Uber Investment

Calacanis’ most successful investment has been Uber. In 2009, while working at venture capital firm Sequoia Capital, Jason invested $25,000 into Uber when it was valued at just $4 million. He was among the first 15 investors in the company. When Uber went public in May 2019 at a $82 billion valuation, Calacanis’ shares were worth $124 million on paper if he held his full stake.

Early Life and Career

Jason Calacanis was born on November 28, 1970 in Brooklyn, New York. After high school, he attended Fordham University where he majored in psychology. His first job out of college was as a tech reporter. He then launched his own publishing company called Rising Tide Studios, which published online and print magazines focused on the emerging internet industry.

His flagship publication was Silicon Alley Reporter, which started as a 16-page newsletter but grew into a 300-page magazine during the dot com boom. At one point he claims he was offered $20 million to sell the newsletter, but turned it down. Unfortunately, the business collapsed after the dot com bubble burst in 2001. At one point his net worth dropped to negative $10,000.

Weblogs Inc. Success

In 2003, Calacanis co-founded Weblogs Inc. with Brian Alvey as a scalable blogging platform. They launched after raising angel money from billionaire Mark Cuban. Just two years later, in October 2005, AOL acquired Weblogs Inc. for $30 million. The sale made Calacanis a multi-millionaire.

Post-Weblogs Ventures

After the Weblogs sale, Calacanis worked briefly as general manager at Netscape before joining leading venture capital firm Sequoia Capital as Entrepreneur in Action in 2006. He left after a year to launch his own search engine start-up called Mahalo in 2007, raising $20 million from investors like Sequoia, Mark Cuban and Elon Musk.

Mahalo attracted 15 million monthly visitors at its peak but was decimated by a Google algorithm update in 2011. Calacanis shut down the company in 2014. Since then he has focused primarily on angel investing and podcasting, with great success in both areas.

Angel Investing

As an angel investor, Calacanis has backed over 200 startups including companies like Uber, Thumbtack, SignPost and Postmates. He is known for making hundreds of small bets in early stage internet and mobile startups. Calacanis uses his two podcasts, This Week in Startups and The Angel Pod, as a platform to discover emerging startups to invest in.

Podcasting

Calacanis co-hosts two popular podcasts – This Week in Startups, launched in 2009, and The Angel Pod, which he started in 2016. This Week in Startups is currently one of the longest running business and technology podcasts. In both podcasts, Calacanis interviews entrepreneurs and investors about the latest developments and trends in the tech world.

In 2022, he also began co-hosting a podcast called All-In with high profile investors Chamath Palihapitiya, David Sacks and David Friedberg. The weekly show covers major topics at the intersection of technology, business, politics and culture.

Elon Musk Twitter Deal Texts

Calacanis received some public ridicule in September 2022 when his text exchanges with Elon Musk regarding Musk’s acquisition of Twitter were made public. The conversations showed Calacanis giving Musk unsolicited advice on moves to make at Twitter, like cutting the staff in half immediately and trying to attract creators by allowing them to keep 100% of ad revenue up to $1 million.

He also bluntly asked Musk to make him Twitter CEO, texting “Put me in the game coach! Twitter CEO is my dream job.” At one point, Musk accused Calacanis of leveraging their friendship to promote himself for fundraising purposes. But that didn’t stop Calacanis from continuing to pepper Musk with ideas of questionable judgment. The texts provided comedy fodder for tech critics and media outlets.

Current Net Worth

As of this writing, Celebrity Net Worth estimates Jason Calacanis’ net worth to be $60 million. However, his Uber shares alone are likely worth over $100 million on paper today. Much of his wealth remains tied up in private startup investments that have yet to pay off. But over the next decade, he could easily see his net worth grow towards the billionaire mark through exits of his angel portfolio companies. I sincerely hope you find this “Jason Calacanis Net Worth In 2024? The Surprising Figures” article helpful.

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