Calacanis is currently the Chairman of The Weblogs, Inc.

In the fall of 2003, Calacanis hatched the concept of the Weblogs, Inc. Network with his longtime friend Brian Alvey. Alvey and Calacanis both attended Xaverian High School. In 1994, Calacanis and Alvey collaborated on their first magazine, CyberSurfer. For a time Alvey was the art director of Silicon Alley Reporter, before taking over as CTO. Alvey helped create Venture Reporter with Calacanis.

Calacanis is bi-coastal, living in Santa Monica and New York City with his bulldog Toro.