Jason Calacanis

Jason Calacanis is an American internet entrepreneur, angel investor, and media personality who maintained a social relationship with both Jeffrey Epstein and Ghislaine Maxwell spanning from at least December 2001 through 2014. The correspondence reveals three key dimensions: a familiar personal relationship with Maxwell dating to 2001, during which Calacanis casually referenced Epstein's most notorious properties — "the island" and "the ranch" — by name; deep embeddedness in John Brockman's Edge Foundation network, which served as a primary conduit between Epstein and the tech elite; and a critical role as intermediary connecting Epstein to Bitcoin's core developers, including lead maintainer Gavin Andresen, in June 2011.

Calacanis's facilitation of Epstein's access to Bitcoin's inner circle represents one of the earliest documented instances of a financial elite figure pursuing direct contact with cryptocurrency's architects. The correspondence shows Epstein and Brockman pursuing this connection with notable urgency, with Brockman telling Calacanis to expect Epstein's call and reporting back when he "struck out with 8 people" trying to find alternative routes to the Bitcoin developers. After Calacanis delivered the contacts, Epstein immediately emailed Gavin Andresen directly, referencing Calacanis by name.

No evidence was found of Calacanis's involvement in or knowledge of any sexual abuse, trafficking, or financial crimes. The relationship appears to be that of a well-connected tech entrepreneur who willingly maintained social ties with Epstein and Maxwell — including after Epstein's 2008 conviction — through the Edge Foundation intellectual circle.

Background#

Jason Calacanis (born November 28, 1970) is a serial entrepreneur and prominent figure in the technology startup ecosystem. In the late 1990s and early 2000s, he was CEO of Silicon Alley Reporter, a New York-based technology publication covering the dot-com era. He later co-founded Weblogs, Inc. (sold to AOL in 2005), the search engine Mahalo.com, and the technology news podcast and conference series "This Week in Startups" (TWiST) and LAUNCH Festival.

Calacanis is known as one of the most active angel investors in Silicon Valley, with early investments in companies including Uber, Robinhood, and Calm. He is the author of Angel: How to Invest in Technology Startups (2017). By the period covered in the Epstein correspondence, he was based in the Los Angeles area (Brentwood) and was well-connected across the tech and media worlds.

His connection to the Epstein network was primarily mediated through John Brockman, the literary agent and founder of the Edge Foundation, whose exclusive intellectual salons and dinners brought together billionaires, scientists, and tech entrepreneurs — and served as a key vehicle through which Epstein cultivated relationships with the technology elite.

Correspondence with Epstein#

Early Social Relationship with Ghislaine Maxwell (2001–2002)

The earliest documented contact places Calacanis in direct, familiar correspondence with Ghislaine Maxwell in December 2001. In a three-email exchange, Calacanis pings Maxwell: "you there?!?!" Maxwell responds: "Receiving loud and clear. Gx." Calacanis then writes:

"where are you? NY, PARIS, the island, the ranch? (hint: please say NY so I can take you to the Knicks game tonight)"

Maxwell replies: "Nope, sorry can't tell you that I am in NY at this moment. Wish I was as the knicks game sounds great. I am in PB returning to NY after the New Year. Plse make seeing me a New Years resolution."

The reference to "the island" and "the ranch" is highly significant. These almost certainly refer to Epstein's Little St. James island in the U.S. Virgin Islands and his Zorro Ranch in Stanley, New Mexico — the two properties most centrally associated with Epstein's sexual abuse of minors. Calacanis's casual, shorthand reference to both properties demonstrates substantial familiarity with Epstein's world, not merely a passing acquaintance. Maxwell's reference to "PB" indicates Palm Beach, the location of Epstein's Florida residence.

In October 2002, Calacanis emailed Maxwell again in a characteristically casual tone, describing a social encounter with Nick Jarecki:

"had Nick Jarecki over my place last night for Sopranos and pasta and he is on my computer and my email was open and he is like 'You know GMAX!' and i was like, 'yeah, you know GMAX?' and he was all like 'yeah', so i was all like 'whoa' and he was like 'cool.'"

Calacanis's use of the nickname "GMAX" for Maxwell — also employed by Jarecki — reveals a social circle in which Maxwell was a familiar, almost celebrity-like figure. Nick Jarecki is the son of Dr. Henry Jarecki, a commodities trader who had extensive correspondence with Epstein's office documented in the archive.

