Jason Calacanis: A Case Study in Creating Resources

Jason Calacanis described himself as a serial entrepreneur, angel investor, and podcaster – and someone who had come a long way from the time he had to talk his way into Fordham University. Later, when finances were tight, he talked the dean into getting the bursar to cut him a break. These early experiences with “being bold,” he believed, encouraged him to keep being bold – and creative.

This case study explores Calacanis’ path to entrepreneurship, a route that took him first into publishing, and later into angel investing, then hosting influential incubator and networking events for investors and entrepreneurs. Throughout all of these activities there was a strong creative thread – Calacanis events were not just about connecting investors and entrepreneurs, but also provided entertainment.