On a recent episode of The Drift, the weekly markets show hosted by thinkorswim and tastytrade founder Tom Sosnoff and trader Adam Mesh, Sosnoff shared a personal story about one of the most talked-about missed opportunities in modern venture history, his early chance to invest in Uber Technologies (NYSE: UBER). "To this day, I'm mad because I had a chance to invest in Uber before their original capital raise. Travis Kalanick was in Chicago and he was going everywhere trying to raise money. He was like knocking on doors. And I just didn't think anybody would ever use this, you know. So I passed and I regretted that for the next 20 years." The context lines up with Uber's actual early history. In October 2010, UberCab, as it was then known, closed a $1.25 million seed round led by First Round Capital at a reported $4 million valuation, with participation from Chris Sacca's Lowercase Capital, Founder Collective, and roughly 30 angel investors. That same month, Kalanick spoke publicly in ...