What you need to know on Wall Street today

Reuters / Shannon Stapleton

Bill Ackman would be right to be worried about his Herbalife short following the company's decision to do a Dutch auction.

Herbalife has a plan that could "squeeze" hedge fund billionaire Bill Ackman.

First and foremost, the company's surging stock - up 11% over two days after a report that it held talks to go private - has cost the Ackman-led Pershing Square Capital Management roughly $115 million on a mark-to-market basis, according to data compiled by the financial-analytics provider S3 Partners.

And Ackman could be in for more pain because of Herbalife's decision to execute a so-called modified Dutch auction, through which the company plans to buy back $600 million in shares at $60 to $68 a pop. The buyback of 8.8 million to 10 million shares could "actually squeeze Ackman out of some of his shorts," S3 says.

In tech news, a $3.4 billion hedge fund is poking holes in conventional thinking over tech behemoths Amazon, Google, and Facebook - and hinting at a potential sell off in the sector.

Fiat Chrysler is reportedly considering breaking itself up. Google and Walmart are joining forces to take on Amazon. And Uber's turmoil has reportedly taken a toll on its valuation.

New York City's famed Plaza Hotel is once again looking for a buyer. And new-home sales tumbled to a 7-month low.

President Trump's obsession with loyalty raises concerns over his preferred pick to lead the Federal Reserve, according to Business Insider's Pedro da Costa.

The Powerball jackpot for Wednesday's drawing is up to $700 million. We did the math to see if it's worth buying a ticket, and it probably doesn't make sense. Still, if you do win, here are the first two things you should do.

Business Insider's Richard Feloni tried the software that uses AI to scan job applicants for companies like Goldman Sachs and Unilever before meeting them. He says it's not as creepy as it sounds.

Lastly, Ferrari has unleashed the new Portofino convertible - its most affordable sports car. And the new BMW M5 is the all-conquering beast we all hoped it would be. Maybe you can buy one if you win the lottery.