Just discovered an old post by Jason... I wanted to attempt to answer..
1. Gut check: Is it just about greed/money, honestly?
No it is not!! I have goals that require money to execute. But I would like to believe that it is not just about getting more money.
2. How do I provide value to the world that's equivalent to a million dollars?
This is a tough one. I have a few random skills but I have life/misc experiences that can yield something useful.
I am certain that the Fear Hacking Journal idea if executed properly can be a million dollar business.
3. How do I serve a million people who'll pay me $1 each? Or 1000 true fans who would pay me $1000 each?
I think $1000 is outrageous. I don't want to pursue that.
$10-$40 is probably the sweet spot for something that gives value on a consistent basis. Like a gym membership.
4. What am I potentially world-class at, or have a chance at making something that's world-class at something?
World-class? I have nothing that I could say is world class.
Maybe I need to be working on being world-class at something.
5. How do I leverage the scalability of technology to get there, as a company of one?
Building a community like 200 words a day around the fear hacking journal is something that can be done by leveraging technology.
6. How do I scale beyond the bottleneck that's me, beyond my own time and my own skills?
Based on my past performance, I tend to leverage outsourcing and hiring experts in things I do not have skills in.
Automation is also another thing that I know can help with time and efficiency when it comes to scaling.