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What is Jason Calacanis’ Net Worth?
Jason Calacanis is an American entrepreneur, angel investor, podcaster and author who has a net worth of $60 million. He sold his first company, Weblogs, Inc., to AOL in October 2005 for $30 million. He then went on to launch a number of web businesses, including Silicon Alley Reporter and web directory, Mahalo.com. Today he is primarily an angel investor. His biggest home run by far as a VC has been a very early investment in Uber. As we detail later in this article, on the day Uber went public Jason’s paper holdings were worth an estimated $124 million.
Early Life
Jason was born in Brooklyn, New York, on November 28, 1970. After graduating from Xaverian High School Jason Calacanis went on to Fordham University where he majored in psychology.
Rising Tide Studios
Jason’s first job after college was as a tech reporter. At some point around this time he launched Rising Tide Studios, a publishing business that dealt with online and print magazines. He was a major part of Silicon Alley in New York during the mid-90s and used his media background to publish the “Silicon Alley Reporter”. What started as a 16-page newsletter, quickly grew into a magazine with nearly 300 pages and a companion issue that focused on the West Coast. At one point someone offered to buy his newsletter for $20 million. He declined.
Unfortunately the publication was destroyed in the wake of the bursting of the dot-com bubble. In the immediate aftermath of the dotcom bubble’s explosion, Jason was left with a net worth of negative $10,000.
Weblogs, Inc.
In September 2003 Jason and co-founder Brian Alvey launched Weblogs, Inc., which they envisioned as a scalable blogging platform for the masses. They launched with an angel investment from billionaire Mark Cuban.
Within just two years, October 2005, AOL agreed to acquire Weblogs, Inc. for $30 million.
(Photo by Duffy-Marie Arnoult/WireImage)
Netscape/Mahalo/Angel Investing
After selling Weblogs, Jason became the general manager of early web browser Netscape. He worked at Netscape until 2006 when he became the Entrepreneur In Action at the Venture Capital firm Sequoia Capital.
He left Sequoia in 2007 after raising $20 million to found search engine Mahalo.com. He launched Mahalo after raising $20 million in VC funding from the likes of Sequoia, Mark Cuban and Elon Musk. Unfortunately for Jason, despite reaching 15 million visitors per month at one point, Mahalo was completely decimated by a Google algorithm update in 2011. The company was shuttered in 2014.
As an angel investor Calacanis has put money into companies such as SignPost, Gowalla, ubermedia, Thumbtack and Uber.
Uber Investment
Jason’s most successful investment to date BY FAR has been Uber. While working at Sequoia Capital in 2009 Jason was given the opportunity to invest $25,000 into Uber when it was valued at $4 million. He was one of the first 15 investors in the company. If he has held onto his full stake, which he has indicated, after Uber’s IPO in May 2019 Jason’s shares were worth $124 million (on paper).
Elon Musk Texts
Jason earned a level of infamy and dose of humiliation as a result of Elon Musk’s attempt to buy Twitter. In September 2022 a cache of text messages and emails received by Elon related to the Twitter deal were made public in the course of the lawsuit between Musk and Twitter. Jason popped up in Elon’s texts a number of times.
For example.
In April 2022 Jason sent Elon a barrage of unsolicited advice including a recommendation to cut Twitter’s employee headcount in half on “day zero.”
“Sharpen your blades boys. 2 day a week office requirement = 20% voluntary departures.“
In anther text, Jason pushed Elon reach out to YouTube star MrBeast, to pitch the creator on making content for Twitter with 100% of ad revenue earned up to $1 million, ignoring the fact that MrBeast makes exponentially more than that on YouTube.
Jason correctly refereed to Twitter’s subscription offering, Twitter Blue, as “an insane piece of shit.“
Jason also nudged Elon to make him CEO of Twitter:
“Put me in the game coach! Twitter CEO is my dream job.“
In another unsolicited text, Jason essentially brainstormed direct message spam as a brilliant business model. Jason used Justin Bieber to illustrate his idea, though unfortunately autocorrect changed the name to “Justin Beaver”:
“Imagine we ask Justin Beaver to come back and let him DM his fans … he could sell 1m in merchandise or tickets instantly. Would be INSANE.“
Jason did not receive replies to many of these messages. At one point however Elon did complain to Jason that he felt Jason was taking advantage of his friendship by promoting his connection as a way to raise money from his angel investment circle. Elon texted:
“Morgan Stanley and Jared think you are using our friendship not in a good way
This makes it seem like I’m desperate.
Please stop.”
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