Sure, it's easy to be successful when you've been successfull and there is no problem using your company as your own virtual playground, when it's your second (or third) company. For the rest of us we just have to work our ass off.
Agreed, he has already achieved financial freedom so it is a lot easier to experiment with throw away companies and projects. Others have to find that balance between working on fun activities and those that earn you income.
Agreed -- there's also the survival bias at play here. We only hear and read the blogs of those that already made it - dabbling in hot springs of financial freedom - in hindsight.
More interesting are the reads of those about to take off, in real-time - e.g. Chris Granger