The Stacking Benjamins Show
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- 1.105
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- Letzte Folge
- 13. Nov. 2026
Über den Podcast
Named Best Personal Finance Podcast by Bankrate.com and Kiplinger — and the only podcast the Plutus Awards retired from competition after winning twice — The Stacking Benjamins Show is personal finance that doesn’t put you to sleep.
Hosts Joe Saul-Sehy (former 16-year financial advisor, ex-WXYZ-TV “Money Man”) and Josh “OG” Bannerman, CFP (Certified Financial Planner, Bannerman Wealth) sit around the card table in Joe’s mom’s half-finished basement in Texarkana and talk money with the smartest guests in personal finance, investing, and behavioral economics. As Fast Company wrote, the show “strikes a great balance of fun and functional.”
Every Monday, Wednesday, and Friday: expert guests, real headlines, listener questions, and Doug’s trivia. Topics include investing, retirement planning, budgeting, real estate, behavioral finance, taxes, and financial independence — for anyone who wants to be smarter about money without being talked down to.
Subscribe to The 201 — the free newsletter that goes deeper than the show — at stackingbenjamins.com/201
Folgen 1.105
How to Turn Retirement Confidence Into a Real Plan (Even If You Feel Behind) SB1923
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 …
Shownotes
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/
See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.
The Advice Pros Give Their Own Families (and How to Tell If Your Advisor Would Too) SB1922
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 …
Shownotes
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
See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.
Year-End Money Moves: What to Do Before December 31 So January Doesn’t Suck SB1921
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 …
Shownotes
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.
Should You Cut Your 401(k) When Money Gets Tight? How to Handle Higher Prices SB1920
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 …
Shownotes
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.
How to Stop Your Brain From Wrecking Your Portfolio With Dr. Daniel Crosby (SB1919)
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 …
Shownotes
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.
How to Build Your Perfect Portfolio With Peter Lazaroff (Plus Who Gets Your Life Insurance) SB1918
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 …
Shownotes
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.
8 Tricky Money Decisions: When to Cosign, Stretch, Take the Job, or Walk Away SB1917
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 …
Shownotes
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.
Why Everyone Needs an Estate Plan (and How to Avoid a Surprise ACA Subsidy Bill) SB1916
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 …
Shownotes
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
See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.
How to Turn Trick-or-Treat Into a Money Lesson (and Choose a Pension Option) SB1915
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 …
Shownotes
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
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 …
Shownotes
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.
Wharton’s Corinne Low on How to Get More Life Out of Your Money, Time, and Career SB1913
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 …
Shownotes
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
See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.
Year-End Money Moves: Student Loan Savings, Roth Conversions, and Disability Insurance SB1912
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 …
Shownotes
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.
How to Build a Career You Won’t Regret (Before You Climb the Wrong Ladder) (SB1911)
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Harvard’s Robert Waldinger on What to Spend Your Money and Time On to Be Happier SB1910
Ask a room of young adults what they want most from life and about eight in ten will say “get rich.” The longest scientific study of adult life, now following the children of its original participants, found …
Shownotes
Ask a room of young adults what they want most from life and about eight in ten will say “get rich.” The longest scientific study of adult life, now following the children of its original participants, found something different about what pays off. Dr. Robert Waldinger leads the Harvard Study of Adult Development, and he explains why one kind of spending keeps making people happier long after a flashy purchase fades, why career achievement doesn’t predict a good life, and the habit he now treats the way he treats the gym. Along the way come a rundown of what SECURE 2.0 changed and a listener question about saving for retirement from overseas.
What You’ll Walk Away With
- What a generation named as its top life goal, and what the data says about chasing it
- The kind of discretionary spending that keeps paying off in happiness, and the kind that doesn’t
- Where money really moves the needle on wellbeing, and the point where it stops
- Why “happiness” is the wrong target, and what the researcher measures instead
- What a couple from one of Boston’s poorest neighborhoods can teach about a rich life
- Why introverts aren’t at a disadvantage, and whether purposeful friendships beat casual ones
- The subway experiment: why strangers who were told to talk ended up happier than they predicted
- “Social fitness”: the weekly habit that works like exercise
- A quick gratitude exercise for a bad mood, built around one question: what if I hadn’t had this?
- Why money you’ve set aside is retirement money even if the account doesn’t say so
Why This Matters Now
Most of us keep score with a number. Waldinger’s research points to a more useful scoreboard: who shows up when it matters and whether your days have a purpose. If you’re saving diligently and quietly wondering whether you’re chasing the wrong things, or you feel behind every time you scroll past someone else’s highlight reel, this is permission to build the plan and the life at the same time, not one after the other.
From the Basement
This one comes out of the basement vault for Greatest Hits week. Doug’s trivia is about the first photograph ever taken of a person, a Paris street so busy that only two men holding still, a customer and a shoe shiner, made it into the picture. OG is also accused of being a curmudgeon, and he does not enjoy it.
Resources Mentioned
- Robert Waldinger: Dr. Waldinger’s site and TEDx talk
- The Good Life: Lessons from the World’s Longest Scientific Study of Happiness: the book by Waldinger and Marc Schulz
- Lifespan Research Foundation: the nonprofit Waldinger co-founded, with more on the study
See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.
