Calacanis: the Tony Robbins of Web 2.0

by Mathew on September 28, 2008 · 20 comments

Update:

Apparently, Jason doesn’t want his email newsletters posted any more because he “doesn’t want to give the haters a platform,” according to a Twitter message. The text of the email has removed from both Silicon Alley Insider and TechCrunch, but you can still find it.

Original post:

Jason Calacanis, the diminutive entrepreneur behind Weblogs Inc. and the “people-powered search engine” known as Mahalo, seems to be attempting to transform himself from just a scrappy CEO into a Web 2.0 cross between Deepak Chopra and Tony Robbins. It’s actually been coming for some time, but really kicked into gear when Jason stopped blogging and started sending out an email newsletter to a select group of followers. Of course, his missives routinely show up on various blogs anyway, which is a nice way to have your cake and eat it too. Which is great, because it means that none of us is denied access to Jason’s words of wisdom.

In his latest missive, Jason gives each of us the benefit not only of his years of startup experience but also of his bachelor’s degree in psychology, both of which taught him a number of key lessons about how to succeed even when everything is going against you. I’ve read through his newsletter several times and extracted some of those key lessons:

  • People are scared, and they should be.
  • Metaphors swing both ways.
  • Sometimes it’s really, really stupid to keep fighting.
  • The darkest hour is, in fact, right before the dawn.
  • If you are suffering from depression or anxiety, go see a professional.
  • Feel free to print this out.
  • You need to access where you’re at, and fight on.
  • If you fail, then by definition you have tried.
  • If your idea is wrong, it really doesn’t matter.
  • The market will tell you what it wants.
  • Execute better.

Really, these just scratch the surface of what you’re going to find in Jason’s missive. There’s so much gold in there, it’s like Fort Knox or something. I’m not kidding (although Jason didn’t include one of the lessons he learned at TechCrunch50, which is to feel free to let people know how you feel, even if the mike is on). So, is Jason a genius whose newsletter is full of useful wisdom, as some would argue, or a putz who strings together bromides and motivational claptrap? That one is up to you. Mahalo.

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