“She’s like a sorceress that writes songs that turn men into crying puddles of regret.”

- Ryan Reynolds

Hey Stackers, it’s Joe's mom's friend Gertrude here, spilling the tea hotter than the one I sip at bridge club! Recently, we took a closer look at the glitter-covered empire of Miss Taylor Swift herself. Now, I may not know all the lyrics to Midnights (okay, I might), but I do know a thing or two about building a brand, negotiating deals, and making smart money moves. Just like Tay-Tay.

So pull up a chair, grab your favorite cardigan (you know which one), and let’s unpack what this savvy songbird can teach us about business brilliance, financial finesse, and how to shake off bad investments.

The 411 on Taylor Swift:

200+ million: Total number of Taylor Swift's album sales.
$2 billion: Revenue generated from her Eras World Tour.
100+ million: Monthly Spotify listeners.
13: Total number one albums.
14: Number of Grammys won.
49: Number of songs that she's had hit the Top 10 on the Billboard Hot 100.
2022: Year in which her songs occupied all Top 10 positions on the Billboard Hot 100 in a single week.

Latest Stacking Benjamins Podcast Episodes:

Harvard Business Review’s Kevin Evers on the Genius of Taylor Swift (SB1670)

Listen here →

Money and Business Lessons from the Career of Taylor Swift (plus a BIG Roth IRA rule clarified) SB1669

Listen here →

Money and Business Lessons from the Career of Taylor Swift (plus a BIG Roth IRA rule clarified) SB1669

Taylor Swift isn’t just a pop superstar. She’s also a masterclass in branding, negotiation, and long-term thinking. From owning her music to building a loyal fan empire, her moves offer powerful money and business lessons for anyone stacking their Benjamins. We explored her journey on the podcast, and now we’re breaking down what her story can teach us about money, mindset, and creating your own success.

Start getting clear as early as you can

Taylor was performing and had a record deal with RCA by the time she was 13. That kind of early focus is rare, but it shows how valuable it is to start exploring your interests and building your skills early. Whether you're launching a business, planning your career, or investing your money, the sooner you begin, the better your odds of long-term success.

Find the work that lights you up
Taylor discovered her passion early and went after it with everything she had. Most of us won’t have that kind of clarity at age 13, but that doesn’t mean we can’t get there. If you’re still figuring out what truly drives you, check out this TED article on 7 lessons to help you uncover the work you’re meant to do (link).

Ask the tough questions. Don’t wait until you’re deep in a bad situation to start asking the hard questions. The sooner you get comfortable with uncomfortable self-reflection, the better prepared you’ll be. Check out this article for insights on the questions you should be asking yourself (link).

"The only thing you should focus on is getting better at what you do."

- Taylor Swift

Collaborators, assemble!

Kevin Evers highlights that from the beginning, Taylor collaborated with people who guided her through the tricky music industry and contributed in meaningful ways.

Know when it's time to move on. Taylor’s first record deal was with RCA, but when she felt she had reached her limit with Robert Ellis Orrall’s guidance, she followed her instincts and joined Scott Borchetta’s startup, Big Machine Records. Want to know when it’s time to leave a job? Check out this article from Forbes (link).
Surround yourself with the right people. Throughout her career, Taylor has surrounded herself with top talent in the industry who have nurtured her creativity. Want to know how to build your own strong network? This piece from Inc. is a great start (link).
Bet on yourself. Taylor’s decision to bet on herself and skip traditional career paths has paid off. Are you ready to take a leap? Here’s a piece from LinkedIn on betting on your own potential (link).
The power of preparation. Taylor has wowed those she’s worked with by showing up prepared to contribute and lead every meeting. Want to run more effective meetings? Learn how with this article from Harvard Business Review (link).

“The greatest victory is that which requires no battle.”

- Sun Tzu, "The Art of War"

Taylor Swift’s smart financial moves

Taylor isn’t just a pop music legend; she’s a business mastermind. She’s built an empire that spans music, fashion, and brand partnerships—all while keeping creative control over her career.

Steal like an artist. Take a look at how your role models approach their businesses and think about how you can apply their strategies to your own financial decisions. Want to learn how to ethically model the strategies of successful entrepreneurs? Check out Austin Kleon’s book, Steal Like an Artist: 10 Things Nobody Told You About Being Creative. You can borrow a copy at your local library, or grab your own copy while supporting the show by using our Amazon affiliate link (link).
Stay at the vanguard. We're not talking about the investment firm Vanguard here; we mean staying ahead of the trends in your industry. Want to stay on top of business trends? This article from Kaizen Consulting Group has some great tips. (link).

The power of negotiation and ownership

Taylor's decision to take ownership of her music catalog speaks volumes about the importance of negotiating terms that prioritize long-term control and revenue. It’s not just about the short-term gains but about setting yourself up for ongoing financial success.