How to Fix Your 401(k): 25 Moves That Work Even If Your Plan Isn’t Great SB1909
Most people check their 401(k) the way they check a gas gauge: a glance, a shrug, and back on the road. Joe and OG pop the hood on the whole engine and work through 25 fixes, from a two-minute change to a phone …
Shownotes
Most people check their 401(k) the way they check a gas gauge: a glance, a shrug, and back on the road. Joe and OG pop the hood on the whole engine and work through 25 fixes, from a two-minute change to a phone call that could cut real money from your fees. The surprise is how many of them have nothing to do with your employer’s plan. A mediocre 401(k) can still do its job if the rest of your accounts pick up the slack, and the bar for “good enough” is lower than the internet makes it sound.
What You’ll Walk Away With
- The one-percent move that takes two minutes, and why nobody ever misses it from a paycheck
- Why risk tolerance quizzes start at the wrong end, and the math problem that should come first
- How often to rebalance, and the point where “rebalancing” quietly turns into market timing
- The way almost everyone sorts their fund list, and why it nudges you into a bad habit
- How to treat your accounts as one household portfolio when your 401(k) is lackluster
- Why getting more conservative as retirement nears can cost you years of compounding
- A rule of thumb for company stock, and why your paycheck and your portfolio shouldn’t share the same risk
- What to do with an old 401(k) when you change jobs, and the rollover detail that makes the choice less permanent than it feels
- What to ask your employer about fees and the match, politely and without withholding cupcakes
- A free tool for checking what your funds really cost
Why This Matters Now
Retirement accounts run on autopilot, which is both the feature and the trap. A plan set up years ago can still carry the fees and funds of that year, and the people paid to run it rarely volunteer that you’re overpaying. The good news is that none of this has a deadline, and one deliberate fix a year beats a panic overhaul. If you worry that one overlooked detail has quietly cost you money, this is a calm, checklist-style way to find it.
From the Basement
This one comes out of the basement vault for Greatest Hits week, so a stray reference or two may be hiding behind Joe’s mom’s water heater, but the fundamentals have held up. Doug’s trivia involves a founding father and a street sweeper, his chores keep multiplying, and his takeaway is to invest like it’s a Chicago election: early and often.
Resources Mentioned
- Morningstar: free fund research on fees and performance versus peers
- FieldKit Finance: a way to see how all your accounts fit together
- Heard it the first time? Tell Joe what you changed at [email protected]
See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.
What the Fed’s Rate Hike Means for Your Money, Plus the Buy Now, Pay Later and Kalshi Traps SB1908
The Fed just raised rates for the first time in more than three years, and the markets barely flinched. Your mortgage, your CDs, and your next car payment may feel it differently than the headlines suggest. The …
Shownotes
The Fed just raised rates for the first time in more than three years, and the markets barely flinched. Your mortgage, your CDs, and your next car payment may feel it differently than the headlines suggest. The panel breaks down what a quarter point actually changes, then turns to two newer ways of borrowing against your future self: buy now, pay later apps that run almost entirely on debit cards, and a prediction market that wants Congress to let you borrow money to bet. One episode, three headlines, and one thread running through all of them.
What You’ll Walk Away With
- What a quarter-point hike does to a $50,000 car loan (the answer is smaller than you’d guess)
- Why your mortgage rate follows the 10-year Treasury more than the Fed, and why that distinction matters
- The three numbers to find in any adjustable rate loan before you decide how much risk it can carry
- Why waiting for a “return” to the rates of 15 years ago may be the most expensive plan available
- How “0% interest” buy now, pay later plans make their money, and what a single missed payment costs
- A simple test for deciding what is worth borrowing against future income and what never is
- How a $22 billion prediction market argues it isn’t gambling, and the odds it never mentions
- What the trader data shows about who actually profits on these platforms
- The meteorite that landed on a $300 car, and how much profit it really made
Why This Matters Now
Borrowing has quietly become easier to start and harder to see. A rate move shows up in a payment you might not notice for months, a payment plan splits a purchase into pieces small enough to ignore, and an app turns a market prediction into something that feels like a game. Each one trades future flexibility for something today. If you worry that one overlooked detail could sneak up on you, this is a plain-English look at where those details hide, and which decisions deserve a pause before you click.
From the Basement
The year-long trivia race enters its final quarter in a dead heat, and the gap that opens up is smaller than anyone’s confidence about it. The question involves a meteorite, a very old Chevy Malibu, and a lesson about waiting for money to fall from the sky. The show also took three tries to start, so you are hearing the one that worked.
Resources Mentioned
- Federal Reserve monetary policy: the source for rate decisions and statements
- Semafor: Kalshi to allow trading on borrowed funds: the report behind the Kalshi headline
- Klarna and Affirm: the two buy now, pay later providers discussed
- Peekskill meteorite: the real story behind today’s trivia
- Afford Anything: Paula Pant's amazing podcast
- Personal Finance for Long-Term Investors: Jesse Cramer's incredible show
See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.
