The Stacking Benjamins Show

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


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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!

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