Begin with the end in mind. Read all contracts meticulously and be sure you understand them fully before you sign on the dotted line; think ahead and ask yourself if this deal is going to move you closer to where you want to be in the future. Learn how to negotiate mutually beneficial deals that will last by reading this piece from Harvard University's Program on Negotiation (link).
Become an owner. Taylor made a fortune by retaining ownership of the intellectual rights of her work. Likewise, think of yourself as an owner of your own venture and use your capital to be an owner rather than only being a consumer. Learn how to invest in stocks, thinking of yourself as a part owner in every company whose stock you own, by reading this piece about investing like Warren Buffett from Morningstar (link).

Building a personal brand with a fan-centric focus

Taylor isn’t just a singer—she’s the CEO of a loyalty empire. Her fan-first strategy turns listeners into lifelong customers and casuals into Swifties.

It's all about genuine connection. Instead of chasing the algorithm, talk directly to the people who already love you, then surprise and delight them like you’re planning their birthday party. Learn how to turn casual customers into raving fans by reading the book Raving Fans: A Revolutionary Approach To Customer Service. You can borrow it from your local library, or you can grab your copy and help out the show by using our Amazon affiliate link (link).
Give your fans the VIP treatment. Treat your fans (or clients, or readers) like VIPs at your backstage meet-and-greet...answer their emails, remember their names, and maybe throw in a metaphorical friendship bracelet. Learn 11 ways to provide exceptional customer service by reading this piece from Indeed (link).

Smart risk-taking and timing

Swift isn’t afraid to take risks, whether it’s reinventing her sound or dropping surprise albums. The timing of her moves shows how important it is to understand market shifts and position yourself at just the right moment to make the biggest impact.

Stick to your (investment) plan. Ok, real talk. Here’s where we can apply Swift's bold moves to our money-nerd universe. When the market takes a dive and you’re starting to worry about the health of the talking heads on financial TV, stick to your plan. It’s essential to create an investment policy statement that acts as your personal guide through all market cycles. Check out this blog entry from 2014 to learn more about building yours. (link).
Be prepared to weather the storm. Not that Taylor has encountered a prolonged downturn in her career, but you should be prepared to withstand a prolonged bear market by maintaining an adequate emergency fund. The size of your emergency stack is entirely up to you, but general guidelines are anywhere between 3 and 12 months' worth of living expenses. Want to know more about building an emergency fund? Check out this piece from Bankrate (link).

Are YOU ready to dig into the genius business lessons that Taylor Swift has laid out for us over the course of her career?

If you're ready to take a page out of Tay Tay's playbook and apply it to your life, grab your copy of Kevin Evers' book, There's Nothing Like This: The Strategic Genius of Taylor Swift

Mom's takeaway

You don’t have to headline a world tour to take control of your story. Whether you're managing your money, your career, or your fan club of two (hi, Grandma), remember: clear values, consistency, and a little sparkle go a long way.

Our Headline:

In our headline segment, we’re talking about the risks of storing cryptocurrency, inspired by reports out of California where wildfires destroyed cold storage devices. It's a clear reminder that whether you're using self-custody options like USB drives or trusting a third-party custodian, both come with security challenges.

The conversation also touches on broader concerns about storing valuables at home, including cash, gold, and jewelry. It’s a good time to revisit what your insurance covers. OG emphasizes the importance of staying vigilant, keeping documentation up to date, and reviewing your policies regularly. This is especially important for older adults who may be more vulnerable to scams or disasters.

Cold storage isn’t foolproof

Storing your crypto offline can protect you from hackers, but that USB drive still isn’t invincible. Fire, theft, or even forgetfulness can erase everything.

Know the risks of your storage method. If you’re using cold storage, keep it in a fireproof, waterproof safe (not just your sock drawer). Learn some of the safest ways to store your Bitcoin by reading this piece from Investopedia (link).
Crypto Wallet. Check out this piece from NerdWallet to learn about 9 of the best crypto wallets in 2025 (link).

Home storage can be a trap

Check your insurance before assuming you’re covered. Storing valuables at home might feel secure, but if you haven't reviewed your policy, you might be in for a surprise. Learn what your options are to insure your cryptocurrency by reading this piece from CNET(link).
Audit your stuff once a year. Pick a date that’s easy to remember, like your birthday or tax season, and do a quick walkthrough of your valuables. Take photos, save receipts, and yes, include your Pez dispenser collection. Make sure everything is backed up digitally and stored off-site. If your laptop vanishes, your spreadsheet won’t be much help. Learn how to document your personal belongings with this guide (link).

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Thanks for Hanging Out with Us!

Whether you’re a Swiftie or just here for the money talk, we’re glad you joined us on this journey through Taylor Swift’s playbook. We hope these lessons spark ideas in your own financial story, because you don’t have to sell out stadiums to take center stage in your life.

If you loved this episode, forward it to a friend, leave us a review, or make mom proud by hitting that subscribe button. Until next time, keep stacking those Benjamins!