Lauryn Williams: What a Four-Time Olympian Learned From Her Biggest Money Mistakes SB1907
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Credit Cards 101: Points, Cash Back, and the Traps Card Companies Want You to Fall Into SB1906
Credit card companies are getting smarter about one thing: making an $800 annual fee feel like a steal. Joe and OG open the vault on how the points-and-perks game actually works, why "free" subscriptions and …
Shownotes
Credit card companies are getting smarter about one thing: making an $800 annual fee feel like a steal. Joe and OG open the vault on how the points-and-perks game actually works, why "free" subscriptions and dining credits aren't really free, and the one simple piece of math that tells you whether a point is worth more than cash. Doug plays referee in a live round of Points, Cash, or Pass, and it turns out his instinct to keep one boring card in his wallet might be the smartest strategy in the room.
What You'll Walk Away With
- The 2% rule that tells you in five seconds whether a points redemption is actually a good deal or just a shiny number
- Why "almost premium" credit cards are the fastest-growing category in the industry, and who they're really designed for
- The real reason card companies give you six months of free DoorDash or Apple TV, and why it costs you more than you think
- How to tell if you're the kind of person who should play the points game at all, and why that's not a bad thing to admit
- The one credit card rule that matters more than any rewards program: pay it off every month or none of this applies to you
- Why transferring points to an airline can either be a smart move or a trap, depending on one thing you do before you transfer
- The behavioral trick retailers use to get your card out of your wallet the second time, not the first
- What "stacking" points actually means, and why it's the one place serious players find real value
Why This Matters Now
Credit card rewards have quietly become their own side economy, with companies spending hundreds of millions of dollars to get you to sign up, swipe, and forget. That's not inherently bad, but it works best when you're the one steering it instead of the other way around. Whether you're the type who wants a system for maximizing every point or the type who just wants one card and zero complexity, knowing the handful of rules that actually matter means you get the benefit without accidentally reshaping your spending to chase it.
From the Basement
Doug gets put through a five-round gauntlet of Points, Cash, or Pass, and somehow nails every single one by refusing to play the game at all. There's also a sticker system involved, a strong opinion about mauve wallets, and a trivia question about Breakfast at Tiffany's that goes about as well as you'd expect.
Resources Mentioned
- The Points Guy — the go-to resource Joe and OG reference for maximizing point redemptions
- Point.me — the tool Joe uses to compare redemption value across multiple loyalty programs
- FieldKit — the budgeting app mentioned for tracking net worth, subscriptions, and credit
- Monster: The Lizzie Borden Story — a mysterious bonus link that may or may not exist, and definitely isn't some kind of secret extra segment. We'd never do that.
FULL SHOW NOTES: https://www.stackingbenjamins.com/how-to-use-credit-card-rewards-1906/
Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.stackingbenjamins.com/201
Enjoy!
See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.
Money Ideas That Sound Great Until You Read the Fine Print (SB1905)
Bigger returns. Guaranteed income for life. Retiring five years early. Every one of these sounds like an obvious yes, until you see the invoice that comes with it. Joe puts Doc G, OG, and Jesse Cramer through a …
Shownotes
Bigger returns. Guaranteed income for life. Retiring five years early. Every one of these sounds like an obvious yes, until you see the invoice that comes with it. Joe puts Doc G, OG, and Jesse Cramer through a rapid-fire "in or out" game: he pitches five genuinely appealing financial ideas, and each of them has to decide whether they'd actually take the deal, and name the worst realistic thing that could go wrong if they did.
What You'll Walk Away With
- Why leveraged ETFs have historically wiped out the vast majority of investors who hold them for more than a few years
- The real, academically-supported case for and against thematic and "beat the market" investment funds
- A clear framework for handling a single stock that's grown into 40% of your portfolio, including a simple trick for spreading a big tax bill across two tax years
- Why "guaranteed income for life" almost always means giving up the one thing that actually protects you from inflation over a multi-decade retirement
- A genuinely helpful explanation of what a Monte Carlo simulation's "80% success rate" actually means, and why it's not the cliff-edge failure people assume
- Why retiring five years earlier isn't automatically the right move, even when the math technically works
- A real cost-benefit gut check on working an extra year or two specifically to fully fund a child's college education
Why This Matters Now
The financial products and strategies that sound the most appealing, guaranteed income, market-beating returns, an earlier retirement, all have a cost that isn't obvious from the pitch alone. That cost isn't always dishonest or hidden on purpose, but it only becomes clear once you ask the right follow-up questions. Learning to instinctively look for that fine print, what you're giving up, what could go wrong, and whether the tradeoff actually serves your specific goals, is a far more useful skill than knowing the name of any single financial product.
From the Basement
A three-way tie atomizes the year-long trivia standings heading into the fourth quarter, decided by a question about how little Charles Schulz was paid for the very first month of Peanuts comic strips.
Resources Mentioned
- Earn & Invest podcast — Doc G's show
- Personal Finance for Long-Term Investors podcast — Jesse Cramer's show
- Granola — AI-powered meeting notes tool mentioned in the sponsor break
- Stacking Benjamins on OG's calendar — for financial planning help
See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.
