Google's Checkout Challenges

But 1% is far too large a number, says a PayPal spokeswoman, for lapses in orders that may be attributable to delays caused by Google Checkout's connection to a vendor's systems.

"That is why we have spent so many resources getting our API [application programming interface] exactly right and connecting our services with a vendor's," says the spokeswoman. "Communication with the vendor needs to be seamless."

Google's trials with Checkout are especially revealing at a time when the company is moving beyond the online advertising market it helped pioneer to more established realms such as radio and print advertising.

Here, the advantage can go to older, more entrenched competitors that have deeper relationships and a better grasp of the landscape.

PayPal, a 7-year-old service that raised more than $250 million in venture capital before being picked up by eBay in 2002, has a big lead over Google Checkout in ironing out the intricacies of the payment business.

And whether it's ensuring seamless integration with vendors or fraud protection, much of the behind-the-scenes heavy lifting in the sector is done best when it goes unnoticed.

Moreover, Google's vaunted technological prowess and tendency for clear-eyed thinking is going to be much less of an advantage in businesses mired in history when compared with fresh, groundbreaking frontiers.