The Stacking Benjamins Show

Your burning questions fuel this episode! Joe Saul-Sehy, OG, and special guest Christine Benz of Morningstar unpack some of the biggest questions facing investors today—especially those just starting out. We kick things off by diving deep into target date funds. They promise simplicity—but do they deliver long-term results? We explore when they work, when they don’t, and what you should consider if they’re part of your portfolio. Then Christine shares a graduation-season masterclass in financial advice: How to begin investing, even when you feel behind Why lifestyle creep is the silent killer of wealth The importance of building habits now that will serve you for decades Resources and reading recs that can actually move the needle for new grads (and not-so-new grads) We also answer listener questions on: Whether refinancing your mortgage is still a smart move How global shifts in labor and supply chains may impact your finances And why it’s time to give your favorite retirement calculator a second look And somewhere in all this… someone may or may not reveal a dream dinner scenario that involves a pair of country music legends. But, you know, that part probably didn’t happen. Probably. Whether you're just graduating, recalibrating, or rethinking your strategy entirely, this episode is your invitation to stack smarter—and have a little fun while you do it. 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

Jen Sincero, bestselling author and success coach, shares her inspiring journey from living in a garage to becoming a seven-figure entrepreneur. She discusses powerful mindset shifts that transformed her relationship with money and offers advice on self-talk as a critical tool for financial success. Listeners learn practical ways to reprogram their spending and saving habits, along with the importance of consistent investing. Plus, she brings humor with anecdotes about marathon filming and quirky trivia, making for an entertaining and insightful conversation.

Join Jesse Cramer, host of the Personal Finance for Long-Term Investors podcast, as he passionately debates the benefits of buying versus renting a home. He reveals surprising truths about renting, dispels myths about homeownership being a guaranteed investment, and shares the hidden costs many new buyers overlook. With anecdotes and spirited discussions, Jesse emphasizes the need for financial flexibility and personal circumstances in the housing decision. Plus, enjoy some lighthearted trivia and banter that keeps the conversation lively!

Retirement might be the goal, but the journey? Full of curveballs. On today’s episode, Joe Saul-Sehy is joined by special guest co-host Len Penzo of LenPenzo.com, along with OG and Neighbor Doug, for a no-holds-barred look at what really derails retirement plans—and how to build a strategy that can handle the chaos. From unexpected job loss to rising long-term care costs, adult kids moving back home, and even changing relationship dynamics, this episode dives into the often-overlooked risks that can chip away at your retirement dreams. Inside the episode: What to consider when evaluating long-term care insurance How job instability late in your career can throw off your timeline The growing trend of adult children impacting their parents’ retirement Grandparents becoming full-time caregivers—and the financial toll that brings Relationship shifts and widowhood in retirement Downsizing, austerity planning, and staying financially flexible Plus, our TikTok Minute features Gary V on why taking a step backward might be the smartest move forward. And as always, Doug brings the trivia heat—this time, with a nostalgic nod to a certain potato-headed toy. With Len Penzo in the basement, the insights (and squirrel references) are extra sharp. Prepare to laugh, learn, and rethink what “retirement ready” really means. FULL SHOW NOTES: https://stackingbenjamins.com/four-things-that-can-derail-your-retirement-plan-1676 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

Join Angelo Poli, CEO of MetPro and nutrition guru, as he shares valuable insights on achieving wellness alongside financial success. He emphasizes the power of consistent habits over extreme diets and dives into popular trends like intermittent fasting. Angelo also offers practical tips to boost energy and manage health despite a busy life, highlighting how wellness can protect future earning potential. Later, the hosts discuss navigating financial uncertainties and understanding HELOCs—balancing smart health with wise money management.

