Jason McCabe Calacanis (born November 28, 1970) is an American Internet entrepreneur,
[ ]angel investor
An angel investor (also known as a business angel, informal investor, angel funder, private investor, or seed investor) is an individual who provides capital for a business or businesses start-up, usually in exchange for convertible debt or owners ...
,[ author and podcaster.]
His first company was part of the dot-com era in New York. His second venture, Weblogs, Inc., a publishing company that he co-founded together with Brian Alvey
Brian Alvey (born March 6, 1970 in Falls Church, Virginia) is an American serial entrepreneur, programmer, designer and blogger. He grew up in Brooklyn and now lives in San Francisco where he is the CEO of Clipisode. He is best known for co-found ...
, capitalized on the growth of blog
A blog (a truncation of "weblog") is a discussion or informational website published on the World Wide Web consisting of discrete, often informal diary-style text entries (posts). Posts are typically displayed in reverse chronological order ...
s before being sold to AOL
AOL (stylized as Aol., formerly a company known as AOL Inc. and originally known as America Online) is an American web portal and online service provider based in New York City. It is a brand marketed by the current incarnation of Yahoo (2017â ...
. Calacanis is also an angel investor in various technology startups, and co-host of the ''All-In Podcast'' & ''This Week in Startups Podcast''.
Early life
Calacanis was born in the Bay Ridge
Bay Ridge is a neighborhood in the southwest corner of the New York City borough of Brooklyn. It is bounded by Sunset Park to the north, Dyker Heights to the east, the Narrows and the Belt Parkway to the west, and Fort Hamilton Army Base and ...
section of Brooklyn
Brooklyn () is a borough of New York City, coextensive with Kings County, in the U.S. state of New York. Kings County is the most populous county in the State of New York, and the second-most densely populated county in the United States, be ...
, New York, to parents of Greek and Irish origin, and has two brothers.
He graduated from Xaverian High School
Xaverian High School is a private Catholic high school located in the Bay Ridge neighborhood of Brooklyn, New York, serving grades 6 through 12. Grades 9-12 offer a college prep program and grades 6-8 are a middle school.
History
The school was ...
in 1988. He then attended Fordham University
Fordham University () is a Private university, private Jesuit universities, Jesuit research university in New York City. Established in 1841 and named after the Fordham, Bronx, Fordham neighborhood of the The Bronx, Bronx in which its origina ...
, where he received a B.A.
Bachelor of arts (BA or AB; from the Latin ', ', or ') is a bachelor's degree awarded for an undergraduate program in the arts, or, in some cases, other disciplines. A Bachelor of Arts degree course is generally completed in three or four yea ...
in psychology
Psychology is the scientific study of mind and behavior. Psychology includes the study of conscious and unconscious phenomena, including feelings and thoughts. It is an academic discipline of immense scope, crossing the boundaries betwe ...
.
Career
Calacanis started his career in the 1990s as a reporter covering the internet industry in New York.
Calacanis was founder and CEO of Rising Tide Studios, a media company that published print and online publications. During the dot-com boom, Calacanis was active in New York's Silicon Alley
Silicon Alley is an area of high tech companies centered around southern Manhattan's Flatiron district in New York City. The term was coined in the 1990s during the dot-com boom, alluding to California's Silicon Valley tech center. The term h ...
community, and in 1996 began producing the ''Silicon Alley Reporter
''Silicon Alley Reporter'' was an American trade publication focused on New York's Silicon Alley.
Founded by Jason Calacanis in 1996, then was renamed the ''Venture Reporter'' in 2001 and was eventually sold to Dow Jones in 2003.
Rafat Ali serv ...
''. 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. Calacanis' socializing earned him a nickname as the "yearbook editor" of the Silicon Alley community. The company also organized conferences in New York, Los Angeles, and San Francisco focused on the Internet, web, and New Media.
