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
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.
10 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.
12 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.
13 snips
Jan 26, 2026 • 1h 13min
When to Trust Your Gut and When to Trust the Math SB1795
Conversations about when to follow intuition versus running the numbers in money decisions. They explore how intuition forms, common biases that mislead, and ways to train better financial instincts. The discussion covers marrying data with creativity, responsible use of AI, practical Costco membership tactics, and tools advisors use to time Social Security and coordinate plans.
10 snips
Jan 23, 2026 • 1h 6min
How to Afford Life Without Living Like a Monk (SB1794)
Justin Brown-Woods, a financial counselor and creator of 'The Price of Avocado Toast,' joins the discussion on tackling chaotic expenses. The crew explores how to make variable costs predictable and identify sneaky spending habits that drain your budget. They dive into practical strategies for cutting food costs and reducing housing expenses, while also addressing the hidden costs of subscriptions. With a focus on mindful spending, they emphasize enjoying life without compromising your finances. A must-listen for anyone feeling financially squeezed!
11 snips
Jan 21, 2026 • 1h 22min
How to Make Your Money Support the Life You Want (SB1793)
Join Dana Anspach, a certified financial planner and retirement expert, alongside Andy Hill, author and creator of the 'Marriage, Kids & Money' podcast. They explore how to prioritize family and flexibility through financial planning. Andy shares his journey from corporate life to a three-day workweek, emphasizing time freedom. Dana dives into life insurance myths following the Kyle Busch lawsuit, clarifying Indexed Universal Life policies and the importance of choosing insurance based on personal goals rather than sales pitches.
10 snips
Jan 19, 2026 • 1h 7min
How to Prioritize Your Money: Listener Q&A (SB1792)
Navigating your financial life with competing priorities can be tricky. Discover how to make better decisions when juggling retirement, insurance, and emergency funds. Get insights on optimizing life insurance and tips for creating an effective gifting strategy. Learn the implications of 401(k) changes and how automatic enrollment can affect your savings. Plus, hear practical advice for building an emergency fund with variable income and the importance of balancing financial goals without losing sight of long-term plans.
