So what does the famously outspoken investor do, maybe to gain a little leverage? He once again floats a possible investment in Uber's chief U.S. rival, Lyft.
"We are positively exploring the opportunity, but whether we make an investment or not — I don't want you to call me a cheater or a liar. And so I say that it depends on the terms and you never know what will happen," Son told investors in a quarterly earnings briefing on Monday. "So depending on the price and the terms, we might change the entity that we would invest in to Lyft."
Son said it is "not decided yet" whether SoftBank would pull the trigger on the Uber deal. SoftBank has a tentative agreement in place with Uber's board to buy 14% to 20% of the company's shares. But Uber shareholders are haggling with the Japanese conglomerate over the price at which those shares would be sold.
Basically, Son wants to pay less and Uber shareholders want more.
If this is familiar, it's because this is the same move Son tried last quarter, when he said "we have not decided which" to invest in. Now, though, there's a specific deal with Uber on the table.
Son on Monday sounded quite uneasy about whether the so-called Uber "tender offer" would succeed — or whether he would be left in need of a different U.S. ride-hailing investment.
"Maybe existing investors don't want to sell or make price up — and if we can't accept the price, maybe we have a different decision," he said. "Again, you never know until the last minute."
Son said that while Uber had "made a good start" as a company, he acknowledged that it was "struggling through some management issues."
Son, in prior remarks on Monday, also shared some behind-the-scenes details of his private sit-down with Donald Trump, who is in Tokyo on the first leg of a five-country tour of Asia. Their tete-a-tete comes almost a full year after the pair met in Trump Tower, when the SoftBank CEO promised the President-elect that he would invest $50 billion in the United States and create 50,000 jobs.
Son said Monday that he was already halfway to achieving that goal.
"Maybe I should've doubled up," Son joked.
Son and Trump also spent some time on Monday complimenting one another's dealmaking ability. Son told investors that Trump was "acting like a top salesman" during his foray to Japan. Trump, for his part, had this to say to Son during their private meeting — at least according to Son:
"Masa, you are great."
—By Theodore Schleifer, Recode.net.
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