
Sign up to save your podcasts
Or


Based on Podcast App listening data
Getting to your first $25,000 saved is harder than anything that comes after it. Not because the math is complicated -- because the habits aren't built yet, the fixed expenses are already set, and the standard advice about cutting small treats completely misses where the real leverage is. Scott Trench, VP of Operations at BiggerPockets and author of Set for Life, brings a roadmap that challenges almost everything you've heard about getting started -- and it begins with a decision most people aren't willing to make.
What You'll Walk Away With
Why This Matters Now
This conversation was originally recorded years ago, but it was pulled from the vault for a reason: saving that first $25,000 feels harder today than it did then. Costs are higher, decisions feel riskier, and it's easier than ever to feel stuck before you even get started. The core framework Scott lays out hasn't changed -- and if anything, it applies more directly now than when it was first recorded.
From the Basement
Scott Trench joins Joe and OG to walk through the early chapters of Set for Life -- the ones that challenge conventional saving wisdom before getting into the real estate strategy BiggerPockets is known for. The headline segment takes on a Bloomberg piece about bad financial advisors and a lawsuit against American Funds, and OG gets considerably more animated than usual about both. Doug arrives with muni bond trivia that turns out to be exactly as straightforward as it sounds -- which is either reassuring or anticlimactic depending on your expectations.
Resources Mentioned
See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.
What if the reason your investment decisions feel so hard isn't the market -- it's how you're wired to think about outcomes? Annie Duke spent years as a professional poker player winning over $4 million in tournaments, then devoted the next chapter of her career to understanding why smart people consistently make bad decisions. The answer has nothing to do with intelligence and everything to do with how we confuse results with quality. She brings the full framework down to the basement today.
What You'll Walk Away With
Why This Matters Now
For Stackers in their 40s watching a volatile market and second-guessing decisions that were perfectly sound six months ago, this episode is a direct intervention. The temptation to call a good decision bad because the market moved against you -- or to abandon a long-term strategy because of a short-term result -- is exactly the bias Annie Duke has spent her career studying. The framework she brings today doesn't just apply to poker. It applies to every financial decision you'll make for the rest of your life.
From the Basement
Annie Duke joins Joe and OG to walk through the decision-making framework behind her book Thinking in Bets -- including the Super Bowl story that reframes how most people evaluate every financial move they've ever made. The headline segment tackles parents spending six figures on kids' extracurriculars and what the trade-off actually looks like for retirement savings. Doug arrives with poker-themed trivia about the all-time tournament earnings leader, gets it mostly right, and declares victory anyway. Whether the basement poker tournament ended in anyone's favor is a matter of some dispute.
Resources Mentioned
See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.
You've seen the ads. Invest like the ultra-wealthy. Get access to what the 1% does. But what does the 1% actually do -- and how much of it should a normal person try to copy? Joe, OG, comedian and finance educator Roxanne Duckels, and Jesse Cramer run every popular "rich people investing" idea through a simple filter: steal it, scale it, or skip it. The answers will surprise you -- especially the one where OG wants to delete an entire asset class from existence.
What You'll Walk Away With
Why This Matters Now
In a noisy market environment, the "invest like the wealthy" pitch gets louder every time volatility spikes. Private credit, non-traded REITs, leveraged real estate, alternative assets -- the marketing machine never stops. For Stackers in their 40s who've built something real and don't want to blow it chasing a category that mostly benefits the people selling it, this episode is a useful reset. The habits worth stealing from the 1% turn out to be remarkably unglamorous.
From the Basement
Joe, OG, Roxanne Duckels from Finance Rox, and Jesse Cramer run the "invest like the rich" playbook through a steal-it-scale-it-skip-it framework -- and nobody agrees on everything, which is exactly what makes it useful. Doug arrives with Mayday trivia about the origin of the distress call and the year it was coined, which turns into one of the cleaner trivia finishes of the season. Whether the basement scoreboard moved in OG's favor or Jesse closed the gap is a question best answered with your earbuds in.
Resources Mentioned
See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.
Haley Sacks didn't grow up knowing what a 401k was. She was nannying for a kid named Winthrop on the Upper East Side, doing comedy at night, and getting paid cash under the table. Then she sat in an HR meeting and her eyes glazed over -- and she decided that was the last time she'd be caught unprepared with her own money. Today she's Mrs. Dow Jones, with millions of followers and a new book. The basement finally got her in the chair, and she did not hold back.
What You'll Walk Away With
Why This Matters Now
