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{{Short description|American businessman}}
{{Use mdy dates|date = October 2022}}
{{Infobox person
{{Infobox person
| name = Jason Calacanis
| name = Jason Calacanis
| image = Jason Calacanis (6723612583).jpg
| image = Jason Calacanis at LAUNCH Festival 2016 (cropped).jpg
| caption = Jason Calacanis, January 2012
| caption = Calacanis in 2018
| birth_date = {{Birth date and age|1970|11|28|mf=y}}
| birth_date = {{Birth date and age|1970|11|28|mf=y}}
| birth_place = [[Bay Ridge, Brooklyn]], [[New York City]]
| birth_place = [[Bay Ridge, Brooklyn]], New York, U.S.
| education = [[Fordham University]] ([[Bachelor of Arts|B.A.]])
| Net worth =
| occupation = {{Hlist|[[Angel investor]]|[[podcast]]er}}
| alma mater = [[Fordham University]] ([[Bachelor of Arts|B.A.]])
| spouse = Jade Li (m. after 2006)
| occupation = Internet entrepreneur / Blogger
| spouse =
| children = 3
}}
|religion = }}


'''Jason McCabe Calacanis''' (born November 28, 1970) is a podcaster, American Internet entrepreneur,<ref name=john/> [[angel investor]],<ref name=reuters/> and author.<ref name="auto"/><ref>{{cite web|title=My retirement party|author=Jason Calacanis|work=Jason Calacanis weblog|date=November 28, 2005|url=http://www.calacanis.com/2005/11/28/my-retirement-party/|access-date=April 21, 2006|archive-date=July 18, 2018|archive-url=https://web.archive.org/web/20180718115100/http://calacanis.com/2005/11/28/my-retirement-party/|url-status=dead}}</ref>
'''Jason McCabe Calacanis''' (born November 28, 1970<ref>{{cite news|title=My retirement party. |author=Calacanis, Jason| work=The Jason Calacanis Weblog|date=28 November 2005 |url=http://www.calacanis.com/2005/11/28/my-retirement-party/| accessdate=2006-04-21}}</ref>) is an American Internet [[Entrepreneurship|entrepreneur]], [[angel investor]], [[author]] and [[Blog|blogger]].<ref>[http://socentex.com/2009/12/business-lessons-from-jasons-twist-this-week-in-start-ups/ Business Lessons from @Jason's TWiST (This Week in Start-Ups) | The Social Entrepreneurship Exchange]. Socentex.com (2009-12-13). Retrieved on 2013-07-19.</ref><ref>[http://www.crunchbase.com/person/jason-calacanis Jason Calacanis | CrunchBase Profile]. Crunchbase.com. Retrieved on 2013-07-19.</ref> His first company was part of the [[Dot-com bubble|dot-com]] era in New York, and his second venture, [[Weblogs, Inc.]], a publishing company that he co-founded together with [[Brian Alvey]], capitalized on the growth of [[blog]]s before being sold to [[AOL]].<ref>[http://labnol.blogspot.com/2006/11/jason-calacanis-timeline-from-weblogs.html Jason Calacanis Timeline: From Weblogs to AOL to Sequoia]. Labnol.blogspot.com. Retrieved on 2013-07-19.</ref> As well as being an [[angel investor]] in various technology startups,<ref>[http://www.huffingtonpost.com/jason-mccabe-calacanis Jason McCabe Calacanis]. Huffingtonpost.com. Retrieved on 2013-07-19.</ref><ref>[http://www.4-traders.com/TESLA-MOTORS-INC-6344549/news/Entrepreneur-Jason-Calacanis-raising-a-$10-million-fund-16999607/ Entrepreneur Jason Calacanis raising a $10 million fund]. 4-Traders. Retrieved on 2013-07-19.</ref>
Calacanis also presents at industry conferences worldwide.<ref>[http://www.conversionrater.com/2006/10/26/jason-calacanis-keynote-at-blog-business-summit/ Jason Calacanis Keynote at Blog Business Summit]. ConversionRater (2006-10-26). Retrieved on 2013-07-19.</ref><ref>[http://ibusinesslogic.com/531/who-is-jason-calacanis-why-should-you-care/ Who is Jason Calacanis – Why Should You care?]. iBusinessLogic.com. Retrieved on 2013-07-19.</ref>


His first company was part of the [[Dot-com bubble|dot-com]] era in New York. His second venture, [[Weblogs, Inc.]], a publishing company that he co-founded together with [[Brian Alvey]], capitalized on the growth of [[blog]]s before being sold to [[AOL]]. Calacanis is also an angel investor in various technology startups and co-host of the [[All-In (podcast)|All-In podcast]] alongside [[David O. Sacks|David Sacks]], [[Chamath Palihapitiya]] and [[David Friedberg]]'','' and the host of ''This Week in Startups Podcast''.
==Early life==
Calacanis was born in the [[Bay Ridge, Brooklyn|Bay Ridge section of Brooklyn]], [[New York (state)|New York]] and has two brothers.<ref>{{Citation|last=carpoolUK|title=Jason Calacanis {{!}} Carpool|date=2010-05-12|url=https://www.youtube.com/watch?v=stDBc8CIh74|accessdate=2017-10-02}}</ref> He graduated from [[Xaverian High School]] in 1988. He then attended [[Fordham University]], where he received a [[Bachelor of Arts|B.A.]] in [[Psychology]].<ref>{{cite web |url= http://www.mediacenter.org/content/5140.cfm |title= Featured Discussion Leaders |publisher= The Media Center |year= 2007 |accessdate= June 6, 2007 |archiveurl= https://web.archive.org/web/20070504112726/http://www.mediacenter.org/content/5140.cfm |archivedate= May 4, 2007}}</ref>


==Career==
== Early life ==
Calacanis was born in the [[Bay Ridge, Brooklyn|Bay Ridge]] section of [[Brooklyn]], New York, and has two brothers.<ref>{{cite news |last1=Drange |first1=Matt |last2=Cheng |first2=Candy |title=Jason Calacanis went from dotcom roadkill to early investor in Uber, Calm, and Robinhood. Here's how he's reshaping venture capital with bluster, ego, and media-savvy. |url=https://www.businessinsider.com/inside-the-world-of-angel-investor-jason-calacanis-2021-5 |access-date=9 June 2024 |work=Business Insider |date=3 June 2021}}</ref> He is of half-[[Greek Americans|Greek]] and half-[[Irish Americans|Irish]] descent.<ref>{{Cite book |last=Remnick |first=David |url=https://books.google.com/books?id=8Ltq9ets9cMC&pg=PT10 |title=The New Gilded Age: The New Yorker Looks at the Culture of Affluence |date=2001 |publisher=Random House Publishing Group |isbn=978-0-375-50705-2 |pages=10 |language=en}}</ref> He graduated from [[Xaverian High School]] in 1988 and attended [[Fordham University]], where he received a [[Bachelor of Arts|B.A.]] in [[psychology]].<ref>{{cite web |url= http://www.mediacenter.org/content/5140.cfm |title= Featured Discussion Leaders |publisher= The Media Center |year= 2007 |access-date= June 6, 2007 |archive-url= https://web.archive.org/web/20070504112726/http://www.mediacenter.org/content/5140.cfm |archive-date= May 4, 2007}}</ref>
[[File:Jason Calacanis3.jpg|thumb|Jason Calacanis in January 2008]]
Calacanis's biggest success to date is [[Weblogs, Inc.]], which was sold to [[AOL]] in 2005.
Before forming Weblogs, Inc., 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]] 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. Calacanis's socializing earned him a nickname as the "yearbook editor" of the Silicon Alley community.<ref>Grigoriadis, Vanessa (March 6, 2000). [http://nymag.com/nymetro/news/media/internet/2285/ "Silicon Alley 10003"]. ''New York''. Retrieved 2010-06-19.</ref> The company also organized conferences in New York, Los Angeles, and San Francisco focused on the Internet, web, and New Media. With the end of the [[Dot-com bubble]], ''Silicon Alley Reporter'' failed, and the company was sold out of bankruptcy to a private equity firm.<ref>Naraine, Ryan (October 8, 2001). [http://www.clickz.com/899091 "Silicon Alley Reporter Goes Under"]. ''ClickZ News''; Incisive Interactive Marketing LLC. Retrieved 2010-06-19.</ref>


