San Francisco-based women-focused online media site Sugar Inc. has made it first significant move into the local market, by announcing its purchase of FreshGuide.

The locally focused FreshGuide makes women-aimed city guides that show off daily offers in a wide range of arenas, such as beauty, health and fitness. Another FreshGuide offering, BookFresh, does online booking for spas and salons.

FreshGuide is in four markets now: San Francisco, Silicon Valley, Los Angeles and Seattle. It will continue to operate as separate brand from Sugar.

Terms of the deal were not released.

Sugar, which runs the flagship PopSugar.com site, is at an interesting juncture right now, in a space that is both competitive and fast-growing.

According to sources, in search of a cogent women’s strategy, Yahoo (YHOO) has given the start-up the once-over several times, including recently.

And a year ago, the company broke off ties with NBC Universal by buying back its shares and got a Series C funding of $16 million from Sequoia Capital.

Sequoia was an earlier venture investor, having put $5 million into the start-up in late 2006.

NBC invested $10 million in 2007. The media giant had been selling online advertising for the site, an arrangement that had previously ended.

Here’s the official press release from Sugar on the purchase:

Sugar Inc. Enters Local Editorial and Advertising Market With Acquisition of FreshGuide

Sugar Inc. Will Rapidly Accelerate FreshGuide’s Growth and Expansion with Its Large Passionate Audience of Women

San Francisco, CA (June 8, 2010)–In its first foray into providing local editorial and advertising, Sugar Inc. (SugarInc.com) today announced it has signed a definitive agreement to acquire FreshGuide Inc., which operates FreshGuide.com and BookFresh (BookFresh.com). FreshGuide.com is an online women-focused city guide that provides access to exclusive daily offers from a well-edited selection of local businesses in beauty, health and fitness, dining, travel getaways and other relevant categories. BookFresh provides an online booking service for local businesses, such as spas and salons.

Sugar Inc. is a leading diversified women’s media company that includes PopSugar Network and PopSugar TV, producing original content and social community for women, and ShopStyle, a social shopping service that brings together the most fashionable stores and the best brands. Sugar has had rapid organic audience growth since inception four years ago and today reaches over 16M monthly unique visitors globally.

“We are constantly striving to add innovative offerings that entertain and delight our audience,” said Brian Sugar, founder and CEO of Sugar Inc. “We felt there were tremendous synergies between Sugar and FreshGuide that could be achieved by combining our large audience with their local service. We are very excited to be able to bring to our readers exclusive daily offers at the best places to eat, exercise, shop and
relax in their local areas.”

FreshGuide was founded in 2008 by Ryan Donahue, a veteran of Pay Pal, and launched its first service, BookFresh, later that year. In January 2010, the company launched Freshguide.com to provide local offers by city. Currently, FreshGuide operates in four markets: San Francisco, Silicon Valley, Los Angeles and Seattle. FreshGuide will continue to operate under Sugar Inc. as a separate brand.

“FreshGuide is focused on providing exclusive, local offers for women. By integrating our service with the PopSugar Network’s addictive editorial content, we are creating a city-based editorial and offers of unmatched quality in the market,” said Donahue. “This acquisition will also allow us to dramatically expand our reach and accelerate our growth. We plan to launch FreshGuide in 30 additional cities over the next 18 months in the U.S. and internationally in the UK, France, Germany and Australia where Sugar Inc. has operations.”

Online local advertising is forecast to grow at a 19 percent annual rate over the next four years and is expected to be a $19 billion market in 2010, according to BIA Kelsey Group. Most of that growth is coming from the decline of the $120 billion traditional local advertising market.

“We believe the winning business model for next generation media companies must include diverse revenue streams. This conviction led to our acquisition of ShopStyle in 2007, which provided Sugar with a new marketing channel for retailers and brands to acquire visitors that met their ROI goals. The acquisition of ShopFlick, now PopSugar Studios, in 2009, enabled Sugar to launch PopSugar TV and provide advertisers a compelling video environment for branded entertainment. Similarly, we believe that FreshGuide will provide local advertisers the ability to advertise to Sugar;s large audience in a high-quality and cost-effective manner.

The FreshGuide service will also provide Sugar’s national advertisers and retailers with a new way to extend their brands into local markets as we develop our local city guides,” added Sugar.

As BoomTown argued yesterday in a piece on the landscape of Yahoo if Microsoft completes its purchase of the Internet portal, Yahoo (YHOO) certainly knows how to make online content.

As we wrote: “For all its history, right down to today, even with all these dumb widgets competing for users’ attention, Yahoo continues to natively understand how to to entertain, inform and serve up their own and others content to consumers.”

