Ross Gerber has a simple message for investors considering a short position on Palantir Technologies Inc. (PLTR): Don't do it.

The Gerber Kawasaki Wealth & Investment Management CEO posted on X recently with unusually blunt advice: "If you learn any lesson today. Don't bet against crazy people. Shorting/puts Palantir is a bad idea… Burry blah blah blah… $PLTR."

A Complete About-Face

What makes this interesting is where Gerber was standing just a few years ago. Back in 2020, he absolutely torched Palantir when it went public. "Just in case you're looking for the most unethical, un-ESG stock since Facebook," he wrote at the time. "We have the evil Palantir going public today. Get a slice of the people surveilling you and giving it to the police and government."

That's quite the journey from "evil surveillance company" to "don't bet against them." So what changed?

The immediate catalyst appears to be a recent SEC filing showing that Michael Burry's Scion Asset Management took massive short positions in both Palantir and Nvidia Corp. (NVDA). We're talking nearly $912 million in puts against Palantir alone. That's not a casual bet.

Karp Fires Back

Palantir CEO Alex Karp had his own colorful response to Burry's move. Speaking to CNBC, he didn't mince words, calling the short position "batshit crazy."

"The two companies he's shorting are the ones making all the money, which is super weird," Karp said. "The idea that chips and ontology is what you want to short is batshit crazy."

Here's where it gets odd: Despite Palantir beating Wall Street expectations in Q3 and issuing positive guidance, its stock dropped 7% the morning after Karp's comments. Nvidia shares slipped nearly 2%. Sometimes defending your company too aggressively can backfire.

Karp wasn't done, though. "I do think these [short-sellers] behavior is egregious and I'm going to be dancing around when it's proven wrong," he added.

The Philosophy Behind Betting on Visionaries

Gerber explained his thinking further in a recent interview with The Information. While discussing Elon Musk's newly approved $1 trillion Tesla Inc. (TSLA) pay package, he laid out why he gravitates toward unconventional leaders.

"I typically bet with crazy people like Elon," Gerber said. "Over the last decade, Elon has helped make me a ton of money."

It's not blind faith, though. Gerber admits he doesn't fully buy into Musk's vision, but he still holds Tesla stock because of the company's uniqueness. "I vote with my dollars. I've sold a lot of stock over the last several years… on the other hand, I've kept a certain amount because there really isn't any company like it."

The same logic seems to apply to Palantir. While Gerber isn't exactly endorsing the company, he's making it clear that betting against it seems unwise, particularly as investor interest in AI continues surging.

Burry's Counterargument

Michael Burry, who famously predicted the 2008 financial crisis, sees the situation very differently. He responded to Karp's CNBC interview with his own post on X: "Doesn't surprise me one bit that Alex Karp and his 'ontology' @PalantirTech cannot crack a simple 13F."

He followed up with a dig at Palantir's data science credentials, noting that a fundamental rule in both philosophy and data science is knowing when you don't have enough information to reach a solid conclusion. Translation: If you're missing key facts, don't pretend you know the answer.

The subtext here is clear. Burry thinks the AI hype has gotten ahead of fundamentals, and he's willing to put serious money behind that conviction.

Who's Right?

Whether Burry's thesis ultimately proves correct or not, Gerber and Karp are aligned on one thing: shorting Palantir right now might not be the smartest play. The company's momentum, its position in the AI boom, and the broader market enthusiasm for the technology create a dangerous environment for short sellers.

Then again, that's exactly when the best short opportunities tend to appear. Sometimes the craziest bet is the one that pays off biggest.