===Weblogs, Inc.===
== Career ==
Calacanis started his career in the 1990s as a reporter covering the internet industry in New York.<ref name="auto">{{Cite news|url=https://www.nytimes.com/2017/09/27/technology/when-tech-disrupts-wealth-and-stability-angels-may-be-solution.html|title=Should the Middle Class Invest in Risky Tech Start-Ups?|last=Manjoo|first=Farhad|date=2017-09-27| archive-date=November 3, 2017 | archive-url=https://web.archive.org/web/20171103143058/https://www.nytimes.com/2017/09/27/technology/when-tech-disrupts-wealth-and-stability-angels-may-be-solution.html |work=The New York Times|access-date=2019-06-04|language=en-US|issn=0362-4331}}</ref>
As a blogger,<ref>[http://www.problogger.net/archives/2004/12/11/the-blogfather-jason-calacanis-expands-family/ The Blogfather? Jason Calacanis expands family : @ProBlogger]. Problogger.net (1970-01-01). Retrieved on 2013-07-19.</ref> Calacanis co-founded [[Weblogs, Inc.]] with [[Brian Alvey]] in September 24, 2003, 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]].<ref>Penenberg, Adam L.. (2007-09-01) [http://www.fastcompany.com/60356/man-vs-machine Man vs. Machine | Fast Company | Business + Innovation]. Fast Company. Retrieved on 2013-07-19.</ref> [[Time Warner]]'s [[America Online]] agreed to buy Weblogs, Inc. in October 2005 for $25–30 million.<ref>{{cite web |author=Arrington, Michael |date=October 5, 2005| url=https://techcrunch.com/2005/10/05/aol-acquires-weblog-inc/ |title=AOL Acquires Weblogs, Inc. |publisher=techcrunch.com |accessdate=2010-06-14 }}</ref>


Calacanis was the 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]] community, and in 1996 began producing the ''[[Silicon Alley Reporter]]''.<ref name=john>{{cite magazine |last1=Heilemann |first1=John |author-link=John Heilemann | archive-url=https://web.archive.org/web/20061230110028/https://nymag.com/news/politics/powergrid/17398/ | archive-date=December 30, 2006 | url=https://nymag.com/news/politics/powergrid/17398/ | title=Suit 2.0: Back in the nineties, Jason Calacanis was a Silicon Alley cowboy. Now, at AOL, he's in full corporate harness. Is that the only way for an entrepreneur to get to the top? |journal=New York |date=3 July 2006 |volume=39 |issue=24 |page=28 |id={{Gale|A148358825}}}}</ref> Originally a 16-page photocopied newsletter,<ref name=reuters/> 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.<ref>Grigoriadis, Vanessa (March 6, 2000). [http://nymag.com/nymetro/news/media/internet/2285/ "Silicon Alley 10003"]. ''New York''. Retrieved 2010-06-19.</ref> The company also organized conferences in New York, Los Angeles, and San Francisco focused on the Internet, web, and New Media.
===Netscape.com===
Eight months into his tenure with AOL, Calacanis was offered the position of General Manager of the new [[Netscape]] website. Calacanis copied the model pioneered by [[Digg]], [[Del.icio.us]], and [[Furl]] and added an editorial layer to the system, like [[Slashdot]]. The project occupied the front page of [[Netscape]]. Calacanis started by hiring a team of eight "anchors" to follow up users' top stories. He then hired some of the top users of [[social bookmarking]] sites like [[Digg]], [[Reddit]], [[Newsvine]] and [[Flickr]] to go to Netscape as Netscape Navigators,<ref>Calacanis, Jason (July 18, 2006). [http://www.calacanis.com/2006/07/18/everyones-gotta-eat-or-1-000-a-month-for-doing-what-youre/ "Paying the top DIGG/REDDIT/Flickr/Newsvine users"]. ''The Jason Calacanis Weblog''. Retrieved 2010-06-19.</ref> which prompted a public debate with [[Kevin Rose]], founder of [[Digg]], most notably during a live taping of the video podcast [[Diggnation]].<ref>{{cite web|url=http://revision3.com/diggnation/2006-07-21|title=July 21, 2006|work=Revision3}}</ref>


Calacanis co-founded the blog network [[Weblogs, Inc.]]<ref name="auto"/> with [[Brian Alvey]] on September 24, 2003, and the startup was supported by an [[angel investment]] from [[Mark Cuban]].<ref>{{Cite web|date=2017-06-06|title=6 Reasons Why You Should Know Jason Calacanis|url=https://startupsd.org/startup-spotlight/6-reasons-know-jason-calacanis/|access-date=2020-06-10|website=Startup San Diego|language=en-US}}</ref>
On November 16, 2006, TechCrunch reported that Calacanis had resigned from his position as CEO of Weblogs, Inc. and General Manager of [[Netscape]].<ref>Arrington, Michael (November 16, 2006). [https://techcrunch.com/2006/11/16/jason-calacanis-resigns-from-aol/ "Jason Calacanis resigns from AOL"]. Tech Crunch. Retrieved 2010-06-19.</ref> Calacanis later confirmed this with a post on his blog.<ref>Calacanis, Jason (November 17, 2006). [http://www.calacanis.com/2006/11/17/yes-its-true-im-leaving-aol/ "Yes it's true, I'm leaving AOL"] ''The Jason Calacanis Weblog''. Retrieved 2010-06-19.</ref><ref>Farber, Dan. (2006-11-17) [http://www.zdnet.com/blog/btl/jason-calacanis-talks-about-leaving-aol-and-whats-next/3979 Jason Calacanis talks about leaving AOL and what's next]. ZDNet. Retrieved on 2013-07-19.</ref>


Two years after its inception, the Weblogs, Inc. blogs business was generating $1,000 a day just from [[AdSense]].<ref>Penenberg, Adam L.. (2007-09-01) [http://www.fastcompany.com/60356/man-vs-machine Man vs. Machine | Fast Company | Business + Innovation]. Fast Company. Retrieved on 2013-07-19.</ref> [[Time Warner]]'s [[America Online]] agreed to buy Weblogs, Inc. in October 2005 for $25–30 million.<ref name="auto"/><ref name=tom/><ref>{{cite web |author=Arrington, Michael |date=October 5, 2005| url=https://techcrunch.com/2005/10/05/aol-acquires-weblog-inc/ |title=AOL Acquires Weblogs, Inc. |publisher=techcrunch.com |access-date=2010-06-14 }}</ref>
===Sequoia Capital===
[[File:Jason Calacanis.jpg|thumb|Calacanis speaking at the 2005 [[Gnomedex]]]]
Calacanis joined [[Sequoia Capital]] as an EIA (entrepreneur in action) in December, 2006,<ref>Arrington, Michael (December 5, 2006). [https://techcrunch.com/2006/12/05/calacanis-takes-position-at-sequoia-capital "Calacanis takes position at Sequoia Capital"]. Tech Crunch. Retrieved 2010-06-19.</ref><ref>Calacanis, Jason (December 5, 2006). [http://www.calacanis.com/2006/12/05/my-new-job/ "My new job"]. ''The Jason Calacanis Weblog''. Retrieved 2010-06-19.</ref>
a position which he held until May, 2007.<ref>[http://www.therisetothetop.com/innovative-broadcaster/jason-calacanis-interview/ Why Jason Calacanis Is Betting All His Chips On Web Video]. The Rise to the Top. Retrieved on 2013-07-19.</ref>


