a year while you figure it out
• A test-drive trick that lets you feel a change before you make it
• A way to compare a big decision by taking the money out first and asking what you’re really trading
• What to do when you need cash and your investments are down
• Why a big tax bill can be worth paying, and what happens when a rule of thumb swallows the reason behind it
• Sunk cost versus switching cost, and why only one of them is a feeling
• The “too small blanket” problem, and the flexibility you can build in from the start

Why This Matters Now

Most of us spend plenty of energy checking whether we’re on track, and very little asking whether we still want to go where the track leads. If you worry about a change you can’t undo, or you’ve outgrown a plan you built with good intentions, this conversation treats changing your mind as a cost you can plan for. Getting good with money was never about living yesterday’s life more efficiently. It was about having more choices tomorrow.

From the Basement

Joe reports that his new tendon came from an Olympian, at his request, and that standing up is now a major athletic event. Doug’s trivia is a cautionary tale about the worst side hustle ever pitched, and the Detroit Lions provide a live demonstration of a plan with an Achilles heel.

Resources Mentioned

• Financial Bliss Coach: Kelley Long’s coaching practice, with links to her podcast and book
• But Who Will Take Care of You When You’re Old? Financial Planning for People Without Kids by Kelley Long: her forthcoming book on planning without children
• Lynda Gratton: What If You Live to 100? Here’s How to Actually Plan For It: our conversation on the hundred-year life

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Most of us are optimizing a number, whether it’s a retirement balance or a job title, and almost never stop to ask what it’s for. Wharton economist Corinne Low measures how people really trade time, money, and love, and she has a short exercise that shows how little of your ideal life depends on that number. Joe Saul-Sehy and guest co-host Anna Allem, CFP, put her ideas to work on careers, partnerships, and the awkward conversations in between. You’ll hear why a house can act as insurance in a marriage, why your job won’t love you back, and how to walk into a hard conversation holding real leverage.

What You’ll Walk Away With

• A two-minute exercise that shows what your money is actually for
• Why almost nobody in that picture is working long weeks, and what that says about your calendar
• What economists mean by “utility,” and why it’s richer than happiness
• The case for “having it almost,” and why dropping perfect can raise satisfaction
• BATNA, a negotiation term worth knowing, and how to build yours before a hard conversation at work or at home
• The coin flip study: why people nudged out of a stuck situation ended up happier
• Why buying a home can act as insurance in a partnership, and who that lets take a step back
• Why your job is a tool for converting time into money, and why that’s good news
• Quick-fire answers on splitting bills 50/50, who gets the last word on big purchases, and whether prenups are only for the wealthy
• One thing to put on your calendar this week that makes you richer without earning a dollar

Why This Matters Now

Most of us are working hard toward a finish line we’ve never described out loud. That makes it easy to keep climbing, keep saving, and keep wondering why the finish line keeps moving. If you worry about making a move you can’t undo, or you feel like everyone else got a rulebook you missed, this conversation is a friendly way to decide what you’re building before you build more of it.

From the Basement

Doug reveals that Mrs. Neighbor Doug exists, which stuns everyone in mom’s basement, and then explains why Joe’s mom’s negotiating style involves a threat to cancel the shrimp appetizer at The Sizzler. Joe also shares a story about a rare Venetian grape that only thrives because of stress.

Resources Mentioned

• Corinne Low at Wharton: faculty page with her research
• Having It All: What Data Tells Us About Women’s Lives and Getting the Most Out of Yours: Corinne Low’s book, in paperback
• “Collateralized Marriage” and “Winning the Bread and Baking It Too”: two of her research papers discussed in the interview

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Some of the best money moves of the year come with a deadline most people never notice. A student loan rate can drop by a full percentage point with one setup step. A window may be open to move retirement money with little or no tax. A gap in your income protection can sit unnoticed until a claim gets denied. Joe Saul-Sehy and guest co-host Anna Allem, CFP, sort the urgent from the merely interesting, using a caller’s real insurance dilemma, a family college decision, and a ringside look at the market’s worst Mondays. It takes a free hour before the calendar flips and no finance degree.

What You’ll Walk Away With

• The deadline that got pushed back, and the one setup step that trims a student loan rate by a full point
• Why one point off a rate is a bigger win than it sounds
• What to check first if your repayment plan changed without you doing anything
• A simple way to show a student what a college choice will cost after graduation, using real salary data
• The question one family asked a kid before agreeing to the pricier school
• Why a year-end Roth conversion deserves a look from some savers, and the Medicare premium surprise to understand before you try it
• What an insurer does when a condition is already on your record, and why shopping around won’t change it
• How to map the “crater” a lost income would leave, and when that math says you can skip the policy
• The employer route that can quietly solve a coverage problem
• Which of three famous Black Mondays hit hardest, and when a mutual fund trade really happens
• A starting point for someone new to saving, military families included, that begins small

Why This Matters Now

Year-end is when quiet deadlines pile up and good intentions slip. You don’t need to master everything on the list. You need to know which items are time-sensitive, which can wait, and which you can cross off. If you worry about making a move you can’t undo, or feel behind because you haven’t looked at your plan lately, this is a low-pressure way to catch up.

From the Basement

Doug turns the trivia into a title bout, with boxing legends and a bowl of queso that did not survive the match. He also makes a Trans Am joke that nobody else in mom’s basement gets.

Resources Mentioned

• Education Department Extends 1% Student Loan Auto-Pay Cut: The College Investor on the extended deadline
• Stacking Benjamins Guides: HR and benefits, college planning, and taxes
• Occupational Outlook Handbook: Bureau of Labor Statistics salary and job data for comparing majors
• The MILMO Show: Lacey Langford’s podcast on money for military families
• Get a Financial Life by Beth Kobliner and The Simple Path to Wealth by JL Collins: the two books recommended for new savers
• Ask a question for the show

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