The Stacking Benjamins Show

Latest Episodes:

How to Turn Retirement Confidence Into a Real Plan (Even If You Feel Behind) SB1923 Nov 13, 2026

Show notes

More of us feel good about retirement than we did a year ago, yet fewer of us are doing the things that get us there. Two new surveys, one on confidence and one on how each generation is tracking, put that gap in plain view. Joe Saul-Sehy and Doug sit down with contributors Paula Pant, Chris Luger, and Evan Raidt to ask what to do about it. The answer is less about willpower and more about swapping a feeling for a plan, then starting before it feels perfect. If you suspect you’re behind, this is a friendly place to begin.

What You’ll Walk Away With

Why confidence is a feeling and “on track” is a number, and how the two can pull in opposite directions
Why popular rules of thumb can leave you falsely comforted or needlessly discouraged
A better starting point than a rule of thumb: define the life you want, then work backward
Why people with a written plan tend to feel more on track, and the honest caveat about cause and effect
What “step zero” looks like before you do any math
How to play with your timeline instead of giving up on it
Why swinging for the fences to catch up usually backfires
Why so many retirements arrive on someone else’s schedule, and what that means for planning
A quick round of Myth or Monster on credit cards, buy now pay later, and more

Why This Matters Now

Rising costs keep tugging at the same dollars we’d like to send toward the future, and it’s easy to confuse a good mood with a good plan. The Confident Explorer in all of us wants to move forward without making an irreversible mistake or feeling judged for where we’re starting. This conversation lowers the stakes. It shows that a rough plan beats a perfect one, and that the smallest first step counts.

From the Basement

Joe Saul-Sehy and Doug (Joe’s mom’s neighbor) keep things playful with horror-movie trivia and a few stories about email and insurance renewals that quietly cost real money. Doug’s closing lesson is a reminder to read the fine print before you buy insurance.

For Financial Coaches

If you’re a financial coach who wants coaching on running your business, write Joe at stackingbenjamins.com.

Resources Mentioned

2026 MFS Global Retirement Survey coverage: https://401kspecialistmag.com/retirement-confidence-surges-despite-financial-pressures-mfs/
Goldman Sachs Asset Management 2026 Retirement Survey press release: https://am.gs.com/en-us/advisors/news/press-release/2026/retirement-survey-press-release
Afford Anything: https://affordanything.com/
Heavy Metal Money and the Extreme Personal Finance Show: https://heavymetal.money
Investing for Beginners and At Any Rate: https://einvestingforbeginners.com/

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The Advice Pros Give Their Own Families (and How to Tell If Your Advisor Would Too) SB1922 Nov 11, 2026

Show notes

What do finance professionals say to their own relatives when nobody is paying them to say it? Joe Saul-Sehy, OG, and Doug sit down with Jenny Harrington, co-author of Investment Wisdom for Our Friends and Loved Ones, to find out. Jenny helped gather lessons from top finance experts, and she shares what she’d tell the people she loves. The conversation then turns to a Stacker’s question about an orphaned retirement account and whether an advisor is worth keeping. You’ll get a practical way to judge the advice you’re getting, minus the jargon and the guilt.

What You’ll Walk Away With

The one question that shows whether an advisor’s guidance is built for you or for their business
Why the advice pros give their own families tends to be simpler than you’d expect
A quick “must know versus nice to know” game that sorts the money basics from the trivia
What to do about an old workplace retirement account that’s been sitting with no one watching it
Why treating your advisor like an investment (and checking what they add) beats just comparing price tags
The case against splitting your money between several advisors, and when it quietly works against you
How to tell whether a lower fee is saving you money or costing you in other ways
Why having people in your corner only helps if they’d give you the advice they’d give their own family

Why This Matters Now

Most of us have someone in our financial corner, whether that’s a pro, a friend, or the loudest voice online. It’s hard to know whether their advice is any good, and nobody wants to make an irreversible mistake or feel judged for asking. A simple test helps: would they say the same thing to their own family? This episode gives you that test and the language to use it, so you can keep good help, move on from the rest, and tackle the leftover accounts you’ve been avoiding.

From the Basement

Joe Saul-Sehy walks Jenny through the book and the big lessons in it. OG and Doug join in with questions from the basement, and Doug keeps Veterans Day in view with trivia about the Vietnam Veterans Memorial. Joe, OG, and Doug then take on Better Call Saul, Sehy and OG, answering a Stacker’s question that carries the advisor conversation from theory into real life. Doug closes with his takeaways, plus a few bathroom-adjacent observations about gas station sushi.

Resources Mentioned

Investment Wisdom for Our Friends and Loved Ones by Jenny Harrington and Rebecca Patterson (Harriman House): https://harriman-house.com/authors/jenny-harrington/investment-wisdom-for-our-friends-and-loved-ones/9781804094426
Jenny Harrington’s author page: https://www.harriman-house.com/authors/jenny-harrington/48930

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Year-End Money Moves: What to Do Before December 31 So January Doesn’t Suck SB1921 Nov 09, 2026

Show notes

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.

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Should You Cut Your 401(k) When Money Gets Tight? How to Handle Higher Prices SB1920 Nov 06, 2026

Show notes

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

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How to Stop Your Brain From Wrecking Your Portfolio With Dr. Daniel Crosby (SB1919) Nov 04, 2026

Show notes

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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How to Build Your Perfect Portfolio With Peter Lazaroff (Plus Who Gets Your Life Insurance) SB1918 Nov 02, 2026

Show notes

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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8 Tricky Money Decisions: When to Cosign, Stretch, Take the Job, or Walk Away SB1917 Oct 30, 2026

Show notes

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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Why Everyone Needs an Estate Plan (and How to Avoid a Surprise ACA Subsidy Bill) SB1916 Oct 28, 2026

Show notes

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) SB1915 Oct 26, 2026

Show notes

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

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

How to Change Your Money Plan When Your Goals Change (Without Starting Over) SB1914 Oct 23, 2026

Show notes

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

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

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