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
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.
Mar 4, 2026 • 1h 11min
Around the World in 80 Days: The Travel Mindset That Makes Retirement Bigger (SB1811)
George Jerjian, a retirement mindset coach and author who took an 80-day round-the-world trip to reinvent retirement. He talks about using intentional travel to push comfort zones and reshape identity. Short planning tips, the DARE method, and vivid stops from Robben Island to Milford Sound and Hiroshima show travel as a catalyst for bold reinvention.
Mar 2, 2026 • 1h 23min
Building Courage One Small Step at a Time SB1810
Jen Drummond, mountaineer and author who completed the Seven Second Summits, shares a story of surviving trauma and choosing to live boldly. She talks about courage as a momentum-builder. She explains breaking massive goals into milestones, the importance of preparation and teams, and how deliberate, safe steps beat recklessness.
9 snips
Feb 27, 2026 • 1h 11min
You Don't Need to Be a Money Genius to Win SB1809
Whitney Hanson, host of the Money Nerds podcast and personal finance educator, shares practical systems to shore up money skills. She highlights using quizzes to find knowledge gaps and theming learning. The team discusses cashflow audits to spot spending leaks, simple automated investing, insurance shopping, and straightforward estate planning. Focus on repeatable habits, not brilliance.
9 snips
Feb 25, 2026 • 55min
How She Eliminated a $43,000 Hospital Bill (SB1808)
Amani Vance, a 19-year-old Coast Guard recruit who faced severe sepsis and a surprise $43,000 hospital bill, shares her medical billing ordeal and fight for relief. She discusses finding nonprofit help via Reddit, how advocates navigated confusing hospital forms, and getting 100% financial assistance that wiped out the debt. The conversation also touches on why medical bills feel uniquely opaque and stressful.
4 snips
Feb 23, 2026 • 1h
Suze Orman Changes Her Mind on Working to 70 (SB1807)
Len Penzo, personal finance writer and retirement-focused blogger, shares his approach to Social Security and planning. He explains why he plans to delay benefits until 70 and walks through the break-even math. The conversation explores stress-testing retirement plans, liquidity vs cash, identity after leaving work, and practical steps to build flexibility rather than chase a perfect retirement date.
10 snips
Feb 20, 2026 • 1h 3min
How to Talk to Kids About Money (Without Making It Weird) SB1806
John Lanza, allowance strategist who designs practical family money systems. Karen Holland, educator behind GiftingSense.org who teaches mindful spending pauses. Livia Roeder, high school senior and Liv Lab host who brings youth perspective. They discuss real moments money becomes real, allowance and jar systems, pausing before purchases, letting kids learn from small mistakes, and making college and big choices price-aware.
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.
