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Fred Wilson

NEW YORK CITY — New York VC Fred Wilson always likes to share his insights to a wide audience. Today at TechCrunch Disrupt NY, not only did he talk about why Foursquare is doing fine, but he also shared what he thinks makes a good entrepreneur — being a little crazy.

Wilson is the cofounder of Union Square Ventures and someone who has placed a lot of smart bets. He’s invested in companies such as Twitter, Tumblr, Foursquare, Zynga, Kickstarter, Etsy, and Dwolla.

“You don’t want a psychopath, but it happens,” Wilson said. “You want someone who is crazy but mentally healthy. … To see things differently requires you to be wired a little differently.”

Wilson refused to name “pyschopaths” that he has funded, but he was willing to name a few people who fit the bill of “good crazy.” Two entrepreneurs he thinks fit that are Kickstarter’s Perry Chen and Zynga’s Mark Pincus. “They just do things differently,” Wilson said. “Perry and Mark have some common traits. … Pincus can drive me crazy.”

What not to do in a pitch session

Wilson also gave insights into things founders and entrepreneurs had done in past pitch meetings that were ill-advised. Here are few tips of what not to do:

  • Don’t give a lengthy background. Get to the point. (“Going through a long backstory is a bad idea.)
  • Don’t pitch something incredibly derivative. (An example of what Wilson hates: “I’m taking a Pinterest model and I’m applying it to automobiles, and there will be flash sales.”)
  • Don’t demo a product that doesn’t always work. (“I had a meeting yesterday with an entrepreneur and the product didn’t work. It was a painful moment for both of us.”
  • Don’t talk for 20 minutes and then show off your product. Show your product for 20 minutes and explain it.
  • Don’t show 20 slides when you can show one really great slide that explains your product.

Photo via Sean Ludwig/VentureBeat

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