Calacanis co-founded the blog network Weblogs, Inc.] with Brian Alvey
Brian Alvey (born March 6, 1970 in Falls Church, Virginia) is an American serial entrepreneur, programmer, designer and blogger. He grew up in Brooklyn and now lives in San Francisco where he is the CEO of Clipisode. He is best known for co-found ...
on September 24, 2003, and the startup was supported by an angel investment
An angel investor (also known as a business angel, informal investor, angel funder, private investor, or seed investor) is an individual who provides capital for a business or businesses start-up, usually in exchange for convertible debt or owners ...
from Mark Cuban
Mark Cuban (born July 31, 1958) is an American billionaire entrepreneur, television personality, and media proprietor whose net worth is an estimated $4.8 billion, according to ''Forbes'', and ranked No. 177 on the 2020 ''Forbes'' 400 list ...
.
Two years after inception, the Weblogs, Inc. blogs business was generating $1,000 a day just from AdSense
Google AdSense is a program run by Google through which website publishers in the Google Network of content sites serve text, images, video, or interactive media advertisements that are targeted to the site content and audience. These advert ...
. Time Warner
Warner Media, LLC ( traded as WarnerMedia) was an American multinational mass media and entertainment conglomerate. It was headquartered at the 30 Hudson Yards complex in New York City, United States.
It was originally established in 1972 by ...
's America Online
AOL (stylized as Aol., formerly a company known as AOL Inc. and originally known as America Online) is an American web portal and online service provider based in New York City. It is a brand marketed by the current incarnation of Yahoo! Inc. ...
agreed to buy Weblogs, Inc. in October 2005 for $25–30 million.[
]
On November 16, 2006, TechCrunch reported that Calacanis had resigned from his position as CEO of Weblogs, Inc. and general manager of Netscape
Netscape Communications Corporation (originally Mosaic Communications Corporation) was an American independent computer services company with headquarters in Mountain View, California and then Dulles, Virginia. Its Netscape web browser was onc ...
. Calacanis later confirmed this on his blog and the Gillmor Gang podcast.
Calacanis joined Sequoia Capital
Sequoia Capital is an American venture capital firm. The firm is headquartered in Menlo Park, California, and specializes in seed stage, early stage, and growth stage investments in private companies across technology sectors. , Sequoia's total a ...
, a venture capital firm, as an EIA (entrepreneur in action) in December, 2006, a position which he held until May, 2007. Through this program, Calacanis invested $25K in Travis Kalanick's company, Uber.[ The deal is now worth about $100 million.]
In 2007, Calacanis started an internet trend he called "fatblogging" after being fed up with being overweight
Being overweight or fat is having more body fat than is optimally healthy. Being overweight is especially common where food supplies are plentiful and lifestyles are sedentary.
, excess weight reached epidemic proportions globally, with mo ...
. 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.
He launched the web directory Mahalo
"Mahalo" is a Hawaiian word meaning thanks, gratitude, admiration, praise, esteem, regards, or respects. According to the Pukui and Elbert Hawaiian Dictionary, it is derived from the Proto-Polynesian ''*masalo.''
Some sources support that the m ...
("thank you" in Hawaiian), which raised $20 million in venture capital from investors[ including ]Sequoia Capital
Sequoia Capital is an American venture capital firm. The firm is headquartered in Menlo Park, California, and specializes in seed stage, early stage, and growth stage investments in private companies across technology sectors. , Sequoia's total a ...
, News Corp
News Corporation, stylized as News Corp, is an American mass media and publishing company headquartered in Midtown Manhattan, New York City. The second incarnation of the News Corporation (1980–2013), original News Corporation, it was formed ...
, CBS
CBS Broadcasting Inc., commonly shortened to CBS, the abbreviation of its former legal name Columbia Broadcasting System, is an American commercial broadcast television and radio network serving as the flagship property of the CBS Entertainm ...
, Mark Cuban
Mark Cuban (born July 31, 1958) is an American billionaire entrepreneur, television personality, and media proprietor whose net worth is an estimated $4.8 billion, according to ''Forbes'', and ranked No. 177 on the 2020 ''Forbes'' 400 list ...
