For just the second time in as many months, Uber Technologies (NYSE:UBER) stock cracked above its IPO price of $45 late last week. Shares of the world's leading ride-hailing service closed above its debutante price on Thursday and Friday, something that investors have never seen since hitting the market nearly two months ago.

Staying above its seemingly arbitrary starting line will be challenging, and for now the question of keeping its chin above the $45 bar is moot. Uber stock did open higher this week -- building on its recent upturn -- only to buckle below its IPO price less than two hours into Monday's trading day. Inertia has been stubborn and cruel. Friday remains the only day in Uber's brief history in which the stock hasn't been a broken IPO at some point in the trading session. The question now becomes if the third time can be a charm, as we learn if Uber can finally fix its rookie season.

An Uber driver on the road with his Uber beacon on.

Image source: Uber.

Hitching a ride

A catalyst to the rise that led to an all-time high on Friday was a Reuters report a day earlier, claiming that Uber was negotiating with regulators about expanding into two West African countries and launching a boat service in Lagos. Market momentum likely played a larger role, as Uber already has a global presence with 93 million monthly active platform consumers already. Pushing into new territories won't necessarily move the needle in a meaningful manner. 

Outside of the predictable wave of Uber underwriters scribing love letters four weeks after the IPO, analysts haven't exactly been smitten by Uber. The platform is huge, popular, and growing, but the gargantuan losses can be a real turnoff. The last two Wall Street pros to initiate coverage of the stock -- Jairam Nathan at Daiwa and and John Healy at Northcoast -- went with neutral ratings despite the depressed stock prices at the time. 

Daiwa's Nathan understands Uber's opportunity for growth, but it's hard for him to get entirely behind a company that isn't likely to turn a profit even on an EBITDA basis until 2023. There will be execution risks between now and then, and it may have to scale up its investments along the way.

Northcoast's Healy accepts Uber's best-in-class standing in the booming niche, but he's not sold on the stock's valuation. Uber's business -- particularly on the personal mobility end that continues to drive the lion's share of its revenue -- is decelerating. He feels that fair value for Uber stock is in the low $40s, slightly below Nathan's price target of $46. 

Uber remains a name to watch. Revenue may be slowing, and the cutthroat nature of where the market is now finds all players heavily incentivizing drivers and riders to keep them on their platforms. Put another way, Uber's weak top-line growth understates the 34% rise in gross bookings in its first quarter as a public company.

The stock's been volatile enough that it may very well bounce on both sides of its $45 starting price. The losses and stiff valuation will weigh on the shares, but its market dominance and the industry's growth will pick it back up. Anything that Uber can do in the next few quarters to convince investors that the meaty deficits won't last forever will go a long way to fixing what has been a broken IPO through most of its first two months of trading. The clock is ticking, and the next $45 stress test will probably come sooner rather than later.

This article represents the opinion of the writer, who may disagree with the “official” recommendation position of a Motley Fool premium advisory service. We’re motley! Questioning an investing thesis -- even one of our own -- helps us all think critically about investing and make decisions that help us become smarter, happier, and richer.