The unpredictability of the next four years has become so intense that it's a punchline in the tech community, entrepreneur and technology investor Jason Calacanis said.
"We have a really interesting joke that's going around Silicon Valley — Trump is going to either last zero terms or seven," Calacanis said of the president-elect on CNBC's "Squawk Alley" on Wednesday.
Entrepreneurs, of course, thrive on risk, and for a California tech start-up, the business climate can go from hot to cold overnight. But even there, Donald Trump's presidency is creating outsized uncertainty, Calacanis said.
"Nobody knows what is going to happen — it's complete chaos. We can all sit here and talk about what Trump's going to do, but we are in 'black swan' territory — it's going to be a crazy ride, buckle up everybody," Calacanis said.
NBC News reported on Wednesday that companies are playing up old decisions around job creation, in part to avoid a Twitter blitz from the president-elect. CNN reported earlier this month that technology CEOs have posted public relations teams at 3 a.m. local time "out of fear that a Trump tweet could crash their stock and put their company into a frenzy."
"Those tweets are effective in the short-term, perhaps, in a negotiation," Calacanis said. "But in the long-term....bullying people and berating people into doing what you want is not as effective as collaborating and inspiring people to solve these big problems."
Indeed, the tens of millions of followers Trump may gain on his personal account during his presidency could amount to an asset of $30 million or more in terms of Twitter advertising power, Calacanis estimates. Calacanis is CEO of Inside.com, which recently started a new "Inside Trump" newsletter.
Still, Trump's policies could yield some positives for Valley, especially when it comes to the discounted repatriation of overseas cash.
"Trump is going to do 2 or 3 amazing things — I think there's a 10 percent chance that he's going to be a great president," Calacanis said.