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

Actor Simu Liu On Diving In The Dark

Fresh Air

Intro

The AI-powered Podcast Player