Certainly:

Person A tries to do something, fails, and in order to not fail again givesup.

Person B tries to do the same thing, fails, then tries again and fails, and tries again and fails, each time learning something more until on the 100th time they succeed.

Person A failed once, person B failed a hundred times, person B is better off for they have learned how to succeed rather than given up.

If you avoid doing something for fear of failure you're worse off than if you fail at it until you get it right.

I believe that you could call this epiphany a change of perception. To his kid, the world is a challenge, and the opinion of others (or the perception of opinions of others), ego, reputation don't matter. Failing, in this new light, does not matter; it is simply the fastest way to discover one less way to try the next time.

Say, for instance, public speaking. We are all familiar with the feeling of fear when speaking in front of a group. However, going on stage and trying different stuff, is (quickly) going to get you better at speaking. I could watch a million YouTube movies about public speaking, but actually trying and failing is the shortest way to getting actually better at it. Only when analyzing what could go better, watching those movies can provide valuable input for a next try (asking an expert is even better). The thing is: negativity and fear (of criticism) often gets the better of us, way before we fail enough to succeed. This often when we hear: "I'm just not a natural born speaker" and stop trying. - Guess what, almost no-one is. Just don't be afraid to fail.

Its not about failing more, its that you cannot be successful at something until you try it, and its likely you wont immediately be great at whatever that is. It will take practice, you will make mistakes - but thats OK as long as you are resilient. How do you get to Carnegie Hall? Practice, Practice, Practice.

You can give people wisdom and advice, but the most important lessons cant be told; until you actually try and fail, you wont listen. Examples include: dont build consumer startups, b2b is way better. Co-founding a startup with someone living 3,000 miles away is a bad idea. Solid legal contracts are very important.

When the fear of failure prevents innovation ans progress. Which is too common in the corporate environment.

I don't believe the text is about failing more, it is rather trying to solve it by yourself first, and if you fail repeatedly and exhausted every solution then ask for help.

Don't know why but this text made me remember Shunryu Suzuki's "Zen Mind, Beginner's Mind".