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I hope that they are actually planning on implementing this and it is not a well-timed PR stunt to get Overstock.com in the news just in time for last minute Christmas shopping. If so, it will be a huge boon for the Bitcoin economy and could be an important catalyst for other companies to follow suit.
Well, the CEO seems pretty convinced that bitcoin is awesome and worth trying. And he's right; why not? If you convert it to dollars with bitpay, there isn't much risk, and there's a PR bonus.
It would be terrible cash management for Overstock to hold onto Bitcoins given the volatile swings. Better to let Bitpay shoulder the burden.
I doubt Bitpay is shouldering the burden, more likely they're just pumping the bitcoin they receive back into one of the exchanges.
They're shouldering the burden between the time the invoice is issued until it's paid. They eat the price change in that (potentially up to 15 minute) window.
That is certainly possible, but the CEO mentioned 1 1/2 months ago that they were considering this move.

See this NY Times article from 10/31/2013: http://www.nytimes.com/2013/10/31/technology/bitcoin-pursues...

What's taking them so long? It's pretty trivial to integrate something like Bitpay or Coinbase for merchant accounts.

Maybe they're negotiating a deal with one of those companies?

From the Marketwatch article:

The project is in an early stage, with no decision yet on whether Overstock.com OSTK would work with bitcoin companies to allow bitcoin payments or create its own system. A team of six to 12 people is expected to work on bitcoin payments at the company, said Byrne.

http://blogs.marketwatch.com/thetell/2013/12/19/overstock-co...

It doesn't sound like they have quite figured out what they are doing yet.

Not so trivial.

* Presumably they need to integrate with their backend systems for reporting, inventory and tax purposes.

* They need to integrate with their customer support system so bitcoin payments are recognized as such.

* They have to update their refund policy and other legal docs to take bitcoin payments into account

It's not just about making the right API call, you know.

it coin pumping site pumps bit coin. Now, that is news.
Based on my companies performance metrics from our Overstock offerings, they are willing to try anything at this point to stop the bleeding.

Overstock was absolutely murdered after a Google update. They went from being a solid source of revenue from our multi-channel division to being virtually non-existent.

How does a merchant go by accepting Bitcoins? Is the price conversion based on the last trade? Average of the day/week/month? Are the Bitcoins going to be converted to $ right way or at certain intervals?

Given the high volatility of bitcoins, there is no way to predict if a transaction will net profit or loss. How do they account for this?

I'm also interested in how this works. I would imagine they would need to use a webservice to get the actual exchange rate at the time of the order processing to give you an exact amount.
Yes, a service like BitPay will allow you to think entirely in USD; a BTC price determined dynamically for the customer and an exchange price locked in for your bank account.
Hedging via insurance, futures, put/call options, etc. The same way companies that deal in commodities like grains and metals handle this sort of risks. I'm sure people like the Winklevi are more than happy to offer this sort of service.
Your going to have to pay a lot of money to someone to take on btc volatility.