18-36 months between each stage? This feels perhaps tenable for VC backed corps but for anyone bootstrapped, this is a long, long road.
I'm not remotely convinced that these steps feed into each other in a more pragmatic way than... I guess any other way? Couldn't you start with enterprise sales and move backwards, releasing your stuff as OSS once you're running a stable business?
The thesis seems to be that without community and a proven track record, you can't make money organically, which is patently false and proven by hundreds of businesses that don't have OSS/communities. Also, SaaS seems tangential to Enterprise sales in many cases, they're often times different segments (i.e. I won't consider your SaaS since I must be on-prem) -- if you only serve one segment, you're only missing out on the other segment, not cannibalizing? This is all hand-wavey of course, but I posit that this is a way to maybe build an open source business, but I'm not sure it's a solid, proven recipe by any means.
Maybe once Ockam knocks it out of the park in their IPO we can look back on this with greater confidence.