There are examples of Beal Aerospace, which closed not long before SpaceX founding, and Kistler Rocket, which also didn't survive around the same time. According to success of SpaceX, the way was there - but somehow not nearly everybody succeeded. Even Virgin Galactic was thought to be easy after successful demonstration of flights in 2004 - the was the way - but today in 2019 we have Stratolaunch closing and Virgin Galactic still not flying with regular passengers.

I think reality is that doing business with space is tricky, and requires complex combinations of luck, money, perseverance, experience - approximately in this order, but still tricky.

Honestly I don't really follow your point.

"Where there is a will, there's a way" means that if you are motivated enough you will find a way to succeed. Which as I understood was your first point. That if billionaires creates these ventures people will be inspired and go on to succeed. That was also Musk's initial idea, that he would do this stunt of sending a plant to Mars and people would get more interested in funding and do space exploration.

"Where there is a way, there's a will" is the opposite. That if you can find a way to do something, people will want to do it. This is what SpaceX ended up doing, trying to be a part of the space industry.

In one of the videos he compares space and the Internet. That the Internet was first created by DARPA who did the ground work and that private companies commercialized and made it accessible. He suggest that space could be similar with NASA doing the ground work and private companies commercializing and making it accessible. That is why he moved the company to Los Angeles instead of the Bay Area, why they got government contracts, why they started with satellites and then cargo etc. And of course it is also luck, timing and everything else. But it was certainly also specifically because the idea wasn't to fund something to inspire or to do space tourism.