jason calacanis

Jason Calacanis is a larger than life personality. He’s had some moderate successes as an entrepreneur, founding Silicon Alley Insider and Weblogs, Inc. He’s also angel invested in companies like Uber, Tumblr, Evernote, and others. But like most investors and entrepreneurs, he’s also missed just as badly.

At tonight’s PandoMonthly fireside chat Calacanis recalled what he describes as the biggest miss of his career. The seminal moment happened while Calacanis was having brunch in with Ev Williams and Biz Stone in the Mission district of San Francisco and they pitched him on the early concept of Twitter.

“I’ve never been more wrong,” Calacanis says.

Twitter was simply an SMS service at the time which Williams and Stone envisioned people using to share inane details like what they’re having for breakfast. Calacanis recalls thinking that Twitter was taking blogging, which he described as a positive force for humanity, and removing the most important part: the actual blog post.

“You’re just leaving the title,” he recalls telling them.

Williams and Stone were resolute in their thesis, arguing that writing a blog post is too intimidating for most people, but headline writing is more approachable. For Calacanis, this was exactly the problem. Not only could everyone write “headlines,” but they would, leaving Twitter as a collection of stupidity.

What Calacanis didn’t understand, he admits, was that in aggregate tweeters would self regulate and that while most tweets would, in fact, be of limited value, the company and the users of the platform would find ways to surface the best content.

Calacanis didn’t invest in Twitter, but took the experience of missing out on that opportunity – the company just went public at a valuation of approximately $16 billion – as a lesson.

“What I realized is that you just never know,” he says.

In the half decade since this fateful meeting, Calacanis’ career as an angel investor has arguably been more successful he has been as an entrepreneurial. He’s since raised a $10 million Launch Fund, aimed at investing in companies that grace the stage at his Launch conference. More recently, Calacanis raised one of the largest, and most highly discussed AngelList Syndicates.

The fact that Calacanis passed on a home run investment opportunity doesn’t make him a rarity. But the way he’s rebounded from is better than most. It will take years to get a generate a final scorecard on his investment portfolio. But given the way that he’s applying his hard knocks lessons to his work today, you can bet that he won’t soon dismiss another moonshot idea from a pair of wide-eyed entrepreneurs.

[Photo by Rebecca Aranda for Pandodaily]