Bill Flagg (who recently sold his company, RegOnline) wrote a great post called Focused Investing on his blog. In it, Bill tries to reconcile his historical mode of investing (full speed on one thing at a time) with what the rest of the world seems to do (diversified asset portfolio theory).
His conclusion: “Wait for the big fat pitches and then focus my energy on hitting them out of the park when they appear.”
In contrast, I’ve been reading Taleb lately, which has (to some extent) validated my own thinking about being “very safe” with the bulk of my investments (that would *not* include startups), and betting on potential black swans with a small portion of my portfolio. If you hear your local angel investor say that she is only looking for deals that have the potential to generate a huge (not just a 10x) return on investment, she may be an idea investor who is a subscriber to this same theory.