The Stacking Benjamins Show

Most of us were never taught this stuff. So, where do you actually start?

Thirty-nine states now require a personal finance course to graduate from high school. That's real progress — and it still might not be enough. Because financial education isn't a one-time event. It's a living curriculum that has to grow with you, stay connected to your actual life, and — crucially — help you get out of your own way when things get emotionally charged.

This week, Joe and the crew build that curriculum from the ground up. Whether you're 22 or 52, there's a starting point here for you.

Rubin Miller — Financial advisor, founder of Peltoma Capital, and author of the Fortunes and Frictions blog. Came from the investment world before financial planning, which means he sees the whole game differently and isn't afraid to say so on LinkedIn.

Paula Pant — Afford Anything host, behavioral finance truth-teller, and the person who goes on record this week with a very confident guess about the trivia answer.

OG — The basement's own financial planner, father of a teenager who wants to day trade, and enthusiastic opponent of giving the government any money he doesn't absolutely have to.

On building the foundation:

Why the first step in any financial plan is an honest accounting of where everything actually stands: income, spending, assets, debt, all of it

What's coming up in the next three to five years and why that question matters more than any abstract retirement calculation

Why teaching a 17-year-old about mortgages probably doesn't stick and what actually does

The one thing traditional savings accounts do really well (hint: it's great for banks, not for you)

Why your behavior matters more than your math and what to do about it

On protecting what you're building:

The insurance mistake most people make: spending too much protecting low-probability events and too little protecting high-probability ones

Why disability insurance is more expensive than life insurance and what that price difference is actually telling you

When improving your credit score should not be your priority (this one surprises people)

Why debt is never really "good," just occasionally less bad

On growing your money:

What an investment philosophy actually is and why you need one before you pick a single fund

The behavioral biases — recency bias, loss aversion, the availability heuristic — that make smart people do dumb things with their portfolios

Why nobody ever thinks they're panicking. They just think the circumstances changed.

Why taxes are a year-round event, not a February problem

The financial media teaches you to chase. New strategy, hot sector, better fund. But the research keeps landing in the same place: most investors' biggest obstacle isn't information. It's themselves. The curriculum that actually helps isn't the one that covers the most ground. It's the one that connects to your real life, your real timeline, and the emotional triggers that quietly blow up even the best-laid plans.

Start there. Everything else builds on top.

Rubin joins the crew for the first time and immediately plays trivia on Jesse Cramer's behalf — which feels both generous and karmic, given that Jesse and his wife Kelly just welcomed a new baby into the world (on Jesse's birthday, no less). Doug brings the Eddie Murphy birthday trivia energy. Paula goes on record with a very confident guess. OG applies his usual ironclad logic to arrive at his number. Someone wins. Someone absolutely should not have said what they said out loud before the answer was revealed.

MENTIONED / RESOURCES

Rubin Miller's blog: fortunesandfrictions.com

Peltoma Capital: palomacapital.com

Rubin on LinkedIn: search Rubin Miller

Paula Pant: Afford Anything podcast, wherever you listen

OG's calendar: stackingbenjamins.com/OG

Wall Street Journal piece on personal finance requirements by state

New to the basement? Subscribe so you never miss an episode — and if this one made you want to finally build your own financial curriculum, that's the whole point.

FULL SHOW NOTES: https://stackingbenjamins.com/looking-at-your-money-report-card-1824

Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.StackingBenjamins.com/201

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Bola Sokunbi didn't start with advantages. She started with a $54,000 salary she never negotiated, a rollover IRA mistake that cost her 40% of her savings, a tenant who stopped paying rent for eight months, and a first year of business that generated exactly $200. She's also built one of the most influential personal finance brands in the country and helped millions of people on the path to becoming millionaires. The gap between those two things isn't luck. It's four pillars -- and she walks through all of them today.

What You'll Walk Away With

The four wealth-building pillars that work in any combination -- and why you only need one to start

Why negotiating your salary isn't about being aggressive -- and the simple strategy Bola used to close a gap between $54,000 and the $70,000+ her peers were already making for the same work

The rollover IRA mistake that cost Bola nearly 40% of her retirement savings in a single tax year -- and exactly how to avoid it

Why the investing pillar isn't just a 401k -- and the specific questions to ask yourself to know if you're actually maximizing it

The honest truth about real estate as a wealth-building vehicle -- including what Bola learned from eight months of unpaid rent and a judge who heard everything

How to get into real estate investing without ever becoming a landlord

The entrepreneurship timeline nobody posts on social media -- and the financial runway strategy that lets you build a business without blowing up your household finances

Why the four pillars aren't meant to be pursued one at a time -- and how stacking them together is where the real wealth acceleration happens

The one mindset shift that separates people who build wealth from people who keep waiting for the right moment

Why starting late is a story we tell ourselves -- and what the math actually says about investors who begin in their 40s or 50s

Why This Matters Now

If you're in your 40s and you've been doing the right things -- contributing to the 401k, avoiding bad debt, building some savings -- but still feel like the millionaire milestone is someone else's story, this episode is the reframe you didn't know you needed. Wealth at this stage isn't about finding a better investment. It's about understanding which pillars you already have, which ones you're leaving on the table, and how to combine them in a way that fits your actual life.