Don't Tell the Car Dealer Your Budget (And Other Money Moves That Actually Work) SB1904
A $12,000 emergency room bill for popping a dislocated shoulder back into place. A car-buying strategy that saved one family $4,000 with a single text message. A college athlete's first taste of NIL money and …
Shownotes
A $12,000 emergency room bill for popping a dislocated shoulder back into place. A car-buying strategy that saved one family $4,000 with a single text message. A college athlete's first taste of NIL money and the tax questions that come with it. Joe and OG spend today answering real questions from real Stackers, the kind of specific, practical situations that don't always fit neatly into a textbook, but come up constantly in real life.
What You'll Walk Away With
- Why you should never tell a car dealer your monthly budget, and the exact three-rule negotiation process that saved one family thousands
- A real, word-for-word example of how to negotiate a hospital bill down, including the specific questions that actually get results
- What to know before buying stock in a private, employee-owned company, including the questions to ask about liquidity and getting your money back out
- Why a college athlete earning NIL revenue-sharing income needs a specialized tax professional, not a generic preparer
- The real difference between qualified and ordinary dividends, and why it matters less than most investors assume
- A nonprofit resource that helped one young Stacker eliminate a $43,000 hospital bill entirely
- Why asset location (which accounts hold which investments) only matters once your portfolio is diversified enough across account types to make a difference
Why This Matters Now
Financial advice often gets taught in tidy, general categories, but real financial life shows up as messy, specific situations: an ER bill with no clear price tag, a car dealer who won't budge on your trade-in, a new source of income nobody prepared you for. Having a framework for these moments, knowing what questions to ask, who to loop in, and where the leverage actually sits, turns a stressful surprise into a solvable problem. None of these situations require perfect expertise, just knowing enough to ask the right question at the right moment.
From the Basement
A Good Neighbor Day detour uncovers the legendary origin of the first-ever Stacking Benjamins meetup: a group of miners in Healy, Alaska, who listened to the show while at work and reached out when they heard Joe was headed to Denali.
Resources Mentioned
- Stacking Benjamins Field Kit — the all-in-one budgeting and net worth tracking tool
- Dollar For — nonprofit that helps eliminate medical debt for qualifying patients
- SB1808: How She Eliminated a $43,000 Hospital Bill — referenced episode on medical debt relief
- SB1899: Should You Graduate From Index Funds to Individual Stocks? — referenced episode with Brian Feroldi
- Yell Down the Stairs — submit a question for a future episode
FULL SHOW NOTES: https://www.stackingbenjamins.com/money-rules-worth-questioning-1904/
Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.stackingbenjamins.com/201
Enjoy!
See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.
Our Top 5 Esoteric Money Strategies That Work (For the Right Person) SB1903
Some financial strategies aren't bad, they're just wildly oversold to people they were never built for. Joe and OG walk through five genuinely legitimate, sometimes powerful tools, cash value life insurance …
Shownotes
Some financial strategies aren't bad, they're just wildly oversold to people they were never built for. Joe and OG walk through five genuinely legitimate, sometimes powerful tools, cash value life insurance, municipal bonds, qualified longevity annuity contracts, net unrealized appreciation, and complex charitable trusts, and draw a clear line between the tiny slice of people these actually help and the much larger crowd who gets pitched them anyway. If you've ever had someone offer you a "special" financial strategy and wondered whether it was genius or a sales tactic, this episode gives you the framework to tell the difference.
What You'll Walk Away With
- Why cash value life insurance almost never makes sense as a savings vehicle, and the very narrow situations where it actually does
- The real math behind municipal bonds, and why the "tax-free" appeal often costs more in lost growth than it saves in taxes
- A clear-eyed look at qualified longevity annuity contracts, and why giving up control of your money rarely makes sense at any wealth level
- The single tax strategy on this list that can genuinely save six figures over a lifetime: net unrealized appreciation on employer stock
- Why "borrowing against your assets instead of selling them" can be brilliant or disastrous depending entirely on how the economy moves
- A blunt reality check on 72(t) distributions for early retirees, and why the five-year commitment trips more people up than the strategy itself
- Why "there's no free lunch" is the single question to ask about any complex financial product before you commit to it
Why This Matters Now
The financial industry has an incentive to make simple problems feel complicated, because complicated problems require expensive solutions. Most people's actual financial life doesn't need any of these five strategies, and that's not a failure, it's just math. But knowing what these tools are, who they're actually built for, and what they cost when misapplied means you can spot the difference between a legitimately smart move and a sales pitch dressed up as sophistication, whether or not you'll ever personally need any of them.
From the Basement
A Good Neighbor Day detour into Ted Williams's legendary 1941 season, when he refused to sit out the final day to protect a rounded-up .400 batting average, becomes a genuinely moving story about doing things the honest way even when nobody would've noticed otherwise.
Resources Mentioned
- Stacking Benjamins Field Kit — the all-in-one budgeting and net worth tracking tool
- Stacking Benjamins Coaching Program — Joe and OG's new cohort program for financial coaches
See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.
Is "This Time Different"? A FinCon Panel on AI, Inflation, and Interest Rates SB1902
Live from FinCon, Joe sits down with historian and bestselling author Joseph Moore, Paula Pant, and Jesse Cramer to talk about what's actually keeping people up at night: AI concentration in the stock market …
Shownotes
Live from FinCon, Joe sits down with historian and bestselling author Joseph Moore, Paula Pant, and Jesse Cramer to talk about what's actually keeping people up at night: AI concentration in the stock market, inflation anxiety that won't fully fade, interest rates that feel "stuck," and a housing market that seems rigged against newcomers. The twist is that almost none of it is new. From a Scottish con man's fake country bonds to the 1830s stock that was over 30% of the entire market, to a refrigerator boom that happened during the Great Depression, this conversation uses 300 years of financial history to put today's anxieties in real perspective.
