Out of the hundreds of thousands of people using my company Open Listings to shop for and buy homes, I thought I knew who our worst users were — even by name.

There was Sarah* in San Diego who went on 134 home tours before finally buying one. Then, there’s Dan in San Francisco who’s asked our in-house agent team questions about nearly 1,000 properties but hasn’t submitted an offer on a home yet. And, there was Chris, who tried to negotiate our already low fee down to zero by blackmailing us with negative online reviews.

As CEO, I cared deeply about all users and every shred of feedback. I read every review, internalized problems, and prioritized solutions. I felt confident that we were super customer-centric and solving the most important p...