Stress-Testing a New Business Idea with ChatGPT

When you’re first starting a business, it’s easy to overestimate how many customers you will have in your first year of operation and, therefore, how much revenue you could potentially generate. As a perpetually optimistic person, this is one of my greatest weaknesses, because once I’ve spotted a problem, for which I believe I have the solution, it then follows in my mind that everyone will want it!

Of course, what I’ve learned over the years, and through building multiple businesses, is that attracting customers takes a considerable amount of time, testing, sometimes pivoting, and always iterating. It’s highly unlikely that the business you start will be the same business after twelve months, especially if you’re struggling to attract clients. It’s a matter of taking what’s working, discarding what isn’t, and building on what you’ve learned. Expecting to do the same thing again and again, and achieve a different result, is the quickest way to fail.

Over the past few months, I’ve been working on a new venture — a directory for premium experiences. Think of it as a place where people can discover high-quality, book-worthy experiences and the small businesses behind them. The site is built, and now comes the hard part: recruiting those businesses to join the platform.

In my mind, everyone would want to list their experience. Why not? There’s a free option, and it costs them nothing. But of course, free won’t sustain a company. The revenue comes from upgraded listings with richer profiles and visibility features.

I knew I needed a reality check before getting carried away — and that’s where ChatGPT became my stress-testing partner.