What is the net worth of Jason Calacanis?
Jason Calacanis is an American businessman, angel investor, podcaster, and author who has a net worth of $80 million. He sold his first company, Weblogs, Inc. to AOL in October 2005 for $30 million. He then launched a number of web businesses, including Silicon Alley Reporter and Web Manager Mahalo. Today he is primarily an angel investor. His biggest investment in his home to date was a very early investment in Uber.
previous life
Jason was born in Brooklyn, New York, on November 28, 1970. After graduating from Xaverian High School, Jason Calacanis attended Fordham University where he majored in Psychology.
High Tide Studios
Jason’s first job after college was as a technical reporter. Sometime around this time, he launched Rising Tide Studios, a publishing company that deals with electronic and print magazines. He was a major part of Silicon Alley in New York during the mid-1990s and used his media background to publish “Silicon Alley Reporter”. What started as a 16-page newsletter, soon grew into a magazine with nearly 300 pages and a companion issue focused on the West Coast. At one point, someone offered to buy his newsletter for $20 million. to reject.
Unfortunately, the post was destroyed in the wake of the dotcom bubble bursting. In the immediate aftermath of the dotcom bubble burst, Jason’s fortune was left with 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 were launched with angel investment from billionaire Mark Cuban.
In just two years, October 2005, AOL agreed to acquire Weblogs, Inc. for $30 million.
(Photo by Davi Marie Arnault/WireImage)
Netscape / Mahalo / Angel Investment
After selling Weblogs, Jason became General Manager of the early web browser Netscape. He worked at Netscape until 2006 when he became an Entrepreneur In Action at Venture Capital 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 hitting 15 million visitors a month at one point, Mahalo was completely destroyed by a Google algorithm update in 2011. The company shut down in 2014.
As an angel investor, Calacanis has invested money in companies such as SignPost, Gowalla, ubermedia, Thumbtack, and Uber.
Invest in Uber
Jason’s most successful investment to date by the Royal Army has been Uber. While working at Sequoia Capital in 2009, Jason was given the opportunity to invest $25,000 in Uber when it was worth $4 million. He was one of the first 15 investors in the company. If he had kept his full stake, which he indicated, after Uber’s initial public offering in May 2019, Jason’s shares would have been worth $124 million (on paper).
Elon Musk texts
Jason earned a level of shame and 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 was made public in the context of the lawsuit between Musk and Twitter. Jason appears in Elon’s scripts several times.
for example.
In April 2022, Jason sent Elon a set of unsolicited advice including a recommendation to cut Twitter’s staff in half on “Day Zero”.
“Boys’ blades sharpened. Office requirement of two days per week = 20% voluntary departure.“
In another text, Jason Elon paid to reach out to YouTube star MrBeast, to convince the creator to create content for Twitter with 100% of the $1 million in ad revenue, ignoring the fact that MrBeast makes twice as much money than that on YouTube.
Jason correctly judged Twitter’s subscription offering, Twitter Blue, as “Crazy piece of crap.“
Jason Elon also urged his appointment as Twitter’s CEO:
“Put me in the game boss! Twitter CEO is my dream job.“
In another spam text, Jason basically devised direct spam as a great business model. Jason used Justin Bieber to illustrate his idea, although the autocorrect unfortunately changed the name to “Justin Beaver”:
“Imagine we ask Justin Beaver to come back and let his fans DM… he can sell 1 million merchandise or tickets instantly. would be crazy.“
Jason did not receive responses to many of these messages. At one point, Elon complained to Jason that he felt Jason was taking advantage of his friendship by cementing his relationship as a way to raise money from the Angel Investment Circle. Elon wrote:
“Morgan Stanley and Jared think you are using our friendship in a bad way
This makes it sound like I’m desperate.
please stop.”
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