The Stacking Benjamins Show

Small company stocks were up nearly 22% in the first six months of 2026. Emerging markets were up 24%. Meanwhile, plenty of people sat on the sidelines convinced those asset classes were dead, chased last year's winners, or just didn't know what they owned. Joe, OG, and Len Penzo break down the first-half scorecard, explain why the lesson isn't about timing -- it's about diversification -- and walk through what an investment policy statement actually is and why having one would have kept most people out of trouble.
What You'll Walk Away With
The first-half 2026 scorecard: Russell 2000 up 21.9%, MSCI Emerging Markets up 24%, S&P 500 up 9.6%, and why the breadth of the rally matters more than the headline number
Why OG's one-sentence takeaway -- "the plan always works" -- is both right and incomplete, and what Len's personal experience this year adds to the conversation
What an investment policy statement actually is: the one-page written decision tree that protects you from making bad moves when markets spike or crash
Why the market closes at an all-time high roughly 30% of the time -- and what that means for the "I'm waiting for it to come down" crowd
How to x-ray your portfolio: the specific inventory OG recommends taking before you make any changes
Why you should rebalance all at once rather than filling in holes slowly -- and the one asterisk that applies before you do anything in a taxable account
Len on the mining sector: why GDX returned 154% last year and is down 10% this year -- and exactly what that pattern teaches about chasing returns
Why trying to explain your investment plan to another human being is the best stress test you have
The allowance micro-economy problem: what happens when you pay kids per task and they start pricing everything in units of dog poop
Jessica's win from the Basement: how one Stacker helped her 25-year-old cousin sign up for her first 401(k), get the full company match, and choose index funds
Why This Matters Now
The second half of 2026 starts now. If you don't know what you own, why you own it, or what you'd do if it dropped 30%, this is the episode to act on before the next six months get away from you.
From the Basement
Joe, OG, and Len Penzo review the first half of 2026, build a case for why diversification beats prediction every time, and explain what an investment policy statement is and how to write one. Doug celebrates the Hollywood sign's origin as a real estate advertisement and shares two things social media actually taught us -- including a TikTok comedian voicing the thoughts in Mark Zuckerberg's ear during a very long beef discussion. Len's annual sandwich survey is about a month away. True Money Stories is climbing the Amazon charts.
Resources Mentioned
True Money Stories by Len Penzo -- available on Amazon; lenpenzo.com
Len Penzo dot com -- lenpenzo.com; 3,000 articles, 18 years of personal finance writing
Stacking Benjamins Field Kit -- stackingbenjamins.com/fieldkit
Stacking Benjamins Newsletter (The 201) -- stackingbenjamins.com/201
Stacking Benjamins Community -- stackingbenjamins.com/basement
OG financial planning calendar -- stackingbenjamins.com/og
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Today's show asks one of the trickiest questions in personal finance: when does a good habit go too far? Saving is great. Cutting expenses can change your life. Earning more can open doors. But what happens when you optimize so hard that you accidentally squeeze the joy out of the whole plan? Joe, Doug, Diana Merriam from EconoMe, New York Times financial writer Paulette Perhach, and Doc G from Earn and Invest dig into the messy middle between YOLO and never spending a dime. Plus, Doug brings hockey trivia, the panel talks odd jobs, and everyone tries to define what "enough" actually means. You'll see very quickly why this episode is an integral part of greatest hits week!
