The Stacking Benjamins Show

• Harvard Business Review's Kevin Evers on the Genius of Taylor Swift (SB1671)

  What Taylor Swift teaches us about strategy, long-term thinking, and building an empire. Taylor Swift isn’t just a pop icon—she’s a master strategist. And in this episode, we unpack exactly how she built a cultural and financial empire with smart moves that offer powerful lessons for any Stacker. Joe Saul-Sehy sits down with Kevin Evers of Harvard Business Review Press to explore: How Taylor’s early partnerships set her on a path most artists never get to walk Why a clear vision—and the discipline to stick to it—can be a superpower How she turned frustration into creative fuel and conflict into leverage The surprising role MySpace and radio tours played in her initial success And what her story teaches us about marketing, risk-taking, and ownership But the show doesn’t stop there. Joe and OG also dive into: Grant Cardone’s 401(k) comments and whether his hot takes hold up The risks and rewards of real estate What crypto storage, insurance, and documentation mean for your financial safety net Plus, Mom’s neighbor Doug jumps in with a tax-themed trivia challenge—and a few surprising family stories to bring it all back home. Whether you’re a Swiftie, a strategist, or someone just trying to make smarter money moves, this episode delivers sharp takeaways and fresh perspectives. FULL SHOW NOTES: https://stackingbenjamins.com/all-about-taylor-swift-business-genius-1671 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

  --------  

  1:15:56
• Money and Business Lessons from the Career of Taylor Swift (and a BIG Roth IRA rule clarified) SB1670

  It’s Taylor Swift week in the basement, and we’re kicking things off by looking at the business behind the beats. Joe, OG, and the gang pull back the curtain on the intentional, savvy moves that took Taylor from breakout teen artist to industry powerhouse—and why her playbook might just work for your financial life, too. We’re talking about more than album drops. This episode covers: The power of controlling your own creative output Why strategic collaborations and timing matter How to avoid your own “sophomore slump”—in music or investing The underrated value of clarity, consistency, and small-but-steady improvements Then, we take a sharp turn toward the world of Roth IRAs, answering a listener question about the five-year rule and clearing up common misconceptions. If you’ve ever been confused by tax rules or unsure when you can touch your money, this one’s for you. Plus, there’s plenty more along the way: A local company stops making yardsticks (and we may be way too interested in that) Salutes to the troops, and a shoutout to basement podcasters A colonoscopy story you didn’t ask for, but will absolutely remember Whether you’re a Swiftie, an investor, or just here for the financial clarity, this episode brings strategy, insight, and unexpected takeaways you can actually use. FULL SHOW NOTES: https://stackingbenjamins.com/the-strategic-genius-of-taylor-swift-1669 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

  --------  

  1:14:51
• Conquering Investment Fears and Risks (SB1669)

  Feeling anxious about where your money’s going? You’re not alone—and you’re not without a plan. In today’s episode, Joe is joined by OG, Mom’s neighbor Doug, and two sharp minds from the personal finance world: Paula Pant from Afford Anything and Dr. Jordan Grumet from Earn and Invest. Together, they take a deep dive into the many faces of investment risk, from the obvious to the overlooked. Because when it comes to your financial future, the real danger isn’t just volatility—it’s misunderstanding the terrain. Whether you're dipping a toe into international markets, piling into real estate, or wondering if your long-term plan can survive a little inflation, this episode will help you better understand the risks that matter—and avoid the ones that don’t. 💡 What’s inside: Why market risk feels scary—but often isn’t the real danger How liquidity and time horizon risks can quietly erode your strategy The danger of overconcentration (ahem, putting all your eggs in one ETF) What inflation, reinvestment, and credit risk mean for your future How to navigate longevity and foreign investment risks without flinching And of course, the basement wouldn’t be the basement without a few detours—including a surprise milkshake debate and Doug’s trivia segment that takes a sharp left into apple peels, Johnny Appleseed, and questionable coalition logic. If you’re ready to face the real dangers of investing—and stop fearing the ones that don’t deserve your attention—this episode’s got you covered. 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

  --------  

  1:11:41
• How To Smooth Out Your Investing Ride...or not (SB1668)

  Market volatility, overthinking portfolios, and why simple might be smarter. Trade wars. Tariffs. Tumbling markets. When headlines scream and your portfolio wobbles, what’s a Stacker to do? Today, we tackle how to invest confidently during uncertain times—without overcomplicating your strategy or losing sleep. We start by breaking down smart ways to manage volatility, whether you’re just getting started or already a seasoned investor. Then we dig into a great question from Stacker Ryan: should you stick with a diversified portfolio or choose a one-stop fund solution like those from Dimensional or Avantis? 🧠 In this episode: How to hedge against market swings without panicking Why keeping it simple could beat fancy fund strategies What most investors get wrong about stock market “danger” The power of a long-term mindset and how it pays off Tips for building confidence in your own investment decisions We also take a break for the TikTok Minute (yes, we found another gem), and Doug brings a trivia challenge that'll take you back to the dawn of the space race. And later, we open the mailbag: A listener asks how to plan solo for retirement ...and also wonders how much is too much for an emergency fund It’s a full basement session—investing insights, listener Q&A, and a few unexpected left turns. FULL SHOW NOTES: https://stackingbenjamins.com/talking-about-taxes-and-tariffs-in-your-investment-plan-1667 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

  --------  

  1:04:21
• Special Episode: Tariff Fallout - What Should You Do?

  Tariffs got you sweating? We’ve got the strategy (and the LaCroix) to help you chill. Markets are wobbling, headlines are screaming, and you’re wondering if your portfolio is about to implode. Take a deep breath—and head down to the basement. In this episode, Joe Saul-Sehy, OG, and Mom’s neighbor Doug tackle the turbulence triggered by recent tariff changes. While others panic, we’re pouring the coffee and walking you through how to think smarter (and sleep better) during uncertain times. 🔍 Inside the episode: What recent tariff changes actually mean for your money How to protect your investments when markets get shaky Why doing nothing might be the smartest move The behavioral traps investors fall into—and how to avoid them Reassurance, real talk, and your weekly dose of Doug Whether you’re tempted to sell it all or just want a little peace of mind, this episode gives you tools to stay cool, stay invested, and stay the course. Because in the basement, we don’t panic—we plan. Learn more about your ad choices. Visit podcastchoices.com/adchoices

  --------  

  26:44

More Business podcasts

Trending Business podcasts

About The Stacking Benjamins Show