Although I’m not a Swiftie myself, I can’t help but admire Taylor Swift’s business instincts. Anyone who can release five versions of the same album and still sell out worldwide tours is clearly doing something right — and plenty of us have been taking notes. The only problem? I don’t personally know Taylor Swift, and I can’t exactly text her for advice.
Enter ChatGPT.
Thanks to OpenAI’s latest updates, the AI’s ability to tone-shift is shockingly strong. So I decided to put it to the test. A lot like my one-word-rule trick, I asked ChatGPT to give me real business advice "like Taylor Swift."
Now, this could work for really anything. Cooking advice in the voice of Gordon Ramsey, fashion advice in the voice of Giorgio Armani, tennis tips in the voice of Roger Federer...I think you get the idea.
What I got back was surprisingly grounded, insightful and delivered with the kind of clarity, vulnerability and brand discipline Swift is known for. Here are the seven prompts I used — and how ChatGPT responded when I told it to “Answer this like Taylor Swift.”
1. Getting started with a business idea
Prompt: What’s the first thing I should do before starting a business?
ChatGPT’s response delivered more than a good business tip; it's a piece of creative writing that performs Taylor Swift-ness. It answers the prompt correctly by providing a solid first step (discovering your purpose/motivation), but what this really shows is how the AI delivers the answer through the crafted persona.
A less skillful AI response might have just said, "Taylor Swift would say to believe in yourself and write a business plan." But ChatGPT built an entire story around the advice, making it feel like it's actually coming from Taylor Swift, not just about her. It's a strong example of how ChatGPT can be used for stylistic imitation.
2. Standing out among the competition
Prompt: How do I stand out in a crowded market?
What was cool with this response was that ChatGPT identified and synthesized key aspects of Taylor Swift’s brand and delivered key ways to stand out, such as leaning into the personal narrative and reinventing yourself when necessary to develop a true connection with your audience. This is actionable business advice, and the response feels uniquely “Taylor” while still being genuinely useful.
This exercise shows how ChatGPT can move beyond surface-level imitation to create a coherent, thematic voice, making the character an effective vessel for delivering a response.
3. Handling competition
Prompt: What’s your advice for dealing with competitors?
ChatGPT has fully embraced the character, demonstrating the advanced capability to maintain a style across multiple chats. For this prompt, it details how strategy is storytelling and ownership is everything. The advice of finding your purpose and focusing on your craft rather than competitors is universally solid.
The “Reputation” album reference provides a unique allegory, and it feels like ChatGPT is performing a kind of creative synthesis, blending known facts about what works in business with thematic extrapolation. Yet, because the business advice is coming “from Taylor,” it seems personal and very on-brand.
4. Building your audience
Prompt: How do I build a loyal customer base?
This answer on building loyalty is perhaps the most meta and self-referential of the prompt responses so far because it directly analogizes from Taylor Swift's core competency: cultivating an unprecedentedly loyal fanbase. The AI goes beyond advising to specifically drawing the blueprint from the persona of Taylor's own greatest success story.
What’s interesting is the result is a hybrid: part aspirational alter-ego of Taylor Swift, part functional business coach. The advice is top-tier strategic and psychological guidance. It perfectly addresses the "heart" and "mind" of entrepreneurship: your motivation, your identity, your mindset and your relationship with your audience.
5. Crisis management
Prompt: What should I do when something goes wrong?
Failure is never easy to discuss, but somehow ChatGPT makes it easier, coming from Taylor Swift. The response outlines a five-stage process for crisis management that is both emotionally intelligent and strategically sound. From emotional acceptance and analytical reflection to narrative control and perseverance, this response offered how to take responsibility and apologize for mistakes.
A typical prompt to ChatGPT on how to overcome a mistake would probably offer some version of this, but the holistic approach here, which blends emotional processing and practical action, is very “Taylor Swift.”
6. Overcoming self doubt
Prompt: How do I overcome fear or impostor syndrome?
The response provides a five-step cognitive-behavioral and narrative framework for overcoming self-doubt. It touches on all the important aspects, including acceptance, reframing and action.
This advice captures the action-before-confidence principle that is the only real antidote to impostor syndrome. Confidence is a result of action, not a prerequisite for it. ChatGPT may have offered this advice, but might have done so more generally. This response synthesizes the broader “business Taylor” philosophy that I was going for.
7. Long-term planning
Prompt: What’s your best advice for long-term growth?
The response outlines a growth model that is organic, intentional and relationship-based, directly opposing the "growth-at-all-costs" and "hustle" mentality. The visionary advice really feels like it embodies Taylor Swift’s own philosophy while also being useful for nearly any entrepreneur to implement into their own strategy.
ChatGPT’s Swift-style responses reveal:
- strong brand strategy
- emotionally intelligent leadership
- thoughtful communication
- practical business fundamentals
- a deeper emphasis on purpose and consistency
Final thoughts
Sure, I could have asked ChatGPT for advice based on Taylor Swift’s success (or Warren Buffett’s or Oprah), but the takeaway here is that ChatGPT can embrace the persona and deliver in the style/voice of a particular individual you choose.
This experiment worked because Taylor Swift’s real-world career is built on clarity, narrative control, connection and reinvention — all things entrepreneurs genuinely need. And, turns out, business advice goes down easier when it feels like someone’s handing you a glitter pen instead of a binder of KPIs.
Give it a try and let me know what you think in the comments.
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