Jason Calacanis is an entrepreneur, angel investor and podcaster. He initially became a notable figure during the dot-com bubble after selling his first startup. His most successful venture was co-founding Weblogs, Inc. Despite his success, most people know him as the host of the “All-In Podcast.”As of 2023, Jason Calacanis has a net worth of $100 million.
Background
Jason was born on November 28, 1970, and was raised in Brooklyn, New York. Calacanis is one of three children and is of Irish and Greek descent. For his secondary education, he went to Xaverian High School and graduated in 1988.
He then earned a degree in psychology at Fordham University which is surprising considering he ended up in space. In the mid-1990s Jason worked as a tech reporter in New York City, documenting the rise of the internet.
Business Career
Calacanis saw huge potential in the internet for business opportunities. So, he founded Rising Tide Studios, a media company that issued print and digital publications. Its publications included Silicon Alley Reporter and the Digital Coast Reporter. The business was booming thanks to the dot-com bubble and he rejected a $20 million offer to sell the company.
Sadly, when the dotcom market crashed it destroyed the company but they rebranded to VentureReporter.net. Jason changed the business of selling advertising to database revenue and it worked! Venture Reporter was acquired by Dow Jones in 2003.
After his first big exit, Calacanis quickly jumped onto another venture. Weblogs, Inc was his next idea and he co-founded it with internet entrepreneur Brian Alvey. Billionaire Mark Cuban invested in the startup. The venture was a success and was making $1,000 per day in ad revenue from Google Adsense.
Two years later, AOL acquired Weblogs for over $25 million. He served as General Manager of Netscape and left the web browser in 2006 to join Sequoia Capital. Here Jason was an early angel investor in Uber, he invested $25,000 at a $4 million valuation and by 2017 his investment was worth over $100 million.
Other Endeavors
Calacanis quit Sequoia Capital to launch a search engine called Mahalo.com and raised $20 million in funding from the likes of Mark Cuban and Elon Musk. Mahalo peaked at 15 million monthly visitors but shut down in 2014 after a Google algorithm update wiped out all the traffic.
In 2009, he started a weekly one-hour podcast called “This Week in Startups”. The show briefly stopped in 2012 but it’s currently one of the most influential podcasts on angel investing. He co-hosts another podcast called “All-In” with Chamath Palihapitiya, David Sacks & David Friedberg.
In 2017, he published his book, “Angel: How to Invest in Technology Startups”. Jason created The Syndicate, an angel investing club that hosts three syndicates. Furthermore, he is behind the creation of Australia’s Sydney Launch Festival, which gives local businesses a chance to go global.
Net Worth and Earnings
In the last decade, Jason Calacanis has invested in more than 300 businesses. He invested early in tech startups such as Trello, Thumbtack, Uber, Calm, Wealthfront, and Robinhood. But before that, he was already a multi-millionaire from selling Weblogs, Inc.
Today, it is reported that the renowned tycoon brings in $4 million every year from his businesses and investments. Of course, there are also his earnings from podcasts, book sales, and other businesses such as Inside.com. This is why he is worth $100 million.
Personal Life
Jason Calacanis is married to Jade Li and they are blessed with three children. They once lived in Los Angeles, California, but the family moved to San Francisco. He is also close friends with Elon Musk and helped support him when Tesla was on the brink of collapse in 2008.