, and Elon Musk
Elon Reeve Musk ( ; born June 28, 1971) is a business magnate and investor. He is the founder, CEO and chief engineer of SpaceX; angel investor, CEO and product architect of Tesla, Inc.; owner and CEO of Twitter, Inc.; founder of The Bori ...
. 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
Google Panda is a major change to Google's search results ranking algorithm that was first released in February 2011. The change aimed to lower the rank of "low-quality sites" or "thin sites", in particular " content farms", and return higher-qual ...
search algorithm update and shut down in 2014.
Calacanis founded ThisWeekIn.com, which shut down in 2012 but is live again and available as a weekly podcast.
'' This Week in Startups'' (also called ''TWiSt'') is a show hosted by Calacanis and co-hosted by Molly Wood.
He also founded a startup Inside.com which focuses on delivering thematic newsletters. The company raised $2.6 million.
In June 2019, Calacanis partnered with the NSW Government
The Government of New South Wales, also known as the NSW Government, is the Australian state democratic administrative authority of New South Wales. It is currently held by a coalition of the Liberal Party and the National Party. The Governmen ...
to create the Sydney Launch Festival for startups to give their pitches to global audiences.
Angel investing
In 2009, Calacanis 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 Calacanis questioning the ethics of pay-to-pitch angel forums. Calacanis 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. Calacanis is an angel investor in Robinhood, Wealthfront
Wealthfront Inc. is an automated investment service firm based in Palo Alto, California, founded by Andy Rachleff and Dan Carroll in 2008. As of September 2019, Wealthfront had $21 billion AUM across 400,000 accounts.
History
Wealthfront was f ...
, Uber
Uber Technologies, Inc. (Uber), based in San Francisco, provides mobility as a service, ride-hailing (allowing users to book a car and driver to transport them in a way similar to a taxi), food delivery (Uber Eats and Postmates), package ...
, Desktop Metal
Desktop Metal is a public American technology company that designs and markets 3D printing systems. Headquartered in Burlington, Massachusetts, the company has raised $438 million in venture funding since its founding from investors such as G ...
, Datastax
DataStax, Inc. is a real-time data company based in Santa Clara, California. Its product Astra DB is a cloud database-as-a-service based on Apache Cassandra. DataStax also offers DataStax Enterprise (DSE), an on-premises database built on Apache ...
, Thumbtack
A drawing pin (in British English) or thumb tack (in North American English) is a short nail or pin used to fasten items to a wall or board for display and intended to be inserted by hand, usually using the thumb. A variety of names is used t ...
, Superhuman
The term superhuman refers to humans or human-like beings with enhanced qualities and abilities that exceed those naturally found in humans. These qualities may be acquired through natural ability, self-actualization or technological aids. Th ...
and Trello
Trello is a web-based, kanban-style, list-making application and is developed by Trello Enterprise, a subsidiary of Atlassian. Created in 2011 by Glitch, it was spun out to form the basis of a separate company in New York City in 2014 and sold ...
.
Calacanis 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
David Sacks is an American television writer and producer.
Biography
He attended Harvard College, graduating with a degree in Government. While there he began his comedy writing career as an editor of the school's humor magazine, ''The Harvard ...
.
Following the success of the Launch conference, Calacanis 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.[Loizos, Connie. (June 3, 2013)]
Entrepreneur Jason Calacanis raising a $10 million fund
Reuters. Retrieved on 2013-07-19.
Calacanis publicly announced in 2018 that he had sold all of his Facebook stock, expressing sharp criticism of company CEO and co-founder Mark Zuckerberg
Mark Elliot Zuckerberg (; born ) is an American business magnate, internet entrepreneur, and philanthropist. He is known for co-founding the social media website Facebook and its parent company Meta Platforms (formerly Facebook, Inc.), o ...
on the Too Embarrassed to Ask podcast. He called Zuckerberg "completely immoral" in how he runs the business and said, "No founder should ever sell a company to him."
Calacanis 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, Calacanis invested in Calm, a meditation app that is valued at $1 billion.
