It has been quite some time since I have seen or heard from Sky Dayton when somehow I stumbled across an episode of Jason Calacanis' This Week in Startups where Sky was interviewed.  

When it comes to all things Internet Sky is one smart cookie with the
perspective of someone that has been involved in the space for 17 years.
He has also knocked a few startups out of the park during this time
frame. I'll never forget his Boingo pitch to me after an EarthLink board
meeting.  It was a single sentence. Lance, wants the biggest issue with
the WiFi? The answer was fragmentation and I immediately understood
the Boingo concept and what he intended to do.

So I listened to all two hours of the show.  With Sky and, the love him or hate him, equally experienced and successful Jason C going back and forth the show is chock full of wisdom. 

"Niche is the new mainstream."

"My test for an idea is I wake up every day and it is the first thing I think of."

"The press is like fun house mirrors."

Both this guys understand what it takes to be an entrepreneur and how to get attention for whatever they happen to be working on.

Personally I find Jason's email newsletter to be a little of a long read.  But this is good stuff so I subscribed to the TWiST podcasts on iTunes. It is easy to listen while you work.