On November 16, 2006, TechCrunch reported that Calacanis had resigned from his position as CEO of Weblogs, Inc. and general manager of [[Netscape]].<ref>Arrington, Michael (November 16, 2006). [https://techcrunch.com/2006/11/16/jason-calacanis-resigns-from-aol/ "Jason Calacanis resigns from AOL"]. Tech Crunch. Retrieved 2010-06-19.</ref> Calacanis later confirmed this on his blog and the Gillmor Gang podcast.<ref>Farber, Dan. (2006-11-17) [https://www.zdnet.com/article/jason-calacanis-talks-about-leaving-aol-and-whats-next/ Jason Calacanis talks about leaving AOL and what's next]. ZDNet. Retrieved on 2013-07-19.</ref>
===Mahalo.com===
{{main|Mahalo.com}}
Calacanis founded [[Mahalo.com]], a "human-powered search engine",<ref>Delaney, Kevin J. (May 31, 2007). [https://www.wsj.com/articles/SB118056234795419124?mod=googlenews_wsj "Start-Up Adds a Human Touch"]. ''WSJ.com;'' [[The Wall Street Journal]]. Retrieved 2010-06-19.</ref> which launched in alpha test in May 2007. During a speech about the site at the [[Gnomedex (conference)|Gnomedex]] conference in August 2007, Calacanis got into a public confrontation with [[Dave Winer]] that led to Winer's resignation from the panel of experts for the TechCrunch20 conference organized by Calacanis. Winer interrupted Calacanis' speech during the event, calling it "conference spam" and igniting a war of words on their blogs. "I'm not interested in having someone berate me like this," Calacanis wrote on his blog.<ref>{{cite news |author=Adario Strange |date= August 13, 2007 |url=https://www.wired.com/epicenter/2007/08/gnomedex-afterm/ |work=Wired News |publisher=Conde Nast Digital |accessdate=2007-08-15 |title=Gnomedex Aftermath: Dave Winer Dropped From TechCrunch20}}</ref>


Calacanis joined [[Sequoia Capital]], a venture capital firm,<ref name="auto"/> as an EIA (entrepreneur in action) in December, 2006,<ref>Arrington, Michael (December 5, 2006). [https://techcrunch.com/2006/12/05/calacanis-takes-position-at-sequoia-capital "Calacanis takes position at Sequoia Capital"]. Tech Crunch. Retrieved 2010-06-19.</ref> a position which he held until May, 2007.<ref>[http://www.therisetothetop.com/innovative-broadcaster/jason-calacanis-interview/ Why Jason Calacanis Is Betting All His Chips On Web Video] {{Webarchive|url=https://web.archive.org/web/20211020104713/https://therisetothetop.com/innovative-broadcaster/jason-calacanis-interview/ |date=October 20, 2021 }}. The Rise to the Top. Retrieved on 2013-07-19.</ref> Through this program, Calacanis invested $25K in [[Travis Kalanick]]'s company, [[Uber]].<ref name=reuters/> As of 2017 the investment was worth roughly $100 million.<ref name="auto"/>
Mahalo ("thank you" in Hawaiian), raised $20 million in venture capital from investors including [[Sequoia Capital]], [[News Corp]], [[CBS]], [[Mark Cuban]], and [[Elon Musk]]. The company's motto: "We're here to help." At its peak, it had 14.1 million global (7.4 million US) unique monthly visitors.<ref>[http://www.quantcast.com/mahalo.com "Quantcast Audience Profile for mahalo.com"]. Quantcast.com. ("Traffic data hidden by owner." Registration and access permission from Mahalo.com required. No archive available.) Retrieved 2010-06-19.</ref><!-- additional cite required, please --> Mahalo shut down in 2014.


In 2007, Calacanis is credited with starting an [[Internet phenemenon|internet trend]] he called "fatblogging" after being fed up with being [[overweight]].<ref name=":1">{{Cite news|last=Pham|first=Alex|date=June 15, 2007|title=On 'fatblogs,' heavy people weigh in|work=Los Angeles Times|url=https://www.latimes.com/la-fi-fatblog15jun15-story.html|url-status=live|access-date=December 27, 2020|archive-url=https://archive.today/20201227180903/https://www.latimes.com/la-fi-fatblog15jun15-story.html|archive-date=December 27, 2020}}</ref> 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.<ref name=":1" />
===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.<ref>Boutin, Paul (December 6, 2009). [https://venturebeat.com/2009/12/06/serial-entropr-calacanis-launches-open-angel-forum-a-free-access-to-investors-program/ "Calacanis Launches Open Angel Forum"]. "VentureBeat.com;" [[VentureBeat]]. Retrieved 2010-08-11.</ref> Calacanis believes startups shouldn't have to pay to pitch angel investors.<ref>Calacanis, Jason (October 9, 2010). [http://calacanis.com/2009/10/09/why-startups-shouldnt-have-to-pay-to-pitch-angel-investors/ "Why startups shouldn't have to pay to pitch angel investors"]. Calacanis.com. Retrieved 2010-08-11</ref>


He launched the web directory [[mahalo.com|Mahalo]] ("thank you" in Hawaiian),<ref name=tom>{{cite journal |last1=Dotan |first1=Tom | url=https://labusinessjournal.com/media/entrepreneur-making-news/ | archive-url=https://web.archive.org/web/20221015144218/https://labusinessjournal.com/media/entrepreneur-making-news/ | archive-date=October 15, 2022 | title=Entrepreneur making news: Jason Calacanis looks to deriver in journalism |journal=Los Angeles Business Journal |date=January 27, 2014 |volume=36 |issue=4 |page=1 |publisher=CBJ |issn=0194-2603 |id={{Gale|A360474368}}}}</ref> which raised $20 million in venture capital from investors<ref name=search/> including [[Sequoia Capital]], [[News Corp (2013–present)|News Corp]], [[CBS]], [[Mark Cuban]], and [[Elon Musk]]. Mahalo 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.<ref name="fastcompany">{{cite web|title=Mahalo.com: Pivot or Die|publisher=Fast Company|author=Adam L. Penenberg|url=https://www.fastcompany.com/1837480/mahalocom-pivot-or-die|date=June 14, 2012|access-date=June 18, 2018}}</ref>
Calacanis raised a $10 million fund to for his own venture investment firm to invest in startups that emerged from the Launch conference.<ref>[http://valleywag.gawker.com/racism-denier-jason-calacanis-is-starting-his-own-vc-f-511058699 Racism Denier Jason Calacanis Is Starting His Own VC Fund] {{webarchive|url=https://web.archive.org/web/20130608102800/http://valleywag.gawker.com/racism-denier-jason-calacanis-is-starting-his-own-vc-f-511058699 |date=2013-06-08 }}. Valleywag.gawker.com. Retrieved on 2013-07-19.</ref><ref>[http://www.financeplus.com/entrepreneur-jason-calacanis-raising-a-10-million-fund/ Entrepreneur Jason Calacanis raising a $10 million fund]. FinancePlus (2013-06-04). Retrieved on 2013-07-19.</ref> Limited partners in the fund include [[David Sacks]].<ref>[http://www.techinvestornews.com/Enterprise/Blogs-and-Tech-Dialogue/launch-founder-jason-calacanis-raising-10-million-venture-fund Launch founder Jason Calacanis raising $10 million venture fund]. Techinvestornews.com (2013-06-03). Retrieved on 2013-07-19.</ref>
Following the success of the Launch conference,<ref>[https://venturebeat.com/2013/06/03/launch-founder-jason-calacanis-raising-10-million-venture-fund/ Launch founder Jason Calacanis raising $10 million venture fund]. VentureBeat (2013-07-15). Retrieved on 2013-07-19.</ref> Mr. Calacanis aims to get closer and more involved in the new ventures that emerged from that conference.<ref>[http://www.foxbusiness.com/news/2013/06/03/entrepreneur-jason-calacanis-raising-10-million-fund/ Entrepreneur Jason Calacanis Raising a $10M VC Fund]. Fox Business (2013-06-03). Retrieved on 2013-07-19.</ref> The approach of investment is around $25,000 to $100,000 in five to 10 startups per year.<ref>[https://www.reuters.com/article/2013/06/04/us-venture-calacanis-newfund-idUSBRE95301W20130604 Entrepreneur Jason Calacanis raising a $10 million fund]. Reuters. Retrieved on 2013-07-19.</ref><ref>[http://www.pehub.com/251362/jason-calacanis-opens-up-about-his-new-venture-fund-launch-fund-i/ Private equity and venture capital news, data and community]. peHUB (2013-06-03). Retrieved on 2013-07-19.</ref>