The Edge Foundation Circle (2009–2011)

Calacanis was deeply embedded in John Brockman's Edge Foundation network, which functioned as one of Epstein's primary pipelines to the tech and scientific elite. In June 2009, Brockman asked Epstein about "backing this year's event" — the Edge Master Class 2009 on Synthetic Genomics, co-taught by Harvard's George Church and J. Craig Venter. The invitation list placed Calacanis (identified with his company "Mahalo") alongside Jeff Bezos, Sergey Brin, Bill Gates, Elon Musk, Larry Page, Sean Parker, Mark Zuckerberg, and Epstein himself.

An internal Edge Foundation document listed Calacanis under "EDGE BILLIONAIRES" — a category that included Jeff Bezos, Sergey Brin, Steve Case, Jeffrey Epstein, Bill Joy, Elon Musk, Pierre Omidyar, Larry Page, Sean Parker, Charles Simonyi, and Mark Zuckerberg, among others. Calacanis was not actually a billionaire at this time, making his inclusion in this tier notable and suggesting Brockman considered him a valued member of the network.

In February 2011, Brockman circulated an invitation for a dinner at Le Cirque's private dining room on February 16, 2011. The confirmed guest list included Jeffrey Epstein (listed as "money manager and science philanthropist") and Ghislaine Maxwell (listed as "Investor"), alongside Daniel Kahneman, Robert Trivers, and others. Under "AWAITING RESPONSE" were "Jason Calacanis/Jade Li Calacanis" — listed alongside Sergey Brin/Anne Wojcicki, Richard Dawkins, Sean Parker, Jack Nicholson, and Marvin Minsky. This dinner invitation placed Calacanis and his wife in a social setting explicitly organized around Epstein and Maxwell's presence, well after Epstein's 2008 conviction and sex offender registration.

In March 2011, Brockman reported to Epstein: "Going to Wired party where I'm guest of honor... Also Calacanis is having a birthday dinner for me Saturday nite." Calacanis was thus not merely attending Brockman's events but actively hosting them, which reveals the depth of the Brockman-Calacanis relationship through which the Epstein connection operated.

The Bitcoin Connection (June 2011)

The most consequential episode in the Calacanis-Epstein correspondence is a June 2011 email chain in which Calacanis served as the key intermediary connecting Epstein to Bitcoin's core developers. At the time, Bitcoin was trading in a volatile range of roughly $10–30, and the cryptocurrency was known primarily to technologists and libertarian activists.

On June 4, 2011, Brockman emailed Epstein from Eastover Farm:

"jason,, ? bitcoin guys? He lives is Bel Air (it's 5am there now). I wrote and told him what you want and to expect a call from you 9am or later PST this morning."

The same day, Epstein emailed Calacanis directly: "I would like to get in touch with the bit coin guys. I m happy to see you doing well." Calacanis replied:

"hey pal... running out to a kids birthday party. will dig up their info. so you know, these are folks who are not trying to build a business. they are the crazy open source folks who are radicals. their motivation is more inline with Wikileaks or wikipedia. i had these guys on my TV show on the web: YouTube - - Startups - Gavin Andresen and Amir Taaki, Bitcoin"

Calacanis's characterization of the Bitcoin developers as "radicals" whose motivation is "more inline with Wikileaks or wikipedia" is notable — he was alerting Epstein that these were ideologically driven individuals, not business-minded people who might be swayed by financial incentives. Yet he proceeded to facilitate the introduction regardless.

When Calacanis didn't deliver immediately, Epstein pushed on June 5–6: "numbers, contacts?" Calacanis responded: "getting them today for you."

Meanwhile, Brockman was pursuing parallel channels. On June 7, Brockman reported to Epstein: "Struck out with 8 people so far on this one and can't find Calacanis. See link. If you haven't gotten anywhere I could try to go directly to Gavin Andresen, who looks like the right guy." The subject line referenced "Bowling for Bitcoins » Meet the Trader 05: Gavin Andresen, Clearcoin." The fact that Brockman had contacted eight people and was still searching shows the urgency Epstein placed on reaching Bitcoin's developers.

