The Taylor Swift Debate, Henry Kissinger Undergrad Thesis, Reading Recommendations
The Sunday Digest
Taylor Swift has built an empire that redefines what it means to be an artist-entrepreneur. Her ownership battles, billion-dollar tours, and mastery of narrative have been hailed as a leadership blueprint for a new generation. Yet critics argue her success rests on singular talent, timing, and cultural lightning strikes that no strategy can replicate.
This episode debates whether Swift offers a replicable playbook for millennial leadership—or whether her empire proves she’s the rare exception who can’t be copied.
For Taylor Swift fans, these are additional readings
How Taylor Swift Works: Magic of Creative Process
We have discussed pop icon Taylor Swift before. If you haven’t read the piece yet, now would be a good time.
If Taylor Swift were a stock, would you invest in her?
Being contrarian isn’t easy but surely worth it. Listen to this Network Capital podcast with Dr. Shashi Tharoor.
Taylor Swift and the Mysteries of Web 3.0
The first era of the web about was about how we process and consume information. Yahoo, Netscape, Craigslist, AOL etc were web 1 companies. Google “won” this era.
Henry Kissinger’s Undergrad Thesis
Kissinger enrolled at Harvard College after serving in World War II and graduated summa cum laude in 1950 with a degree in Government. His senior thesis, famously over 300 pages long, led Harvard to set a maximum word limit for future theses (sometimes jokingly called the “Kissinger rule”).
Introductory Note
The Argument (Introduction and Summary)
History-as-Intuition (Spengler)
History-as-an-Empirical-Science (Toynbee)
History and Man’s Experience of Morality (Kant)
The Sense of Responsibility
When we outsource the core work that defines us, we disconnect from what energizes us.
When European companies abandon perfectionism, they dominate globally.
Spotify didn't wait for perfect audio quality or complete music catalogs: they shipped with 256kbps streams and limited content, then iterated based on user behavior. Today they control 31% of global music streaming.
Supercell's Helsinki team prototypes mobile games in weeks, kills 99% of them, and ships the survivors with basic graphics and gameplay. Result? $2.3 billion revenue from games that looked "unfinished" at launch.
Revolut started as a prepaid card with currency exchange: no lending, no savings, no business accounts. Seven years and 100+ rapid feature releases later, they're worth $33 billion.
TransferWise (now Wise) launched with manual bank transfers and a basic website, ignoring regulatory complexity. They perfected the experience through 10,000+ customer interactions, not compliance meetings.
Even BioNTech broke European pharmaceutical traditions. Instead of decade-long development cycles, they designed their COVID vaccine in two days and shipped for trials within months.