Morgan Stanley nabbed the biggest United States (US) initial public offering of the past five years. Now it gets to field the second-guessing after Uber Technologies Inc tumbled 18 per cent in its two painful first days of trading.

Across Wall Street, questions are flying: Why did bankers including Morgan Stanley’s suggest a $120 billion valuation last year that Uber could not deliver? Did the syndicate led by the firm set the IPOs price too aggressively? And did they steer too much stock to big investors who made hollow pledges to hold it long term?

In retrospect, the underwriters should have done a better job at figuring how strong the true demand was, said Jay Ritter, a professor at the University of Florida’s Warrington College of Business who specializes in IPOs. But underwriters in general have a hard time finding out how much buy-and-hold demand there is, versus flippers.

The debate over how well Morgan Stanley and other banks handled the marquee offering is complicated by a lot of bad luck, including the abrupt flare-up last week in US-China trade negotiations that drove markets down around the globe, as well as the recent dismal performance of Uber’s main rival, Lyft Inc. There’s also a broad, gnawing concern about Silicon Valleys penchant for delaying public listings until startups achieve full size: Who’s left to buy?

Many top-tier investors already owned shares of Uber before last week, potentially curbing some appetite for the $8.1 billion of stock sold. Holders included clients of Morgan Stanley’s wealth management division, such as family offices that had opportunities to buy in privately, one person familiar with the matter said. Even some within Uber’s leadership began to view the round more as a follow-on investment than a fresh public offering, two people said.

Still, people with knowledge of the situation have said the order book was at least three times oversubscribed.

One investor at a multi-billion-dollar shop recalled other misgivings heading into the sale.

He said he grew suspicious days before the pricing because the syndicate of banks kept seeking reassurances that his firm would not flip the stock. Yet, the bankers also kept telegraphing there were ample retail investors hoping to buy in after the debut, which could cause the price to pop at least briefly, offering a chance for a quick and easy profit, the investor said. His firm ended up slashing its final order.

The stock fell more than seven per cent on Friday and then 11 per cent on Monday.

Price stabilization

Morgan Stanley has been trying to steady Uber’s price, according to people briefed on its efforts. As the lead underwriter and stabilization agent, Morgan Stanley has a right to sell additional shares via a so-called green-shoe option. Typically, banks can either get those shares from sellers in the IPO, or by snapping them up in the open market, which helps to support the price as it begins trading. Its unclear to what degree Morgan Stanley has done so.

At least one of Uber’s largest investors, now in the red and speaking under the condition of anonymity, voiced frustration, suggesting the bank should have propped up the price more from the start. Yet that could have left the investment bank with less fire-power to support the stock if it were to keep sliding in the days that followed.

Morgan Stanley has built a reputation for wresting megawatt technology IPOs from major rivals including Goldman Sachs Group Inc, which was listed second on Uber’s offering documents. Some credit the tenacity -- and others the showmanship -- of Morgan Stanley tech banker Michael Grimes and his equity capital markets counterpart Colin Stewart. Both are veterans of the industry, able to reassure clients by saying, “We have been here before.”

Uber, perhaps the player whose opinion matters most, has not faulted the bank. In a letter to employees, Chief Executive Officer (CEO) Dara Khosrowshahi blamed the poor opening on the markets: Obviously our stock did not trade as well as we had hoped post-IPO. Today is another tough day in the market, and I expect the same as it relates to our stock.

Uber's $45 stock price in the IPO gave the company a $75.5 billion valuation. The shares closed at $37.10 on Monday. A $120 billion market valuation would help Khosrowshahi and other executives unlock equity awards.

Its possible that the early trading travails wont last. Morgan Stanley has handled some of the most famous and infamous tech IPOs of all time -- Facebook Inc, for example -- that initially fell before fully emerging as once-in-a-generation companies.

Uber looks kind of like what happened after Facebook, said David Erickson, a finance professor at the University of Pennsylvanias Wharton School. The balloon got deflated on the first day.

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