Calacanis founded ThisWeekIn.com,<ref name=search>{{cite journal |via=Cengage | last1=Dotan |first1=Tom |title=Ex-search engine finds way to video: Mahalo to produce YouTube channels as [[Inside.com]] |journal=Los Angeles Business Journal |date=January 7, 2013 |volume=35 |issue=1 |page=1 |id={{Gale|A315221432}}}}</ref> which shut down in 2012 but is live again and available as a weekly podcast.<ref>{{cite web|url=https://techcrunch.com/2012/12/14/this-week-in-wind-down/|title=Jason Calacanis Says He Will Shut Down Podcast Network ThisWeekIn.com, This Week In Startups Will Continue|author=Anthony Ha|publisher=AOL|work=TechCrunch}}</ref>
According to [[AngelList]], Calacanis' list of investments includes: [[Tumblr]], [[Cozy (company)|Cozy]], [[gdgt]], [[Gowalla]], [[Blippy]], [[Backupify]], [[Boxbee]], [[UberMedia]], [[LeadGenius]], [[Thumbtack (website)|Thumbtack]], [[Rapportive]], [[NewHound]], [[StyleSeat]], [[LAUNCH Media|LAUNCH]], [[Wanderfly]], [[Tout (company)|Tout]], [[AdStage]], [[Uber (company)|Uber]], [[Chartbeat]], [[Groundcrew (company)|Groundcrew]], [[ChallengePost]], [[Evernote]], [[Pen.io]], [[Red Tricycle]], [[Nimble (CRM)|Nimble]], [[BetterCompany]], [[Circa (news app)|Circa]], [[JIBE]], [[15Five]], [[Crossfader (company)|Crossfader]], [[Robinhood Markets|Robinhood]], [[Signpost (company)|Signpost]], [[HandUp]], [[Mouth (company)|Mouth]], [[HomeHero]], [[Swell Radio]], Brilliant, [[Stowaway Cosmetics]], [[MyTime]], [[Ramen (company)|Ramen]], [[Calm (wellness company)|Calm]], [[Frequency (company)|Frequency]], [[Fresh Radio|Fresh]], [[Backyard]], [[Birdi]], [[This Week In]], [[Red Clay (company)|Red Clay]], [[Skift]], [[Connect (social media)|Connect]], [[Butterfleye]], [[Datastax]], [[Density (company)|Density]], [[Whisper (company)|Whisper]], [[CAUSECAST]], [[Nimble CRM]], [[WizzyWig]], [[StorkBrokers]], [[Bento (company)|Bento]], [[VUE (app)|VUE]], [[ThisWeekIn]], [[ThisNext]], [[Tweetup]], [[SpaceMonkey]], Requested.


''[[This Week in Startups]]'' (also called ''TWiSt'') is a show founded and hosted by Calacanis. The show was co-hosted by [[Molly Wood]] from 2021 to 2023.<ref>{{cite web|url=http://www.avc.com/a_vc/2011/07/this-week-in-startups.html|title=This Week In Startups|author=Fred Wilson|work=avc.com|date=2011-07-09}}</ref> Molly left the podcast in 2023 for unnamed reasons.
===ThisWeekIn.com===
Calacanis is the founder of ThisWeekIn.com,<ref>http://www.crunchbase.com/company/this-week-in</ref> a podcast network, and the host of the live streamed "This Week In Startups" show, one of the featured podcasts.<ref>Second Annual Twistee Awards (June 17th, 2011). [http://thisweekinstartups.com/blog/the-second-annual-twistee-awards-152-1.html "This Week in Startups"] Retrieved 2011-6-21</ref>
In 2010, the company raised a seed round of about $300,000 from Matt Coffin, Sky Dayton, and Calacanis himself.


He also founded a startup Inside.com which focuses on delivering thematic newsletters.<ref name=":0">{{Cite web|url=https://www.businessinsider.com/investor-jason-calacanis-worth-millions-thanks-to-uber-2017-7|title=How a founder went from being worth millions to -$10,000 almost overnight — then rebounded to a $100 million fortune|last=Mazarakis, Shontell|first=Anna, Alyson|date=2017-08-03|website=Business Insider|access-date=2019-10-27}}</ref> The company raised $2.6 million.<ref>{{Cite web|url=https://www.niemanlab.org/2019/02/inside-insides-new-local-newsletters-and-its-plans-to-keep-scaling-with-750000-active-subscribers-on-board/|title=Inside Inside's new local newsletters and its plans to keep scaling (with 750,000 active subscribers on board)|website=Nieman Lab|access-date=2019-10-27}}</ref>
On December 14, 2012, Calacanis announced that he would be shutting down his podcast network ThisWeekIn.com.<ref>{{cite web|url=https://techcrunch.com/2012/12/14/this-week-in-wind-down/|title=Jason Calacanis Says He Will Shut Down Podcast Network ThisWeekIn.com, This Week In Startups Will Continue|author=Anthony Ha|publisher=AOL|work=TechCrunch}}</ref> The shut down of the company did not mean the end of its three most popular shows, which are still in live production: This Week In Startups, This Week In Web Design and Kevin Pollak’s Chat Show.


In June 2019, Calacanis partnered with the [[NSW Government]] to create the Sydney Launch Festival for startups to give their pitches to global audiences.<ref>{{Cite web|url=https://www.crowdfundinsider.com/2019/06/148512-jason-calacanis-launch-festival-takes-place-in-sydney-australia-this-week/|title=Jason Calacanis' Launch Festival Takes Place in Sydney Australia this Week|last=Alois|first=J. D.|date=2019-06-18|website=Crowdfund Insider|language=en-US|access-date=2019-06-26}}</ref>
===ThisWeekInStartups.com===
[http://thisweekinstartups.com/ This Week in Startups] (also called TWiSt) is a show hosted by Jason that has published more than 780 episodes. Typically, TWiSt produces two episodes a week, one on Tuesday and one on Friday. Tuesday shows generally feature founders, CEOs, entrepreneurs, angel investors and venture capitalists talking about startups, entrepreneurship and the Web industry in general.<ref>{{cite web|url=http://ethanbeute.com/wordpress/who-how-many-this-week-in-startups-calacanis-audience-twist/|title=Who Trumps How Many: This Week in Startups with Jason Calacanis - ethanbeute|work=ethanbeute}}</ref> Friday shows feature a round table format show<ref>http://readwrite.com/2010/04/09/this-week-in-venture-capital-jason-calicanis-latest-podcast-creation</ref> that usually runs over an hour of conversation about the web startup industry with a rotating panel of commentators. The show has gained popularity amongst the startup community, averaging 100,000 regular listeners {{Citation needed|date=February 2015}}, and routinely attracts well-known speaker-guests.<ref>{{cite news| url=https://www.forbes.com/sites/tjwalker/2011/05/10/is-jason-calacanis-the-best-talk-show-host-on-tv-today-media-training/ |title=Is Jason Calacanis the best talk show host on tv today media training?work=Forbes | first=TJ | last=Walker}}</ref><ref>{{cite web|url=http://www.avc.com/a_vc/2011/07/this-week-in-startups.html|title=This Week In Startups|author=Fred Wilson|work=avc.com}}</ref> Calacanis and a continuous fresh group of speaker-guests<ref>{{cite web|url=http://www.tubefilter.com/2009/05/12/jason-calacanis-covers-startups-with-a-twist/|title=Jason Calacanis Covers Startups With a 'TWiST'|work=Tubefilter}}</ref><ref>{{cite web|url=http://magazine3.com/demo/generalpress/this-week-in-startups-with-jason-calacanis-with-tyler-crowley/|title=GeneralPress WordPress theme - This Week In Startups With Jason Calacanis with Tyler Crowley|work=magazine3.com}}</ref> that are well known within the industry, sometimes experts, share their stories and thoughts on the Web industry, their ventures andcompanies and trends.<ref>{{cite web|url=http://venturevillage.eu/berlin-v-london-june-8|title=Berlin to battle London on Jason Calacanis's show This Week in Startups (Apply now!)|work=VentureVillage}}</ref><ref>{{cite web|url=http://www.imdb.com/title/tt1950991/|title=This Week in Startups (TV Series 2009– )|work=IMDb}}</ref> including the live broadcast<ref>http://thisweekin.com/live/</ref><ref>{{cite web|url=http://www.justin.tv/thisweekin|title=Goodbye from Justin.tv|work=justin.tv}}</ref>
on its main site<ref>{{cite web|url=http://thisweekin.com/thisweekin-startups/|title=This Week In Startups|work=thisweekin.com}}</ref> as well as iTunes/Audio & iTunes/Video.


