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All the irresponsible things Marissa Mayer could do with Yahoo’s Alibaba IPO windfall

Once the dust from Alibaba’s mammoth IPO is settled, Yahoo is going to have a lot more cash to play with. The US internet company was expected to sell nearly 140 million shares into the eagerly anticipated offering last night, raising $9 billion, for after-tax proceeds of at least $6 billion.

The company has already pledged to return half of the IPO proceeds to shareholders (presumably through dividends and buybacks.) That will leave CEO Marissa Mayer with $3 billion-plus to play with (in addition to the $4 billion in cash already sitting on Yahoo’s balance sheet.)

Just to stress, these are entirely speculative options. We reached out to Yahoo for comment, but (unsurprisingly) did not get any response. At any rate, here is what she could do:

Buy AOL

A tie-up between Yahoo and AOL has been talked about for years (paywall), although Yahoo flat out denied any interest as recently as two months ago. It is not a particularly inspiring option, and talking to observers, you do not get the sense it would excite people. Yahoo is still the second-biggest digital property in the US, according to the latest numbers from comScore. Its problem isn’t traffic, it is making money from its traffic. And it’s not clear how buying AOL, the owner of the Huffington Post and a bunch of other websites, would change that.

Still, the talk won’t go away and, yesterday, AOL shares even shot up on vague analyst speculation that it would make sense. Jefferies internet analyst Brian Pitz has been pushing the idea for years but now thinks it might be difficult.”The complicating factor of Marissa in the CEO seat now makes it much more challenging as we are not sure [AOL CEO] Tim [Armstrong] is ready to give up the post to Yahoo,” he tells Quartz in an email. “But anything could happen, especially if it would make an Alibaba divestiture tax free” Pitz said that while a tie up makes sense on paper there would likely be many other complicating factors, including board approval, cost savings, and of course, agreeing a price.

Buy Yelp

Earlier this year, Yahoo was linked with Yelp by Re/Code’s well-connected editor Kara Swisher. The companies went on to establish a strategic partnership, which may mean there is no reason for Yahoo to consider an acquisition anymore. The other problem: Yahoo probably can’t afford it. Yelp is currently valued at about $5.5 billion by the stock market. Assuming a decent takeover premium and you get pretty close to wiping almost all of Yahoo’s cash.

Sign up more expensive talent; order more comedies

One area where Yahoo, under Mayer, has been investing heavily internally is in video. Despite its huge overall traffic, Yahoo lags Google in video traffic and in video advertising (where rates are generally higher than Yahoo’s traditional display ads.)

The company hired TV news anchor Katie Couric to spearhead a new live news channel. It struck deals with Live Nation and Taylor Swift to stream live concerts online. It has even ordered its own, Netflix-style original series—both comedies—and they actually sound quite promising. Other Space is a galactic adventure set in the 22nd century, made by the people behind Freaks and Geeks, while Sin City Saints is described as “an off-beat comedy set in the front office of a fictional pro basketball expansion team.” If Yahoo really wanted to be irresponsible, why not go all out on original video content, an area that is starting to look increasingly crowded?

Continue the acqui-hire binge

Yahoo has actually bought about 40 companies since Mayer took over. The only one that was significant from a shareholder perspective was its $1.1 billion purchase of the blogging platform Tumblr. For the most part, the rest have been acqui-hires of engineers and product managers, acquisitions Yahoo thinks have helped solve its talent problem. But it would take a long time to burn through all of its money by sticking to small deals like these, and not do anything to help its revenue problem.

Do nothing

Yahoo’s core business is shrinking. Revenue has declined for 13 of the past 16 quarters and four of the past five fiscal years. Yahoo’s share price is up about 170% in the Mayer era—but that’s mainly due to its stake in Alibaba. Yes, Yahoo will retain a 16% stake in the Chinese e-commerce giant, but starting from tomorrow, if an investor wants exposure to the Alibaba story, there is no need to bother with Yahoo anymore, it can just simply buy shares of Alibaba. That means the easy ride higher is probably over, and more scrutiny around Yahoo’s core business in the months and quarters ahead. Doing nothing would not be a sensible option. Many shareholders probably would like to see all of the Alibaba proceeds returned to them. But that is probably not going to happen either.

Buy something in advertising technology

Yahoo has talked at length about helping make the complicated online-advertising world easier to navigate and took steps to reboot its ad technology business earlier this year. Video-ad technology startups are among the speculated possibilities. Valuations are relatively cheap and companies actually generate revenue.”The good news about ad tech is there are a lot of real businesses,” Pivotal Research Group’s Brian Wieser told Reuters yesterday.

Actually, this sounds quite sensible.

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