Jason Calacanis Net Worth

Net Worth:$60 Million
Date of Birth: November 28, 1970 (53 years old)
Profession:Businessperson, Television producer and Entrepreneur
Nationality:United States of America

What is Jason Calacanis’ Net Worth?

Jason Calacanis is an American Podcaster, internet entrepreneur, and investor who has a net worth of $60 million. For a whopping $30 million, he offered for sale Weblogs, Inc., his first and foremost firm to AOL in October 2005.

The Silicon Alley Reporter and the website directory Mahalo.com were among the online ventures he subsequently started. He invests in angel groups now largely.

Jason’s extremely early investment in Uber has been his biggest success to date as a VC. The value of Jason’s paper holdings on the day Uber went public was estimated to be $124 million, as we go into more depth about that later in this piece.


On November 28, 1970, Jason Calacanis was born in Brooklyn, New York. For his education, he attended Xaverian High School and after his graduation, he majored in a degree in psychology at Fordham University.

Rising Tide Studios

Moreover, after leaving college, Jason worked as a tech reporter where he started a publishing business named ”Rising Tide Studios” which mainly dealt with print and online magazines.

He was a key contributor to the growth of Silicon Alley in New York City in the middle of the 1990s and used his media connections to start the “Silicon Alley Reporter.” What started as a 16-page newsletter quickly grew into a magazine with nearly 300 pages and a sister issue that focused on the West Coast.

Someone once made a $20 million bid to purchase his publication unfortunately he turned the offer down. Sadly, after the dot-com boom broke, the publication was destroyed. Jason’s net worth was negative $10,000 as soon as the dotcom boom burst.

Weblogs, Inc.

A scalable blogging platform for the general public was the motivation behind the founding of Weblogs, Inc. in September 2003 by Jason and co-founder Brian Alvey.

Millionaire angel investor Mark Cuban contributed to their start-up. AOL and Weblogs, Inc. agreed to be acquired by each other for $30 million just two months later, in October 2005.

Netscape/Mahalo/Angel Investing

Jason became the general manager of the pioneering web browser Netscape after selling Weblogs. He worked with Netscape before joining Sequoia Capital as the Entrepreneur In Action in 2006.

Jason left Sequoia in 2007 after lending $20 million to start the Mahalo.com search engine. Elon Musk, Mark Cuban, and Sequoia contributed $20 million to the venture capital money that went towards the creation of Mahalo.

He regrettably lost everything when, in 2011, a Google algorithm update completely decimated Mahalo, which had previously received over 15 million visitors each month. 2014 saw the closure of the business.

As an angel investor, Calacanis has funded businesses like SignPost, Gowalla, uber media, Thumbtack, and Uber.

Uber Investment

By FAR, Uber has been Jason’s most profitable investment to date. Jason had the chance to invest $25,000 in Uber in 2009 while working at Sequoia Capital when the company was valued at $4 million.

One of the company’s original 15 investors, he was. If Jason had kept all of his investment after the IPO of Uber in May 2019, as he has stated, his shares would have been valued at $124 million (on paper).

Texts From Elon Musk

Jason received some notoriety and some degree of embarrassment as a result of Elon Musk’s unsuccessful attempt to purchase Twitter. In September 2022, as a result of Musk’s legal battle with Twitter, a number of texts and emails that Elon received in connection with the Twitter transaction were made public.

Elon’s letters frequently mentioned Jason.

For example;

Jason bombarded Elon with unsolicited suggestions in April 2022, advising him to slash Twitter’s workforce in half on “day zero.”

“Boys, sharpen your tools. 20% of voluntary absences when a 2-day workweek is required.”

In another communication, Jason encouraged Elon to approach YouTube celebrity MrBeast and propose that the creator create content for Twitter with 100% of ad money collected up to $1 million, despite the fact that MrBeast earns far more on YouTube.

Twitter Blue, a membership service offered by Twitter, was appropriately described as “a crazy piece of junk” by Jason.

Jason also urged Elon to appoint him as CEO of Twitter:

“Coach put me on the field! My ideal job would be CEO of Twitter.”

In a subsequent unsolicited text, Jason effectively came up with the wonderful business idea of spamming direct messages. Although autocorrect mistakenly spelled Justin Bieber’s name as “Justin Beaver,” Jason chose Justin to demonstrate his point:

“Just for fun, let’s beg Justin Beaver to return so that he may DM his followers. Instantaneously, he could sell $1,000,000 worth of goods or tickets. A CRAZY idea.”

Many of these messages went unanswered, and Jason noticed it. Elon did, however, at one point express his displeasure to Jason that he believed Jason was abusing their friendship by using their relationship to solicit funding from his network of angel investors. Elon sent the following text:

You are allegedly misusing our friendship, in the opinion of Morgan Stanley and Jared.

This gives the impression that I’m in a desperate situation.

Please put an end to this.”

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While we always strive to ensure that our figures are as accurate as possible, please note that they are only estimates, unless otherwise indicated.

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