Taylor Swift for President, may sound like a farfetched thing but if you look historically at how she outmaneuvered people seeking to control her intellectual property, her brand, and her music, she is executing a brilliant business strategy.
In this post, I’ll touch upon a few concepts about close trusted relationships on strategic thinking and execution that aren’t generally highlighted in books.
Quick Reflection on Taylor Swift
In 2023, her tour generated over 1.4b in revenue. Her movie is slated to see almost 100m and this doesn’t include other forms of income. Prior to 2023, she learned about business the hard way but was underestimated in her calculus.
- Masters of Her Early Music: When Taylor Swift’s former record label, Big Machine Label Group, was sold, she lost the rights to her early music catalog. In response, she decided to re-record her first six albums, allowing her to regain control over her master recordings and potentially divert some revenue away from the original masters.
- Exclusivity with Apple Music: In 2015, Swift wrote an open letter to Apple, criticizing the company for not paying artists during the free trial period of Apple Music. Her public stance led to Apple changing its policy and paying artists during the trial, showcasing her influence and advocacy for artists’ rights.
- Strategic Album Releases: Swift has been known for her strategic album releases. She often surprises her fans with new albums and singles, building anticipation and creating a buzz. This has led to successful album launches and high chart positions.
- Merchandise and Branding: Taylor Swift has been very successful in creating her own brand through merchandise, including clothing and accessories. Her branding and merchandising strategies have enabled her to connect with her fan base and generate additional income.
- Touring Strategies: Swift’s tours are known for their intricate stage designs, engaging performances, and marketing tactics. She has consistently broken attendance and revenue records with her tours, making them some of the most successful in the music industry.
- Streaming Services: After a public dispute with Spotify in 2014, Swift temporarily removed her music from the platform. She returned to Spotify in 2017 on her own terms, which is an example of her ability to negotiate favorable deals with streaming services.
- Partnerships and Endorsements: Swift has collaborated with various brands and companies, including Diet Coke, Apple, and Keds, to expand her reach and increase her income through endorsements and partnerships.
- Ownership of Her Work: With her transition to Republic Records and Universal Music Group, Taylor Swift negotiated terms that allow her to retain ownership of her future master recordings. This move gives her more control over her music and its usage.
- Social Media Presence: Taylor Swift has a strong presence on social media platforms, directly connecting with her fans and promoting her music. Her approach to engaging with her audience has been a key component of her success.
- Philanthropic Initiatives: Swift is also known for her philanthropic efforts, including donations to various causes and charities. Her charitable endeavors contribute to her positive public image and fan loyalty.
Not Obvious
While companies are trying to figure out how to get their business moving, some people have figured out “cheat codes.” If we look again at Tayor, we can see a few things she did to understand, act on and strategically manage conditions and execution. I am not suggesting that she cheated anything but she used the fact that people underestimated her. Her understanding of the situation gives her an advantage.
- She understands her talent and she knows how to use it.
- She knows that people underestimate her and think she isn’t smart. She actually uses this to her advantage and publically calls it out. (Shake it off)
- She has a loyal fanbase. She can stick to her personal values and inspire millions along the way.
- While she doesn’t have a college education, she’s outperformed brilliant business school grads in her age group.
One 2 Three
I wouldn’t call it a hard rule but it is something I’ve seen consistently. Many successful strategic thinkers have very close people they keep in a trusted circle. Generally 3 or less….

It probably looks more like

As an outsider, it is very difficult to know for sure who is in her “inner circle” but if the reports are true, she has her parents, her brother in the first circle. The trust circle closest to her. There are also conditions to the trusted relationships. For x, she may go to y and there are also considerations of timing.
While there may be others that I don’t know about, it is safe to say that her “close thinking” would be done by herself and the smaller group. For the sake of this post, I am keeping it very high level but there are factors like events, timing, psychology that come into play. For example, if my son has me as his closest advisor generally but he may have a life event that he doesn’t want me to know about. He may pull someone closer to him for this event and this “thing” until he figures out what to do. There are also “King Henry VIII” situations. Think about former President Trump. In historical times, you may have made the advisor “cut” and literally lost your head. Today, you go to jail as an expendable advisor who may have been useful for a moment.
Conditions, Tools and Practice
History books are filled with names of the popular person who “did a thing” but not so much the people who helped them do it. Do you know who Octave Chanute is? How about Robert Wayne? Rev. Ralph David Abernathy? Anyone .. ??
Ok, so if you look these folks up, you’ll find they were in close proximity and advisors to greatness. History has a way of mostly ignoring “advisors” but more often than not, ideas come from close conversations with trusted people.
Understanding that trusted advisors can help keep a person aware of their blindside.
Beyond the trusted advisors, stategists need to think and understand what conditions exist in their world, timing, tools they have at their availability which include resources and practices of (how to) use the tools.
Achieveing Greatness Alone
If we look all throughout history, it is highly unlikely that any one person achieved anything great or impactful wholly alone. We often see people alone in the history books. We see the names of great business leaders, political leaders, military leaders and so on. They had help, they didn’t do it all alone. The lesson here is to “find your people.”
I have worked closely with brilliant leaders, well read, highly capable and in some cases polymaths. Being smart does NOT mean the same thing as being “aware.” A lack of awareness can blindside the most brilliant leaders and strategists.
Some people talk about strategy as if it is a game of chess. While chess may require a strategy, it is NOT a strategic tool per se.
Let’s get back to the Presidency of Taylor Swift!
Aside from the fact that she is a little young for this next election, she would be a viable candidate.
People might question her political experience, knowledge and views along with her ability to handle the pressures of being president.
If she were to be surrounded by knowledgable trusted advisors, she would likely be a great president.
Why?
1) She unites people.
2) People aren’t threatened by her (in fact they underestimate her.)
3) She understands how to run a business.
4) She cares about the environment.
5) She shows kindness and fairness in her behavior.
She gets my vote!
By the way, little known fact that Machiavelli and da Vinci were friends! Could you imagine those converstions?!!!!!
FIND YOUR TRUSTED CIRCLE
Great post Howie. I’ll vote too. The biggest issue for me as an American is we are stuck in the mud of our dual parti model. We know that diversity of thoughts is a way to provide better harmony. How to break that current structure?