Posted this over on the blog, but interested to hear views:

Having read Outliers, what struck me about it was that - despite being a very interesting read - you could only really define the path and circumstances leading to Outlier success with the benefit of hindsight.

Whilst you can argue it is a good time to start up, it is hard to see until years down the line if a particular skill set and particular market conditions did actually lead to the success seen by the people mentioned in the book.

The power of hindsight makes all things obvious with time. Uncertainty of an idea or skill in a market will always be there.

So it's always pretty accurate to say "now", because "later" is rarely a good time to start.