From the Basement

Bola Sokunbi joins Joe and OG to walk through the four pillars of her new book, Clever Girl Millionaire -- and yes, the guys are allowed in today. Doug arrives with April Fools trivia involving the Tower of London and a very old prank about lion-washing that somehow still worked on Londoners in 1856. Joe and OG also spend the headline segment making what is either a very compelling case for strategic debt -- or the most elaborate April Fools bit in Stacking Benjamins history. The basement scoreboard had nothing to do with any of it.

Resources Mentioned

Clever Girl Millionaire by Bola Sokunbi -- available wherever books are sold

Clever Girl Finance -- free courses, worksheets, and resources at clevergirlfinance.com

Clever Girl Finance on YouTube and Instagram -- @CleverGirlFinance

Grind by (coffee shop founder) -- referenced by Joe during the entrepreneurship discussion

Stacking Benjamins Scorecard -- assess your financial strategy at stackingbenjamins.com/scorecard

Stacking Benjamins Meetups -- find a local group at stackingbenjamins.com/bad

Live Show -- Stacking Benjamins and Afford Anything joint live recording, April 7th at Texas A&M Texarkana; details at stackingbenjamins.com/meetup

FULL SHOW NOTES: https://stackingbenjamins.com/clever-girl-how-to-become-a-millionaire-1823

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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Markets are down. Social media is loud. And somewhere in the back of your mind, a voice is asking if you should do something. That voice has cost investors more money than any bear market in history. Joe and OG dig into what actually separates disciplined investors from everyone panic-refreshing their brokerage account -- and how to build the guardrails that keep you from making the one mistake that derails everything you've built.

What You'll Walk Away With

Why the average intra-year market decline is 14% -- and what that means for how seriously you should be taking a 5% dip right now

The real reason financial news channels make you feel like you need to act -- and how understanding their business model changes everything

How to build a simple investment policy statement that removes emotion from the equation before the next market drop hits

Why setting arbitrary calendar dates to review your portfolio might be the single most underrated investing strategy available to anyone

The case for checking your portfolio less often -- including a real example of how last April's market chaos looked completely different depending on how often you were watching

How to set automatic triggers that tell you when it's actually time to rebalance -- so you're never guessing in the middle of a storm

A powerful perspective shift: look at your tax returns from 2003 or 2010 and then look at your balance today -- what that exercise does to your decision-making in volatile markets

Why your only real job as a long-term investor is to not interrupt the compounding -- and how systems make that easier than willpower ever could

A four-factor framework for calculating exactly how much emergency fund you actually need -- built around your income, job stability, reemployment risk, and expense flexibility

Why the standard three-to-six month emergency fund rule is the wrong starting point -- and what a personalized risk-based approach looks like instead

Why This Matters Now

If you're in your 40s and you've been building toward something -- a retirement account that finally has real weight to it, a financial plan that took years to assemble -- a volatile market feels personal. Because it is. The stakes are higher than they were in your 30s and the noise is louder than ever. The investors who come out ahead aren't the ones who reacted fastest. They're the ones who had a plan written down before things got uncomfortable.

From the Basement

Joe and OG work through what a real investment policy statement looks like in plain language -- rules, triggers, and all. OG and Anna return with the second installment of the financial planning basics series, this time tackling exactly how much emergency fund you need using a four-factor framework that replaces the three-to-six month rule of thumb with something actually built around your life. Doug arrives with insurance trivia that is technically about premiums and practically about Joe's unregistered vehicle situation in Texarkana. Whether the basement scoreboard survived the week is a separate matter entirely.

Resources Mentioned

JP Morgan Guide to the Markets -- monthly research report tracking S&P 500 returns and intra-year declines (Google "JP Morgan Guide to the Markets" for the latest edition)

Stock Market Maestros by Claire Flynn Levy and Lee Freeman-Shor -- referenced throughout; available wherever books are sold

SSA.gov -- Social Security earnings history lookup, referenced as a tool for tracking long-term financial progress

Stacking Benjamins Scorecard -- rate your overall financial strategy at stackingbenjamins.com/scorecard

Stacking Benjamins Vault -- budgeting and net worth tracking tool at stackingbenjamins.com/vault

Stacking Benjamins Voicemail -- share your investment policy statement questions at stackingbenjamins.com/voicemail

Stacking Benjamins Meetups -- find a group near you at stackingbenjamins.com/bad

FULL SHOW NOTES: https://www.stackingbenjamins.com/how-to-protect-your-money-for-when-times-turn-bad-1822/

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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Willpower has a terrible track record with money. It works until it doesn't, and then your good intentions are the first thing to go when life gets busy. The investors and savers who actually make consistent progress aren't trying harder. They've built systems that keep running in the background whether they're paying attention or not. Joe Saul-Sehy, OG, Paula Pant, and Jesse Cramer break down the small, repeatable habits that quietly move the needle -- and why simpler usually wins.

