We've discussed Miles Davis on a number of occasions here at HN. It's exactly up our alley...or, at least, the upvotes seem to indicate it is, and I agree that it is.

Here's why I think he's interesting:

1. He was an astonishingly good businessman in a time when black men were rarely given opportunities in business, even in the music industry. He is nearly unique even in the jazz world (which was better for black folks than most other industries of the time) for the level of his business success.

2. He was a great leader. He's regarded as one of the best jazz band leaders ever. He helped nurture multiple generations of jazz greats. If you can name a jazz legend from any time until his death, they probably played with Miles before they were a legend. An executive at a startup would do well to learn from him how to pass on skills and help develop even greater talents than their own (many people who played with Miles ended up being better musicians than Miles, and pretty much all became better than they were before they played with Miles).

3. He's interesting. Which could be enough. Nerds like interesting people and things.