Bill Gates said in 1995: "Paul Allen makes high-risk investments. He’d be the first to say some will do well, others will not. That’s a risk you take.” Paul understood that it is magnitude of success and not frequency of success that matters in venture investing.
In 2000 Paul asked Craig McCaw and I to meet with him about making Metricom's business model a success. At the time his investment was $500M. We met a few times, but unfortunately the unit economics couldn't be made to work. He wasn't afraid to swing the bat seeking a grand slam.
Paul Allen's offices has a curved Window which has a shade that would lower to allow showing slides like it was a bat cave. In the Mercer Island conference room he had incredible art of the walls that made it a bit hard to concentrate. He did not have small thoughts.
In one of my 25iq blog posts write I about the “wired world” which was the investing thesis of Paul Allen who was Starwave’s primary shareholder. Mike Slade said once: "The whole concept was to take various bets on the future of a wired world." 25iq.com/2017/07/07/how… 
Slade took the idea to Allen. “I went to Paul and said, ‘We’re going to build this thing on the World Wide Web, because we don’t know what else to do,’ Slade said, recounting the dialogue. ‘He goes, ‘What’s the business model?’ I go, ‘I have no idea.’ He goes, ‘OK.’”
Slade: "The first people to run a crawl of a Web site that you were supposed to go to was us and ESPN." Starwave never turned a profit on ESPN during the five years of the deal, but it became the bridge toward a larger relationship with Disney, which eventually bought Starwave.
