Inkling Markets, a prediction market software company, posts about startups, persuasion, management and the accuracy of prediction markets.
HN links it for startup and psychology essays; commenters here mostly point to the authors' own posts rather than judging them.
Hugh's been a favorite of mine too. One of the only newsletter's I've subscribed to. You might dig this blog post of mine that was up on HN awhile ago that mentioned Hugh and Jobs and the effort of going against the grain.
http://blog.inklingmarkets.com/2010/01/ignore-everbody.html
Here's a blog post we wrote a few years ago about it: http://blog.inklingmarkets.com/2008/05/judging-prediction-markets-accuracy.html