(Ladylike) Fun and Games: BoomTown Visits Sugar HQ for an Update!

It’s been a dog’s age since BoomTown revisited Sugar Inc., the scrappy women-focused content start-up run by Brian and Lisa Sugar.

I first paid a visit to the San Francisco headquarters of Sugar three years ago to check out the flagship PopSugar (celebs), GeekSugar (tech), CasaSugar (home) and YumSugar (food) sites.

Since then, it has moved into a range of other arenas, via acquisition, such as:

ShopStyle.com for Web commerce; FreshGuide, which makes women-aimed city guides that show off daily offers in a wide rage of arenas, such as beauty, health and fitness; and video shopping start-up Shopflick, which is now a Los Angeles-based branded entertainment unit called Sugar Digital Entertainment.

And, most recently, in mid-July, it launched a fashion game on Facebook called Retail Therapy. where you run your own fashion boutique.

While mine would be all jeans, T-shirts and Puma Mostros, it is an interesting idea from a content company, injecting into the content model doses of virality, commerce and user passion.

And, of course, Sugar has launched the requisite Apple (AAPL) iPhone and iPad apps.

Last summer, Sugar also cut its ties with NBC Universal by buying back its shares and got a Series C funding of $16 million from Sequoia Capital.

Sequoia has been an existing venture investor, having put $5 million into Sugar in late 2006. NBC invested $10 million in 2007.

And while Sugar has had serious acquisition flirtations with Yahoo (YHOO), it currently remains on the road to building a new media content company of the future from scratch.

Here’s a talk I had with Brian Sugar last week about that and more, as well as a tour of Sugar’s office.

Also below, a very funny video called “The Zoeinator,” which Sugar did for Rachel Zoe’s Zoe Report, as an example of its branded content efforts:

Enjoy: