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by amplification 4606 days ago
If the challenge is to "think of successful entrepreneurs or CEOs who blog", I can think of a bunch off the top of my head:

Leo W. at Buffer - http://blog.bufferapp.com/author/leo

Ryan Carson at Treehouse - http://ryancarson.com/

Jason Fried & DHH - http://37signals.com/svn

Matt Mullenweg - http://ma.tt/

Patio11 - http://www.kalzumeus.com/

9 comments

Tobi Lütke of Spotify - http://tobi.lutke.com/

Dalton Caldwell of App.net - http://daltoncaldwell.com/

Suhail Doshi of Mixpanel - http://sufficientlyadvanced.net/

Jack Groetzinger of SeatGeek - http://jackg.org/

Eric Koester of Zaarly - http://ekoester.com/

I wouldn't necessarily add Dalton to the category of "Successful" just yet. Although he is a great influencer and a great technologist.
ZING (too true though)
minor edit. Tobi is the founder of Shopify, not Spotify.
Sridhar Vembu of Zoho - http://blogs.zoho.com/author/sridhar

Craig Newmark - http://craigconnects.org/blog

Mark Cuban - http://blogmaverick.com

Tim O'Reilly - http://radar.oreilly.com/tim

Yeah, I'm pretty sure evidence to the contrary is stronger. A little googling tells me C-levels and founders of forbes 100 are often proflic bloggers. Novell, Cisco, Oracle, a lot of founders of big companies in India, and many here in the non-tech sector blog as well.

Insofar as commenting on HN and other similar sites is quite similar to blogging, there's a lot of others here too.

Craig and Mark are owners of companies or sports franchises (or own large amounts of equity in them), but are not CEOs. I'm not aware of the CEO of Craigslist, Jim Buckmaster, blogging. Nor am I aware of 2929 Entertainment's CEO, Todd Wagner (co-owned by Mark), blogging.

Also on some of the other folks listed in sibling comments, like Richard Branson, I'd be very surprised if he were the one posting on the Virgin "blog" under his name. Just as executives and politicians have speechwriters, they also have exec comm and marketing staff to write blog posts.

Just clicking on the last few posts, Cuban didn't blog from March to October.
I can also think of KissMetrics CEO Neil Patel http://quicksprout.com/
Joel Spolsky of StackExchange - http://www.joelonsoftware.com/
A significant number of these people and those mentioned in the sibling comments here are not CEOs (if you seek out their job title carefully) and/or don't have startups.
Let's not forget to add Richard Branson http://www.virgin.com/richard-branson
Tom Preston-Werner - http://tom.preston-werner.com/
Looks like Tom hasn't actually blogged in 2 years though. That's not really very regular...
Adii Pienaar of WooThemes — http://adii.me

Collis Ta'eed of Envato — http://notes.envato.com/author/collis/, http://inside.envato.com

Who's that a smart bear guy? Jason Cohen of WP-engine? He blogs all the time.
Vinicius Vacanti of Yipit - http://viniciusvacanti.com/

Dan Shipper - http://danshipper.com/