What You'll Walk Away With
- Why "this time is different" has been true in every single era of financial history, and why that's actually reassuring, not alarming
- The real reason today's AI-heavy stock market concentration isn't as extreme as people fear, compared to genuine historical outliers
- Why equal-weighted index funds tend to underperform market-weighted ones, and what that reveals about betting against your own winners
- A fascinating historical parallel between AI infrastructure spending today and the railroad boom of the 1800s, and where that comparison breaks down
- Why the fastest way to build real wealth during a technological boom is often working in the industry, not investing in it
- How the "golden handcuffs" of low mortgage rates are quietly fueling a broader sense of economic pessimism, even during a strong economy
- Why increasing your income is one of the few truly controllable levers in your financial life, and why it usually takes longer than people expect
Why This Matters Now
Every generation convinces itself that its economic moment is uniquely unprecedented, uniquely uncertain, uniquely dangerous. History suggests otherwise: markets concentrate around a handful of winners, technology booms take decades to actually change daily life, and financial anxiety tends to track personal experience more than actual data. None of that means today's concerns aren't real. It means the emotional weight of "this has never happened before" is usually misplaced, and understanding that can be the difference between panicking through a normal cycle and staying invested through one.
Resources Mentioned
- How to Get Rich in American History by Joseph Moore — Joseph's USA Today bestselling book on 300 years of financial advice, what worked and what didn't
- Afford Anything podcast — Paula Pant's show
- Personal Finance for Long-Term Investors podcast — Jesse Cramer's show
- Men Go To Mars — sponsor mentioned in the episode
See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.
Robin Wigglesworth: The Boring Market That Actually Runs the World SB1901
In April 2025, the bond market did something the stock market couldn't: it made a sitting president reverse course within days. Financial Times journalist Robin Wigglesworth, author of the new book A Fabulous …
Shownotes
In April 2025, the bond market did something the stock market couldn't: it made a sitting president reverse course within days. Financial Times journalist Robin Wigglesworth, author of the new book A Fabulous Debt, joins Joe and OG to explain why bonds, dismissed for centuries as the dull corner of finance, are actually the bedrock everything else sits on. From a murdered medieval ruler in Venice to a Scottish con man who sold bonds for a country that didn't exist to the hedge fund collapse that nearly took down the global financial system, this is 900 years of history explaining exactly why the "boring" market is the one that actually moves empires.
What You'll Walk Away With
- Why the bond market, not the stock market, is what actually forced a change of course during 2025's "Liberation Day" tariff chaos
- The surprisingly wild origin story of the very first government bond, issued in 1171 Venice, and how it got its ruler killed
- How the Dutch turned Venice's basic invention into a true market, and used it to fund their independence from a much larger empire
- The incredible true story of a con man who sold real bonds for a fictional country and lured hundreds of settlers to their deaths
- Why Long-Term Capital Management, staffed with Nobel laureates and legendary traders, collapsed almost overnight in 1998
- The biggest misconception most Americans have about U.S. government debt, and why the reality is more nuanced than the doom headlines suggest
- Why the oldest investing mistake in 900 years of financial history is still the simplest one: borrowing too much
Why This Matters Now
Most people never think about bonds until something breaks, a rate spike, a market scare, a headline about the national debt, and by then it can feel too complicated to catch up on. But bonds quietly determine mortgage rates, corporate borrowing costs, and government policy in ways that touch daily life far more than most people realize. Understanding even the basics of how this market works, and how consistently it has shaped history, turns a vague sense of unease about "the economy" into something you can actually follow and make sense of.
From the Basement
A Bond-adjacent trivia detour (the James Bond kind, not the financial kind) reveals that Ian Fleming borrowed his spy's name from a real-life ornithologist, proof that even a show about medieval Venetian debt can't resist a pun. Plus, a Wall Street Journal headline on why the job market has quietly flipped in favor of workers without a college degree.
Resources Mentioned
- A Fabulous Debt by Robin Wigglesworth — Robin's new book on the 900-year history of bonds
- Trillions by Robin Wigglesworth — Robin's earlier book on the history of index funds
- Stacking Benjamins Field Kit — the all-in-one budgeting and net worth tracking tool
See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.
Five Signs Your Financial Advisor Might Not Be Great SB1900
"How do I know it's time to fire my advisor?" That question came up over and over at a recent retreat, enough that Joe knew it needed its own episode. Today he and OG walk through five real, specific red flags …
Shownotes
"How do I know it's time to fire my advisor?" That question came up over and over at a recent retreat, enough that Joe knew it needed its own episode. Today he and OG walk through five real, specific red flags, not vague warnings about fees, but concrete signs that your advisor might be coasting, out of their depth, or simply not built for where your life is headed. If you've ever sat in a meeting with your advisor and wondered whether you're getting real value or just really good small talk, this one's for you.
