I've actually never come across Larry Osterman before, but he's got a whole lifetime of experiences at Microsoft. He joined in 1984 in the heady days of MS-DOS, and has progressed through most of the teams. He has an infectious sense of enthusiasm and of course a crazy number of war stories about Microsoft through the years.
Robert Scoble has posted a series of three interviews with him: actually they're barely interviews as Larry does almost all the talking and veers from product to product with barely a prompt. If you can bear half an hour of staring at his florid shirt, this is the perfect thing to listen to over a lunch hour whilst munching a sandwich.
What I enjoy is that Larry is completely politically incorrect - I can think of at least 100 people in marketing who would go wild if they listened to the first video in particular (and could understand what he's talking about!) And yet, when you listen to this, you understand far more about the heart and soul of Microsoft than you would from reading 100 whitepapers or pushy presentations. He's my new role model of the week (albeit not for sartorial elegance!).
If you've not given Channel 9 a go recently, you should take a look - the guys continue to work on improving the site and making it the ultimate insiders' guide to Microsoft.
Take a break for a few minutes and listen to the latest from Larry Osterman on Channel 9. Fascinating