Jason Calacanis launched the Silicon Alley Reporter ten years ago [1], then co-founded Weblogs, which he sold to AOL in 2005, and now runs Netscape for AOL. Over the weekend Calacanis participated in a podcast hosted by Dave Winer, and he had some interesting things to say about reinventing yourself:
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, 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 liar," [laughter] and then he turns around to his band and he says, "Play real fucking loud," 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. I'll have to kill Weblogs 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. [1]
I don't think you have to be a founder/entrepreneur who's personally identified with your business for this to be relevant. We all have a professional persona, a set of characteristics and concepts that our colleagues associate with us as individuals, and that persona can be helpful as we make our way along our chosen path. But a pre-existing persona can also be a hindrance when you need to make a major change, and sometimes you need to kill it and reinvent yourself.
However, as reader Seth Finkelstein asked me, "What if you tend to tenaciousness and dogged persistence?" How do we know when to reinvent ourselves? And here again I think Calacanis' comments offer some useful guidance. He held onto the Reporter too long and sold it for much less than he could have. This wasn't just poor timing for the transaction–he was too slow to let go of his identity as the Reporter's founder and that aspect of his professional persona. So if you're asking "When should I make a change?" the answer may simply be, "Sooner than you think."
A key here is recognizing that our weaknesses are often overused strengths. If you "tend to tenaciousness and dogged persistence," those strengths turn into weaknesses when you fail to let go and move on. You may not feel ready, but waiting until you're ready may mean waiting too long and missing an important opportunity. You may need to take that leap.
Footnotes
[2] Morning Coffee Notes (Dave Winer, Mike Kowalchik, Doc Searls and Jason Calacanis, August 5, 2006)
- The historic moment in 1966 when Dylan was heckled in Manchester is captured in this 30-second video.
For Further Reading
Taking the Leap (Dealing with Risk and Uncertainty)
William Bridges on Transitions
You Quit. You're Free. Now What?
Do You Have to Leap…Or Can You Grow?
It's Time to Stop Interviewing
Updated February 2022.
Photo by Eva Rinaldi.
2 Responses
Indeed, what if you tend to tenaciousness and dogged persistence? Suppose you don’t do very well at re-invention? (it’s taken me long enough to have one “self”!). As advice goes, there’s certainly truth to what he says – but there’s really no help in it to guide you as to when reinvention is helpful or harmful.
Seth, I agree that the question of whether (and when) to make a fundamental change is a profoundly difficult one. But I do think Jason’s comments offer some guidance in that regard.
He notes that he held onto Silicon Alley Reporter too long and eventually sold it for much less than he could have earlier. This may have been the result of poor timing and some “irrational exuberance” on his part, but he also suggests that he was slow to let go of his identity as the Reporter’s founder, of that aspect of his “personal brand.”
So if you’re asking “When should I make a change?” the lesson I’d draw from Jason’s experience is, “Probably sooner than you think.”
I don’t mean to be flippant, and I realize that’s hardly a perfect guide to decision-making. But when it comes to issues like this, I think the most important thing is to know ourselves, our characteristics and tendencies, and to determine when our strengths turn into weaknesses.
If you tend to “tenaciousness and dogged persistence,” those strengths turn into weaknesses when you fail to let go, cut your losses, and move on. Not knowing you, I’m not offering any specific advice here, but I wonder if “Sooner than you think” might resonate with you.
And I think it’s important to realize that there’s no guarantee of success. No advice, no guide, will insure that a risky change is worth making. But I’m reminded of my recent post on risk-taking and Doug Sundheim’s thoughtful advice–the outcome of a risk we’ve taken is often less important than the process we went through to take it. Taking a risk may be an essential step in expressing yourself fully, in being yourself.