Michael Arrington’s “Twice Shy” One Year Later

December 13th, 2008 Sean Murphy

Last December Michael Arrington wrote “The Twice Shy Entrepreneur” lamenting that entrepreneurs like himself who had lived through the dotcom meltdown were more cautious. They were “once bitten, twice shy.”

Silicon Valley these days is made up of two kinds of entrepreneurs (I’m painting with broad strokes, bear with me). The first group is the old guard. These are people who started companies during the late nineties and up until the 2000 stock market crash. The second group was either in school during that period, or doing something other that working in the tech world, and have started companies after the fallout from the crash.

Generally speaking, experience counts for something. So you’d expect entrepreneurs who’ve been through the ups and downs of a tech startup to have an advantage over the newcomers. Or at least have an equal chance at success. But in fact the opposite may be true. A number of venture capitalists I’ve spoken with have said that too many “old guard” entrepreneurs are not being bold enough in their business decisions, and it’s hurting their startups.

What a difference a year makes. Now the “newcomer entrepreneurs” have had the chance to lay employees off and are encouraged by the VC’s on their boards to focus on profit and survival instead of bold growth. And the experienced entrepreneurs–like Arrington–are probably feeling a little less out of sync with the environment.

A year ago I wrote “Entrepreneurs, Luck, and Silicon Valley” which closed with  Richard Wiseman’s four principles for improving your luck from “The Luck Factor: Changing Your Luck, Changing Your Life: The Four Essential Principles.” They bear repeating:

1. Maximize Chance Opportunities: Lucky people are skilled at creating, noticing, and acting upon chance opportunities. They do this in various ways, which include building and maintaining a strong network, adopting a relaxed attitude to life, and being open to new experiences.
2. Listen to Your Lucky Hunches Lucky people make effective decisions by listening to their intuition and gut feelings. They also take steps to actively boost their intuitive abilities — for example, by meditating and clearing their mind of other thoughts.
3. Expect Good Fortune Lucky people are certain that the future will be bright. Over time, that expectation becomes a self-fulfilling prophecy because it helps lucky people persist in the face of failure and positively shapes their interactions with other people.
4. Turn Bad Luck Into Good Lucky people employ various psychological techniques to cope with, and even thrive upon, the ill fortune that comes their way. For example, they spontaneously imagine how things could have been worse, they don’t dwell on the ill fortune, and they take control of the situation.

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