I sent $100 to Jason Calacanis last week as a gag mostly for a mention on the Gillmor Gang. I have to say Jason is a hysterical marketer and gave HelpSpot a long plug. He got a few of the facts mixed up, but hey what do you want for $100! One thing to clear up is that you can run HelpSpot on your own server, hosting is optional.
You can hear the show here: http://www.gillmorgroup.com/media/TheGang-2008.01.04-1.mp3
HelpSpot is mentioned at 39:10