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Jason Calacanis Net Worth: How Much Money Did Jason Invest in Uber?

Jason McCabe Calacanis is an Internet business owner, angel investor, author, and podcaster who lives in the United States. His first business was started in New York during the dot-com era.

Weblogs, Inc., a publishing company he started with Brian Alvey, took advantage of the growing popularity of blogs before it was sold to AOL. Calacanis is also an angel investor in a number of tech startups and a co-host of the All-In Podcast and the This Week in Startups Podcast.

Early Life of Jason Calacanis

Jason was born on November 28, 1970, and he grew up in the area of Brooklyn New York City. Calacanis is the second of three children. They are all boys with roots in Ireland and Greece. He went to Xaverian High School for high school, and in 1988 he got his diploma.

Then, he went to Fordham University to get a degree in psychology. Jason didn’t go right into business when he got out of college. In the 1990s, he started his career as a reporter in New York. He wrote about how online businesses were growing. Calacanis married Jade Li sometime between 2006 and 2009

Jason Calacanis’s Net Worth

According to Celebrity Net Worth, American entrepreneur, angel investor, podcaster, and author, Jason Calacanis has a net worth of $100 million. In October 2005, he sold his first company, Weblogs, Inc., to AOL for $30 million. He then started a number of web businesses, such as Silicon Alley Reporter and, a web directory.

Jason Calacanis Net Worth

He is mostly an angel investor now. By far, his best investment as a venture capitalist was an early bet on Uber. As we’ll talk about later in this article, Jason’s paper holdings were worth about $124 million on the day that Uber went public.

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After college, Jason’s first job was as a tech reporter. Around this time, he started Rising Tide Studios, a company that published magazines online and in print. During the mid-1990s, he was a big part of Silicon Alley in New York. He used his experience in the media to publish the “Silicon Alley Reporter.”

What started out as a 16-page newsletter quickly grew into a magazine with nearly 300 pages and a companion issue that focused on the West Coast. Someone once gave him a $20 million offer to buy his newsletter. He said no. After the dot-com bubble burst, the publication was unfortunately destroyed.

After the dot-com bubble burst, Jason had a negative net worth of $10,000. Jason and Brian Alvey started Weblogs, Inc. in September 2003. They wanted it to be a platform for blogging that could be used by a lot of people. Mark Cuban, who is worth a lot of money, gave them a start-up loan.


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In just two years, in October 2005, AOL agreed to pay $30 million to buy Weblogs, Inc. After selling his Weblogs, Jason became the general manager of Netscape, which was one of the first web browsers. He worked for Netscape until 2006 when he joined Sequoia Capital as the Entrepreneur In Action.

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How Much Money Did Jason Invest in Uber?

By FAR, Jason’s best investment so far has been in Uber. When Jason worked at Sequoia Capital in 2009, he had the chance to put $25,000 into Uber, which was worth $4 million at the time.

He was one of the first 15 people to put money into the business. If he had kept all of his shares, as he said he would, after Uber went public in May 2019, Jason’s shares would have been worth $124 million.

Which Was Jason’s First Web Browser?

Jason became the general manager of Netscape, which was one of the first web browsers, after selling his Weblogs. He worked for Netscape until 2006 when he became the Entrepreneur In Action at Sequoia Capital. In 2007, he left Sequoia after getting $20 million to start the search engine

Jason Calacanis Net Worth

He started Mahalo after getting $20 million from venture capitalists like Sequoia, Mark Cuban, and Elon Musk. In 2011, a change to Google’s algorithm killed Mahalo, which was bad news for Jason. At one point, 15 million people went there every month. In 2014, the business closed.

Making Money by Writing Books

Also, Jason Calacanis is a good writer. In 2017, he wrote a book about how he invested and made money. Angel: How to Invest in Tech Startups: Timeless Advice from an Angel Investor Who Turned $100,000 into $1,000,000 was the title of the book. The book was also made available by HarperCollins.

Frequently Asked Questions

Is Jason Calacanis a Billionaire?

How much does Jason Calacanis have in the bank? American entrepreneur, angel investor, podcaster, and author Jason Calacanis has a net worth of $60 million. In October 2005, he sold his first company, Weblogs, Inc., to AOL for $30 million.

What is Jason Calacanis Known for?

Jason Calacanis, who is known for betting early on companies like Uber and Robinhood, is putting together money to invest in Twitter as part of Elon Musk’s plan to buy the company. Calacanis has known and liked Tesla’s CEO for a long time. He went to New York with him last year when he was a guest host on Saturday Night Live.

How Did Jason Calacanis Get Rich?

Before he became an angel investor, Jason Calacanis was known for his business ventures during the dot-com bubble. Weblogs, Inc., which he helped start, was his most successful project. He went on to write books and host podcasts. Jason Calacanis is worth $100 million as of 2023.


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