Stacking Benjamins: Your Gateway To Money And Personal Finance

What if the scariest part of retirement isn’t running out of money—but losing your sense of identity? This week on The Stacking Benjamins Show, we tackle the fears that hold so many people back from financial independence and a joyful, purpose-filled retirement. Joe Saul-Sehy and Doug are joined by an all-star panel of financial thinkers: Mark Trautman (Mark’s Money Mind) Paula Pant (Afford Anything) Jesse Cramer (Personal Finance for Long-Term Investors) Together, they unpack the emotional, practical, and strategic side of planning your next chapter—whether you're closing in on retirement or still working toward it. The biggest fears about retirement: from running out of money to running out of meaning. The “one more year” syndrome: why it's so tempting to delay and how to break through. Time freedom vs. financial freedom: how to align your life goals with your money strategy. Tactics to conquer fear: income layering, diversified portfolios, annuities, and rental