The Stacking Benjamins Show
StackingBenjamins.com | Cumulus Podcast Network
Named the Best Personal Finance Podcast by Bankrate.com and Kiplinger, The Stacking Benjamins Show features a light and friendly tone. Hosts Joe Saul-Sehy and OG aim to make financial literacy fun for all as they sit around the card table in Joe's Mom's half-finished basement and talk with experts about personal finance, saving, investing, and important money trends. As Fast Company once wrote, the Stacking Benjamins podcast "strikes a great balance of fun and functional." So join Joe and OG every Monday, Wednesday and Friday as they read your letters, discuss major headlines, and throw in some trivia and laughs for free.
Episodes
Mentioned books
10 snips
Dec 1, 2025 • 1h 13min
The Tax Basics You Should've Learned Years Ago (But Nobody Taught You) SB1768
Hannah Cole, a tax professional and author of *Taxes for Humans*, shares her journey from artist to tax expert. She simplifies the tax code for freelancers and small business owners, explaining deductions versus credits, the essentials of bookkeeping, and when to pay estimated taxes. Hannah emphasizes the importance of tracking startup costs and maintaining organized records. The hosts also engage in a lively debate about the AI market hype, urging caution for investors as the financial landscape shifts. Plus, a fun trivia tidbit about Richard Pryor!
4 snips
Nov 28, 2025 • 1h 16min
Board Games That Make You Smarter With Money (Without Feeling Like School) SB1767
Join board game expert Kylie Prymus, owner of Games Unlimited, as he reveals how fun games can teach financial literacy without the boring lecture. Discover strategic games like Dominion and Food Chain Magnate that illustrate money management concepts through engaging play. Kylie shares tips for selecting holiday games that suit mixed skill levels, ensuring laughter and connection at your gatherings. From delightful two-player games like Boop to party hits like Monikers, elevate your game nights with lessons cleverly disguised as fun!
29 snips
Nov 26, 2025 • 1h 9min
Black Friday Tech: What's Worth Buying (And What's Just Hype) SB1766
Bridget Carey, a seasoned technology journalist from CNET, joins the conversation to decode Black Friday's tech landscape. She shares insights on smart buying, highlighting Nintendo's impressive line-up and the pros of handheld gaming devices like the Steam Deck. Bridget warns against gimmicky AI appliances and stresses the importance of understanding what tech truly enhances our lives. The discussion also delves into Robinhood's gamified investing, cautioning that it may not be suitable for serious long-term investors.
16 snips
Nov 24, 2025 • 1h 22min
The Smart Person's Guide to Black Friday Deals (SB1765)
Regina Conway, Senior Deal Expert from Slick Deals, shares her insider tips for maximizing Black Friday savings, including strategic shopping times and gift card stacking. Comedian Josh Liston humorously critiques American Thanksgiving traditions while participating in lively banter. The two also delve into the risks of Buy Now Pay Later schemes, comparing them to the fleeting delight of Halloween candy. From apparel discounts to clever holiday gift ideas, the conversation serves as a savvy guide to conquering the post-Thanksgiving shopping frenzy.
16 snips
Nov 21, 2025 • 1h 15min
How to Actually Use Money Apps the Right Way (According to FinTech Pros) SB1764
In this insightful discussion, Peter Polson, founder of Tiller, emphasizes data privacy in finance apps, while Aaron Froug of Griffin reveals how everyday spending can fuel investing. Ryan Ruff from Array dives into the backend tech of banking, shedding light on user experience and simplicity. The trio addresses common misconceptions about money apps, the role of AI in finance, and the ethics of gamification. They also share valuable tips on choosing FinTech tools, fostering community learning, and making small habits lead to big financial results.
24 snips
Nov 19, 2025 • 1h 18min
How to Actually Listen (Not Just Wait to Talk) SB1763
Katie O'Malley, an executive coach and TEDx speaker, shares her expertise on effective listening. She introduces the AIR framework—Attention, Intention, Recognition—that transforms communication. Katie explains how truly listening enhances personal relationships and financial decision-making. She discusses the importance of financial literacy for kids and provides tips on navigating tough discussions during family gatherings. Plus, discover how practicing reflective listening can alleviate misunderstandings and foster connection, especially in high-stakes scenarios.
11 snips
Nov 17, 2025 • 1h 14min
Should You Actually Use a Catastrophic Health Plan? (& more questions from YOU!) SB1762
Is switching to a catastrophic health plan a smart move? The hosts dissect the ins and outs of these plans, revealing what they truly cover and whether it's worth the gamble. They also delve into the tricky timing for 529 withdrawals, including clever strategies to maximize tax benefits. Meanwhile, market fears arise as they explore Japan's lost decade and share tips on surviving market crashes. And don't miss some light-hearted chaos with trivia about counterfeiting and a charity challenge to support financial literacy!
10 snips
Nov 14, 2025 • 60min
Why You Feel Broke Even When You're Doing Everything Right (SB1761)
In this conversation, Erin Lowry, author of Broke Millennial, shares her journey to financial stability, while Paula Pant, creator of Afford Anything, emphasizes the importance of earning more through side hustles. Greg McFarlane, author of Control Your Cash, offers blunt insights on personal finance. They discuss why some families feel broke despite saving, the systemic issues with big banks, and unusual ways to make extra money. Expect laughter and practical advice that transforms the way you think about income and budgeting!
9 snips
Nov 12, 2025 • 1h 23min
Jonathan Clements: Why Simple Beats Complicated Every Time (SB1760)
In a heartfelt conversation, Jonathan Clements, a former Wall Street Journal columnist and founder of Humble Dollar, shares his insights on building wealth through simplicity and consistent habits. He emphasizes that true financial success isn't about complex strategies, but rather about steady saving and making informed choices—like renting vs. buying based on your lifestyle. Jonathan also discusses the importance of preparing for life's uncertainties with insurance and the compelling stories behind his book, My Money Journey, illustrating the power of everyday financial decisions.
9 snips
Nov 10, 2025 • 60min
What a 12-Hour Walk Teaches You About Money (And Life) SB1759
Colin O'Brady, an endurance athlete and author of The 12-Hour Walk, shares his incredible adventures, including a solo trek across Antarctica. He discusses how challenging your mental limits can transform your approach to goals and money. Colin highlights the importance of the 'not yet' mindset, encouraging listeners to reconnect with their aspirations. He also introduces the 12-hour walk as a practice for mental clarity. Plus, Joe and OG dive into listener questions about Roth vs. Traditional 401(k) contributions, illustrating the parallels between financial and physical endurance.
