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Owning Your Legacy– What We Can Learn from Taylor Swift's Re-Recordings and Business Strategy

Keep reading for a masterclass in owning your legacy. Learn from Taylor Swift's re-recordings, keen business strategy, and estate planning.

Who knew that being an antihero could look so good?

Known for sharing deeply personal stories through her lyrics, Taylor Swift is arguably one of the greatest songwriters of our generation. (Swifties, members of her fanbase,  would argue that she’s the best songstress of all time.) 

While she is world-renowned for her artistry, it’s time that she is recognized as a business mogul as well. At just 33 years old, she has managed to build an impressive empire that blows other musicians out of the water. Swift has demonstrated that she is just as meticulous about her business dealings as she is regarding her artistic choices.

From Taylor Swift’s re-recordings to real estate, Trust & Will explores important lessons we can glean from the songstress when it comes to taking control over your own legacy by protecting your property.

How much is Taylor Swift worth?

Before we examine what we can learn from Taylor, let’s talk about her success in terms of net worth. According to Forbes, the Pennsylvania native is currently worth $570 million. Elton John is an example of a recording artist who is worth roughly the same. The difference here is that Sir Elton’s music career is over three times longer than Taylor’s. 

Much of her income comes from her music, including record deals and concert ticket sales. That’s no surprise. However, other important segments of her wealth include partnerships and endorsements, merchandising, and an extensive real estate portfolio.

Let’s take a look at some smart decisions that have contributed to Taylor’s legacy thus far.

Building an empire (Taylor’s Version)

She might marry you with just paper rings, but that’s likely because Taylor can buy herself as many shiny things as she likes. At $570 million and counting, Taylor is on a trajectory of leaving behind a massive legacy one day. She’s only 33 years old and has shown no signs of slowing down or faltering since she launched her music career at just the age of 14. 

Much of her success should be attributed to her musical talent and songwriting genius,  but her amassing of wealth has a lot to do with her razor sharp business acumen. 

Here are some notable examples:

1. Taylor Swift re-recording

Taylor signed with Big Machine Records when she was just 15 years old. Due to this contract, Big Machine Records owned all of the music that she recorded. She began re-recording her old albums when she left the label in 2018, after her 13-year contract ended. She then signed with Republic Records under the condition that she owned her own music.

Why is Taylor’s re-recording of her older albums a big deal? 

Although Taylor quietly began to re-record her music that she made under Big Machine Records several years ago, the project began to make headlines when the label was sold to Scooter Braun. He is a big-name manager who manages the likes of Kanye West and Justin Bieber. He then sold her recordings for $300 million to Shamrock Holdings. Because Taylor doesn’t own any of the albums she recorded with Big Machine, payments go directly to Braun and Shamrock. 

Swift publicly spoke against the sale, claiming that Braun bullied her on numerous occasions. She began to release re-recorded versions of her songs under the name “Taylor’s version.” These new recordings sound almost exactly the same as the original versions. The key difference is that any time a fan plays Taylor’s version of the song, the money goes to the artist instead of some big holding corporation that has nothing to do with the artist.

Because Taylor has such a huge fanbase, streaming platforms like Spotify have a reason to promote her new recordings. 

2. Trademarking

Another clue to Taylor’s sharp business acumen is her extensive trademarking efforts. A trademark is a “word, phrase, symbol or design that identifies your goods and services,” according to the U.S. Patent and Trademark Office. Trademarks are a helpful way to distinguish your brand from that of competitors. Further, having a registered trademark prevents competitors from using something that is the same or very similar to yours. Some of Taylor’s revenue comes from merchandise sales and therefore it was a smart decision for her to obtain legal protection for some of her most famous phrases associated with her likeness.

Here are Taylor’s trademarks as of 2023:

  1. 1989

  2. … READY FOR IT?

  3. 1989 TAYLOR’S VERSION

  4. A GIRL NAMED GIRL

  5. AND I’LL WRITE YOUR NAME

  6. BIG REPUTATION

  7. BLANK SPACE

  8. CAUSE WE NEVER GO OUT OF STYLE

  9. CHRISTMAS TREE FARM

  10. COULD SHOW YOU INCREDIBLE THINGS

  11. FEARLESS TAYLOR’S VERSION

  12. FOLKLORE

  13. FOLKLORE ALBUM

  14. LOOK WHAT YOU MADE ME DO

  15. LOVER

  16. LOVER FEST

  17. LOVER FEST EAST

  18. LOVER FEST WEST

  19. MEREDITH & OLIVIA SWIFT

  20. MEREDITH, OLIVIA & BENJAMIN SWIFT

  21. NICE TO MEET YOU. WHERE YOU BEEN?

  22. PLAYERS GONNA PLAY

  23. RED TAYLOR’S VERSION

  24. REPUTATION

  25. REPUTATION TAYLOR’S VERSION

  26. SHAKE IT OFF

  27. SPEAK NOW

  28. SPEAK NOW TAYLOR’S VERSION

  29. SWIFT

  30. SWIFTIE

  31. SWIFTIES

  32. SWIFTMAS

  33. T. S.

  34. T.S. 1989

  35. TAYLOR NATION

  36. TAYLOR SWIFT

  37. TAYLOR SWIFT (Her Signature)

  38. TAYLOR SWIFT EVERMORE ALBUM

  39. TAYLOR SWIFT FEARLESS

  40. TAYLOR SWIFT TAYLOR’S VERSION

  41. TAYLOR SWIFT TOURING

  42. TAYLOR’S VERSION

  43. TAYMOJI

  44. THE 1989 WORLD TOUR

  45. THE OLD TAYLOR

  46. THE OLD TAYLOR CAN’T COME TO THE PHONE RIGHT NOW

  47. THIS SICK BEAT

  48. TS

  49. WELCOME TO NEW YORK, IT’S BEEN WAITING FOR YOU

3. Taylor Swift real estate

What the general public may not know is that Taylor also owns an impressive portfolio of real estate properties worth over $150 million

