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
Nov 12, 2025 • 1h 23min
Jonathan Clements: Why Simple Beats Complicated Every Time (SB1760)
In a heartfelt conversation, Jonathan Clements, a former Wall Street Journal columnist and founder of Humble Dollar, shares his insights on building wealth through simplicity and consistent habits. He emphasizes that true financial success isn't about complex strategies, but rather about steady saving and making informed choices—like renting vs. buying based on your lifestyle. Jonathan also discusses the importance of preparing for life's uncertainties with insurance and the compelling stories behind his book, My Money Journey, illustrating the power of everyday financial decisions.
9 snips
Nov 10, 2025 • 60min
What a 12-Hour Walk Teaches You About Money (And Life) SB1759
Colin O'Brady, an endurance athlete and author of The 12-Hour Walk, shares his incredible adventures, including a solo trek across Antarctica. He discusses how challenging your mental limits can transform your approach to goals and money. Colin highlights the importance of the 'not yet' mindset, encouraging listeners to reconnect with their aspirations. He also introduces the 12-hour walk as a practice for mental clarity. Plus, Joe and OG dive into listener questions about Roth vs. Traditional 401(k) contributions, illustrating the parallels between financial and physical endurance.
10 snips
Nov 7, 2025 • 1h 11min
What Retirees Wish They'd Known 10 Years Ago (SB1758)
Join Jill Sirianni, co-host of Frugal Friends and author on values-based spending, Jesse Kramer, a personal finance podcaster and CFP-adjacent expert, and Doc G, host of Earn & Invest, as they delve into the five biggest retirement regrets people face. They discuss the pitfalls of poor investment strategies, tax blunders, and the importance of estate planning. The guests share valuable insights on enjoying your money rather than hoarding it, making this a must-listen for those planning ahead!
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!
