Calacanis on reinventing yourself

in On Entrepreneurship

A transcript from a podcast with Jason Calacanis, Doc Searles and Dave Winer, emphasis mine:

You tend to fall in love with your first brand, and you can’t let it go. And I did that with Silicon Alley Reporter magazine, and it’s well documented that I could have sold it for 20 million bucks, and I didn’t, and I got a fraction of that [when I eventually sold it], and then when the next [opportunity] came around, Weblogs, Inc., I sold it after 18 months, instead of holding the other brand [Silicon Alley Reporter] for six years, and I did much better in 18 months than I did in six years…

You have to always be confident that you are able to create another hit, you’re not a one-hit wonder, and that your future is always brighter than your past. You can’t live with this fear of losing this monster you created. And sometimes you gotta kill it, and I always give people the example of Bob Dylan, because when Bob Dylan took folk music as far as his interest in it…could go and then he said, “I want to do electric, it’s more interesting to me,” and there’s that famous thing at Royal Albert Hall where somebody yells at him and says, “You’re Judas,” and [Dylan] says, “I don’t believe you, you’re a liiiiiiar,” [laughter] and then he turns around to his band and he says, “Play real fuckin’ louuuuuud,” and then he turns around and he plays “Like a Rolling Stone,” which is arguably his best song ever and he did some of his best work after that.

You have to reinvent yourself, and sometimes you have to kill your previous persona. I had to kill [my] Silicon Alley Reporter persona to become Weblogs, Inc. I’ll have to kill Weblogs, Inc. to be Netscape, kill Netscape to be whatever comes after that. You can’t live on your past brand, or else it owns you, and you no longer own it.

Links: the MP3 of the podcast, the original transcript of the podcast from Ed Batista, Jason comments.

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