Blogs of the Year: Ask the Wizard and Fortuitous

Today’s Blog of the Year Picks: Ask the Wizard and Fortuitous.


Between these two blogs, there have barely been twenty posts this year. Yet either one alone could be the best small-business (or small tech business) site of the year. Dick Costolo, co-founder and CEO of FeedBurner (now part of Google) writes Ask the Wizard, and Matt Haughey, proprietor of MetaFilter, is behind Fortuitous. Both these guys are a little too busy running their businesses to post more often than they do, but I’ll take what I can get. And both are creative, funny, honest writers whose openness and candor are inspiring.

Ask the Wizard is about the financial and organizational building blocks for creating and launching a company that is venture-backed and designed for growth. Dick’s done what a lot of tech entrepreneurs consider the holy grail, starting up a little tech firm, getting some first-rate funding, and then flipping it to Google. He and his team even did it in Chicago, of all places. And it’s not the first-time this team’s built a successful company. (Shout out to Spyonit!) So there’s a level of credibility and experience here that goes way beyond the endless sea of would-be tech business pundits who are mostly just talking out their asses.

And from the side of the independent entrepreneur who worked his ass off for years and self-funded a business into being a nice little stable company with a great set of ethics, nobody’s got better credentials than Matt Haughey. MetaFilter has grown from one of the earliest and most influential group blogs into a whole network of related sites, including Ask MetaFilter, which I raved about last year for beating Google and for being one of the best sites on the web. Appropriately, Matt’s not talking about venture capitalists and boards of directors — he’s talking about the nuts and bolts of starting up a company and running it every day. And this stuff can be downright nerve-wracking, since there isn’t exactly a school you can go to for this kind of stuff. If you have a little company, tasks like talking to the press and hiring an accountant are the kind of things that can keep you up for a lot of long, sleepless nights. So Matt walks through his own process of how he figured those things out, accompanied by a remarkable honesty about the intimidating situations and neophyte’s mistakes he encountered along the way.

Best of all, both of these guys are great storytellers. You don’t have to be an entrepreneur or a geek to get into the narrative of what they’re saying; It’s just a really modern retelling of a story as old as the American dream.

Pick of the Posts:

If you like this, try: Worst name ever for an amazingly good blog. Marc Andreessen should have been blogging, oh, about ten years ago. But I guess he was busy. He’s made up for lost time with an astoundingly frequent set of posts that are up-to-the-minute in their topicality but informed by the fact that no matter what part of the geek business world you’re in, he’s done it bigger, louder, and earlier. I usually try to play it cool with the name-dropping and the fanboyism, and I’m very fortunate that I get to meet and work with a lot of my inspirations, but I’m not ashamed at all to admit that I was totally geeked out to see one of my posts referred to by Marc as “the smartest thing anyone has said today“, even if it was only in the context of Open Social.

This is one in a series of posts about Blogs of the Year for 2007. They’re my subjective picks about blogs that inspired or influenced me this year, and you can check out my introductory post to find more.