The Stacking Benjamins Show

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

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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

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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

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This is a different kind of episode. No trivia, no headlines, just Joe and longtime health and wellness expert Angelo Poli having an honest, unscripted conversation about what happened when a training injury, a missed diagnosis, and months of frustration sent Joe into a spiral he didn't see coming. It's a personal story, but the reason it belongs on a money show is simple: your ability to earn, think clearly, and actually enjoy what you've built depends on your health just as much as it depends on your portfolio.
What You'll Walk Away With
Why a setback in one area of your health or life can quietly spiral into others, and the exact moment that turnaround has to happen
The science behind why doing "one thing" well beats trying to overhaul everything at once
Why having someone else to be accountable to changes follow-through far more than willpower alone
A candid explanation of why almost nobody follows through on "I'll think about it and get back to you," and what to do instead
Why acting early in the day and early in the week measurably increases your odds of sticking with a health goal
How physical health directly affects financial outcomes, through energy, focus, decision-making, and the years you get to actually enjoy what you've saved
Why This Matters Now
It's tempting to treat health and money as two completely separate categories of adulting. But the connection runs deeper than most people realize: poor sleep, low energy, and physical pain make it harder to think clearly, work efficiently, or make good financial decisions. And the whole point of building financial security is having the health to actually enjoy it, time with family, travel, the ability to do the things you're saving for. Taking care of one without the other only gets you halfway to the life you're actually working toward.
Resources Mentioned
MetPro — Angelo Poli's concierge nutrition, fitness, and lifestyle coaching program, free session for Stacking Benjamins listeners

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What actually makes for a happy retirement? Today, Joe sits down with retirement expert Wes Moss, author of The Retire Sooner Method, to explore the research behind America’s happiest retirees. Wes explains why money is only part of the equation, how community and “super activities” give retirement purpose, why eliminating debt can create more freedom, and how a clear retirement plan can help reduce the fear of running out of money.
Then Joe and OG tackle one of retirement’s most popular investing strategies: living off dividends so you never have to sell your investments. They break down why dividends feel so appealing, where the strategy can fall short, and why building your retirement income plan around your goals may matter more than chasing a particular yield. Plus, Doug celebrates the anniversary of the ATM with some cash-dispensing trivia.
Resources mentioned
Wes Moss
The Retire Sooner Method: The 5 Secrets Behind America’s Happiest and Unhappiest Retirees
You Can Retire Sooner Than You Think
Retirees Love Dividends, but the Stock Market Surge Is Making Them Think Again — The Wall Street Journal
Field Kit Finance
The 201 newsletter — stackingbenjamins.com/201
Field Kit Finance webinars: Sign up for The 201 to get the full schedule.
The Clark Howard Show
FinCon
Dana Anspach
Ben Carlson
Attorney Tim Semro’s recent Stacking Benjamins appearance

FULL SHOW NOTES: https://www.stackingbenjamins.com/wes-moss-retire-sooner-method-1892/
Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.stackingbenjamins.com/201
Enjoy!
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