Alibaba’s IPO could put $15.4 billion into Yahoo’s pocket

Yahoo made an incredible investment when it paid $1 billion for 40% of Alibaba Group back in 2005. Times have changed and now Alibaba is the bigger fish. Last year, a subset of Alibaba’s properties, two web portals, together did more business than eBay and Amazon combined.

As of today Yahoo owns about a 24 percent stake of Alibaba, a portion that could be worth as much as $37 billion, according to an average of analyst’s estimates compiled by Bloomberg News. Yahoo will experience its windfall as a mixture of cash and continued equity. Because of agreements between the two companies, Yahoo has to get rid of a significant portion of its holdings the minute Alibaba goes public, selling those shares at the initial price and missing out on the first-day market bump.

Kenneth Goldman, Yahoo’s chief financial officer, recently told investors that Yahoo would likely sell 10 percent of Alibaba and hold on to 14 percent. Such a sale would mean $15.4 billion in cash, added to the $5 billion in cash that Yahoo had as of the end of last year.

This wouldn’t be the first time Yahoo has bolstered its coffers by selling off a portion of Alibaba. Yahoo made $4.6 billion in 2012 by selling shares back to Alibaba itself, valuing the company at a fraction of what it would be today. “Forgive me for using hindsight here, but clearly I wish we hadn’t done that,” said Goldman at a conference earlier this month.

A great investment.