After Elon Musk acquired Twitter in 2022 and re-organized the management and governance structure, Calacanis helped run the company Twitter along with David Sacks.<ref>{{Cite web |last=O'Sullivan |first=Clare Duffy,Oliver Darcy,Donie |date=2022-11-15 |title=Twitter chaos spills into public view as Musk clashes with and fires employees on the platform {{!}} CNN Business |url=https://www.cnn.com/2022/11/15/tech/elon-musk-twitter-employees/index.html |access-date=2023-11-18 |website=CNN |language=en}}</ref>
===LAUNCH Conference===
Calacanis announced the creation of the [[LAUNCH Conference|Launch Festival]] to spotlight unannounced start-ups. The first Festival was held on February 23 and 24, 2011, and featured 140 startups. A number of companies received funding at the event and the winners included [[Room 77]] and [[GreenGoose]]. LAUNCH Festivals are held each year in the spring.


===Dyn===
=== 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.<ref name="venturebeat2009">{{cite web|author=Paul Boutin|date=December 6, 2009|url=https://venturebeat.com/2009/12/06/serial-entropr-calacanis-launches-open-angel-forum-a-free-access-to-investors-program/|title=Calacanis Launches Open Angel Forum|publisher=VentureBeat|access-date=August 11, 2010}}</ref> 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.<ref name="observer">{{cite web|title=Pay-to-Pitch Comes Creeping Back: How Much Is Too Much?|url=https://observer.com/2011/12/pay-to-pitch-how-much-is-too-much/|author=Adrianne Jeffries|publisher=Observer|date=December 12, 2011|access-date=June 21, 2018}}</ref><ref name="calacanis2010">{{cite web|title=Why startups shouldn't have to pay to pitch angel investors|author=Jason Calacanis|date=October 9, 2010|url=http://calacanis.com/2009/10/09/why-startups-shouldnt-have-to-pay-to-pitch-angel-investors/|access-date=August 11, 2010|archive-date=July 21, 2011|archive-url=https://web.archive.org/web/20110721153543/http://calacanis.com/2009/10/09/why-startups-shouldnt-have-to-pay-to-pitch-angel-investors/|url-status=dead}}</ref> Calacanis is an angel investor in [[Robinhood (company)|Robinhood]], [[Wealthfront]], [[Uber]],<ref name="auto"/> [[Desktop Metal]], [[Datastax]], [[Thumbtack (website)|Thumbtack]], [[Superhuman]] and [[Trello]].<ref>{{Cite web|url=https://qz.com/1043958/angel-uber-investor-jason-calacanis-had-dim-sum-to-promote-his-book-on-investing-in-unicorns/|title=At dim sum with angel investor Jason Calacanis, buying his book is mandatory|last=Griswold|first=Alison|website=Quartz|date=August 3, 2017 |language=en|access-date=2019-07-30}}</ref>
Calacanis joined the Board of Directors of [[DynDNS|Dyn]] in late 2012.
<ref>{{cite web|url=http://dyn.com/dyn-receives-38-million-investment-from-north-bridge/|title=Dyn Receives $38M Investment From North Bridge|author=Dyn News|date=2 October 2012|work=dyn.com}}</ref>


Calacanis raised a $10 million fund for his own venture investment firm to invest in startups that emerged from the Launch conference.<ref>[http://valleywag.gawker.com/racism-denier-jason-calacanis-is-starting-his-own-vc-f-511058699 Racism Denier Jason Calacanis Is Starting His Own VC Fund] {{webarchive|url=https://web.archive.org/web/20130608102800/http://valleywag.gawker.com/racism-denier-jason-calacanis-is-starting-his-own-vc-f-511058699 |date=2013-06-08 }}. Valleywag.gawker.com. Retrieved on 2013-07-19.</ref><ref>[http://www.financeplus.com/entrepreneur-jason-calacanis-raising-a-10-million-fund/ Entrepreneur Jason Calacanis raising a $10 million fund]. FinancePlus (2013-06-04). Retrieved on 2013-07-19.</ref> Limited partners in the fund include [[David O. Sacks|David Sacks]].<ref>[http://www.techinvestornews.com/Enterprise/Blogs-and-Tech-Dialogue/launch-founder-jason-calacanis-raising-10-million-venture-fund Launch founder Jason Calacanis raising $10 million venture fund] {{webarchive|url=https://archive.today/20130618033721/http://www.techinvestornews.com/Enterprise/Blogs-and-Tech-Dialogue/launch-founder-jason-calacanis-raising-10-million-venture-fund |date=2013-06-18 }}. Techinvestornews.com (2013-06-03). Retrieved on 2013-07-19.</ref>
===Tesla===
Following the success of the Launch conference,<ref>[https://venturebeat.com/2013/06/03/launch-founder-jason-calacanis-raising-10-million-venture-fund/ Launch founder Jason Calacanis raising $10 million venture fund]. VentureBeat (2013-07-15). Retrieved on 2013-07-19.</ref> 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.<ref name=reuters>Loizos, Connie. (June 3, 2013). [https://www.reuters.com/article/us-venture-calacanis-newfund-idUSBRE95301W20130604 Entrepreneur Jason Calacanis raising a $10 million fund]. Reuters. Retrieved on 2013-07-19.</ref><ref>[http://www.pehub.com/251362/jason-calacanis-opens-up-about-his-new-venture-fund-launch-fund-i/ Private equity and venture capital news, data and community]. peHUB (2013-06-03). Retrieved on 2013-07-19.</ref>
During a dinner meeting between Calacanis and [[Elon Musk]], Musk mentioned that the second Space X rocket had exploded and that [[Tesla Motors]] had only two weeks of funding left. Calacanis enquired about any good news; Musk confided in him that a new car ([[Tesla Model S]]) was close to development and might cost $50,000. Upon arriving home, Calacanis wrote out two $50,000 cheques to Tesla with a note stating "E looks like a great car. I will take two". Two years later the cheques were cashed and Calacanis took delivery of two Tesla Model S cars. The first has the serial number 00001 and the second 00073.<ref>{{cite web|url=http://twit.tv/show/this-week-in-tech/508|title=Shows - TWiT|work=TWiT.tv}}</ref>


In 2016, Calacanis was banned from attending [[Y Combinator|Y Combinator's]] Demo Day. According to a post on ''[[Hacker News]]'' by then-president of Y Combinator [[Sam Altman]], the decision to exclude Calacanis was driven by feedback received from YC founders regarding their interactions with him.<ref>{{cite news |last1=Black |first1=Julia |title=The Besties’ Revenge: How the ‘All-In’ Podcast Captured Silicon Valley |url=https://www.theinformation.com/articles/the-besties-revenge-how-the-all-in-podcast-ate-silicon-valley |access-date=13 February 2024 |work=The Information |date=15 December 2023}}</ref>
As such Calacanis is interviewed as a 'Tesla Customer' in the 2011 documentary, ''[[Revenge of the Electric Car]]''.


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]] 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."<ref name="recode">{{cite news|title=Why did Jason Calacanis sell all his Facebook stock?|author= Eric Johnson|newspaper= Vox|publisher=Recode|url=https://www.recode.net/2018/5/4/17317824/jason-calacanis-facebook-mark-zuckerberg-immoral-instagram-copying-snapchat-kara-swisher-podcast|date=May 4, 2018|access-date=June 15, 2018}}</ref>
Calacanis has received an offer of $250,000 for the vehicle with serial number 00001, but he has expressed interest in donating the car to the [[Smithsonian Institution]].


