If any of his companies were making him a good enough living, I don't think he would have gotten a day job at Stripe.
"when he didn't have the 'fire in his belly'y any longer"
I've been running my own company for almost 5 years after 5 years of side-projects and failures. To actually go from a project to a successful company, you need to do lots of boring work that has nothing to do with technology or development. Most of it is a slog, but is still required. You can eventually outsource this and hire other people, but this will take some time.
You will lose your fire at some point, but you still need to push through this. I've tried to partner with many different friends over the years on different business ideas and ventures. They all failed at some point because my partner (usually another developer) would get bored when things got tough or they had to work on something other than a cool library.
If you can't get through this, it's probably better to stick to working a job.
The other problem with Patrick is that everything he builds is from a developer perspective. Starfighter was a cool concept, but much too complicated for most people (from the business side of things. You need to spend time and money with tutorials attempting to convince business owners why this new concept is better than what they are currently using).