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
13 snips
Feb 18, 2026 • 1h
Best Tax Software for 2026 (And Handling Market Drops) SB1805
Robert Farrington, founder of The College Investor and personal finance expert, gives a no-nonsense take on tax software and market turbulence. He compares top tax apps, who should pay for features, and crypto reporting pitfalls. They also unpack recent drops in gold, silver, and crypto and what volatility and concentration risk mean for long-term investors.
15 snips
Feb 16, 2026 • 1h 12min
The Boring Plan That Built $2 Million SB1804
A real-life case study of a Wisconsin couple who quietly turned ordinary retirement accounts into $2 million over 22 years. They started at zero, used employer matches, and escalated contributions slowly. The conversation covers why workplace 401(k)s often win, reframing goals into months, fee tradeoffs versus just saving, gamifying Roth contributions, and balancing post-tax flexibility with long-term care planning.
14 snips
Feb 13, 2026 • 1h 4min
Love It or Leave It: Financial Edition (SB1803)
Jesse Kramer, long-form investor who digs into retirement rules and strategy, and Paula Pant, entrepreneur focused on financial independence and real estate, spar over hot-button money moves. They debate paying off low-rate mortgages, whether FIRE frees or traps people, the reality of real estate as passive income, the 4% rule, lifestyle inflation, and if budgeting apps actually change behavior.
20 snips
Feb 11, 2026 • 1h 1min
How to Talk About Money Without Fighting SB1802
Douglas Boneparth, financial planner and author, teams up with Heather Boneparth, financial planning pro and co-author, to tackle money and relationships. They discuss spotting financial secrecy, scheduling short money check-ins, adapting conversations to different learning styles, teaching kids about delayed gratification, and using calendars to avoid tax pitfalls. Practical, relationship-first money talk without the drama.
10 snips
Feb 9, 2026 • 57min
Are You Investing or Just Placing Bets? SB1801
A lively breakdown of why many people confuse investing with high-stakes betting. Short, vivid examples contrast speculative trends and prediction apps with long-term strategies. The conversation flags risky products like Indexed Universal Life and explains why isolating bets matters. Plus a quirky detour into Costco perks and practical reminders about probability and patience.
20 snips
Feb 6, 2026 • 1h 11min
The Worst Money Advice Ever (Episode 1800!)
Sarah Catherine Gutierrez, a CFP and founder of Aptis Financial who builds workplace financial-wellness programs for middle-income Americans. The conversation rips into the worst money clichés people keep repeating. Short, punchy rounds debate buy vs rent, tax myths, credit-card reward traps, YOLO spending, and a trivia-fueled game that keeps things lively.
13 snips
Feb 4, 2026 • 1h 15min
Building a Wealth Machine That Lasts Generations (SB1799)
Whitney Elkins-Hutton, entrepreneur and investor who builds cash-flowing real estate and business systems, discusses creating income engines that scale and outlast you. She covers shifting from flips to recurring revenue, underwriting true cash flow, scaling operations after crises, diversifying with businesses like car washes, and practical steps to start building generational income systems.
11 snips
Feb 2, 2026 • 52min
Stop Leaving Money on the Table at Tax Time (SB1798)
They walk through seven major tax changes for 2026 and who actually benefits. Topics include the expanded SALT cap, a new senior deduction, and a tip-income deduction. They cover auto loan interest, HSA triple-tax benefits, retirement account tactics for tax savings, tax-loss harvesting tradeoffs, charitable giving rules, 529 optimization, and practical year-round planning moves.
11 snips
Jan 30, 2026 • 1h 9min
How to Get 1% Better Without Burning Out (SB1797)
David Gillis, creator of the 1% Better Conference and speaker coach, and Paula Pant, personal finance podcaster behind Afford Anything, explore tiny, sustainable improvements. They discuss why 1% gains beat overhaul approaches. Short takes cover spotting energy drainers, saying no to protect progress, simple daily practices, and how rest and relationships quietly compound into real change.
9 snips
Jan 28, 2026 • 1h 3min
The Science of Better Ideas with George Newman SB1796
George Newman, behavioral scientist and creativity researcher at Rotman, explains how great ideas arise from relaxed states, expertise, and systematic searching. He argues for surveying options, copying to learn, iterating with small experiments, and relying on 1% improvements rather than forced breakthroughs. Short, practical takes on where ideas show up and how to shape them into better decisions.
