I started CollegeHumor.com when I was still in school and I ended up coming up with BustedTees and Vimeo in 2003 and 2004. In 2006 I sold the companies to IAC.
While, I don't want to say it was a mistake to do the deal or to sell my company...because I wouldn't be here if I didn’t make that decision. But, I think the mistake that I made and what I didn't understand then was the implications of not being aligned with your strategic partner—in this case it was a majority investor.
There was moment when a top executive at IAC, someone who doesn't hold punches, yelled at me for the first time. It was sort of like, you're not doing a good enough job...it wasn't just about the business, it was directed at me—maybe you're not good enough to do this for us. It was that first moment of realizing, "Oh wait. Maybe I'm not actually the best person for this job anymore or maybe I am failing."
And it was because after we did our deal, the first few months we were continuing on a good trajectory. Everybody was giving us high-fives and we felt really good. And then, we missed our projections for a couple months here and there.
I can remember walking out of the meeting and being like, "Oh wow. This got real." And then, having to come to terms with that...and not being sure, is it him, is it me, is it the business? All the sudden having to question that, which is really hard.
I think the ambition I had for the business and what was going to make it a success or feel like a success to me was very different to what my new boss' expectations were. And I think that having to work everyday in that organization where it is such a different ambition level takes its toll on you.
Sell 40 percent or sell 80 percent, but don't sell 51 percent. If you can.
Generally speaking if you can sell a minority or a vast majority do that. Sell 40 percent or sell 80 percent, but don't sell 51 percent. If you can.
I learned that through experience and doing that deal. And I will not put myself in that situation again. I would never sell 51 percent of my company. 100 percent guaranteed. I would never ever do that kind of a deal again.
So while, it is not a mistake in that I still had a positive outcome as a result. I also had many years of feeling like I was failing at something that was objectively a success on a certain level. But, not exactly a success by my boss' standards. So, I went from feeling like this successful entrepreneur to feeling like someone that was not successful, someone that was not doing a good job for a long time.
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Photo courtesy of Josh Abramson.