If you're in your 40s and you still feel like the millionaire milestone belongs to someone else's story -- someone who started earlier, earned more, or just had better instincts -- this episode is a direct challenge to that belief. Hailey Sacks didn't have better instincts. She had a glazed-over HR meeting and a determination not to be caught unprepared twice. The foundation she built after that moment is exactly what she walks through today.
From the Basement
Mrs. Dow Jones herself -- Haley Sacks -- finally makes it down the stairs and does not disappoint. Joe and OG close the episode with a Wall Street Journal headline on mortgage rate volatility and what it actually means for anyone trying to buy, move, or refinance right now. OG lands what may be the cleanest take of the season: when should you borrow money? When you need to borrow money. Doug arrives with Dow Jones trivia about the longest-tenured company in the index, which turns out to have been added in 1932 and is hiding in plain sight on every household shelf. Whether the basement scoreboard had anything to do with Procter & Gamble is a question best answered with your earbuds in.
Resources Mentioned
See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.
Most investors spend their energy asking the wrong question. It's not which fund is best -- it's which combination of funds gets you to your actual goal at a cost and complexity level you'll actually maintain. Joe and OG break down the full index investing playbook: where to start, when to add complexity, what Wall Street calls indexing that really isn't, and the one number that should change how you think about your entire portfolio.
What You'll Walk Away With
Why This Matters Now
In your 40s, the portfolio is finally big enough to matter -- and that's exactly when the temptation to complicate things gets strongest. New products, new strategies, and new buzzwords show up constantly, each promising a smarter approach. The investors who come out ahead aren't the ones who found the best fund. They're the ones who built something simple enough to maintain, scientific enough to optimize, and sturdy enough to hold through the moments when everything feels like it's falling apart.
From the Basement
Joe and OG dig into the full index investing playbook -- from the first fund a beginner should buy to the asset class combinations that actually improve long-term outcomes once the portfolio gets big enough to warrant it. OG and Anna close out their seven-week financial planning basics series with a full recap and the surprise release of a free downloadable workbook at stackingbenjamins.com/basicsguide. Doug arrives with Nolan Ryan trivia that connects strikeout records to index investing in a way that only the basement could pull off. Whether the analogy fully lands is a question best answered with your earbuds in.
Resources Mentioned
See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.
Most people glance at their balance and move on. Joe Saul-Sehy, OG, Paula Pant, and Jesse Cramer argue that's exactly where the money quietly disappears. This week they go statement by statement, credit card through brokerage, and share what actually deserves your attention and what you can safely ignore.
In this episode:
The one thing on your credit card statement that trips up even careful spenders, why focusing on your 401k rate of return is the wrong move, the underinsured coverage gap most homeowners and drivers don't know they have, and the tax planning opportunities hiding inside your brokerage account.
Biggest takeaways:
Sort your credit card transactions highest to lowest. The leak with a comma in it will find you faster than you'll find it.
Your 401k contributions matter more than your returns. Contributions are within your control. Returns aren't. Check that your payroll deductions are actually landing in the account, because the IRS does not look kindly on companies that miss that.
Check your homeowner's insurance rebuild value every few years. Labor and material costs have changed dramatically. If you bought your policy when you bought your house and never revisited it, there is a good chance you are significantly underinsured.
In a taxable brokerage account, understand whether you're holding short-term or long-term gains before you make any moves. The difference in what you'll owe can be substantial.
Also in this episode:
Jesse Cramer previews an upcoming episode of Personal Finance for Long-Term Investors on why target date funds may be underperforming by more than you think.
Resources mentioned:
See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.
Blockchain. Stablecoins. Wallets. Staking. Halvings. If you've spent the last few years nodding confidently through crypto conversations while quietly hoping nobody asks a follow-up question -- this episode is for you. Retired anesthesiologist and trading veteran Joe Duarte went from crypto skeptic to informed pragmatist, and today he brings the plain-English breakdown that most crypto content assumes you don't need. No hype. No moon talk. Just the vocabulary, the mechanics, and the honest risks.
What You'll Walk Away With
Why This Matters Now
Whether you've been crypto-curious for years or you've actively avoided the conversation, the landscape has changed enough that staying completely uninformed carries its own risk. Regulation is arriving, major brokerages now offer access, and the vocabulary has leaked into mainstream financial planning. You don't have to become a believer -- but understanding what you're looking at puts you in a much better position to decide whether any of it belongs in your financial life.
