Don’t Call It a Comeback

Eryn Brown’s Revenge of the Dotcom Poster Boy, which is featured in, talks about Jason McCabe Calacanis. Calacanis’ story is very exciting. He pushed for content long before its recent surge in demand, which is driven by businesses looking to rank highly on popular search engine result pages. Calacanis’ publications allowed him to deal with the big time players of the technology industry during the dotcom era. His inspiring persistence allowed him to continue looking for opportunities at the dotcom era’s end.

Although Calacanis was not the first to develop a content network, he has been very successful in monetizing the network that he helped develop. Eryn Brown compares Calacanis with Gawker Media’s Nick Denton, noting that “Denton kept Gawker relatively small and focused, but Calacanis and Alvey went unabashedly for scale.” Taking on those kinds of risks requires some degree of confidence that may very well be confused with arrogance. He expresses his confidence by stating:

There’s no limit to how far I could go in AOL – it’s just the limits they put on me. I’m not in line to be CEO of AOL, but it’s obvious that’s where I’ll end up, if I stay focused. Somebody’s got to be the next CEO of AOL.

I would have loved the opportunity to hear Calacanis talk “about scaling up startups with in earnestness that would make a boom-era dotcommer blush.” Like Calacanis, I actively seek the opportunity to bring startups to the next level with some equity for my team.

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