A lot of people here seem to focus on reasons why startups won't hire Dave Winer, but the this isn't a Winer-specific situation. Startups aren't filled with personable JSON-loving 50 year olds, or even 40 year olds.
One reason may be that most current web startups just don't do work that is difficult or innovative enough to warrant that level of experience/cost. You don't need 20 years' experience to create Reddit, for example, and even though a veteran team might have avoided pick the wrong language initially or storing users' passwords in plaintext, these didn't really hurt Reddit that much.
There's also the employee's side. In my late thirties I already find it hard to get excited about self indulgent social-location-based-nano-blogging apps aspiring to get mentioned at Wired. When you look for something that's either really challenging or tries to solve a real problem, your range of choice is greatly limited.
One reason may be that most current web startups just don't do work that is difficult or innovative enough to warrant that level of experience/cost. You don't need 20 years' experience to create Reddit, for example, and even though a veteran team might have avoided pick the wrong language initially or storing users' passwords in plaintext, these didn't really hurt Reddit that much.
There's also the employee's side. In my late thirties I already find it hard to get excited about self indulgent social-location-based-nano-blogging apps aspiring to get mentioned at Wired. When you look for something that's either really challenging or tries to solve a real problem, your range of choice is greatly limited.