Jason Calacanis - CEO of Mahalo.com
One really great story about web entrepreneurship with Jason Calacanis. Be a Samurai not a rice picker!
Some of my favorite episodes:
TWiST #61 All Jayter Show (the Jason Calacanis hater episode)
TWiST #46 with David Heinemeier Hansson (Do a single best product or finish a project and start a new one)
TWiST #40 Bonus Interview with Penn State (the video above)
TWiST Interview with 100 Things (for bloggers and seo)
TWiST #24 with Gary Vaynerchuck ( "get off the bitch train" )