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I am not sure how you scale this business. People are not often in-market, and they don't stay there very long. The ads to reach people in-market are prohibitively expensive.

I think I would take the money and blow it on a Super Bowl commercial. I think that is how Lending Tree got off the ground.

Carwoo is a service that matches customers with dealers.

Why should there be any dealership ads? Brand/model ads make sense, but customers on the market for the best deal ought to be able to quickly find which dealer in a convenient radius is willing to offer the best deal. No hassle, no misleading price quotes, no bs.

Disclaimer: I bought my last car via carwoo after reading about it here and I will definitely use it again for future car purchases.

I don't doubt it is a good and useful service, but how do they get their name out there? Advertising to people who are searching for new cars is insanely expensive.
word of mouth. I saved around $1000 and have told tons of people about it.
If the business plan is "word of mouth" then why raise money? This is a company that has a good product, customers that are willing to recommend it, and plenty of dealers signed up. Now they need scale. "word of mouth" is not a very good plan for new auto sales because not many people are in-market, and they aren't in-market for very long. To put that in a simple way, let's pretend I am your friend, and I want to buy a new car. I will likely complete the transaction before me and you are at the pub, and I tell you that I am shopping for a car, and you tell me about carwoo.
honestly, it's difficult to buy cars from dealers? that's one of the easiest (and more expensive) i can think of.

but i think 6mm tells me i'm wrong.

i'd like to see someone solve the problem of buying used cars. solving buying new cars just get a meh from me.

i'd like to see someone solve the problem of buying used cars

What do you feel is the problem?

There are lots of problems, but I think they can be largely segmented by demographic.

Edit: The problems also extend to dealers and there are many demographics that have problems there. Many women, in fact. Dealers are unfriendly places, I spent a very short tour of duty within the industry and have lots of experience as an enthusiast and consumer.

This is an interesting concept and more interesting is that this is something that had been tried successfully a long time back.

In 1997, at Trilogy Software, a bunch of new employees as part of their training program (Trilogy University) pitched this idea. The CEO wasn't sure about it but the team went ahead and implemented it. It was an insanely successful project until due to some political lobbying by car dealers there was some law passed or something due to which they had to shut it down.

It would be interesting to see how big car dealerships in US react to this now.

Ref - http://www.cyberwink.com/don/reading_trilogy.html