The Stacking Benjamins Show

Ever wondered how to tailor financial advice to your net worth? This conversation breaks down the wealth ladder, offering insights for every stage—from $10K to $10 million. Discover why following generic tips can hinder your progress and learn when a Roth IRA conversion truly benefits you. The hosts mix humor with valuable lessons on diversification, risk management, and the pitfalls of impatience in wealth building. Plus, enjoy community stories of triumph and nostalgic trivia celebrating Robin Williams, keeping the tone light and engaging.

Join hospice doctor Jordan Grumet, also known as Doc G, and financial guru Paula Pant as they dive into the essence of living a purposeful life. They discuss the detrimental effects of hustle culture and the importance of taking action now. From strategies to overcome indecision to the surprising link between choices and regret, these experts share valuable insights on goal setting and productivity. Their humorous and relatable banter makes exploring life's time-wasters both entertaining and enlightening.

Retired Lieutenant Commander Gary MacDermid, a business coach with a military background, shares his insights on goal-setting with unyielding discipline. He emphasizes the importance of defining SMART goals to avoid burnout from borrowed aspirations. The conversation covers techniques for sustainable habit formation and developing multiple income streams. Additionally, they tackle the often-overlooked topic of long-term care insurance, discussing when it’s necessary and how to evaluate your options. Packed with actionable advice, this chat helps you take charge of your goals and financial future.

Reflect on your financial trajectory as the year unfolds. Discover insights on risk management from successful entrepreneurs and the importance of intentional spending. Understand the flawed connection between money and happiness, and explore how your community can enhance your financial well-being. Dive into joyful retirement planning and the significance of setting realistic milestones. Embrace a proactive mindset as you reassess your goals, making this your moment to recalibrate without the guilt.

Paula Pant, founder of Afford Anything, and Len Penzo, personal finance guru and TikTok legend, bring hilarity and wisdom as they tackle what we should stop buying. Discover why your treadmill may just be a fancy coat rack and the hidden costs of seasonal decorations that drain your wallet. They dive into magazine subscriptions as budget vampires and reveal unexpected items that quietly suck away your cash. With trivia and personal anecdotes, their lively banter makes decluttering your finances both fun and insightful!

In this engaging discussion, Ken Honda, Japan's bestselling personal development guru and author of 'Happy Money,' dives into how gratitude can transform your relationship with finances. He shares insights on emotional finance, revealing that small mindset shifts can lead to significant life changes. The conversation also uncovers hidden fees in real estate commissions, urging listeners to be vigilant. Plus, practical tips on maximizing Health Savings Accounts and the complexities of hiring your kids for Roth IRA contributions add to the mix.

In this enlightening discussion, organizational expert Tracy McCubbin, author of "Making Space, Clutter Free," navigates the emotional ties we have with clutter. She reveals why letting go can be liberating and offers strategies for donating intentionally. The conversation also touches on crucial financial advice, emphasizing the significant losses retirees face by claiming Social Security too early. Plus, a whimsical look at the Taco Bell Hotel promises some laughs! Tune in for practical tips on decluttering and securing your financial future.

Join Dorethia Kelly, a TikTok content creator and money coach, who transformed her financial life as a single mom, as she shares insightful strategies for smart money choices. Jesse Cramer, a personal finance expert, discusses the importance of intentional investing and budgeting to achieve financial independence. Steve Stewart reveals his journey toward mortgage freedom and the pivotal moment that changed his financial outlook. Together they tackle debt, lifestyle creep, and the need for open family discussions about money, all while keeping it fun and engaging.

Julie Wainwright, founder of luxury consignment store The RealReal, shares her journey from setbacks like Pets.com to billion-dollar success. She discusses overcoming ageism in entrepreneurship and how your past failures can inform future triumphs. Julie emphasizes the importance of risk-taking and confidence while revealing the untold story of luxury resale markets. Listeners will gain insight into building a brand against the odds, and how perseverance can redefine one’s career path, regardless of age.

How much can you really spend in retirement without running out of money—or worse, running out of fun? In this deeper-than-usual dive, Joe Saul-Sehy and OG examine the classic 4% retirement rule and whether it’s time for an upgrade. With new commentary from Bill Bengen, the original architect of the 4% rule, the team explores emerging research that suggests a withdrawal rate closer to 5.5% might be possible—if you’ve got the right mix of investments, a solid plan, and a bit of courage. But we don’t stop there. Because with greater freedom comes greater risk (especially if you're leading with vibes instead of strategy). The guys tackle the sequence of returns risk that can derail early retirement years, and how to build a portfolio that helps you sleep at night—even during a market storm. Meanwhile, Doug drops in with an unexpected (and very British) culinary experience, Joe fields a listener question comparing financial plans to workout routines (is your Roth IRA doing enough reps?), and yes... we revisit our fan-favorite segment on how food waste is wrecking your budget. Why the 4% rule might be too conservative (or maybe just outdated). What diversified portfolios and asset class strategy have to do with a longer-lasting nest egg. How to prepare for market downturns before they happen—and what to do if you're already in one. Why retirement joy isn’t just about spreadsheets—it’s about the psychology of spending with confidence. Which type of green tea is the superior kind (depending on which side of the TikTok aisle you're on). How to reduce food waste and put that extra savings toward your bigger financial goals. If you’re approaching retirement—or even just dreaming about it—understanding how much you can safely spend without sabotaging your future is the question. This episode combines historical insight with today’s market realities to give you the real math and mindset you need to retire well…and maybe even with a smile. FULL SHOW NOTES: https://stackingbenjamins.com/problems-with-the-4-percent-rule-1702 Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.stackingbenjamins.com/201 Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices