Inc.

How to Not Become Dumb Money

Y our problem just got bigger. Think, what have you done?

Not long ago, that “fortune” spilled out of a cookie to me at the end of a meal. My first response was that it was hilarious— and so different from the typical platitudes in fortune cookies. But I’ve since realized just how closely it echoes what I often find myself thinking when I meet with founders.

Making mistakes is inevitable. It’s impossible to succeed in business without stepping in muck somewhere—sometimes repeatedly. In my experience, each day spent growing a company is 30 minutes of exhilaration and hours of having your ass handed to you for some decision that, looking back, can go directly to the file marked “Stupid.”

At Unorthodox Ventures, my investment company, we frequently see missteps where startup financing is concerned. And even more disturbing is the fact that in some cases,

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