On June 11, 2011, Calacanis delivered, CC'ing Brockman:

"tech lead: Gavin Andresen: [REDACTED] escrow guy -- Amir Taaki: [REDACTED] will be in Europe this summer and in September i think... will ping you for coffee."

Gavin Andresen was at this time the lead maintainer of Bitcoin Core — effectively the most important developer in the entire Bitcoin ecosystem, having been designated by Satoshi Nakamoto as Bitcoin's lead developer. Amir Taaki was an anarchist coder and early Bitcoin developer known for his radical political views.

The very next day, June 12, 2011, Epstein emailed Andresen directly:

"gavin.. I spoke with Jason calacanis,, I would like to speak with you, call my office in ny [REDACTED]. The idea is great, the execution as you are now aware has some serious risks."

Epstein's comment that "the execution as you are now aware has some serious risks" is cryptic and significant. It could refer to Bitcoin's regulatory vulnerabilities, security risks, or Epstein's assessment of the technology's practical challenges. Regardless, it demonstrates Epstein was already thinking strategically about Bitcoin at a very early stage, and that Calacanis's facilitation gave him direct access to the person who controlled Bitcoin's development.

Ongoing Contact (2011–2014)

In July 2011, shortly after the Bitcoin exchange, Calacanis emailed Epstein: "will be in paris on Tuesday to Thursday if you want to get coffee." Epstein replied: "sorry, in ny today through fri." The casual offer to meet in Paris suggests a comfort level with seeking out Epstein's company internationally.

Epstein maintained Calacanis in his digital contacts. A Skype contacts export lists Calacanis (ID 91183), and Epstein's Mac Address Book contained Calacanis's entry with a work email (created February 1, 2012). In June 2012, Google+ suggested both Calacanis and Gavin Andresen to Epstein as contacts. This reflected their digital connection.

Calacanis continued to appear in Epstein's inbox through automated feeds — LinkedIn updates and LAUNCH newsletters. In January 2014, someone forwarded Calacanis's LAUNCH Festival 2014 newsletter to Epstein with the note: "This might be fun. Not really your scene, but super interesting group of people!!" In March 2015, another forwarded a LAUNCH Festival 2015 newsletter with the comment: "Fun to read." These forwards suggest that people in Epstein's circle continued to associate Calacanis with Epstein's interests.

Connections#

Calacanis's correspondence reveals connections to the following individuals in the Epstein network:

• Jeffrey Epstein — Direct correspondent (~6 unique emails, with additional duplicates across DOJ volumes). Addressed as "hey pal." Calacanis provided Bitcoin developer contacts at Epstein's request and proposed meeting for coffee in Paris and New York.

• Ghislaine Maxwell — Direct correspondent (3 emails). Calacanis had a familiar social relationship with Maxwell dating to at least December 2001, referencing Epstein's properties by shorthand ("the island, the ranch") and using the nickname "GMAX." Invited her to a Knicks game.

• John Brockman — Primary intermediary (2 direct emails, multiple indirect references). Brockman facilitated the Epstein-Calacanis connection through Edge Foundation events and dinners, and actively coordinated Calacanis's role in the Bitcoin introduction. Calacanis hosted Brockman's birthday dinner.

• Nick Jarecki — Social acquaintance who recognized Maxwell's email on Calacanis's computer. Son of Henry Jarecki, a figure with extensive Epstein correspondence in the archive.

• Gavin Andresen — Bitcoin lead developer whose contact information Calacanis provided to Epstein, leading to direct contact between Epstein and Andresen.

• Amir Taaki — Anarchist Bitcoin developer whose contact information Calacanis also provided to Epstein.

Document References#

Visits to Epstein Properties#

While no visits are directly documented in the correspondence, Calacanis's December 2001 email to Ghislaine Maxwell — "where are you? NY, PARIS, the island, the ranch?" — demonstrates detailed familiarity with Epstein's portfolio of residences, including his private island (Little St. James, U.S. Virgin Islands) and ranch (Zorro Ranch, Stanley, New Mexico). The casual, shorthand nature of these references suggests either prior visits or extensive social knowledge of Epstein's properties and Maxwell's movements between them. Maxwell's response that she was in "PB" (Palm Beach) further confirms the conversational familiarity with this network of properties.