I think net worth of a leader and “in touchness” with the user are not necessarily related.
First, your user may be not be a typical consumer if, say, you are making an enterprise product. So you can never “be the user” in that business in the same way you might be able to “be the user” in a consumer business.
Second, permit a tangent: I think “being the user” is somewhat overrated in general.
Of course there are many tales of companies running afoul because the products teams had no interest in actually using the product they were making, and went ahead and made something useless or dumb. On the other hand, product teams are never really the user — not really. That’s because the product team is spending way more time obsessing over the product than the user ever will. The antidote for all this is product management and customer development — that is, a (more) methodological approach to product design and prioritization than simply trusting one’s instincts on product direction in the case that the product team really does or will use the product. In other words, there is no excuse for avoiding customer development and understanding.