Here is a list of the real estate she currently owns:

  • The Goldwyn Estate: An 11,000 square-foot historic estate located in Beverly Hills, California. It was purchased in 2015 for $25 million but could sell for roughly $70 million in today’s market.

  • The Holiday House: An 11,700 square-foot mansion in Rhode Island. She purchased it for $17.75 million but has a price tag of $30 million today.

  • Sugar Loaf: In 2014, Taylor purchased two penthouses in the famed Sugar Loaf Building in Tribeca, New York City,  for $19.95 million and combined them into a duplex.

  • Sugar Loaf Part Deux: Taylor wasn’t done combining properties in the Sugar Loaf Building. In 2017 she purchased a townhouse for $18 million, and then a $9.75 million apartment. She connected the two properties, using the townhome as a garage so she could enter directly into the apartment using the garage as a private entrance. (Quite an expensive garage!)

  • Music Row: Taylor made her first real estate purchase when she was just 19 years old. For $2 million, she purchased a luxury condo in Nashville near Music Row. The purchase was made through a Trust.

  • Music Row II: Shortly after her first real estate purchase, Taylor purchased another unit below the condo for $387,000.

  • Northumberland Estate: In 2011, Taylor bought the Northumberland Estate, a 7,700 square-foot home in Tennessee. The $2.5 million estate sits on 6 acres of land.

While these properties were pricey to begin with, they have increased significantly in value in just a few short years. Taylor’s personal desire to combine and expand properties to make them her own has rendered her a real estate developer in some sense, making her properties even more desirable. Celebrity properties also tend to increase in intrinsic value, creating a much greater pool of buyers when they are listed.

4. Aligned partnerships

Taylor is also known for strategic brand endorsements and aligned partnerships. 

While there is no word on how much each of these endorsements and partnerships are worth, she reportedly makes between $418,970 to $698,283 for a single sponsored Instagram post. She has partnered with major brands such as:

  • Coca-Cola

  • CoverGirl

  • Keds

  • AT&T

  • Target

  • Sony Electronics

Swifties love the fact that Taylor isn’t what you would call a “sell-out” because she only associates herself with brands that she personally loves. For example, one of her brand endorsement deals is with Coca-Cola and she is a known Diet Coke addict. She also does her due diligence to make sure that she only strikes good deals. For example, in 2022, FTX offered her a $100 million sponsorship deal. She walked away, and later, there was a class action lawsuit against the company involving celebrities such as Tom Brady, Larry Davis, and Shaquille O’Neal, where celebrity endorsements were believed to drive billions of dollars in damages. 

Lessons you can learn from Taylor about owning your legacy

While most of us won’t be able to amass a fortune as large as Taylor’s, we can still pull several lessons from her strategies thus far.

First, we have seen that Taylor will go extra lengths to ensure that she is the legal owner of her artistic expressions. From trademarking to copywriting and re-recording music, she is making sure that no other entity can take profits that aren’t theirs to take. She likely learned her lessons when she felt utterly powerless when her own music was bought then sold for hundreds of millions of dollars without her having any say in it. When she signed with Republic Records, she likely read the fine print on her contract and asked many questions and made negotiations before she would sign the dotted line.

This brings us to the second point, which is asking the right questions. Taylor doesn’t sign on with just any brand. As we saw with the FTX case, she was the only celebrity influencer who asked the right question and avoided a very sticky class action lawsuit that could have tarnished her reputation. While we might not be playing in Taylor’s same arena, she exemplifies what it means to be a smart businessperson. You don’t say “yes” to every opportunity; you only say yes to the ones that are truly aligned with your personal brand and always ask the tough questions, even if it means you might have to walk away from a big deal.

The final lesson is regarding Estate Plans. These are legally-binding documents that can help protect your assets and ensure that you can pass them down to future generations.  While there is no word regarding the contents of Taylor’s Estate Plan, she has left some easter eggs that hint about it. For starters, we know that it’s at least on her mind. In her hit song “Anti-Hero,” there is a line that says “I have this dream my daughter in-law kills me for the money / she thinks I left them in the will.” It insinuates that Taylor has some anxiety about her wealth and what will happen to it. More concretely, we do know that her real estate was purchased through a Trust. (Read our guide here on the benefits of transferring real estate into a Trust.) This is a smart move that allows you to protect your assets from creditors and certain taxes, as well as keep your estate hidden from the public eye when you pass away. 

With all that Taylor has done, we can confidently say that she has done a great job of protecting her assets, and thus her legacy, and will be able to pass them on to future generations one day.

At Trust & Will, we’re here to help keep things simple. You can create a fully customizable, state-specific estate plan from the comfort of your own home in just 20 minutes. Take our free quiz to see where you should get started, or compare our different estate planning and settlement  options today!

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