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"''<ref name="auto"/> on angel investing published by HarperCollins in 2017.<ref>{{Cite book|title=Angel : how to invest in technology startups-timeless advice from an angel investor who turned $100,000 into $100,000,000|author=Calacanis, Jason|isbn=9780062560711|edition= First |location=New York, NY|oclc=993752430|date = 2017-07-18}}</ref>
===Angel===
On July 18, 2017, Calacanis released his first book ''Angel: How to Invest in Technology Startups'', published by Harper Business imprint of [[HarperCollins]].<ref name=harpercollins>{{cite web |url=https://www.harpercollins.com/9780062560704/angel |title=Angel - Jason Calacanis - Hardcover |publisher=HarperCollins |date=July 18, 2017}}</ref>


In 2018, Calacanis invested in [[Calm (company)|Calm]], a meditation app that is valued at $1 billion.<ref>{{Cite web|url=https://www.cnbc.com/2018/03/26/calm-raising-over-25-million-from-insight-at-250-million-valuation.html|title=This meditation app is now worth $250 million and has Trump-related stress to thank|last=Levy|first=Ari|date=2018-03-26|website=CNBC|language=en|access-date=2019-06-11}}</ref><ref>{{Cite web|url=https://www.cnbc.com/2019/02/05/calm-raises-88-million-valuing-the-meditation-app-at-1-billion.html|title=Relaxation app Calm raises $88 million, valuing it $1 billion|last=LaVito|first=Angelica|date=2019-02-06|website=CNBC|language=en|access-date=2019-07-30}}</ref>
==Controversy==
During a speech about his company [[Mahalo.com|Mahalo]] at [[Gnomedex]] in 2007, Calacanis was heckled from the audience. The heckler was [[Dave Winer]]. Winer accused Calacanis of "spamming the audience" with a Mahalo pitch.<ref>{{cite web|url=http://www.businessinsider.com/2007/8/jason-calacanis|title=Jason Calacanis vs. Dave Winer Pissing Match, Round By Round|date=13 August 2007|work=Business Insider}}</ref> Winer later reiterated his disdain for Calacanis, stating "It's all about Jason and his investors making money. Why should I care about that?"<ref>{{cite web|url=http://scripting.com/stories/2007/08/10/heresWhatBothersMeAboutMah.html|title=Here's what bothers me about Mahalo (Scripting News)|work=scripting.com}}</ref>


== Podcasting ==
Calacanis was involved in a 2010 Internet hoax regarding his Twitter postings about the introduction of the Apple iPad. In his tweets, he claimed to have a "reviewer's copy" of an iPad device describing in great detail the features of such device. The device in question was not in his possession nor did it exist. It was explained to have been an attempt by Calacanis to expose the hysteria regarding Apple product launches. The hoax also called into question the fact checking and verification processes of the mainstream media who published the hoax story as true.<ref>Dunagan, Jake (January 31, 2010). [http://www.iftf.org/future-now/article-detail/calacanis-hoax-guerrilla-futures-as-persuasion/ "Calacanis Hoax: Guerrilla Futures as Persuasion"]. ''iftf.org''; Institute For The Future. Retrieved 2010-06-19.</ref><ref>Swisher, Kara (February 1, 2010). [http://kara.allthingsd.com/20100201/prankster-jason-calacanis-talks-about-his-apple-ipad-hoax-warning-cute-baby-alert/?mod=ATD_iphone "Prankster Jason Calacanis Talks About His Apple iPad Hoax"]. ''allthingssd.com''; [[The Wall Street Journal]]. Retrieved 2010-06-19.</ref>


=== ''This Week in Startups'' ===
[[Leo Laporte]], founder of the [[TWiT.tv]] network, and netcasts ''[[This Week in Tech]]'', ''[[This Week in Google]]'', ''[[This Week in Computer Hardware]]'', ''[[This Week in Enterprise Tech]]'', and ''[[This Week in Law]]'', expressed disdain for Calacanis' use of the term "This Week in".<ref>{{cite web|url=http://www.quora.com/Did-Jason-Calacanis-screw-over-Leo-Laporte-when-he-started-his-podcasting-network|title=Did Jason Calacanis screw over Leo Laporte when he started his podcasting network?|work=quora.com}}</ref> Prior to starting ThisWeekIn.com, Calacanis had been a guest on Laporte's show ''This Week in Tech'' 29 times, and Laporte reported feeling betrayed,<ref>{{cite av media|url=https://www.youtube.com/watch?v=kEihhjJC9jI|title=Leo Laporte rants about Jason Calacanis 11/07/10|date=7 November 2010|work=YouTube}}</ref> suggesting that the use of the same name was intended to confuse advertisers and viewers. Since 2015, Calacanis has returned to making regular appearances on TWiT podcasts, including guest co-hosting ''[[The New Screen Savers]]'' alongside Laporte.<ref>{{Cite web|url=https://twit.tv/shows/this-week-in-tech/episodes/508|title=This Week in Tech 508 Calacanis Returns {{!}} TWiT.TV|website=TWiT.tv|language=en-US|access-date=2016-09-22}}</ref><ref>{{Cite web|url=https://twit.tv/shows/new-screen-savers/episodes/57|title=The New Screen Savers 57 Twitter's 'Fail Whale' Creator {{!}} TWiT.TV|website=TWiT.tv|language=en-US|access-date=2016-09-22}}</ref>
{{Infobox podcast
| title = This Week in Startups
| image = This Week in Startups logo.jpg
| alt =
| caption =
| italic title = no
| hosting = Jason Calacanis and Molly Wood
| website = {{URL|https://thisweekinstartups.com}}


}}
==Bibliography==


''This Week in Startups'' is a weekly podcast created and hosted by Calacanis.<ref name=search/><ref>{{Cite web|url=https://www.businessinsider.com/jason-calacanis-offers-startup-500k-and-podcast-time-dm-fail-2019-5|title=A famous startup investor had a DM fail and accidentally revealed his clever strategy for getting into super competitive funding rounds|last=Hernbroth|first=Megan|website=Business Insider|access-date=2019-08-23}}</ref> ''[[The Wall Street Journal]]'' contributor Cecilie Rohwedder described the podcast as "an influential Web series filmed in the U.S."<ref>{{cite news|title=Careers: Learning the Art of the American Pitch --- Coaches Teach International Entrepreneurs to Deliver Persuasive Presentations to Investors, Clients|author=Cecilie Rohwedder|work=[[The Wall Street Journal]]|date=November 17, 2013|page=B6}}</ref>

==== 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]], CEO and founder of the content management and hosting system Crowd Fusion, as its first guest..<ref>{{Cite web|url=https://www.phillymag.com/business/2018/02/12/podcasts-business-leaders-philadelphia/|title=Podcasts Business Leaders in Philadelphia|last=|first=|date=12 February 2018|website=Philly Mag|access-date=}}</ref>

==== Reception ====
''This Week in Startups'' was listed in an article at [[Fortune (magazine)|Fortune.com]] titled "The Ultimate Guide to the Best Business Podcasts".<ref>{{Cite web|url=https://fortune.com/2018/09/11/best-business-podcasts/|title=The Ultimate Guide to the Best Business Podcasts|website=Fortune|language=en|access-date=2019-08-23}}</ref>

=== ''All-In'' ===
As of 2022, Calacanis is co-host of the ''[[All-In (podcast)|All-In]]'' podcast, alongside [[Chamath Palihapitiya]], [[David O. Sacks]], and [[David Friedberg]].<ref>{{Cite web | url=https://nymag.com/intelligencer/2022/01/chamath-palihapitiya-has-deep-business-ties-to-china.html | title=Chamath Palihapitiya is 'Not Even Sure That China is a Dictatorship' | date=18 January 2022 }}</ref><ref>{{Cite web | url=https://deadline.com/2022/01/golden-state-warriors-owner-chamath-palihapitiya-uyghurs-china-1234913951/amp/ | title=Golden State Warriors Co-Owner: "Nobody Cares About What's Happening to the Uyghurs" in China | date=17 January 2022 }}</ref><ref>{{Cite web | url=https://www.npr.org/2022/01/17/1073705516/co-owner-of-the-nbas-warriors-lambasted-after-saying-nobody-cares-about-the-uygh | title=Co-owner of NBA's Warriors slammed after saying 'nobody cares about the Uyghurs' | website=NPR | date=17 January 2022 | last1=Jones | first1=Dustin }}</ref> 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?"<ref>{{Cite web |title=All-In Summit |url=https://www.aedeapartners.com/aneta-key-calendar/2022/all-in-summit-miami |access-date=2022-07-16 |website=Aedea Partners LLC — Strategy Consulting and Training with Aneta Key |date=May 15, 2022 |language=en-US}}</ref>

