After perhaps the most sluggish journey ever, the penny finally dropped with investors on Wall Street that the grand stock-pumping parade of Alibaba Group was soon coming to an end for Yahoo.

And what a party it has been, with shares of the Silicon Valley Internet giant tripling over the last two years. This happened right after hedge fund dandy Dan Loeb first came to the in-plain-sight-but-no-one-saw-it realization that the giant stake in the Chinese Internet juggernaut — presciently bought by Yahoo co-founder Jerry Yang in 2006 — was the hidden treasure of Yahoo.

A treasure that will finally be cashed in when Alibaba goes public in a few months and Yahoo’s CEO Marissa Mayer is handed about $10 billion, depending on how the offering goes, if the company sells any more of its stake and how CFO Ken Goldman can finesse the taxes on the haul.

And it is most definitely a dreamy mountain of dough, a bet that Yahoo made that paid off big time through exactly no efforts of its own. Not to overuse the metaphors — well, why not? — it feels like the Internet equivalent of that old barb about the trust fund kid who is born on third base but thinks he has hit a triple.

This is a concept that investors have suddenly woken up to, causing Yahoo stock to drop close to eight percent over the last five days in the wake of the Alibaba IPO filing.

Their main worry: It is long past time that Yahoo be judged on the basis of Yahoo alone and what Mayer has done and will do to turbocharge its business.

That's gotta hurt.

That’s gotta hurt.

This is a drum I have been banging on for a while, which some think has been unfair. Perhaps it is just me, but I believe that the benefits of a canny investment almost a decade ago is not what counts in the end for Yahoo. What does is if and how it can reinvent its “core” business.

Despite some small improvements, that core is still troubled enough in a way that would make a Pilates instructor cry.

Make no mistake, since she arrived, the very energetic Mayer has indeed been trying hard to create pockets of strength at Yahoo. She’s bought almost two dozen companies — including forking over $1.1 billion for blogging platform Tumblr; she has said the word “mobile” an awful lot, as she has tried to shift the company into being a mobile-first organization and attract mobile developers; she has made splashy content hires to get advertisers excited about Yahoo’s editorial offerings (Bobbi Brown! Katie Couric! That guy from Elle!); she has pushed forward an ambitious effort in search, designed to extricate Yahoo from its lackluster partnership with Microsoft.

And yes, the free smartphones, the free food, the persistent attempts to make Yahoo seems like a cool place to work with the young Silicon Valley brogrammers, although — having covered it since its inception — I can assure you Yahoo was never actually cool, nor did it ever try to be.

All impressive, if perhaps exhaustingly manic and possibly unfocused, which is why a lot of people are asking now about the overall strategy and wondering if it makes any sense at all.

A piece today in the New York Times was typical:

“More than ever, Marissa Mayer needs to find the exclamation point in Yahoo’s business,” wrote Richard Beales, making a pun on the famous banger used by the company. “To persuade her shareholders, Ms. Mayer needs a clearer sentence or two when it comes to defining Yahoo’s business — before splashing out on punctuation.”

That has become more urgent given the money Mayer is about to get — billions with which she has to do something. And that’s why she hauled out the old financial maxim on the stage of TechCrunch Disrupt this week: “We intend to be good stewards of capital.”

The wise words of Queen B

The wise words of Queen B

But, other than that tired CEO doublespeak, she was unspecific in the extreme, hinting only that there may be multi-billion-dollar share buybacks as before. But take note: That stock will be pricier than ever since Yahoo stock has risen so much.

And there will be acquisitions, although who knows what that will mean, especially since Mayer has to compete with the moneybags of Google and Facebook for the really tasty ones like Pinterest and Snapchat. And even those — which are exciting — are not enough to move any really critical needle at Yahoo when it comes to true growth.

Of course, Mayer could buy an established revenue-generator like AOL, which CEO Tim Armstrong would sure love to have happen. But that transaction has all kinds of complications, and seems too retro for many on Wall Street to ever like enough (although you can read a different take here).

This is not just an issue for Mayer, of course, because tech is most definitely about to see some tougher sledding ahead, as the valuation chickens — much too fat now on overfunding — are coming home to roost.

With overtired consumers saturated in new apps, new devices, new concepts (if someone says wearables or “Internet of Things,” including me, once more, I will scream), there is a palpable sense that there is about to be one of the periodic lulls in tech that happen every so often.

Thus, “What now, Marissa?” will be the meme Mayer will have to deal with every day from here on out. What will she buy? If she does not buy, what can she make out of the ingredients in the cupboard of Yahoo? What happens if what is in that cupboard is not enough?

And worse: If she can’t come up with a winner, why doesn’t she just fork over all the money to shareholders? What’s with all those employees she had once promised the board to cut? Will less-patient investors now take aim again at cash-rich Yahoo to fork over the dough?

Could he return? Let's hope not.

Could he return? Let’s hope not.

In other words, paging Carl Icahn (again)!

You see the problem for Mayer, who is a very smart executive dealing with a puzzle that is perhaps beyond her very clever machinations.

I don’t envy her at all and, frankly, would have no idea what to do either at this point beyond more jazz hands or the true cutting and pruning at Yahoo — shedding most of its businesses — that she has largely avoided.

But what Mayer is really facing is not something a can-do, ex-Google exec likes to hear and is that oldest of cliches: Money really can’t buy happiness.



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