What You'll Walk Away With
- Why an advisor who knows your portfolio better than they know your actual life is a warning sign, not a compliment
- The real reason a "free" advisor should make you more suspicious, not less
- Why an advisor working with literally anyone, instead of a defined type of client, often means shallower expertise
- How to tell the difference between a collaborative advisor relationship and one where you're quietly doing all the driving
- Why outgrowing your advisor isn't always about more money, sometimes it's about more complexity, and that's worth a real conversation
- A simple question to ask about fees that costs you nothing and might save you real money
- The single clearest red flag of all: an advisor who leads with products instead of questions
Why This Matters Now
Most people have no natural way to judge whether their financial advice is actually good, since the whole reason you hired someone was that you didn't have the expertise to evaluate it yourself in the first place. That's not a flaw in you, it's exactly why concrete, observable signs matter more than a vague gut feeling. Knowing what a good advisor relationship actually looks like, real collaboration, a defined specialty, clear communication about fees and process, gives you a way to check in on that relationship without needing a finance degree to do it.
From the Basement
An Earth, Wind & Fire trivia detour uncovers the real, long-hidden meaning behind "the 21st night of September," and a listener question from someone getting her first-ever 401k at 50 sparks a genuinely useful conversation about target-date funds, Roth versus pre-tax decisions, and the often-overlooked Rule of 55.
Resources Mentioned
- Stacking Benjamins Field Kit — the all-in-one budgeting, privacy, credit and net worth tracking tool
- Stacking Benjamins Benjamins After Dark meetups — local in-person Stacker meetup groups
- Yell Down the Stairs — submit a question for a future OG and Anna episode
See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.
Should You Graduate From Index Funds to Individual Stocks? SB1899
You've done everything right. Emergency fund, employer match, maxed-out retirement account, boring diversified index funds quietly compounding in the background. And now some part of you is wondering: is there …
Shownotes
You've done everything right. Emergency fund, employer match, maxed-out retirement account, boring diversified index funds quietly compounding in the background. And now some part of you is wondering: is there a next level? Financial educator Brian Feroldi joins Paula Pant and Jesse Cramer for a genuinely useful gut-check on whether picking individual stocks is a smart next step, a fun hobby, or a trap dressed up as ambition, and how to tell the difference before you put real money on the line.
What You'll Walk Away With
- The single question that determines whether you're actually ready to buy individual stocks: do you have real interest in the process, not just the potential payoff
- Why working in an industry doesn't automatically make you qualified to invest in it
- The real statistics behind stock picking: roughly two-thirds of individual stocks underperform the market average
- Why losing money on your first few stock picks might be the best possible outcome, and why winning right away can be dangerous
- A clear framework for position sizing, so a stock-picking hobby never puts your actual financial plan at risk
- The real opportunity cost of stock picking as a "side hustle," and why it competes with your time as much as your money
- Why a great company and a great stock investment are often two completely different things
Why This Matters Now
There's a point in a lot of people's financial journeys where the basics start to feel almost too simple, and that itch to do something more advanced is worth taking seriously, not dismissing. But "more advanced" doesn't automatically mean "individual stocks," and jumping in without genuine interest or a clear framework can turn a healthy curiosity into an expensive mistake. Knowing honestly whether you're drawn to the actual process of researching and following businesses, not just the idea of beating the market, is the difference between a rewarding new hobby and a costly detour from a plan that was already working.
From the Basement
A tight, competitive trivia round on Bank of America's 1958 "Fresno Drop," the unsolicited mass credit card mailing that eventually led to the creation of Visa, shakes up the year-long standings in a genuinely dramatic way.
Resources Mentioned
- Stock Simplifier — Brian Feroldi's AI-powered stock research tool
- Why Does The Stock Market Go Up? by Brian Feroldi — Brian's bestselling book on how the market works
- Afford Anything podcast — Paula Pant's show
- Personal Finance for Long-Term Investors podcast — Jesse Cramer's show
See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.
Lynda Gratton: What If You Live to 100? Here's How to Actually Plan For It SB1898
The traditional life plan, learn, work for four decades straight, retire once and for all, was built for a much shorter life than many of us are actually going to live. Lynda Gratton, London Business School …
Shownotes
The traditional life plan, learn, work for four decades straight, retire once and for all, was built for a much shorter life than many of us are actually going to live. Lynda Gratton, London Business School professor and bestselling author of The 100-Year Life, has spent years studying what happens when that old blueprint stops matching reality. Her answer isn't a bigger retirement number. It's a completely different way of thinking about how work, rest, learning, and relationships fit together across a much longer stretch of time, and what that means for how you actually fund it.
What You'll Walk Away With
- Why a single, long block of retirement often backfires, and what tends to happen to people's sense of purpose and friendships when it does
- The "weaving" framework: eight threads, four about staying productive and four about nurturing yourself, that Gratton argues need ongoing attention throughout life, not just at the end
- Why a "flexibility fund" might matter more than a traditional retirement account for anyone planning to take real breaks, sabbaticals, or career pivots along the way
- A simple four-option framework (stay, switch, scale back, or sail away) for deciding what to do when a chapter of work stops feeling right
- Why the fastest way to burn out is neglecting the "nurture" side of life, and why neglecting the "productivity" side leaves you financially fragile instead
- A genuinely useful reframe on AI: not a threat to outrun, but a reason to double down on the specifically human parts of work and life
Why This Matters Now
Longer lifespans sound like good news until you realize the traditional financial and career plan never accounted for them. A forty-year runway to retirement followed by thirty-plus years of doing nothing structured often turns out to be less fulfilling, and harder to fund, than a life built with more transitions built in along the way. Planning for that kind of life means thinking further ahead than most retirement calculators do, and building in the flexibility to actually use the extra years well, not just survive them.