Podcasting
''This Week in Startups''
''This Week in Startups'' is a weekly podcast created and hosted by American internet entrepreneur and angel investor Jason Calacanis.[ '']The Wall Street Journal
''The Wall Street Journal'' is an American business-focused, international daily newspaper based in New York City, with international editions also available in Chinese and Japanese. The ''Journal'', along with its Asian editions, is published ...
'' contributor Cecilie Rohwedder described the podcast as "an influential Web series filmed in the U.S."
History
Plans for the podcast were announced on March 16, 2009, through a blog post. The 60-minute program premiered on May 1, 2009, featuring Brian Alvey
Brian Alvey (born March 6, 1970 in Falls Church, Virginia) is an American serial entrepreneur, programmer, designer and blogger. He grew up in Brooklyn and now lives in San Francisco where he is the CEO of Clipisode. He is best known for co-found ...
, CEO and founder of the content management and hosting system Crowd Fusion, as its first guest. The show is one of the longest running podcasts on the topic of startups and angel investing.
Reception
''This Week in Startups'' was listed in an article at Fortune.com titled "The Ultimate Guide to the Best Business Podcasts".
''All-In''
As of 2022, Calacanis is co-host of the ''All-In Podcast'', alongside Chamath Palihapitiya
Chamath Palihapitiya (born 3 September 1976) is a Sri Lankan-born Canadian and American venture capitalist, engineer, SPAC sponsor, founder and CEO of Social Capital. Palihapitiya was an early senior executive at Facebook, working at the compan ...
, David O. Sacks, and David Friedberg
David Albert Friedberg (born 1 June 1980) is an American entrepreneur, businessman, and angel investor. He founded and was chief executive of The Climate Corporation, whose $1.1 billion sale to Monsanto in 2013 made it the first unicorn in the ...
. In May 2022, the ''All-In Podcast'' team hosted their first ''All-In Summit'' in Miami, where leaders in business and tech attended to discuss the central theme of "What problem do you want to solve right now?"
Personal life
Calacanis married Jade Li sometime between 2006 and 2009. Calacanis' name was found in Jeffrey Epstein
Jeffrey Edward Epstein ( ; January 20, 1953August 10, 2019) was an American sex offender and financier. Epstein, who was born and raised in Brooklyn, New York City, began his professional life by teaching at the Dalton School in Manhattan, des ...
's little black book on page 9. On 5 August 2020, he addressed this discovery by stating that he met Epstein at a Ted Talk
TED Conferences, LLC (Technology, Entertainment, Design) is an American-Canadian non-profit media organization that posts international talks online for free distribution under the slogan "ideas worth spreading". TED was founded by Richard Sau ...
, when Epstein wanted to invest in Calacanis' magazine. Calacanis also added that he has "played ping pong with Ghislaine Maxwell
Ghislaine Noelle Marion Maxwell ( ; born 25 December 1961) is a British convicted sex offender and former socialite. In 2021, she was found guilty of child sex trafficking and other offences in connection with the financier and convicted sex o ...
once".
Politics
Calacanis was an early supporter and funder for the effort behind the successful recall election
A recall election (also called a recall referendum, recall petition or representative recall) is a procedure by which, in certain polities, voters can remove an elected official from office through a referendum before that official's term of offi ...
of former San Francisco DA Chesa Boudin.
Publications
* Jason Calacanis, ''Angel: How to Invest in Technology Startups'', Harper Business, 2017
References
; General
* Brown, Eryn (January 2006)
"Revenge of the Dotcom Poster Boy"
''Wired''; Conde Nast Digital. Retrieved 2010-06-19.
External links
This Week in Startups
– podcast
All In
– podcast
*
*
*
{{DEFAULTSORT:Calacanis, Jason
1970 births
Living people
American bloggers
American computer businesspeople
Fordham University alumni
Angel investors
Weblogs, Inc.
People from Bay Ridge, Brooklyn
Xaverian High School alumni
American technology company founders
AOL employees
American technology chief executives