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
Aug 22, 2025 • 1h 2min
Estate Planning, Charitable Giving, and Financial Hot Takes (SB1725)
Paula Pant, a negotiation expert from Afford Anything, teams up with Jesse Cramer, a financial strategist for long-term investors. They dive into the intriguing debate of giving now versus later and the benefits of donor-advised funds. Discover whether anonymous donations are underrated superpowers or publicity lost. The conversation takes a lighthearted turn with humor and relatable anecdotes, making complex topics like estate planning more accessible, while encouraging you to start those important financial legacy conversations.
16 snips
Aug 20, 2025 • 1h 15min
Donor Advised Funds 101 (with Adam Nash) SB1724
In this engaging discussion, Adam Nash, founder and CEO of Daffy, shares his insights on donor-advised funds as a revolutionary approach to charitable giving. He explains how these funds can simplify and enhance your generosity. The hosts also dive into practical advice on handling car insurance claims, blending humor with serious financial strategies. Listeners will learn the advantages of consistent giving, navigate the complexities of insurance policies, and walk away with valuable tools for effective philanthropy and financial safety.
14 snips
Aug 18, 2025 • 1h 1min
3 Questions You're Dying To Know about Estate Planning (with attorney Tim Semro) SB1723
Tim Semro, an estate planning attorney, breaks down the often-misunderstood world of wills and trusts. He explains the critical differences and when to use each one, highlighting common pitfalls with beneficiary designations. The conversation dives into tricky scenarios, like managing probate across state lines and the complexities of life insurance. Tim dispels myths, offers peace of mind strategies, and shares captivating stories that illustrate the real-world importance of planning. Tune in for laughter and insightful tips!
10 snips
Aug 15, 2025 • 1h 2min
Is Chasing Work-Life Balance Worth the Investment? (SB1722)
Paula Pant, a personal finance expert and host of the Afford Anything podcast, teams up with Jesse Cramer, a financial analyst and host of Personal Finance for Long-Term Investors, to discuss the elusive quest for work-life balance. They explore why chasing this balance may hinder fulfillment, promoting alignment and integration instead. The conversation includes hilarious anecdotes, personal insights into managing productivity, and practical advice for creating a fulfilling work-life dynamic. Get ready to rethink your priorities and laugh along with their Nautica nostalgia!
11 snips
Aug 13, 2025 • 1h 5min
How One Entrepreneur Constructed a Better Tomorrow (with Cheryl McKissick Daniel) SB1721
Cheryl McKissick Daniel, President and CEO of McKissick & McKissick, shares her family's remarkable journey in construction, emphasizing entrepreneurship across generations. She reveals strategies to turn challenges into opportunities, highlighting the value of reputation as a currency in networking. Cheryl discusses the importance of adapting financial plans and building strong teams to succeed. With insights on negotiation and resilience, listeners gain practical advice to thrive in their careers and businesses while navigating life's unpredictabilities.
28 snips
Aug 11, 2025 • 1h 2min
How To Fix 8 of the Most Common 401k Mistakes (SB1720)
Learn about the most expensive mistakes people make with their 401(k)s and how to fix them quickly. Discover why employer matches are basically free money and explore smart strategies for rolling over old 401(k)s. The conversation shifts to the emotional challenges of transitioning from saving to spending in retirement, offering practical tips to spend guilt-free while aligning withdrawals with personal values. Understand how to turn your nest egg into a meaningful income stream and embrace financial freedom for a fulfilling life.
10 snips
Aug 8, 2025 • 55min
Hot Financial Takes: Are You In or Out? SB1719
Joining for a lively roundtable are Paula Pant, host of the Afford Anything podcast, Jesse Cramer from Personal Finance for Long-Term Investors, and Don McDonald of Talking Real Money. They dive into hot financial topics, like whether cash or credit is best for beginners and the real trade-offs of delaying homeownership. The conversation covers essential insurance needs, the impact of hiring a CPA, and insights on Roth vs. Traditional 401(k) strategies. Plus, they debate target date funds and whether to keep collision insurance on older cars, all with a fun twist!
23 snips
Aug 6, 2025 • 1h 16min
Master the Art of Negotiation with Paula Pant (SB1718)
Paula Pant, host of the Afford Anything podcast and a negotiation instructor, shares powerful insights to help listeners master the art of negotiation. She discusses overcoming fears in negotiations, emphasizing aspiration and reservation points for successful outcomes. Topics range from tackling salary discussions to everyday negotiations, like avoiding chores. The conversation also touches on innovative strategies for workplace retirement plans and the realities behind viral financial advice, all sprinkled with humorous anecdotes and nostalgic TV references.
7 snips
Aug 4, 2025 • 1h 21min
A Sandwich Guide to Navigating Inflation (plus how to plug 401k "leakage") SB1717
Len Penzo, an award-winning personal finance expert, joins the hosts to explore the quirky intersection of inflation and sandwiches through his Annual Sandwich Survey. They discuss surprising shifts in sandwich prices and how to keep enjoying affordable lunches despite rising costs. The conversation then shifts to troubling trends in 401(k) hardship withdrawals, offering valuable insights on how to secure retirement savings. Plus, Stacker community member Christine shares essential tips for reducing college expenses—definitely worth a listen!
7 snips
Aug 1, 2025 • 1h 6min
What Would YOU Do With $50,000? (SB1716)
Join Paula Pant, founder of Afford Anything and a savvy real estate investor, along with Jesse Cramer, founder of The Best Interest, as they dive into the capital conundrum of what to do with a sudden $50,000. They emphasize starting with mindset and goals before addressing high-interest debt, investing, or splurging. The conversation reveals common pitfalls in managing windfalls and tackles the 401(k) match dilemma. Expect playful banter mixed with valuable insights on navigating unexpected financial blessings.
