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Great post.

Another benefit of this approach is it’s simply much easier. If you’re trying to act like some smooth corporate salesperson or be overly formal or whatever and that’s not really you, interacting with customers and prospects and… everyone… will feel tiring and painful.

But if you drop the pretense and just act like yourself? Minimal extra energy required. As a bonus, it opens you up to make real connections with people who you click with as you run your business.

So it works, it’s easier, and it’s more fun. And has basically no downsides. But still something that most founders seem to have to learn the hard way for some reason.



I agree with your comment and couldn’t agree more with this article. It’s solid advice for anyone just starting out with a product or service.

Speaking authentically and admitting you don’t have all the answers is genuine, not weak. That kind of honesty has always worked best for me.

People respond better to real conversations, concrete examples, and the feeling that you’re building with them, not just selling at them.

In my experience, working with smaller businesses has opened more doors than chasing big corporate clients. Smaller companies tend to be more curious, open to new ideas, and quick to take action.

That said, “dress to impress” can work, but in my experience, it’s often a short-lived win. It grabs attention, but rarely builds lasting trust or real traction. Not a playbook I buy into.

For example, I recently sat through a 3-hour pitch from a so-called “AI consultant.” The presentation was packed with buzzwords, vague promises, and a sleek slide deck. Every time someone asked how AI would actually solve a specific problem, the answer was basically: “AI will handle that,” followed by name-dropping a popular AI company like it was the solution to everything. It was clear the consultant didn’t fully understand the tech, but the leadership team still ate it up.

This article was a great reminder that trying to sound big and impressive might get attention early on, but it often backfires later. Being honest and straightforward has always been my real strength, even if it keeps me small.


Taleb has written about dressing to impress and looking the part: https://medium.com/incerto/surgeons-should-notlook-like-surg...


Thanks for sharing, packed with solid insights.


Paywalled? Needs a signup apparently.


I don't find it paywalled, but here is an archived version for you to read: https://archive.is/e4O1W




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