Chad Dickerson, a long time Yahoo exec and the head of their Brickhouse special projects group, is leaving the company to become the CTO of Etsy, a a website that allows users to buy and sell handmade items. Mike Folgner, the former GM of Yahoo Video, will take Dickerson’s place at the head of Brickhouse.

We first covered Brooklyn-based Etsy, which has a cult-like following, back in 2005. Since then the company has raised over $30 million in venture capital. The most recent Comscore stats show nearly 2 million monthly visitors and 83 million page views worldwide.

This is a blow to Yahoo on par with the loss of Bradley Horowitz, Dickerson’s former boss, earlier this year. Dickerson ran Yahoo’s developer platform and oversaw their various internal and external Hack Days.

Dickerson joins the ranks of departed Yahoo execs, which gets larger every week. He wrote a long post on his personal blog about his reasons for leaving, but he doesn’t say the one thing that is on every Yahoo’ers mind: they crave leadership, and they aren’t getting it.

Putting a value on private companies is hard enough for insiders and venture capitalists who have full access to the company’s financial statements. When outsiders try to do it, even well-informed ones, it is nothing more than a guessing game. But it is nonetheless perhaps one of Silicon Valley’s favorite parlor activities.

Today, Henry Blodget & Co. at Silicon Alley Insider try to peg valuations on 25 private Web companies. Facebook is at the top of the list, but it is valued at $9 billion instead of the $15 billion that Microsoft’s investment put on the company. Why? Because everyone knows that the $15 billion is too high, so SAI decided to apply a 25X multiple on Facebook’s 2008 revenue forecast of $350 million. Does that make its valuation correct? Probably not. But in the absence of any true market pricing, anyone can go ahead and make a guess.

The same goes for any of the valuations on the SIA 25 list, which puts Wikipedia’s worth at $7 billion, Craigslist’s at $5 billion, Mozilla’s at $4 billion, LinkedIn’s at $1.3 billion, Ning’s at $560 million, RockYou’s at $325 million, and Spot Runner’s at $250 million. Note that three of the top five (Wikipedia, Craigslist, Mozilla) are essentially not-for-profits sitting on very valuable assets. The valuations for those three are based on what they would be worth if they were run differently with an eye towards maximizing revenues—which, of course, could impact how consumers interact with them, which in turn would impact their valuations.

Another 25 startups make up the contenders list, which includes Federated Media ($245 million), Yelp ($225 million), Meebo ($220 million), Mahalo ($150 million), Digg ($125 million), Etsy ($115 million), Powerset ($80 million), and Twitter ($75 million). A full list that changes dynamically every 20 minutes, based on changes in the Nasdaq, can be found here (although, exactly how the valuations are linked to the Nasdaq is never clearly explained)

Some of these valuations have more merit than others. Some have none whatsoever. For instance, SAI gets at its $125 million valuation for Digg by “splitting the difference” between a $200 million buyout rumor we reported and the $60-to-$80 million that Kara Swisher came up with. Splitting the difference between two rumors is not exactly the height of financial analysis.

But what are you gonna do? At least SAI acknowledges that the list is an imperfect work in progress. Don’t get too caught up in the actual numbers. It is more useful really as a starting point to think about relative valuation between different startups. Is Meebo really worth three times as much as Twitter? Is Ning worth as much as Slide? Let the parlor game begin.

Etsy, the anti-eBay shopping site for handcrafted goods, raised $27 million in a series C round. It previously raised a total of $4.6 million from Union Square Ventures and angels Caterina Fake, Stewart Butterfield, Joshua Schachter, and Albert Wenger. Union Square Ventures invested again in this round, as did new investor Acel Partners. Accel partner Jim Breyer will take a seat on Etsy’s board (he is also a board member of Facebook). Fake, a founder of Flickr with her husband Butterfield, and Union Square’s Fred Wilson are existing board members. Since launching in June, 2005, Etsy now has 650,000 members, 120,000 of which are craft sellers, in 127 different countries. The Brooklyn-based startup employs 50 people.

Etsy founder Rob Kalin says in a blog post:

This means that we now have the resources to extend Etsy’s reach in this world, to enable so many more people to make a living making things. We want Etsy to exist for hundreds of years. Our goal is for Etsy to be an independent, publicly traded company, focused on all things handmade.

He says that Etsy is “almost break-even” on profits, but he plans on using the money to:

—Buy $5 million worth of hardware and hosting over the next two years.
—Support more currencies and languages other than the U.S. Dollar and English.
—Fix the checkout system (there is none now, every buyer has to pay every seller on an individual basis. There is no Etsy payment system that works across all sellers).
—Fix search.
—Provide a cushion in case of a recession.
—Offer customer service
—Provide competitive wages and take care of his employees.

In other words, Etsy is growing up. And it needs cash to do so. The site reached 1 million unique visitors in the U.S. last month, according to comScore (1.6 million worldwide), doubling from last April.

Update: the word on the street is that etsy was valued at $90 million pre money in this round. wow.

A relatively new company called Etsy has recently captured my attention. Etsy is a P2P ecommerce company (like ebay) that currently limits sales to handmade items. It’s smart to focus on a niche to iron things out…and Etsy could easily expand into other categories as well.

Etsy does lots of things like ebay – They charge sellers a listing fee and final sale percentage (although at $.10 and 3.5% they are way below what ebay charges), there is an ebay-like feedback system (side note: there is a huge market waiting out there if someone would create an independent third party feedback system with open data and APIs), and they have integrated paypal as a payment option.

Unlike ebay, Etsy has architected the buyer experience from the ground up using web 2.0 priciples.

Tagging

First, Etsy has a very flat taxonomy – top level categories such as Bags & Purses, Toys, etc. Everything underneath these top level tags is based on seller tagging. For instance, look at the “Bags & Purses” category and note the tags (called subcategories) on the right hand side. Click on anyone of these and you go deeper into the taxonomy…although really it is a folksonomy. Further refine items by clicking on additional tags, or on a different set of tags based on materials used to produce the product. The benefit of this folksonomy is that it is user generated and based on popularity. If a new item gets hot fast, the folksonomy will take that into account. It’s a beautiful use of tags and the first launched product I’ve seen that does this.

Flash

Etsy also does some amazing things with flash – the geolocator on the home page is a great way to find sellers by location. You can also use their “shop by color” widget…less useful but an interesting feature. Finally, they have a time machine feature, although I can’t figure out what it does.

Nice product. It looks like more features are coming, too. Check out their blog.