From the Basement
A Dolly Parton headline turns into a genuinely sharp personal finance lesson: how she turned down Elvis, kept the rights to "I Will Always Love You," and built Dollywood, her literacy program, and her entire business empire on the exact same core talents rather than chasing unrelated ventures. Old-school diversification, but the boring kind that actually works.
Resources Mentioned
- Living the 100-Year Life by Lynda Gratton — Lynda's book, workbook, and free diagnostic on the eight life threads
- Life Threads podcast — Lynda's eight-episode podcast series exploring each thread
- The 100-Year Life by Lynda Gratton and Andrew Scott — the original million-copy bestseller that started this line of research
See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.
Can You Retire With $500,000? $750,000? A Million? SB1897
Someone with half a million dollars confidently retires and thrives. Someone else with a full million dollars runs into trouble within a few years. The dollar amount alone never tells the whole story, and …
Shownotes
Someone with half a million dollars confidently retires and thrives. Someone else with a full million dollars runs into trouble within a few years. The dollar amount alone never tells the whole story, and today's episode proves it with three real scenarios side by side. Joe and OG walk through exactly what changes the math: your age, whether Social Security has kicked in yet, how much of your spending is already covered by guaranteed income, and how many years that portfolio actually needs to stretch.
What You'll Walk Away With
- Why the question to start with isn't "how much do I have," it's "what's the gap between my expenses and my guaranteed income"
- A real comparison of three retirement scenarios (500k, 750k, and 1 million) that shows why the smallest portfolio can actually be the least risky
- Why the "safe withdrawal rate" debate among experts (ranging from under 4% to over 5%) matters less than having a plan for flexibility
- The often-overlooked lumpy expenses, property taxes, insurance premiums, home repairs, that can quietly wreck an otherwise solid retirement budget
- Why retiring early and taking Social Security ahead of schedule creates a double reduction that compounds for both you and a spouse
- A clear breakdown of how many years you actually have left to "practice" your retirement spending before you commit to it
Why This Matters Now
A specific dollar figure feels like it should provide an answer, but retirement security depends on the relationship between that number and your actual life: your fixed expenses, your guaranteed income, your timeline, and your flexibility if plans change. Two people with wildly different account balances can have equally solid plans, and two people with the same balance can be in completely different positions depending on when they start drawing from it. The real work isn't chasing a bigger number. It's understanding exactly what gap that number needs to fill.
From the Basement
A Social Security deep dive digs into a genuinely useful and underdiscussed detail: how retiring early doesn't just shrink your own benefit, it can shrink a spouse's spousal benefit too, and by how much. Plus, a Golden Girls trivia detour and a listener note that sparks a good, honest conversation about teaching kids to give.
Resources Mentioned
- Stacking Benjamins Field Kit — the all-in-one budgeting and net worth tracking tool
- SSA.gov — create an account to download your official Social Security earnings statement
- The 201 Newsletter — deeper dives on topics covered in the show
See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.
Why "Doing It Yourself" With Money Is Costing You SB1896
Collaboration is celebrated everywhere else. Musicians collaborate. Athletes have training partners. Businesses merge their best ideas together. But mention teaming up on your finances, and suddenly it sounds …
Shownotes
Collaboration is celebrated everywhere else. Musicians collaborate. Athletes have training partners. Businesses merge their best ideas together. But mention teaming up on your finances, and suddenly it sounds suspicious, like you're doing something wrong. Joe sits down with Paula Pant, Jesse Cramer, and OG to ask why personal finance is the one area where going it alone gets treated as a virtue, and what exactly gets left on the table when nobody's allowed to help.
What You'll Walk Away With
- Why financial blind spots are nearly impossible to see on your own, no matter how much you already know
- A real story about a stranger who handed over his entire real estate renovation system, no strings attached, simply because that's how a good community works
- Specific, practical answers for who to actually collaborate with on earning more, spending less, saving more, and investing better
- Why "the best collaborator" is sometimes the person most willing to tell you you're wrong
- A surprisingly effective incentive system for getting family members genuinely invested in cutting shared expenses
- Why competitors can make some of the most valuable collaborators of all, if you're willing to see them that way
Why This Matters Now
There's a quiet assumption in a lot of financial advice that asking for help is a sign of weakness, that a truly capable person should be able to figure it all out solo. But nobody expects a musician, an athlete, or a business to succeed in total isolation, and money isn't actually any different. The people who make the fastest progress usually aren't the ones with the most willpower. They're the ones surrounded by others willing to share a system, question an assumption, or simply say "that seems like a lot of money for fish."
