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HD Moore is another good one. A long time ago he got caught hacking NRL (or somewhere on navy.mil my memory isn't as good as it was), something which isn't mentioned all that much any more, funnily enough.
He decided to parlay his five minutes of script kiddie fame into creating an open source version of Core Impact, in which exploits are packaged as modules into this all-singing all-dancing centralized hacking program.
Unlike core impact, however, he didn't hire a bunch of skilled guys to write reliable useful exploits, rather he encouraged other wanna be hackers and fame-seekers on IRC to port public exploits to metasploit (the resulting modules rarely working outside the "author's" own computer) while he just sat around and took all the credit (and Matt Miller did all the actual work on the framework itself).
Rapid7 acquired metasploit (and Moore) in 2009, turning the erstwhile exploit cataloger into a millionaire overnight.
Moore is now on more boards of directors, advisory councils, and conference panels than I can even begin to count. A pillar of the security community, who the media will always go to for a quote... and all while having a mere fraction of the security knowledge of the people who built his program for him. Oh, and they'll even sell you a dodgy certification in advanced metasploit click-monkeyry to boot:
Actually just go and watch the HBO documentary "Silicon Valley" and imagine that they're doing infosec instead of compression and that there's like 10,000 Bigheads.