From the Basement
Joe Duarte joins Joe and OG to translate the crypto dictionary for everyone who's been faking it at dinner parties for the last decade. In the headline segment, Joe and OG dig into a sobering new AARP report on long-term care costs -- and the conversation gets uncomfortably real about what most retirement plans are quietly missing. Doug arrives with trivia about the Bitcoin halving process, which turns out to have a name that required approximately zero creativity to invent. Whether the basement scoreboard reflects informed decision-making or something closer to Doug's personal net worth is a question best answered with your earbuds in.
Resources Mentioned
See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.
Most people think about investing in terms of what to buy. Joe Saul-Sehy, OG, and CFP Anna Allem argue the more important question is where you put it. This week they break down the three-bucket tax triangle that could save you thousands in retirement, plus answer listener questions on Trump accounts, UTMAs, and how to pull together a home down payment when your money is locked up in all the wrong places.
In this episode:
The difference between pre-tax, brokerage, and tax-free investing and why you need all three, what the new Trump account actually does and who it makes sense for, how to build a home down payment when your assets are tied up in retirement accounts, and why flexibility in your tax strategy matters as much as the investments themselves.
Biggest takeaways:
Draw a triangle. Label each corner pre-tax, brokerage, and tax-free. Then draw your buckets to scale based on where your money actually sits. If one bucket dwarfs the others, that's your problem to solve before you touch anything else.
The Trump account is not a traditional IRA, despite what the website implies. Money goes in after tax, grows tax deferred, and comes out taxable. For most people with a 529 and an UTMA already in place, keep going with what you have.
When your money is locked in retirement accounts and you need a down payment, the math has two sides. What does pulling it out cost you today in taxes and penalties, and what does it cost you in thirty years of lost compounding? Know both numbers before you decide.
Resources mentioned:
See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.
What would you ask about money if you had the mic?
Live from Texas A&M Texarkana, Joe Saul-Sehy, Paula Pant, and financial educator Jay Davis take questions from students facing real-world money decisions—like choosing between passion and paycheck, avoiding lifestyle creep, investing safely, and building a financial future from scratch.
If you're in your 20s—or wish you could do them over—this episode is packed with the advice we wish we knew earlier.
Plus: Doug climbs into the rafters (again) for a trivia showdown you won’t forget.
💡 What We Cover in Today’s Episode
🧠 The Big Takeaways
🎤 Special Guests
Enjoy!
See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.
The same mental patterns that cause investors to panic-sell during a downturn, chase validation through status purchases, or freeze up when facing big financial decisions -- those are the exact patterns performance coach Jim Murphy has spent decades helping elite athletes overcome. His framework isn't about trying harder. It's about getting aligned. And today he brings it down to the basement to help Stackers apply it to the one game that matters most -- the one you play with your own money and your own life.
What You'll Walk Away With
Why This Matters Now
In your 40s, the financial pressure is real -- but so is a quieter kind of pressure that rarely gets named. Am I building the right life? Am I making decisions because they matter to me, or because of what other people will think? Jim Murphy's work sits at the intersection of those two questions, and the answer he keeps arriving at is the same one the best investors, the best athletes, and the most contented people share: stop optimizing for the scoreboard and start arranging your days around what actually makes you feel fully alive.
From the Basement
Jim Murphy joins Joe and OG to walk through the framework behind his new book, The Best Possible Life -- including the desert solitude, the FedEx job, the homeless harpist, and the cancer diagnosis that field-tested everything he teaches. Joe and OG close out the episode with a Psychology Today headline on AI and financial trust -- and OG's story about nearly committing accidental tax fraud because Claude was being extremely encouraging about a box he absolutely should not have checked. Doug arrives with McDonald's trivia in honor of Tax Day and Ray Kroc's first store. Whether the basement scoreboard survived the week is a question best answered with your earbuds in.
Resources Mentioned
Enjoy!
See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.
From the publisher's feed
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…
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
Ranked by our users in the last 21 days

3,565 Listeners

22,874 Listeners

1,243 Listeners

3,234 Listeners

1,964 Listeners

1,171 Listeners

800 Listeners

781 Listeners

1,302 Listeners

458 Listeners

539 Listeners

980 Listeners

1,753 Listeners

5,135 Listeners

10,188 Listeners

697 Listeners

2,958 Listeners

3,059 Listeners

6,469 Listeners

729 Listeners

448 Listeners

829 Listeners

201 Listeners

2,195 Listeners

2,936 Listeners

85 Listeners

357 Listeners

17 Listeners

56 Listeners

793 Listeners

3 Listeners

2 Listeners

7 Listeners