When is a CIO ready to become a VC?

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Director in Manufacturing, 1,001 - 5,000 employees
When their bank account is overflowing?
Director - IT Infrastructure - Databases and eBusiness Specializing in Information Technology in Retail, 1,001 - 5,000 employees
When they are in a better position financially and come up with great ideas are coming across the great teams with wonderful concepts 
Director of Information Security Operations in Consumer Goods, 1,001 - 5,000 employees
When he can really start to aim high and run as deep as needed to be "worthy" the vc title 
GVP in Software, 10,001+ employees
No better person to answer this than
CISO (CISO) in Healthcare and Biotech, 5,001 - 10,000 employees
I assume VC means "venture capitalist" and will answer that.

A CIO lacks the skill set to be a VC.  It is a completely different world.

Best would be if they are a consultant for a VC first for a few years before sticking a toe in.  I personally worked with multiple VC companies during my time at Siemens.  Siemens has its own VC group and partners with VC companies across the world.  I learned a lot during that time, you need to invest a lot of time and research appropriately.

You need to have a good base of knowledge in economics, preferably a masters degree.  You need to be able to financially evaluate a company, you need to know or research the business you are looking at.  You need reliable and trustworthy partners and subject matter experts.

Also you need access to significant funds of course...

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Chief Technology Officer in Software, 51 - 200 employees
My personal experience. 

I usually get the feedback and go back with data driven analysis providing details to cross leaders to understand the context and make decision basis data and and not gut feeling. 
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