Standout Branding Starts Here

A few months ago, I found myself on a call with the founder of AI Toast — a promising, yet relatively unknown, AI newsletter.

It wasn’t a cold call or a job pitch. Instead, it started with a single question I asked during a public discussion: “In the sea of AI newsletters like Rundown AI, Superhuman, and Neat Prompts, how do you stand out?”

That question changed everything. It led to an invitation to write and consult with them and, ultimately, play a key role in shaping their brand.

But it also reminded me of a vital truth: the path to building a standout brand isn’t paved with generic tips or trends. It starts with asking the right questions.

Most people assume branding is about colors, logos, or slogans. But those are just byproducts of a deeper process. The strongest brands stand out because they answer questions that matter, questions customers themselves might not know to ask.

Let’s return to AI Toast for a moment. The inboxes of AI enthusiasts are flooded with newsletters making nearly identical promises: “Get the latest AI trends every morning!” My initial question pierced the veil.

Instead of asking, “What AI topics do you cover?” (which yields the same answers as everyone else), I pressed into, “How do you make readers feel differently from the competition?”

This shift from superficial to strategic questions is where brand-building begins.

Great brands aren’t built on generic answers. They’re built on clarity about why they exist. That clarity comes from asking harder questions:

• Why should anyone care?

• What are we willing to do differently, even if it’s risky?

• What’s the bigger change we want to help people make?

When working with AI Toast, our key breakthrough wasn’t a new design or a catchy catchphrase. It was drawing out their real motivation: creating space for AI curiosity, not AI hype.

This then shaped everything, the tone, the rhythm, and the stories. It became their backbone.

Sometimes brands stall because they fall in love with their own story. By continuously asking “What am I missing?” or “What about this doesn’t make sense to a new reader?” we expose assumptions that can limit growth.

During workshops, I often ask founders to pretend they’re outsiders encountering their brand for the first time. What would confuse them? What big promises are easy to make but difficult to keep? These questions hurt, but they’re supposed to. Growth starts on the other side of honest answers.

For a moment, imagine you’re trying to take a great photo in a crowded market. You can’t just snap a wide shot and hope your subject stands out. You need to zoom in, adjust your focus, and change your angle.

In the same way, asking sharper, more intentional questions allows you to zoom past surface-level branding and find what’s truly unique about your story.

Brands willing to do this end up with images that can’t help but draw attention.

If there’s one lesson I’ve learned, both in my own companies and with hundreds of brands, it’s this: you can’t “position” a brand in the market by force. You have to keep peeling back layers with questions, daring to confront uncomfortable truths until what’s left is something only you can say.

So the next time you sit down to build a brand, or simply want your work to stand out, don’t start with answers.

Start with questions. Ask until you feel a little uncomfortable, a little exposed.

That’s usually where the real magic starts.

— Shashank

P.S. 

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