What You'll Walk Away With
Why reducing expenses works best when it removes waste -- not when it turns your life into a deprivation contest
Diana's throw-pillow test: how to ask whether you actually want something or just inherited the idea that you're supposed to want it
The difference between frugal and cheap -- and why ironing hotel toast or stealing dealership coffee might be a sign you've crossed the line
Why Doc G says saving money is only useful if it eventually becomes fuel for the life you want to live
The case for "YOLO responsibly": automate the saving first, then give yourself room to spend without turning every purchase into a morality play
Why high savings rates can be powerful in your 20s -- especially when friends turn frugality into a shared goal instead of social isolation
Paulette's reminder that money habits aren't just math; ADHD, dopamine, entrepreneurship, and self-compassion can all change how saving feels
Why earning more often matters more than cutting more -- and how Diana's denied raise helped push her toward building her own thing
Doc G's hospice-doctor warning: nobody gets to the end wishing they had worked more nights and weekends to hit a slightly bigger net worth
Why Coast FI may be the healthier goal for some people: save enough to create options, then stop tolerating work or lifestyles that no longer fit
The guardrails idea: avoid both extremes -- wasting your future and wasting your present
Why This Matters Now
It's easy to turn personal finance into a scoreboard: lower expenses, higher savings rate, bigger income, faster FI date. But the real goal isn't winning the spreadsheet. It's building a life that feels secure, flexible, and worth living while you're still living it. This conversation is a reminder to use money as a tool, not a dare.
From the Basement
Joe Saul-Sehy gathers a rare Friday card table with Diana Merriam, Paulette Perhach, and Doc G to talk about saving too much, spending too much, working too hard, and finding the middle before the middle finds you. Doug is salty about not going to FinCon, the panel debates FIRE extremes, someone brings up homemade Gatorade, and the trivia question involves hockey nets. No word yet on whether Mom has removed the throw pillows upstairs.
Resources Mentioned
MrStingy.com -- "Too Much of a Good Thing: Taking It Too Far"
Diana Merriam -- EconoMe Conference; economeconference.com
Diana Merriam -- Optimal Finance Daily
Paulette Perhach -- pauletteperhach.com
Paulette Perhach -- New York Times personal finance writing, including ADHD and money
Doc G / Jordan Grumet -- Earn and Invest podcast
Doc G -- Wealth with Purpose
The Fioneers -- referenced in the lifestyle design conversation
Frugalwoods -- referenced during the throw-pillow/minimalism discussion
Stacking Benjamins Newsletter, The 201 -- stackingbenjamins.com/201
Stacking Benjamins Community, The Basement -- stackingbenjamins.com/basement
See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

Scott Galloway doesn't do soft-pedal advice. In this Greatest Hits conversation, the NYU professor, entrepreneur, investor, and author of The Algebra of Wealth joins Joe to talk about why building wealth is less about chasing passion, picking the perfect stock, or waiting for retirement -- and more about focus, discipline, diversification, time, and relationships. Before that, Joe and OG dig into a 401(k) lawsuit involving AllianceBernstein and why comparing your portfolio to the wrong benchmark can send your plan sideways. Later, Alex calls in with a big early-retirement question: how do you access retirement money before age 59 and a half without triggering penalties?
What You'll Walk Away With
Why Scott Galloway says money is not the story -- it's the ink in the pen that can help you build deeper relationships with less anxiety
The "follow your passion" problem: why Scott believes young people should look first for talent, certification, and industries where they can become excellent
Why boring careers can create extraordinary lives -- especially when they offer income, stability, and room to build options
Scott's wealth equation: focus, stoicism, diversification, and time -- and why each piece matters more than trying to look brilliant for one lucky moment
The savings muscle: why measuring spending, gamifying saving, and surrounding yourself with the right people can change behavior faster than good intentions alone
Why diversification is financial Kevlar -- it may not make you look like a hero, but it can keep one bad investment from becoming a fatal wound
The retirement myth Scott wants to burn down: why the goal isn't necessarily to stop working, but to make work a choice instead of a trap
The 401(k) benchmarking lesson: why Joe and OG say your benchmark should be your goal, not whichever index happened to win over the last decade
Why chasing the S&P 500 because it recently crushed everything else can become dangerous when you forget that market leadership rotates
What the AllianceBernstein lawsuit teaches participants: ERISA protects against imprudence, not against every disappointing stretch of market performance
Alex's early-retirement question: the difference between accessing 401(k) money after separation from service at age 55 and using SEPP rules before then
Why substantially equal periodic payments can work -- but also why OG says you want experienced help before touching those rules
Why splitting IRA assets into separate buckets may create more flexibility for early-retirement income planning
Why This Matters Now
A lot of people want the shortcut: the best stock, the best index, the perfect retirement number, the magic career move. Scott Galloway's message is more durable than that. Build skills. Save consistently. Avoid lifestyle traps. Diversify. Give time room to work. Keep the people around you strong. That's not flashy, but it is the kind of advice that still works when the market, the economy, and your life refuse to cooperate.
