Opendoor Bull Eric Jackson Shorts CRM, DOCU, TEAM, FIVE, ASAN – Here’s Why

• Jackson said he tested the theory on over 700 earnings calls over the last two decades.
• The hedge fund manager argued that many SaaS companies are overvalued and vulnerable, as they are trading largely on AI hype.
• Stocktwits sentiment was ‘bearish’ for TEAM, CRM, ASAN and DOCU, and ‘neutral’ for FIVE.

Hedge fund manager and crypto entrepreneur Eric Jackson on Tuesday revealed short positions in Salesforce, Five9, DocuSign, Atlassian, and Asana — backed by a provocative thesis: the companies talking most about AI tend to deliver the weakest forward returns.

Jackson, best known for his bullish Opendoor call, said he analyzed 147 earnings call transcripts across 21 enterprise software firms, then expanded the study to 716 SaaS earnings calls spanning the past two decades to test the idea.

‘AI Paradox’

“The result: companies in the top quintile of AI language density underperformed the bottom quintile by 5.4 percentage points over the following 90 days,” Jackson said in his Substack blog, calling the trend the “AI Paradox.”

He argued that certain SaaS companies are overvalued and vulnerable because their growth narratives are increasingly driven by AI hype rather than underlying demand, masking a broader slowdown in core business momentum. 

Those companies are facing weakening organic growth, rising customer acquisition costs, and deteriorating pricing power, especially as enterprise spending tightens. 

“Chegg was a $14 billion company. Management said "AI is an opportunity." Stock went from $115 to $0.67. The same language pattern is now showing up in five enterprise software companies,” he said in an X thread about his blog. He added that certain companies, such as CrowdStrike, Zscaler, and Palo Alto, are benefiting as well, with AI making their products “more necessary, not less.”

But, “the market is punishing both groups equally. That's the mistake.”

Jackson’s SAAS Shorts Already In Doldrums

To be sure, all the companies Jackson has shorted are trading at multi-year lows. Asana shares are at their lowest point on record, while Atlassian stock was the biggest loser on Nasdaq in the first quarter of 2026. CRM declined nearly 30% last quarter, its worst since the 2008 financial crisis.

Jackson, who runs EMJ Capital and a crypto treasury company, last month said he had invested in Palantir after the AI company's blowout fourth-quarter results. He has previously taken long positions on Carvana, Better Home & Finance, IREN, and BTQ Technologies, among others.

On Stocktwits, the retail sentiment was ‘bearish’ for TEAM, CRM, ASAN and DOCU, and ‘neutral’ for FIVE on Tuesday.

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