The Stacking Benjamins Show

December has a way of arriving all at once. Joe Saul-Sehy and OG each bring a top-five list of money moves to make before the calendar flips, and compare them in real time while Doug watches for overlap. The lists cover taxes, retirement accounts, investments, and one move that has nothing to do with money and everything to do with how 2027 will feel. Do the work now,before Thanksgiving sneaks up on us and the holidays are off and running.
What You’ll Walk Away With
Why a quick tax projection now can spare you an April surprise
How tax-loss harvesting works, why most of its value shows up earlier in the year, and the wash sale rule that trips people up
Which retirement and HSA deadlines hit December 31, and which ones you can finish after New Year’s
How to max out contributions by leaning on your cash cushion, and when that is smart or risky
Why buying into a taxable mutual fund in December can hand you a tax bill on gains you never earned
What an FSA deadline really means, and how to avoid a contact lens stockpile
Why Roth conversions come down to an educated guess, and how to make a choice you will not regret
How giving to charity straight from a retirement account can lower your taxes, and what changed this year for charitable deductions
The calendar move that has nothing to do with money, and why it came in at number one
What a retirement plan that sailed off the map teaches about planning for the unexpected
Why This Matters Now
Year-end deadlines do not move, and the holiday season is when budgets get tested. A few hours of attention before the spendiest month of the year means January starts with a clean sheet instead of a cleanup. This episode is general education, and a tax professional can apply it to your situation.
From the Basement
Doug challenges everyone to say a very difficult tongue twister about Bitcoin five times fast, then runs trivia about the back of the $5 bill. OG explains his holiday budget approach, which involves fun coupons, and Joe Saul-Sehy and OG debate whether one-click shopping is genius or a trap. Doug also offers a “Dougalicious” tip for next year.
Resources Mentioned
Planning for charitable contributions in 2026: a guide to what changed this year
Endless cruise goes broke: coverage of the story about retirees stranded abroad
Your own top five: share yours at stackingbenjamins.com/basement
If you heard a rumor about a children’s book on what money really means, Mama, Are We Poor?, we can neither confirm nor deny where. But if you happen to want a copy, here’s a link.
See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

Social Security checks are getting a raise because everything costs more. Joe Saul-Sehy, OG, and Doug are joined by a Brooklyn financial planner who works with creative people on lumpy incomes and Jesse Cramer of Personal Finance for Long-Term Investors to ask whether you should trim retirement savings when the budget squeezes. They play “Cut It, Keep It, or Crank It” and “Who Gets the Next Dollar?” with realistic households. The goal is to keep a temporary squeeze from turning into a permanent setback.
What You’ll Walk Away With
Why a Social Security raise is both good news and a sign your costs went up
What a single inflation number misses about how prices actually hit your household
The first signs your budget is leaking if you have never tracked your spending
A quick way to see price changes by scrolling through your online shopping carts
What “enoughness” means and how to use it when prices shift
When to cut your 401(k) contribution, when to keep it, and why many of the panelists would hold it at the employer match
Why it is easier to keep a small retirement contribution going than to restart a stopped one
A financial triage order for deciding where each new dollar goes
Whether to pay a car repair from cash or a credit card
Why a 401(k) loan is rarely better than pausing contributions
Why retirement comes before college savings, even for loving parents
How to handle lumpy income and set aside taxes before a windfall arrives
Why asking for what you need in a negotiation costs you nothing
Why This Matters Now
Prices are rising unevenly, with groceries, gas, and airfare moving in different directions, and many people are trimming retirement savings to cope. Year-end is when budgets get reset and benefit elections get made, which makes it a natural time to decide your plan before the squeeze decides it for you. This episode gives you a framework you can use without feeling judged for being behind.
From the Basement
Doug’s trivia goes back to a sailor in 1492 who brought smoking home to Spain and got locked up for it, then to the giant settlement that came centuries later. He also confesses to once trying to smoke a Slim Jim, and nearly gets the guest’s name right while inventing a few new words. Everyone swaps stories about their love of the Sizzler salad bar, and OG tries to hold on to his lead for the “You suck the least” trophy.
Resources Mentioned
Creative Money: New Financial Rules for Artists, Innovators, and Misfits: the guest’s new book, out Tuesday, Nov 10
Personal Finance for Long-Term Investors: Jesse Cramer’s podcast

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

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

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

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.