The Stacking Benjamins Show

StackingBenjamins.com | Money Podcast | Cumulus Podcast Network
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Apr 8, 2026 • 1h 17min

Why You Should Stop Saving for Retirement 3 Years Early (SB1826)

Jamie Hopkins, retirement expert and author of The Retirement Sketchbook, argues retirement is an identity shift, not just math. He challenges last-minute saving, urges practicing spending before you retire, and warns about home bias and geographic concentration. He also covers preparing for forced retirement and creative uses of home equity.
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15 snips
Apr 6, 2026 • 1h 9min

You Don't Need a Huge Income to Build Real Wealth SB1825

Len Penzo, personal finance blogger and author, shares practical frugality habits and money stories. He explores Midwest millionaire traits anyone can adopt. Short, actionable habits—from a 20-minute monthly money check to intentional spending choices—are highlighted. The conversation also covers interviewing financial advisors and balancing generosity with smart saving.
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27 snips
Apr 3, 2026 • 1h 8min

Building Your Personal Finance Curriculum (At Any Age) SB1824

Ruben Miller, financial advisor and founder of Paloma Capital who writes Fortunes and Frictions, helps build a lifelong personal finance curriculum. He covers honest money inventories, planning around the next 3–5 years, sensible protection priorities like disability over unlikely risks, modern cash placement, and why behavior beats math. Short, practical building blocks for any age.
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11 snips
Apr 1, 2026 • 1h 6min

You Don't Need a Big Break to Become a Millionaire -- You Need a Better System (SB1823)

Bola Sokunbi, founder of Clever Girl Finance and author of Clever Girl Millionaire, is a personal finance educator who teaches women money, investing, and entrepreneurship strategies. She outlines four wealth-building pillars and shares stories about salary negotiation, a costly rollover IRA mistake, real estate lessons from a bad tenant, and how stacking income, investing, real estate, and entrepreneurship accelerates wealth.
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10 snips
Mar 30, 2026 • 50min

What to Do With Your Money When the Market Is Scaring Everyone Else (SB1822)

They explain why normal intra-year drops make small dips unimportant. They show how a written investment policy and automated rebalancing rules stop emotional trades. They demonstrate how checking less often changes your perspective on volatility. They introduce a four-factor, risk-based method for sizing emergency funds instead of the generic three-to-six month rule.
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12 snips
Mar 27, 2026 • 1h 8min

Stop Relying on Willpower (Build This Instead) SB1821

Jesse Cramer, investor and long-term planning guide, and Paula Pant, financial independence advocate and habit designer, explain why willpower fails and systems win. They discuss automating savings, choosing start-small vs start-big strategies, simplifying accounts and cards, the joy budget to align spending with values, and using AI to spot forgotten subscriptions.
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20 snips
Mar 25, 2026 • 1h 10min

Even the Pros Are Wrong Half the Time. Here's What They Do Differently SB1820

Lee Freeman-Shor, an investment manager and author who studies fund manager behavior, and Claire Flynn Levy, founder of Essentia Analytics and former CIO, discuss how top investors win by process not pick accuracy. They cover why pros are often wrong, rules-based selling and sizing, handling losers and letting winners run, and real-world case studies on repeatable systems and market quirks.
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22 snips
Mar 23, 2026 • 1h 6min

The Real Return on Your Emergency Fund Has Nothing to Do With Interest Rates SB1819

They reframe emergency savings as protection that prevents panic selling and costly, emotional decisions. They compare places to hold cash like high-yield savings, CDs, money markets, and T-bills. They explain CD laddering, FDIC limits, and tax differences for Treasuries. They promote a “good enough” cash plan, a five-column cashflow framework, and practical rules for liquidity versus yield.
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10 snips
Mar 20, 2026 • 1h 10min

How to Build a Financial Plan That Holds Up When Life Doesn't SB1818

Paul Merriman, longtime investor and educator known for practical portfolio strategies, lays out how to build resilient financial systems. He talks about avoiding flashy "sports car" portfolios, improving simple one-fund approaches, and why diversification can feel like failure before it protects you. Also covers cash reserves, insurance, job‑loss risk, and skills that keep plans intact under pressure.
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9 snips
Mar 18, 2026 • 59min

What to Build After You Hit "The Retirement Number" (SB1817)

Amy Minkley, FI traveler and community builder who runs retreats in Bali, retired early and now crafts purpose-driven gatherings. She describes trading the spreadsheet for community, creating retreats that blend meaning and giving back, and why designing life beats simply escaping. The conversation also covers how to size emergency savings around essentials and avoid common cash-and-credit mistakes.

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