What You'll Walk Away With

Why motivation fades and willpower fails -- and the structural shift that keeps your finances moving forward anyway

The real debate between starting small and going big with savings -- and how to know which approach actually sticks for your personality

A practical framework for automating your finances so progress happens whether you're paying attention or not

When tracking every budget category helps -- and when narrowing your focus to just one creates faster, more lasting wins

How to dump a year's worth of spending data into an AI tool and get back a categorized breakdown that surfaces forgotten subscriptions and leaks you've stopped seeing

The surprising relief that comes from consolidating accounts -- and why mental buckets sometimes matter more than the actual number of accounts

Why brand loyalty and fewer cards aren't just convenient -- they quietly reduce the decision fatigue that erodes financial consistency

The "joy budget" reframe that changes how you think about spending -- and makes it easier to spot what's actually worth keeping

The shift that changes everything -- from cutting spending to aligning spending with what actually matters to you

How small habit changes, repeated without fanfare, compound into financial progress that eventually surprises you

Why This Matters Now

In your 40s, mental bandwidth is the real scarce resource. Work, family, and a hundred competing priorities mean complicated financial systems tend to break down exactly when you need them most. The edge doesn't come from trying harder -- it comes from simplifying, automating, and setting up defaults that keep working on your busiest days, when you're not thinking about money at all.

From the Basement

Joe, OG, Paula Pant, and Jesse Cramer trade strategies on building better financial habits while the crew debates whether you should start small or go big -- and nobody agrees. Doug arrives with a Beatles trivia question that shifts the basement scoreboard in ways the current leader did not anticipate. Whether the points hold or the margin call changes everything is a question best answered with your earbuds in.

FULL SHOW NOTES: https://stackingbenjamins.com/diving-into-the-all-weather-portfolio-with-paul-merriman-1821

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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The best investors in the world are wrong -- a lot. Researchers Claire Flynn Levy and Lee Freeman-Shor spent over a decade studying elite money managers and found that being right about stock picks isn't actually what separates the winners. What separates them is what happens after the pick. The discipline, the rules, the willingness to act when the data changes -- and the ability to remove emotion from decisions most people make entirely on feeling.

What You'll Walk Away With

Why top investors can be wrong more than half the time and still dramatically outperform -- and what that means for how you evaluate your own strategy

The critical shift from obsessing over what to buy to building a repeatable process around what you do next

Three behavioral tribes investors fall into when a position moves against them -- and which one quietly destroys long-term returns

Two distinct ways investors handle winning positions -- and why the more comfortable approach tends to leave serious money on the table

How elite investors use predefined rules to decide when to sell, trim, or hold -- and why removing emotion from that decision is the whole game

A real-world example of a rules-based system built around earnings surprises and data-driven holding periods -- one you can actually learn from

Why planting tiny "seed" positions can preserve massive upside while keeping risk almost invisible on the downside

The hidden cost of a pattern so common it barely registers -- holding losers too long while cutting winners too early

What makes China's market behave unlike anywhere else -- and how one maestro built an entire strategy around it

The AI cautionary tale hiding inside this episode -- a real advisor, a real client presentation, and math that was off by a factor of 12

Why This Matters Now

For investors in their 40s, the goal quietly shifts. Finding the next big winner starts to matter less than building something that actually holds up over time. Markets feel noisier, AI tools feel more powerful, and the promise of faster answers has never been louder. But long-term results still come down to behavior, discipline, and repeatable systems -- the same unglamorous edge the pros have been using all along. Knowing that changes how you listen to the noise.

From the Basement

Joe and OG press Claire and Lee on what a decade of studying elite investors actually reveals -- and the answers are more behavioral than most people expect. The crew then turns to AI in financial advice, and OG shares a story that should give every advisor and DIY investor pause before they hit send on anything they haven't personally verified. Doug arrives with a trivia question that somehow connects Michael Jackson's moonwalk to one giant leap for your bragging rights. Whether the basement scoreboard sticks the landing is best discovered with your earbuds in.

FULL SHOW NOTES: https://stackingbenjamins.com/diving-deep-into-stock-market-research-1820

Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.stackingbenjamins.com/201

Enjoy!

Learn more about your ad choices. Visit podcastchoices.com/adchoices