Jason Calacanis

Jason Calacanis
Born	(1970-11-28) November 28, 1970 Bay Ridge, Brooklyn, New York City, U.S.
Occupation(s)	Entrepreneur, angel investor, podcast host, writer
Known for	Co-founder of Weblogs, Inc., host of This Week in Startups podcast, co-host of All-In podcast

Jason McCabe Calacanis (born November 28, 1970) is a prominent American entrepreneur in the Internet sector, angel investor, podcast host, and writer.

His initial venture arose amid the Dot-com bubble in New York City. He co-established Weblogs, Inc., a publishing enterprise that capitalized on the expanding popularity of blog platforms before being acquired by AOL. Calacanis has invested as an angel in a wide array of tech startups and co-hosts the All-In podcast alongside David Sacks, Chamath Palihapitiya, and David Friedberg. Additionally, he is the host of the This Week in Startups Podcast.

Early life

Calacanis was born in Brooklyn’s Bay Ridge neighborhood. He possesses Greek and Irish heritage. He completed his secondary education at Xaverian High School in 1988 and holds a Bachelor of Arts degree in psychology from Fordham University.

Career

Calacanis embarked on his professional journey during the 1990s as a journalist reporting on the internet sector based in New York.

He founded Rising Tide Studios, a media company producing both print and digital content. During the dot-com era, he was deeply involved in New York’s Silicon Alley scene, launching the Silicon Alley Reporter in 1996. This publication expanded from a modest 16-page newsletter into a comprehensive 300-page magazine, accompanied by a West Coast counterpart named the Digital Coast Reporter. His company also hosted internet-centric conferences across New York, Los Angeles, and San Francisco.

In 2003, Calacanis co-launched the blog network Weblogs, Inc. with Brian Alvey, supported by angel investor Mark Cuban. By 2005, this network was earning $1,000 daily through AdSense revenue. In October 2005, Time Warner's America Online purchased Weblogs, Inc. for an estimated $25–30 million. Calacanis stepped down as CEO of Weblogs, Inc. and general manager at Netscape in November 2006.

From December 2006 to May 2007, he served as an Entrepreneur In Action (EIA) at venture capital firm Sequoia Capital. During this tenure, he invested $25,000 in Travis Kalanick’s startup Uber, an investment that was valued near $100 million by 2017.

In 2007, Calacanis popularized "fatblogging," a trend where blogging was used as a tool to encourage weight loss.

He founded Mahalo.com, a web directory that secured $20 million in funding from investors such as Sequoia Capital, News Corp, CBS, Mark Cuban, and Elon Musk. Mahalo reached its peak with 15 million unique monthly visitors and achieved profitability by 2011 but experienced a significant downturn following Google's Panda algorithm update and ultimately ceased operations in 2014.

Calacanis created ThisWeekIn.com; although it closed in 2012, it was later revived as a weekly podcast.

This Week in Startups (TWiSt), which Calacanis both founded and hosts, featured Molly Wood as co-host from 2021 until 2023.

He also established Inside.com, a platform providing curated newsletters focused on specific themes; the company raised $2.6 million and grew to serve 750,000 active subscribers.

In June 2019, Calacanis collaborated with the New South Wales Government to introduce the Sydney Launch Festival, offering startups opportunities to present to international audiences.

Following Elon Musk’s acquisition of Twitter in 2022, Calacanis assisted David Sacks in overseeing the company during its restructuring phase.

Angel investing

In 2009, Calacanis established the Open Angel Forum, a platform designed to connect early-stage startups with angel investors. This initiative was created in response to the controversial pay-to-pitch schemes that required startups to pay fees ranging from $1,000 to $8,000 for short presentation opportunities. Calacanis firmly believes that entrepreneurs should not be charged to present their ideas to potential investors.

Among the companies he has invested in as an angel are Robinhood, Wealthfront, Uber, Desktop Metal, Datastax, Thumbtack, Superhuman, and Trello. He launched a $10 million investment fund focused on startups emerging from his Launch conference, with notable limited partners including David Sacks. His typical investments fall between $25,000 and $100,000, targeting five to ten startups each year.

In 2016, Calacanis was prohibited from attending Y Combinator's Demo Day following feedback from founders regarding their experiences with him. Two years later, in 2018, he publicly divested all of his Facebook shares, condemning CEO Mark Zuckerberg’s leadership as "completely immoral."

Calacanis authored the book Angel: How to Invest in Technology Startups—Timeless Advice from an Angel Investor Who Turned $100,000 into $100,000,000, which HarperCollins published in 2017.

That same year, he made an investment in Calm, a meditation application that reached a valuation of $1 billion.

This Week in Startups

Created and hosted by Jason Calacanis, This Week in Startups is a weekly podcast. Cecilie Rohwedder, contributor for The Wall Street Journal, described it as "an influential Web series filmed in the U.S."

History

The show was announced on March 16, 2009, and debuted on May 1, 2009. Its first guest was Brian Alvey, CEO of Crowd Fusion. The earliest known episode on YouTube is dated June 3, 2010, titled "This Week in Venture Capital - Mark Suster and Jason Calacanis."

Reception

Fortune.com featured This Week in Startups in its "The Ultimate Guide to the Best Business Podcasts," recognizing its significant impact within the startup community.

All-In

By 2022, Calacanis co-hosted the All-In podcast alongside Chamath Palihapitiya, David O. Sacks, and David Friedberg. In May of that year, the podcast hosts organized the first-ever All-In Summit held in Miami. The event brought together leaders from business and technology sectors to deliberate on critical issues under the theme "What problem do you want to solve right now?"

Personal life

Between 2006 and 2009, Calacanis married Jade Li. He played a foundational role as an early supporter of the successful 2022 recall election of San Francisco District Attorney Chesa Boudin. Additionally, Calacanis appeared as a contact in Jeffrey Epstein's "little black book," which attracted attention following Epstein's conviction and subsequent death.

Publications

• Jason Calacanis, Angel: A Guide to Investing in Technology Startups, Harper Business, 2017

References

General

• Brown, Eryn (January 2006). "The Comeback of the Dotcom Poster Boy". Wired; Conde Nast Digital. Accessed 2010-06-19.

External links

• All In – podcast series