Venture Capitalist And Podcaster Jason Calcanis Claimed He Only Knew Epstein In The 90s, Email Dump Shows They Were Chummy Even After The Conviction

Tech entrepreneur and podcast host Jason Calacanis has disabled comments on his X account following recent scrutiny over his relationship with convicted businessman Jeffrey Epstein.

The controversy centers on discrepancies between Calacanis’s public statements about when he knew Epstein and what recently surfaced emails appear to reveal.

Calacanis co-hosts the popular All-In Podcast and is married to Bitcoin investor Jade Li Calacanis. He has repeatedly stated that his contact with Epstein was limited to brief encounters in the 1990s.

However, newly released correspondence suggests their connection continued well into the 2000s and 2010s, even after Epstein’s 2008 conviction for soliciting prostitution from a minor.

The disclosures have sparked particular criticism from Palmer Luckey, the billionaire founder of Anduril Industries and creator of the Oculus VR headset.

Luckey posted on X that Calacanis “said 10+ times that he only knew Epstein in the 90s. He was actually helping Epstein through the 2000s and 2010s, even after the child s*x trafficking conviction.”

The contrast has not been lost on observers familiar with Calacanis’s public commentary. Luckey highlighted what he characterized as inconsistent standards, noting Calacanis’s harsh criticism of him over political donations while apparently maintaining ties with Epstein after his legal troubles became public.

The situation escalated when Calacanis accused Matt Grimm, Luckey’s business partner at Anduril, of using manipulated images.

In a detailed post, Calacanis wrote: “And now @mttgrmm, @PalmerLuckey’s partner, is using a photoshopped photo of me being twice as fat as I ever was AND trying to slander me by insinuating that I was involved with Epstein.”

He continued: “Like thousands of others, I met Epstein in NYC and TED in the 1990s. I am in his black book, which has been out for a decade and has hundreds of TED/Tech/finance/New Yorkers in it. I am not in the flight logs because I never flew on his plane. I never went to his island, and I probably talked to him for 30 minutes in my whole life.”

X users quickly added context noting the image in question was an unaltered screenshot from a CNBC interview, contradicting Calacanis’s claim of manipulation. Calacanis has not issued a correction regarding the photoshopping allegation.

According to reports, Calacanis may have used his Epstein connections to facilitate introductions to influential investor networks, positioning himself as a well-connected figure in elite financial circles.

The revelations have drawn attention from other prominent figures in business and social media. Real estate mogul Grant Cardone questioned publicly: “Why did @Jason turn off his comments?”

Venture capitalist Sheel Mohnot recently shared a 2011 email from Calacanis that listed his investment portfolio at the time. The email, preserved as what Mohnot called “a fun time capsule,” demonstrated Calacanis’s early stake in Uber, among other companies.

Mohnot calculated that the portfolio, assuming equal $25,000 investments, would have grown from $625,000 to approximately $128 million, driven primarily by Uber’s massive valuation increase.

Calacanis has built his public profile partly on taking strong positions on moral and political issues through his podcast and social media presence. He has frequently criticized political figures and business leaders for what he characterized as ethical failings and dishonesty.

Those past statements now face renewed examination in light of questions about the completeness of his own disclosures regarding Epstein.

As of now, Calacanis has not provided additional clarification about the timeline of his interactions with Epstein or addressed the specific evidence presented in the email releases.