When I was early in my career, I casually mentioned to an older VC that I had yet to lose money on an investment. He replied "that's not good, you aren't taking enough risk." I have gone on to lose a lot of money over the years. And made a fair bit too.
The mistake young Fred made was not testing the boundaries. To his mentor, not losing was a sign of over-conservatism, with the result of missing out on potential big wins. This reminds me of the hockey skating story Ashley Good related earlier this year.
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