What do zipper injuries, holiday party mishaps, and servant leadership have in common? They’re all part of today’s wide-ranging look at careers—what to do, what not to do, and how to make your next move smarter (and safer).Joe Saul-Sehy, OG, and Neighbor Doug are joined by contributors Sandy Smith, Jesse Cramer, and a few classic career stories from the SB vault. Together, they explore: The surprising power of likability in the workplace How consistency and personal branding can open big doors Why some leadership styles flop and others inspire The real-life career missteps that made us all a little wiser A closer look at the Elevate Conference, which champions financial literacy for Black women And of course, it wouldn’t be a basement episode without a trivia challenge. This time, Doug delivers a stat that’ll make every listener squirm—let’s just say it involves zippers and emergency rooms.Whether you're climbing the corporate ladder, considering a leap, or just trying to avoid HR’s bad side, this episode packs in real advice and memorable stories from people who’ve been there, done that, and got the awkward email to prove it.Smart moves, cautionary tales, and Doug’s very specific warning about pants—this one's got it all.FULL SHOW NOTES: https://www.stackingbenjamins.com/improve-your-career-trajectory-1674/Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.StackingBenjamins.com/201Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

Lorraine Lee, a former LinkedIn and Prezi leader and sought-after keynote speaker, shares her insights on building a standout career brand. She introduces the EPIC framework—Experiences, Personality, Identity, Community—guiding listeners on personal branding without self-promotion fatigue. Lorraine emphasizes the power of feedback and offers practical tips for mastering virtual interactions. The conversation also touches on financial strategies during uncertain times, including home-buying tips and investment advice, delivering a mix of career and money-savvy insights.

Today’s episode blends career strategy with financial know-how, because who says you can’t build your personal brand and your balance sheet at the same time?Joe Saul-Sehy and OG explore what it really means to shape your professional reputation—from the way you show up in meetings to how you set (and measure) your career goals. Whether you're climbing the ladder, shifting industries, or mentoring others, this episode delivers practical ways to take control of how you're seen and what you stand for at work.Inside this conversation: The “RAVE” model for boosting your brand Why being a cheerleader for your colleagues makes you a standout How appearances and visibility (yes, even your Zoom background) impact your path Real-world tips for growing your influence without bragging—or burning out We also get into the intersection of tech and money: Is AI ready to replace financial advisors? (Short answer: not quite.) What metrics every financially literate person should understand And why your credit card points strategy might need a second look Plus, Doug breaks out a trivia challenge involving coin collecting, and we unravel the very weird truth behind the 1 cent piece.Whether you’re building a career, managing your money, or trying to do both with a little more polish—this episode’s packed with insights that stick.FULL SHOW NOTES: https://www.stackingbenjamins.com/your-career-brand-sb1672Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.stackingbenjamins.com/201Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

Some people master reinvention. They move from one stage of life to the next with confidence, purpose, and an eye on long-term success. What if your financial plan could do the same?In today’s roundtable, Joe is joined by Alyssa Maes, Roger Whitney (The Retirement Answer Man), and OG to talk about what it takes to build wealth that lasts—not just through one season of life, but through all of them.🎯 Inside the episode: What starting strong in your 20s and 30s really looks like How to fight lifestyle creep and sharpen your personal brand mid-career Why simplifying cash flow in retirement can be a game-changer The power of habits, automation, and adaptability across all stages And what consistent, thoughtful choices can do for your long-term success The thread running through it all? Knowing who you are, where you're going—and letting your financial decisions reflect that.We also sneak in a bit of trivia involving the most expensive comic book ever sold and a certain pop icon with a track record of breaking records (you can probably guess who).This episode is about more than music or money—it’s about making every era of your life count.Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.StackingBenjamins.com/201Enjoy! Learn more about your ad choices. Visit podcastchoices.com/adchoices

Kevin Evers, a Senior editor at Harvard Business Review Press, unpacks Taylor Swift's strategic brilliance in building her empire. He reveals how her early partnerships shaped her career and the superpower of a clear vision. Discover how she transformed adversity into creativity and leveraged initial setbacks. Evers also discusses insights into risk-taking, marketing strategies, and the importance of ownership. Along with intriguing takes on real estate and crypto safety, this conversation offers sharp lessons for anyone looking to navigate their financial journey.