== Personal life ==
Calacanis married Jade Li sometime between 2006 and 2009.<ref>{{Cite magazine|title=Revenge of the Dotcom Poster Boy|language=en-US|magazine=Wired|url=https://www.wired.com/2006/01/blogger-2/|access-date=2021-06-11|issn=1059-1028}}</ref><ref>{{Cite web|url=https://calacanis.com/2009/05/29/jades-first-show-invitation-to-out-there-exhibit-june-12/|title=Jade's first show! Invitation to OUT THERE Exhibit, June 12|date=May 29, 2009|website=Jason Calacanis|access-date=November 21, 2021|archive-date=December 20, 2022|archive-url=https://web.archive.org/web/20221220155821/https://calacanis.com/2009/05/29/jades-first-show-invitation-to-out-there-exhibit-june-12/|url-status=dead}}</ref>

Calacanis was an early supporter and founder for the effort behind the successful recall election of the San Francisco District Attorney [[Chesa Boudin]] in 2022.<ref>{{cite web |last1=Akela |first1=Lacy |title=What's Stopping Chesa Boudin? |url=https://theintercept.com/2022/06/03/san-francisco-chesa-boudin-recall/ |website=The Intercept |date=June 3, 2022 |publisher=First Look Institute |access-date=3 November 2022}}</ref><ref>{{cite web |last1=Akela |first1=Lacy |title=A Tech Investor Is Raising Funds to Investigate San Francisco Prosecutor's Decarceral Approach |url=https://theintercept.com/2021/01/26/chesa-boudin-recall-san-francisco-prosecutor/ |website=The Intercept |date=January 26, 2021 |publisher=First Look Institute |access-date=3 November 2022}}</ref>

== Publications ==
* Jason Calacanis, ''Angel: How to Invest in Technology Startups'', Harper Business, 2017 {{isbn|9780062560704}}
* Jason Calacanis, ''Angel: How to Invest in Technology Startups'', Harper Business, 2017 {{isbn|9780062560704}}


==References==
== References ==
{{Reflist|30em}}
{{Reflist}}


;General
; General
{{Refbegin}}
{{Refbegin}}
*Brown, Eryn (January 2006). [https://www.wired.com/wired/archive/14.01/blogger.html "Revenge of the Dotcom Poster Boy"]. ''Wired''; Conde Nast Digital. Retrieved 2010-06-19.
* Brown, Eryn (January 2006). [https://www.wired.com/wired/archive/14.01/blogger.html "Revenge of the Dotcom Poster Boy"]. ''Wired''; Conde Nast Digital. Retrieved 2010-06-19.
{{Refend}}
{{Refend}}


==External links==
== External links ==
* {{Instagram}}<!--- [[WP:ELOFFICIAL]] --->
{{commons category|Jason Calacanis}}
*[http://www.calacanis.com/ The Jason Calacanis Weblog]
* [https://www.allinpodcast.co ''All In''] – podcast

*[http://inside.com/ Inside.com]
{{Authority control}}
*[http://thisweekinstartups.com/ This Week in Startups]
*[https://angel.co/jason/ AngelList Investments]
*[http://angelthebook.com/ Angel]


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{{DEFAULTSORT:Calacanis, Jason}}
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[[Category:Angel investors]]
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[[Category:Xaverian High School alumni]]
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Latest revision as of 04:12, 1 December 2024

Jason Calacanis
Calacanis in 2018
Born (1970-11-28) November 28, 1970 (age 54)
Bay Ridge, Brooklyn, New York, U.S.
EducationFordham University (B.A.)
Occupations
SpouseJade Li (m. after 2006)
Children3

Jason McCabe Calacanis (born November 28, 1970) is a podcaster, American Internet entrepreneur,[1] angel investor,[2] and author.[3][4]

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, capitalized on the growth of blogs before being sold to AOL. Calacanis is also an angel investor in various technology startups and co-host of the All-In podcast alongside David Sacks, Chamath Palihapitiya and David Friedberg, and the host of This Week in Startups Podcast.

Early life

[edit]

Calacanis was born in the Bay Ridge section of Brooklyn, New York, and has two brothers.[5] He is of half-Greek and half-Irish descent.[6] He graduated from Xaverian High School in 1988 and attended Fordham University, where he received a B.A. in psychology.[7]

Career

[edit]

Calacanis started his career in the 1990s as a reporter covering the internet industry in New York.[3]

Calacanis was the 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 community, and in 1996 began producing the Silicon Alley Reporter.[1] Originally a 16-page photocopied newsletter,[2] 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.[8] 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.[3] with Brian Alvey on September 24, 2003, and the startup was supported by an angel investment from Mark Cuban.[9]

Two years after its inception, the Weblogs, Inc. blogs business was generating $1,000 a day just from AdSense.[10] Time Warner's America Online agreed to buy Weblogs, Inc. in October 2005 for $25–30 million.[3][11][12]

Calacanis speaking at the 2005 Gnomedex

On November 16, 2006, TechCrunch reported that Calacanis had resigned from his position as CEO of Weblogs, Inc. and general manager of Netscape.[13] Calacanis later confirmed this on his blog and the Gillmor Gang podcast.[14]

Calacanis joined Sequoia Capital, a venture capital firm,[3] as an EIA (entrepreneur in action) in December, 2006,[15] a position which he held until May, 2007.[16] Through this program, Calacanis invested $25K in Travis Kalanick's company, Uber.[2] As of 2017 the investment was worth roughly $100 million.[3]

In 2007, Calacanis is credited with starting an internet trend he called "fatblogging" after being fed up with being overweight.[17] 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.[17]

He launched the web directory Mahalo ("thank you" in Hawaiian),[11] which raised $20 million in venture capital from investors[18] including Sequoia Capital, News Corp, CBS, Mark Cuban, and Elon Musk. Mahalo 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.[19]

Calacanis founded ThisWeekIn.com,[18] which shut down in 2012 but is live again and available as a weekly podcast.[20]

This Week in Startups (also called TWiSt) is a show founded and hosted by Calacanis. The show was co-hosted by Molly Wood from 2021 to 2023.[21] Molly left the podcast in 2023 for unnamed reasons.

He also founded a startup Inside.com which focuses on delivering thematic newsletters.[22] The company raised $2.6 million.[23]

In June 2019, Calacanis partnered with the NSW Government to create the Sydney Launch Festival for startups to give their pitches to global audiences.[24]

After Elon Musk acquired Twitter in 2022 and re-organized the management and governance structure, Calacanis helped run the company Twitter along with David Sacks.[25]

Angel investing

[edit]

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.[26] 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.[27][28] Calacanis is an angel investor in Robinhood, Wealthfront, Uber,[3] Desktop Metal, Datastax, Thumbtack, Superhuman and Trello.[29]

Calacanis raised a $10 million fund for his own venture investment firm to invest in startups that emerged from the Launch conference.[30][31] Limited partners in the fund include David Sacks.[32] Following the success of the Launch conference,[33] 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.[2][34]

In 2016, Calacanis was banned from attending Y Combinator's Demo Day. According to a post on Hacker News by then-president of Y Combinator Sam Altman, the decision to exclude Calacanis was driven by feedback received from YC founders regarding their interactions with him.[35]

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 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."[36]

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"[3] on angel investing published by HarperCollins in 2017.[37]

In 2018, Calacanis invested in Calm, a meditation app that is valued at $1 billion.[38][39]

Podcasting

[edit]

This Week in Startups

[edit]
This Week in Startups
Presentation
Hosted byJason Calacanis and Molly Wood
Related
Websitethisweekinstartups.com

This Week in Startups is a weekly podcast created and hosted by Calacanis.[18][40] The Wall Street Journal contributor Cecilie Rohwedder described the podcast as "an influential Web series filmed in the U.S."[41]

