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.” Manily due to angel investing, Jason Calacanis has accumulated a net worth of $100 million.
Born on November 28, 1970, Jason grew up in Brooklyn, New York. He’s one of three children and is of Irish and Greek descent. After graduating in 1988, he studied psychology at Fordham University. In the mid-1990s, Jason worked as a tech reporter in New York City, documenting the rise of the internet.
Early on, Calacanis spotted the potential of the internet and capitalized on the hype by launching Rising Tide Studios, a media company with publications such as Silicon Alley Reporter and the Digital Coast Reporter. During the dot-com bubble, business was booming and he rejected a $20 million takeover offer.
Sadly, when the dotcom market crashed it destroyed the company but they rebranded to VentureReporter.net. Jason changed the business model of selling advertising to database revenue and it worked! In 2003, Venture Reporter was acquired by Dow Jones for an undisclosed sum.
After his first big exit, Calacanis co-founded Weblogs alongside internet entrepreneur, Brian Alvey and Mark Cuban was an investor. Weblogs was a network of 90+ blogs that covered tech news, gaming, entertainment and more. The business was making $1,000 per day in ad revenue from Google Adsense at its peak.
Two years later, AOL acquired Weblogs for over $25 million. He served as General Manager at Netscape and left the web browser in 2006 to join Sequoia Capital. Here Jason was an early angel investor in Uber and invested $25,000 at a $5 million valuation. By 2017 his investment was worth over $100 million.
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” and is still one of the most influential podcasts on angel investing. He co-hosts another podcast called “All-In” with Chamath Palihapitiya, David Sacks & David Friedberg.
Net Worth and Earnings
Over the last decade, Jason Calacanis has invested in more than 300 businesses. He made the majority of his fortune through early angel investments in startups including Uber, Calm, Trello, Thumbtack, Wealthfront, and Robinhood. Before this, he was already a millionaire from selling Weblogs, Inc.
It’s estimated that the entrepreneur makes $10 to $20 million every year. In addition, there are his earnings from podcasts, book sales, and other businesses such as Inside.com. This is why he is worth $100 million.
Jason Calacanis is married to Jade Li, a successful film director. They are blessed with three children and currently live in San Francisco. Jason is also close friends with Elon Musk and helped support him when Tesla was on the brink of collapse in 2008. He rarely mentions it!