For the startup story Mike mentioned below, we paired each founder with a seasoned entrepreneur, having the wiser one critique the newer one. The story I wrote was on GreenPrint, a printing-software company. It paired GreenPrint's Hayden Hamilton with Tim Gill, the founder of Quark.
Both entrepreneurs were lovely. Tim, who's mostly stayed out of the press since leaving Quark, was thoughtful and humble. Hayden was really enthusiastic and eager, a natural pitchman.
The way we set it up, we—the writers—acted as the conduit between the two entrepreneurs; except in the Gauri Nanda-Gordon Segal case, they didn't talk directly. Now I'm thinking this wasn't the best way to go, swayed in part by Hayden's blog entry responding to Tim's critique. Tim's reaction to the GreenPrint idea was tepid, so obviously Hayden needs to respond vigorously. He does so in his blog, going through Tim's points and explaining why he found them unconvincing.
I think it would have been more effective, and better for both entrepreneurs, to have had them to talk directly. Hayden could have done his pitch for Tim, and even if Tim still had the same quibbles about GreenPrint, he could have given advice directly to Hayden and answered the questions Hayden has about starting up a software company. The transcript of their conversation would have been pretty illuminating. Ah, well; maybe for next year's package, when—who knows?—your company could be one of the cool startups.