Jason Calacanis

Angel investor and Founder and CEO of Launch.co and Inside.com

Jason McCabe Calacanis is an American entrepreneur, angel investor, author, teacher, and podcaster. 

Jason founded Rising Tide Studios, a media company that published print and online publicationsduring the dot com era in New York. He co-founded the blog network Weblogs, Inc with Brian Alvey, a startup angel invested by Mark Cuban capitalising on the growth of blog. Currently, he is the Founder and serves as Chief Executive Officer at Inside.com and Launch, an early-stage investment firm and media company. 

A graduate from Xaverian High School, Jason attended Fordham University, where he received a B.A. in psychology.

As an Entrepreneur in Action at Sequoia Capital, a venture capital firm, Jason invested $25K in Travis Kalanick's company, Uber. 

His web directory, Mahalo, raised $20 million in venture capital from investors including Sequoia Capital, News Corp, CBS, Mark Cuban, and Elon Musk. Jason is also associated with various startups including Massive, Dexter, Calm, Preventure, Grin, STEEZY Studio, DensityKippo, Lead IQ, Neyborly, Sceneer, Solesavvy, and Vincent as their Board Member. 

Jason authored a book titled "Angel: How to Invest in Technology Startups—Timeless Advice from an Angel Investor Who Turned $100,000 into $100,000,000" on angel investing published by HarperCollins in 2017.

Jason created and hosts a weekly podcast on angel investing, This Week In Startups. The podcast was listed in an article at Fortune.com titled "The Ultimate Guide to the Best Business Podcasts". He is also the co-host of the All-In Podcast, alongside Chamath Palihapitiya, David O. Sacks, and David Friedberg.

As a teacher at Founder University, a division under the Launch umbrella, Jason offers a 12-week course for founders who want to learn how to turn transform their startup into a reality. 


Jason was born in the Bay Ridge section of Brooklyn, New York, to parents of Greek and Irish origin. He graduated from Xaverian High School in 1988. He then attended Fordham University, where he received a B.A. in psychology. 

He started his career in the 1990s as a reporter covering the internet industry in New York. Jason was the founder and CEO of Rising Tide Studios, a media company that published print and online publications. During the dot-com boom, Jason was active in New York's Silicon Alley community, and in 1996 began producing the Silicon Alley Reporter. Originally a 16-page photocopied newsletter, it eventually expanded into a 300-page magazine, with a sister publication called the Digital Coast Reporter for the West Coast. The company also organised conferences in New York, Los Angeles, and San Francisco focused on the Internet, web, and New Media.

Jason co-founded the blog network Weblogs, Inc. with Brian Alvey on September 24, 2003, and the startup was supported by an angel investment from Mark Cuban. 

Two years after inception, the Weblogs, Inc. blogs business was generating $1,000 a day just from AdSense. Time Warner's America Online agreed to buy Weblogs, Inc. in October 2005 for $25–30 million.

Jason joined Sequoia Capital, a venture capital firm, as an EIA (entrepreneur in action) in December, 2006, a position which he held until May, 2007. Through this program, Jason invested $25K in Travis Kalanick's company, Uber. The deal is now worth about $100 million. 

In 2007, he started an internet trend he called "fatblogging" after being fed up with being overweight. Fatblogging is when a person loses weight by exercising and then posting their weight afterwards onto their blog for encouragement and support from commenters and other fatbloggers. 

In 2009, Jason founded the Open Angel Forum, an event that connects early-stage startups with angel investors. The forum was the culmination of a series of public comments by Jason questioning the ethics of pay-to-pitch angel forums.  

In 2009, he also founded a startup, Inside.com, that focuses on delivering thematic newsletters. It provides business intelligence in the form of events, newsletters, and an online SLACK community. The company raised $2.6 million. 

He launched the web directory Mahalo ("thank you" in Hawaiian), which raised $20 million in venture capital from investors including Sequoia Capital, News Corp, CBS, Mark Cuban, and Elon Musk. The company hit a peak of 15 million unique visitors a month and achieved profitability in 2011, but suffered a sharp decline in traffic that year from the Google Panda search algorithm update and shut down in 2014. 

In 2011, Jason founded Launch, an early-stage investment firm and media company. Jason raised a $10 million fund for his own venture investment firm to invest in startups that emerged from the Launch conference. Limited partners in the fund include David Sacks.  

Jason founded ThisWeekIn.com, which shut down in 2012 but is live again and available as a weekly podcast, his Week in Startups (also called TWiSt), co-hosted by Molly Wood. The podcast is now a part of media division at Launch. 

He also introduced Founder University under the Launch umbrella for delivering education to startups from founding to maturity. He also introduced Launch Accelerator to invest in 7 startups in one cohort of 15 weeks, where founders meet more than 700 investors and master growth strategies.

He also established the Launch Fund that directly invests in deals, and a syndicate with more than 10,000 accredited investors. 

Jason authored a book titled "Angel: How to Invest in Technology Startups—Timeless Advice from an Angel Investor Who Turned $100,000 into $100,000,000" on angel investing published by HarperCollins in 2017. 

In 2018, Jason invested in Calm, a meditation app that is valued at $1 billion. 


Jason believes startups shouldn't have to pay to pitch angel investors, calling out fees that can range from $1,000 to $8,000 for a single 10- or 15-minute presentation. While establishing Launch, an early-stage investment firm, he said:

"We support founders & inspire innovation by backing builders. 
We do this through a series of free events, podcasts, books, research products, and by investing millions of dollars a year into promising, early-stage startups."

Following the success of the Launch conference, Jason declared his intent to get closer and more involved in the new ventures that emerged from that conference. The level of investment was around $25,000 to $100,000 in five to 10 startups per year.

In June 2019, Jason partnered with the NSW Government to create the Sydney Launch Festival for startups to give their pitches to global audiences.

Jason has made 50 investments. His latest investment was the Funding Round for Bonjuur on Nov 24, 2022, when Bonjuur raised $25K.

Recognition and Awards
Jason is an angel investor in Robinhood, Wealthfront, Uber, Desktop Metal, Datastax, Thumbtack, Superhuman and Trello. To date, Launch has successfully invested in over 300 startups, eight of which have gone on to achieve valuations over a billion dollars: Uber, Thumbtack, Calm, Datastax, Wealthfront, Robinhood, Desktop Metal & Density. The company invests in ~100 startups per year through our LAUNCH Fund & Syndicate. Its check sizes range from $25k to $5M. Jason was also an early supporter and funder for the effort behind the successful recall election of former San Francisco DA Chesa Boudin.

Jason Calacanis
American entrepreneur, angel investor, author, teacher, and podcaster.
B.A (Psychology), Fordham University
Social Media
Sat Mar 02 2024

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