From the Basement
A fiercely competitive year-long trivia race gets even tighter with a question about the Volkswagen Beetle's original 1949 price tag, complete with a brand-new (and delightfully cheap) trophy that finally dethrones the old one.
Resources Mentioned
- Afford Anything podcast — Paula Pant's show, referenced episode featuring 9/11 survivor Michael Hingson
- Personal Finance for Long-Term Investors podcast — Jesse Cramer's show
- Stacking Benjamins on OG's calendar — for financial planning help
See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.
Todd Havens: Why Most People Don't Have a Money Problem, They Have a Thinking Problem SB1895
Todd Havens spent decades dreaming of a net worth of zero, just breaking even felt like an impossible finish line. Then, in 2021, at the height of COVID, a doctor delivered news that would reframe everything …
Shownotes
Todd Havens spent decades dreaming of a net worth of zero, just breaking even felt like an impossible finish line. Then, in 2021, at the height of COVID, a doctor delivered news that would reframe everything: incurable blood cancer, tumors too numerous to count. What follows is one of the most honest, wide-ranging conversations this show has had about money, mortality, and the difference between being rich and actually being wealthy. Todd is now in remission, a self-made millionaire, and the author of a book built entirely around one idea: the biggest obstacle to financial security usually isn't a spreadsheet problem. It's what's happening between your ears.
What You'll Walk Away With
- Why disability insurance and life insurance, the coverage nobody wants to pay for, turned out to matter more than almost anything else when the worst actually happened
- The "money dam" framework for deciding, moment by moment, what's actually worth spending on
- Why believing you "deserve" financial security might be the single most important money belief there is
- A game that separates helpful money beliefs from dangerous ones, and why "I'll save more when I make more" quietly sabotages people for years
- Why net worth, not salary, is the number that actually matters, and how that shift changed Todd's entire trajectory
- A genuinely difficult story about saying no to a parent's request for money, and why it was ultimately an act of love
- Why gratitude, generosity, and integrity are money topics, whether people realize it or not
Why This Matters Now
It's tempting to think financial struggle is purely a math problem: spend less, save more, invest wisely. But plenty of financially literate people still feel stuck, and the reason is rarely a lack of information. It's an old story about not deserving security, about money meaning lack, about identity getting tangled up with a bank balance. Untangling that story doesn't require a windfall or a perfect plan. It requires deciding, the way Todd did at forty, that today is the day the narrative changes, and then building simple systems that don't depend on willpower to keep working.
From the Basement
A headline on the four things you should never order in front of your boss turns into a genuinely useful (and very funny) etiquette lesson, complete with a real story about a twenty-year-old nephew calmly ordering the most expensive steak on the menu without blinking. A listener question on Robinhood also gets a thorough, unflinching answer on why the platform's marketing has repeatedly crossed lines other brokerages haven't.
Resources Mentioned
- Think Wealthy by Todd Havens — Todd's book on the mindset behind financial freedom
- The Simple Path to Wealth by JL Collins — companion read referenced as the "systems" counterpart to Todd's "mindset" focus
- The Psychology of Money by Morgan Housel — referenced book on the behavioral side of money
See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.
You're Doing Risk Tolerance Backwards SB1894
Every brokerage account asks the same question: how comfortable are you with a 20% decline? Are you conservative, moderate, or aggressive? Joe and OG argue that's exactly the wrong place to start, and it's why …
Shownotes
Every brokerage account asks the same question: how comfortable are you with a 20% decline? Are you conservative, moderate, or aggressive? Joe and OG argue that's exactly the wrong place to start, and it's why so many people panic-sell at the worst possible moment. The real question isn't how you feel about risk. It's what rate of return your actual goals require, and whether you can stomach the volatility that comes with getting there. Once you flip the order, risk tolerance stops being a personality quiz and becomes a math problem you can actually solve.
What You'll Walk Away With
- Why "risk" and "volatility" are two completely different things, and confusing them leads to bad investing decisions
- The real order of operations for building a portfolio: goal first, required return second, risk tolerance last
- How standard deviation can turn scary market swings into something you expected all along, instead of something that panics you
- Why concentration risk quietly builds up in portfolios, even for people who think they're diversified
- A genuinely surprising take on why "getting more conservative as you age" often doesn't make sense, once you think in decades instead of birthdays
- Real answers to listener questions on emergency fund sizing, late-start Roth conversions, disability insurance coverage, and whether the 4% retirement rule still holds up
Why This Matters Now
A risk tolerance quiz can't tell you what you actually need your money to do. It just measures a feeling in the moment, and feelings change the second the market gets scary, which is exactly when a plan built on feelings falls apart. Building your investment strategy around your actual goals and time horizon, instead of a gut reaction to hypothetical losses, gives you something sturdier to hold onto when the inevitable rough year arrives. That's the difference between panic-selling at the bottom and staying the course long enough to actually reach the life you're investing for.
From the Basement
A Labor Day trivia detour into the 1916 origins of workers' compensation somehow spirals into a bit about an "employee named Al" being replaced by AI, which is either brilliant wordplay or a sign the basement crew needs a vacation. Possibly both.
Resources Mentioned
- Stacking Benjamins Field Kit — the all-in-one budgeting and financial tracking tool
- Yell Down the Stairs — submit a question for a future OG and Anna episode
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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