From the Basement
Joe and OG start with a retirement-plan lawsuit that turns into a bigger conversation about how Stackers should judge their own portfolios. Then Scott Galloway pulls up a chair at the card table to talk about wealth, work, saving, relationships, his mom, Sizzler, bourbon, Tom Petty, and why you don't need to be a hero to build real financial security. Doug brings trivia about the first camera phone, plus a few modeling notes of his own. Later, Alex asks how early retirees can tap retirement accounts before 59 and a half, and the basement joke-off marches toward its dramatic, deeply mathematical conclusion.
Resources Mentioned
Scott Galloway -- The Algebra of Wealth
Stacking Benjamins Newsletter, The 201 -- stackingbenjamins.com/201
OG financial planning calendar -- stackingbenjamins.com/og
Stacking Benjamins voicemail line -- stackingbenjamins.com/voicemail
Stacking Benjamins Community, The Basement -- stackingbenjamins.com/basement
Stacking Benjamins YouTube channel -- youtube.com/stackingbenjamins
InvestmentNews article by Emil Halasz on the AllianceBernstein 401(k) lawsuit
JL Collins -- The Simple Path to Wealth
Paul Merriman and Peter Mallouk -- referenced during the benchmarking and diversification discussion
IRS Rule 72(t) / SEPP rules -- referenced for early retirement account withdrawals
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Should you invest money you're saving for a house, or keep it in cash? How does an inherited IRA actually work when it's split between siblings? What should a single person think about differently when planning for retirement? And is SGOV a reasonable place to park your emergency fund? Joe and OG dig in. These aren't questions from this week. They're questions Stackers sent in over a year ago -- and people are still asking every single one of them.
What You'll Walk Away With
The house down payment question: why OG flips it around and asks what happens if the market is down 20% when you need the money -- and how the answer tells you exactly what to do
Why the juice-worth-the-squeeze question matters more than the optimal investment question when your timeline is three to five years
How inherited IRAs actually work: the 10-year rule, required minimum distributions, what happens when multiple siblings inherit the same account, and when it might make sense to just pay the tax and be done with it
Why a spouse inheriting an IRA follows completely different rules -- and why you cannot add to an inherited IRA even if you don't have one of your own
The single person's financial plan: why disability insurance is the most important protection nobody thinks about, why your estate plan needs different beneficiary logic than a married person's, and why being your own backstop means advocating harder for your own income
Michelle's numbers run through the Rule of 72: why a 35-year-old with $270,000 already saved may be closer to Coast FI than she realizes
SGOV as an emergency fund: when treasury ETFs make sense as a cash alternative, when they don't, and why over-optimizing your cash flow can cost you more in overdraft fees than you ever gained
Why keeping one to two months of expenses in your checking account isn't lazy -- it's a system that protects you from the chaos of a missed transfer
The student loan bankruptcy debate: why Ron's argument has more merit than most people admit, and what the real structural problem is
The Edward Jones response: what's actually Joe's job in the headline segment and what belongs to a company's PR department
Why This Matters Now
Good financial advice doesn't have an expiration date. These questions were relevant a year ago, they're relevant today, and they'll be relevant next year. If you've been putting off answering any of them for yourself, this is the episode.
