Mastery by Robert Greene also mentions in a few pages this story about the Wright Brothers (they started from their expertise in bicycles, that’s how they got planes right) and it’s def a book the OP might be interested in.
I think it's deeper than bicycles. They never went to college or university (though their sister did), but they were extremely well read and researched everything they did. Their first business was a weekly newspaper and printing press. They built the press from scratch using scavenged materials, and they wrote most of the newspaper articles themselves. They sold advertising and set the type. When they went into bicycles they were again the entire staff. They sold to customers, repaired bicycles, and manufactured their own model of bicycle right in the back room of their shop. And now they were the ones making up advertising slogans and buying space in the papers.
They were raised with the understanding that they could learn anything, build anything, discover anything that they set their mind to. And once they had set their minds on flight it was only a matter of time.