Case in point, an attractive new site it launched today called Shine, which is aimed at women from their mid-20s to their mid-50s.

As you can see from the image below, it is a very well-done site, incorporating a lot of the good stuff in the same genre from around the Web.

Does it look a bit like the sassy properties of Sugar Inc.? Is it light and frothy like Glam Media? Does it feel a bit like DailyCandy, in its focus on the shopping as a sport? And, is it as helpful as iVillage (and does it even “borrow” a wiggly “i”)?

Yes indeedy to all!

Imitation is a form of flattery, I suppose, although Yahoo’s site feels fresher than any out there and it has an aspirational and hip feel that women will like, I think.

I’d call it an Eat-Pray-Love mood, with a lot of Oprah mixed in.

More importantly, it is clearly a good market for Yahoo’s advertisers, who all aim to reach this high-spending but underserved demographic online.

Yahoo is trying to reinvigorate its lackluster efforts here, as well as making plans to further drill down into related topics like parenting, sex, food and wellness that are present on the Shine site now.

While it looks a lot like a blog plus, Shine obviously has social written all over it and a wide range of communications tools will be easy to layer over the service.

It also is smart in its partnering with lots of media companies like Hearst and in pointing across the Web to give users a more comprehensive offering.

But can Yahoo compete in a very crowded field with such a late entrant? Probably. It recently put up a celebrity site called OMG, which has grabbed significant traffic quickly.

And while we honestly could care less if men look bad in skinny jeans (um, yes!), there is probably something on the very-full page of interest to everyone.

The Shine site has Brandon Holley as its editor-in-chief, but the effort in the arena is being helmed by Amy Iorio, who is the VP/GM of Yahoo’s Lifestyles unit. It all rolls up under Yahoo Media SVP Scott Moore.

While Yahoo PR will probably blah-blah too much about “starting points,” which is the latest buzz word from top brass, related to Shine, it should just hush up and realize Yahoo’s many owned-and-operated media conglomerations just need decent support and promotion to stay as strong as they are and to keep them as one of the bright spots at the company.

Here’s a screen shot of the site (click on the image once to make it appear on another page and then again to make it larger):

After a year of manic site creation, Brian Sugar actually bought his first company, rather than extend his name further in the online women-focused arena.

Yesterday, Sugar’s San Francisco-based Sugar Publishing–which includes the flagship PopSugar (celebs), GeekSugar (tech), CasaSugar (home), YumSugar (food), well, we could go on but won’t for fear of lapsing into a diabetic coma–changed its name to Sugar Inc. and also acquired ShopStyle.com.

The all-equity deal for the Los Altos, Calif.-based social-shopping site will give Sugar a nice bit of technology to play in the Web commerce space more aggressively, with features that allow the quick creation of shopping widgets using products grabbed from all over the Internet.

Think of a digital version of one of those massive kitten-heel shoe spreads in Lucky magazine that also allows you to instantly buy stuff you see and you’ve got the right idea.

We sat down with the jumpy (really, he is) Brian Sugar and made a video interview recently, after noticing the tear he and his wife Lisa have been on since they founded their mini-empire last year.

Their activity has caused notice–last year, Yahoo almost bought the network of sites. The Sugars were probably glad they missed that bullet now, as their sites seem to be growing faster without a big partner.

The start-up is backed by Sequoia Capital and also NBC Universal, which have both sunk $15 million in total into the company, which uses a unique cross-pollinating style to grow its audience to about 5 million unique visitors a month.

NBC, via its iVillage subsidiary, sells the Sugar Network’s ads in a guaranteed deal for the company.

While it is a crowded space in all of Sugar’s subsidiaries, it’s also nice to see a sassy effort from the Sugars, who use a sweeter (sorry!) approach to coverage–some might call it saccharine (sorry again!) even–in the blog genre.

In other words, Lindsay Lohan is still a drunken, drug-addled mess, but don’t those super white nails look amazing!!!

The new buy is in keeping with Brian Sugar’s background of online commerce (top stints at J. Crew online and also Kmart’s ill-conceived BlueLight.com) and give Sugar sites another tool in an interesting arsenal.

“We’re aimed at an ADD culture,” said Sugar to me yesterday, and he is not kidding.

Each of his more than a dozen sites–yes, there is also a social network called TeamSugar, as well as a tagging site called, yep, Sugarlicio.us–has from 15 to 25 posts a day, with the user-generated content numbering upward of 15,000 items.

It all makes us feel like we’ve gained five pounds by just lingering on the sites. (Sorry once again, but these sugar puns are hard to resist!).

See Sugar in action: