The Stacking Benjamins Show
StackingBenjamins.com | Money Podcast | 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
12 snips
Mar 27, 2026 • 1h 8min
Stop Relying on Willpower (Build This Instead) SB1821
Jesse Cramer, investor and long-term planning guide, and Paula Pant, financial independence advocate and habit designer, explain why willpower fails and systems win. They discuss automating savings, choosing start-small vs start-big strategies, simplifying accounts and cards, the joy budget to align spending with values, and using AI to spot forgotten subscriptions.
20 snips
Mar 25, 2026 • 1h 10min
Even the Pros Are Wrong Half the Time. Here's What They Do Differently SB1820
Lee Freeman-Shor, an investment manager and author who studies fund manager behavior, and Claire Flynn Levy, founder of Essentia Analytics and former CIO, discuss how top investors win by process not pick accuracy. They cover why pros are often wrong, rules-based selling and sizing, handling losers and letting winners run, and real-world case studies on repeatable systems and market quirks.
10 snips
Mar 23, 2026 • 1h 6min
The Real Return on Your Emergency Fund Has Nothing to Do With Interest Rates SB1819
They reframe emergency savings as protection that prevents panic selling and costly, emotional decisions. They compare places to hold cash like high-yield savings, CDs, money markets, and T-bills. They explain CD laddering, FDIC limits, and tax differences for Treasuries. They promote a “good enough” cash plan, a five-column cashflow framework, and practical rules for liquidity versus yield.
10 snips
Mar 20, 2026 • 1h 10min
How to Build a Financial Plan That Holds Up When Life Doesn't SB1818
Paul Merriman, longtime investor and educator known for practical portfolio strategies, lays out how to build resilient financial systems. He talks about avoiding flashy "sports car" portfolios, improving simple one-fund approaches, and why diversification can feel like failure before it protects you. Also covers cash reserves, insurance, job‑loss risk, and skills that keep plans intact under pressure.
9 snips
Mar 18, 2026 • 59min
What to Build After You Hit "The Retirement Number" (SB1817)
Amy Minkley, FI traveler and community builder who runs retreats in Bali, retired early and now crafts purpose-driven gatherings. She describes trading the spreadsheet for community, creating retreats that blend meaning and giving back, and why designing life beats simply escaping. The conversation also covers how to size emergency savings around essentials and avoid common cash-and-credit mistakes.
13 snips
Mar 16, 2026 • 1h 12min
The One About 401k Loans (and How To Stay Away From Them) SB1816
They dig into why people increasingly tap retirement accounts and the hidden system pressures that make loans seem necessary. They compare 401(k) loans to hardship withdrawals and outline the career and tax risks involved. Practical topics include building buffers, emergency funds, expense tracking, tripwires, and a six-area framework to prevent raiding retirement savings.
9 snips
Mar 13, 2026 • 1h 11min
Why Doing Less With Your Money Is the New Investing Edge (SB1815)
Doc G, creator of Earn & Invest and financial commentator, and Jen Smith, co-host of Frugal Friends and frugality advocate, dive into millennial money moves. They debate automation vs gamification, why fewer decisions can win, the dangers of frictionless trading, budgeting app pitfalls, career risk and where to take big swings. Short, lively, and practical.
14 snips
Mar 11, 2026 • 1h 2min
When Money Rules Don't Match Real Life (Your Questions!) SB1814
Anna Allem, a Certified Financial Planner who clarifies tax and retirement puzzles. She tackles real-life twists on savings-rate rules, when to revisit inflation assumptions, backdoor Roth paperwork scares, whether to stay in a poor 401(k), and why fund splits usually aren’t dramatic. Short, practical takes on messy money decisions.
10 snips
Mar 9, 2026 • 58min
Private Equity for Regular People: Higher Returns or a Very Expensive Lesson? SB1813
Doug, Joe's mom's neighbor and frequent contributor who brings trivia and perspective, joins the conversation. They dig into why private equity and private credit are being sold to everyday investors now. Short, punchy takes cover illiquidity traps, who gets targeted by aggressive marketing, regulatory and Ponzi risks, and what practical steps to consider before chasing exclusive-sounding deals.
10 snips
Mar 6, 2026 • 49min
Should You Invest When the Market Feels Too High? SB1812
Greg McFarlane, author and pragmatic budgeting commentator; Paula Pant, financial independence podcaster and lifestyle investor; Len Penzo, frugal personal finance blogger with a witty take. They debate whether to invest when markets feel high. Short takes on sell losers fast vs letting winners run. Talk about tuning out financial media, cash versus credit habits, risks of a cashless society, and how to explain money to kids.
