[jasonkester]

A bit meta, but it's interesting to see how much this guy has reinvented himself over the years. Going from running the biggest, loudest, and most profitable software consulting firm in the world... to retiring to play with photography and airplanes... to junior pilot at a small airline.

Some might say going from $MM/year CEO to $18k/year new guy would be a step down, but he seems to be genuinely enjoying the ride. I especially like how he keeps the whole "dot com millionaire" thing hidden on his aviation resume:

http://philip.greenspun.com/narcissism/resume

http://philip.greenspun.com/flying/resume

If you haven't read about the guy, it's worth picking up a copy of Founders at Work just for his interview.

[zachbeane]

"Retiring" is an interesting way to describe it. He took VC money, didn't like VC control, got into a court battle. He then settled for millions with the VCs, while his partners got nothing out of the settlement (http://www.assureconsulting.com/articles/arsdigitahisone.sht...).

It's interesting to see him slightly back in the public eye as an aircraft nerd.

[adolph]

Especially as an interviewee on an NPR story about Groupon. If I remember correctly NPR made no mention of Greenspun as having founded a seminal social media web app, before there was language to describe it that way.

http://www.npr.org/templates/story/story.php?storyId=1293863...

[rdouble]

the biggest, loudest, and most profitable software consulting firm in the world

At its apex aD had 200 employees and 20m in funding and maybe 10m in invoices. However, I'm going to update my resume with your version.

[ajaxian]

I think it's safe to say that Greenspun isn't working as a junior pilot for the money since not too many people making $18k/year have their own plane, helicopter and Acura NSX.

[goatforce5]

Bruce Dickinson of Iron Maiden got his commercial pilots license. You can assume he didn't do it for the money:

http://en.wikipedia.org/wiki/Bruce_Dickinson#Aviation