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
22 snips
Nov 5, 2025 • 1h 9min
Financial Literacy for Kids + Are Annuities Actually Safe? SB1757
Karen Holland, an economist and founder of Gifting Sense, joins the discussion to emphasize the importance of teaching financial literacy to kids. She highlights the ideal age for financial lessons, explains the DIMM score calculator, and shares strategies for mindful spending. The conversation shifts to annuities, questioning their safety and the hidden fees that often accompany them. With practical insights and engaging trivia, listeners gain valuable advice on educating the next generation about money and navigating modern financial products.
18 snips
Nov 3, 2025 • 60min
What to Do When Money Gets Tight SB1756
When finances get tight, a solid plan can save you. Discover the first crucial steps to take, like assessing your pantry and building an effective emergency fund. Learn smart budgeting tips to stretch food and utilities without living on ramen. The hosts discuss the importance of local assistance and avoiding quick loans that can complicate finances. Plus, insights on risky financial moves seen on TikTok will keep your strategy grounded. It's about staying afloat, even in tough times!
13 snips
Oct 31, 2025 • 1h 1min
Tales of Financial Horror (and how we exorcised them) SB1755
Join Doc G (Jordan Grumet), a physician and host of the Earn and Invest podcast, Jesse Cramer, creator of Better Interest, and Emily Egashira, personal finance coach known as 'Hey Friend, It's Em', as they dive into spine-chilling financial horror stories. They share cautionary tales from impulse buys that haunt them to the terrible traps of overspending and luxury leasing. The panel emphasizes learning from these mistakes and implementing strategies like cooling-off periods to avoid future financial frights, proving that even the scariest stories can lead to valuable lessons.
11 snips
Oct 29, 2025 • 1h 10min
Banishing Money Monsters: How to Talk Money With Anyone (Partners, Roommates, or Coworkers) SB1754
Doug and Heather Bonaparte, a dynamic husband-wife team, tackle the often scary conversations around money in relationships. They share personal experiences, like navigating Heather's career shift from corporate law to their family business, and highlight how childhood money scripts shape adult beliefs. Discover practical tactics for smooth money talks, the balance between joint vs. separate accounts, and the crucial need for personal introspection before tackling financial discussions. Their tips ensure financial teamwork doesn't turn into a horror show!
12 snips
Oct 27, 2025 • 1h 4min
Real Money Horror Stories (And How Not to Star in Your Own) SB1753
Chuck Jaffe, a financial journalist and host of Money Life with Chuck Jaffe, joins to share his creative Halloween Money Game that teaches kids about risk, reward, and decision-making through fun. He also discusses the value of choices—like candy versus cash—and how to gamify money lessons. The show takes a spooky turn as real listeners share their financial horror stories, illustrating the dangers of procrastination and bad advice. Jaffe emphasizes practical money lessons that can be learned during the holiday season.
10 snips
Oct 24, 2025 • 1h 6min
You've Got Enough Money to Quit. Should You? SB1752
Join Paula Pant, founder of the Afford Anything podcast, and Jordan Grumet (Doc G), host of Earn & Invest, as they explore the concept of Reverse FIRE. They delve into why some financially independent individuals choose to keep working, emphasizing that purpose often outweighs the desire to retire. The guests discuss the hidden costs of quitting too soon, the importance of autonomy in work, and how retirement should be redefined as a design challenge, not an end point. Plus, they share personal anecdotes on maintaining a sense of purpose while navigating post-financial independence choices.
13 snips
Oct 22, 2025 • 1h 14min
Your Money Problems Aren't Math Problems (They're People Problems) SB1751
In this discussion, Carl Richards, a financial planner and New York Times columnist known for his insightful 'Sketch Guy' drawings, shares invaluable insights on why money problems are often about emotions rather than equations. He emphasizes the importance of personal stories in financial decisions and suggests starting conversations with intimate questions. The hosts also delve into the complexities of options trading, debating their legitimacy as a risk management tool versus just financial gimmickry. Tune in for practical advice on simplifying your financial life!
10 snips
Oct 20, 2025 • 1h 11min
Should You Drain Your Emergency Fund? (And 4 Other Money Questions Keeping You Up) SB1750
In this discussion, financial planner Anna Allem shares her expertise on emergency funds and insurance. They debate whether draining your emergency fund to pay off debt is wise and evaluate the real necessity of whole life insurance for children. The conversation also dives into how much life insurance one actually needs and the risks of investing part of an emergency fund. Through differing opinions and practical tips, listeners gain insight into navigating their own financial dilemmas.
13 snips
Oct 17, 2025 • 1h 7min
What Lucky People Do Differently With Money (SB1749)
Join Paula Pant, founder of the Afford Anything podcast, and Chris Luger from Heavy Metal Money, as they explore what sets lucky individuals apart financially. They reveal that creating luck hinges on curiosity, generosity, and flexibility. Discover how helping others can enhance your financial strategy, and why being persistent can open up new opportunities. Learn about the importance of building genuine relationships over transactional ones, and how to adapt your financial plans when faced with unexpected changes.
11 snips
Oct 15, 2025 • 1h 12min
How to Deliver the “WOW” in Everyday Life (with longtime former Royal Caribbean Chairman and CEO Richard Fain) SB1748
Join Richard Fain, the former CEO of Royal Caribbean, as he shares insights on leading with purpose and creating memorable experiences. He reveals how to transform ordinary moments into opportunities to 'deliver the WOW' in life. Richard discusses the importance of long-term vision over quick gains and how to foster intentional company culture. Learn about engaging diverse teams and retaining talent through example-setting. Get inspired with practical tips to bring creativity and generosity into your everyday life!
