The Stacking Benjamins Show

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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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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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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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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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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