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How did Dave McClure start investing in startups?

After leaving PayPal around 2004, Dave started investing recreationally. After he'd invested in about 13 companies over the next four year, some of them turned into 100M+ exists.

Dave ended up working for Founder's Fund with Peter Thiel and Sean Parker for about 1.5 years, and eventually got together with Christine Tsai to raise their own fund, 500 Startups.