I've been following Ben Thompson for a few years. His comments are usually insightful on both his blog and podcast.

He has a different advertising model. He has one advertised at a time. His last advertiser MailChimp sponsored the podcast for an entire year.

He also has a decently popular paid email newsletter. The only time he spoke about the number of subscribers was about two years ago and he had a little over 2000 then paying $100 a night.

He's worked at Microsoft and Apple.