From the Basement
Joe and OG work through the mailbag -- house down payments, inherited IRAs, single-person planning, SGOV, student loans, and a spirited defense of Edward Jones from an actual Edward Jones employee who has some notes. The trivia question is about Michael Jackson's best solo hit according to Billboard. Mom has the curtains drawn.
Resources Mentioned
Stacking Benjamins voicemail line -- leave your question; stackingbenjamins.com/voicemail
SGOV -- iShares 0-3 Month Treasury Bond ETF; referenced for emergency fund and cash management discussion
Stacking Benjamins Newsletter (The 201) -- stackingbenjamins.com/201
OG financial planning calendar -- stackingbenjamins.com/og
Stacking Benjamins Community -- stackingbenjamins.com/basement

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Most retirement content talks about what to do. This episode talks about what actually goes wrong -- and how often it happens to people who thought they had it figured out. Joel Larsgaard of How to Money, Paula Pant of Afford Anything, and Jesse Cramer of Personal Finance for Long-Term Investors each nominate their worst retirement mistake for the wall of shame. Some make it. Some get argued off. All of them are more common than you'd think.
What You'll Walk Away With
Why "everything's going to go according to plan" is the most dangerous assumption in retirement -- and the gray swan events nobody sees coming that quietly derail otherwise solid plans
The difference between a black swan and a gray swan: why divorce, health changes, and job loss in your early 60s aren't surprises exactly, and yet almost nobody plans for them
Why most people retire two to three years earlier than they expected -- and why those lost years tend to be peak earning years
The pre-tax wealth trap: why the number in your 401(k) isn't the number you actually get to spend -- and the planning that closes the gap
Joel's RV warning: why the most regretted retirement purchase is almost always the one that seemed most exciting at the moment of retirement
The copy-paste retirement: why doing what other retirees do -- epic trips, vacation homes, the shiny version of leisure -- often produces a quietly miserable result
Why the 4% rule is a starting point, not a sentence: how lumpy real-world expenses, medical costs, and changing needs make a fixed withdrawal rate more aspiration than reality
The lifestyle design question underneath all of it: why Fritz Gilbert's polling of actual retirees found that finances barely make the top concerns list once you're actually retired
Paula's fix for the go-go years: how a dedicated travel bucket with a deliberate spend-down timeline lets you enjoy early retirement without quietly mortgaging the rest of it
Why the 18-month retirement honeymoon often ends in the biggest depression of someone's life -- and what to do before you retire to prevent it

Why This Matters Now
Every mistake on this wall is more common than it should be -- and most of them are fixable with a little planning before the moment arrives. This episode is the conversation to have while you still have time to change something.
From the Basement
Joel Larsgaard, Paula Pant, and Jesse Cramer build the retirement wall of shame live, with Joe trying and failing to get anyone to argue anyone else off the board. Paula tries to win the trivia competition for the second week in a row with a guess of $500 on George Washington's Continental Army salary -- was she right???? Happy Fourth of July from mom's basement, and Stephen Merchant has some thoughts about the holiday.
Resources Mentioned
How to Money podcast -- Joel Larsgaard; greatest hits in July; available wherever you listen to podcasts
Afford Anything podcast -- Paula Pant; July 1st episode on the New York City rent freeze and its downstream consequences
Personal Finance for Long-Term Investors (FILTI) -- Jesse Cramer; recent episode with Frank Vasquez on risk parity; upcoming AMOT on Roth conversions
The Retirement Manifesto -- Fritz Gilbert; retirement research and polling referenced in the episode; theretirementmanifesto.com
Living Off Your Acorns by Dana Anspach -- referenced for the go-go, slow-go, no-go framework; available wherever books are sold
Stacking Benjamins Newsletter (The 201) -- stackingbenjamins.com/201
Stacking Benjamins Community -- stackingbenjamins.com/basement
OG financial planning calendar -- stackingbenjamins.com/og
See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.