History

[edit]

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, CEO and founder of the content management and hosting system Crowd Fusion, as its first guest..[42]

Reception

[edit]

This Week in Startups was listed in an article at Fortune.com titled "The Ultimate Guide to the Best Business Podcasts".[43]

All-In

[edit]

As of 2022, Calacanis is co-host of the All-In podcast, alongside Chamath Palihapitiya, David O. Sacks, and David Friedberg.[44][45][46] 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?"[47]

Personal life

[edit]

Calacanis married Jade Li sometime between 2006 and 2009.[48][49]

Calacanis was an early supporter and founder for the effort behind the successful recall election of the San Francisco District Attorney Chesa Boudin in 2022.[50][51]

Publications

[edit]
  • Jason Calacanis, Angel: How to Invest in Technology Startups, Harper Business, 2017 ISBN 9780062560704

References

[edit]
  1. ^ a b Heilemann, John (July 3, 2006). "Suit 2.0: Back in the nineties, Jason Calacanis was a Silicon Alley cowboy. Now, at AOL, he's in full corporate harness. Is that the only way for an entrepreneur to get to the top?". New York. Vol. 39, no. 24. p. 28. Gale A148358825. Archived from the original on December 30, 2006.
  2. ^ a b c d Loizos, Connie. (June 3, 2013). Entrepreneur Jason Calacanis raising a $10 million fund. Reuters. Retrieved on 2013-07-19.
  3. ^ a b c d e f g h Manjoo, Farhad (September 27, 2017). "Should the Middle Class Invest in Risky Tech Start-Ups?". The New York Times. ISSN 0362-4331. Archived from the original on November 3, 2017. Retrieved June 4, 2019.
  4. ^ Jason Calacanis (November 28, 2005). "My retirement party". Jason Calacanis weblog. Archived from the original on July 18, 2018. Retrieved April 21, 2006.
  5. ^ Drange, Matt; Cheng, Candy (June 3, 2021). "Jason Calacanis went from dotcom roadkill to early investor in Uber, Calm, and Robinhood. Here's how he's reshaping venture capital with bluster, ego, and media-savvy". Business Insider. Retrieved June 9, 2024.
  6. ^ Remnick, David (2001). The New Gilded Age: The New Yorker Looks at the Culture of Affluence. Random House Publishing Group. p. 10. ISBN 978-0-375-50705-2.
  7. ^ "Featured Discussion Leaders". The Media Center. 2007. Archived from the original on May 4, 2007. Retrieved June 6, 2007.
  8. ^ Grigoriadis, Vanessa (March 6, 2000). "Silicon Alley 10003". New York. Retrieved 2010-06-19.
  9. ^ "6 Reasons Why You Should Know Jason Calacanis". Startup San Diego. June 6, 2017. Retrieved June 10, 2020.
  10. ^ Penenberg, Adam L.. (2007-09-01) Man vs. Machine | Fast Company | Business + Innovation. Fast Company. Retrieved on 2013-07-19.
  11. ^ a b Dotan, Tom (January 27, 2014). "Entrepreneur making news: Jason Calacanis looks to deriver in journalism". Los Angeles Business Journal. 36 (4). CBJ: 1. ISSN 0194-2603. Gale A360474368. Archived from the original on October 15, 2022.
  12. ^ Arrington, Michael (October 5, 2005). "AOL Acquires Weblogs, Inc". techcrunch.com. Retrieved June 14, 2010.
  13. ^ Arrington, Michael (November 16, 2006). "Jason Calacanis resigns from AOL". Tech Crunch. Retrieved 2010-06-19.
  14. ^ Farber, Dan. (2006-11-17) Jason Calacanis talks about leaving AOL and what's next. ZDNet. Retrieved on 2013-07-19.
  15. ^ Arrington, Michael (December 5, 2006). "Calacanis takes position at Sequoia Capital". Tech Crunch. Retrieved 2010-06-19.
  16. ^ Why Jason Calacanis Is Betting All His Chips On Web Video Archived October 20, 2021, at the Wayback Machine. The Rise to the Top. Retrieved on 2013-07-19.
  17. ^ a b Pham, Alex (June 15, 2007). "On 'fatblogs,' heavy people weigh in". Los Angeles Times. Archived from the original on December 27, 2020. Retrieved December 27, 2020.
  18. ^ a b c Dotan, Tom (January 7, 2013). "Ex-search engine finds way to video: Mahalo to produce YouTube channels as Inside.com". Los Angeles Business Journal. 35 (1): 1. Gale A315221432 – via Cengage.
  19. ^ Adam L. Penenberg (June 14, 2012). "Mahalo.com: Pivot or Die". Fast Company. Retrieved June 18, 2018.
  20. ^ Anthony Ha. "Jason Calacanis Says He Will Shut Down Podcast Network ThisWeekIn.com, This Week In Startups Will Continue". TechCrunch. AOL.
  21. ^ Fred Wilson (July 9, 2011). "This Week In Startups". avc.com.
  22. ^ Mazarakis, Shontell, Anna, Alyson (August 3, 2017). "How a founder went from being worth millions to -$10,000 almost overnight — then rebounded to a $100 million fortune". Business Insider. Retrieved October 27, 2019.{{cite web}}: CS1 maint: multiple names: authors list (link)
  23. ^ "Inside Inside's new local newsletters and its plans to keep scaling (with 750,000 active subscribers on board)". Nieman Lab. Retrieved October 27, 2019.
  24. ^ Alois, J. D. (June 18, 2019). "Jason Calacanis' Launch Festival Takes Place in Sydney Australia this Week". Crowdfund Insider. Retrieved June 26, 2019.
  25. ^ O'Sullivan, Clare Duffy,Oliver Darcy,Donie (November 15, 2022). "Twitter chaos spills into public view as Musk clashes with and fires employees on the platform | CNN Business". CNN. Retrieved November 18, 2023.{{cite web}}: CS1 maint: multiple names: authors list (link)
  26. ^ Paul Boutin (December 6, 2009). "Calacanis Launches Open Angel Forum". VentureBeat. Retrieved August 11, 2010.
  27. ^ Adrianne Jeffries (December 12, 2011). "Pay-to-Pitch Comes Creeping Back: How Much Is Too Much?". Observer. Retrieved June 21, 2018.
  28. ^ Jason Calacanis (October 9, 2010). "Why startups shouldn't have to pay to pitch angel investors". Archived from the original on July 21, 2011. Retrieved August 11, 2010.
  29. ^ Griswold, Alison (August 3, 2017). "At dim sum with angel investor Jason Calacanis, buying his book is mandatory". Quartz. Retrieved July 30, 2019.
  30. ^ Racism Denier Jason Calacanis Is Starting His Own VC Fund Archived 2013-06-08 at the Wayback Machine. Valleywag.gawker.com. Retrieved on 2013-07-19.
  31. ^ Entrepreneur Jason Calacanis raising a $10 million fund. FinancePlus (2013-06-04). Retrieved on 2013-07-19.
  32. ^ Launch founder Jason Calacanis raising $10 million venture fund Archived 2013-06-18 at archive.today. Techinvestornews.com (2013-06-03). Retrieved on 2013-07-19.
  33. ^ Launch founder Jason Calacanis raising $10 million venture fund. VentureBeat (2013-07-15). Retrieved on 2013-07-19.
  34. ^ Private equity and venture capital news, data and community. peHUB (2013-06-03). Retrieved on 2013-07-19.
  35. ^ Black, Julia (December 15, 2023). "The Besties' Revenge: How the 'All-In' Podcast Captured Silicon Valley". The Information. Retrieved February 13, 2024.
  36. ^ Eric Johnson (May 4, 2018). "Why did Jason Calacanis sell all his Facebook stock?". Vox. Recode. Retrieved June 15, 2018.
  37. ^ Calacanis, Jason (July 18, 2017). Angel : how to invest in technology startups-timeless advice from an angel investor who turned $100,000 into $100,000,000 (First ed.). New York, NY. ISBN 9780062560711. OCLC 993752430.{{cite book}}: CS1 maint: location missing publisher (link)
  38. ^ Levy, Ari (March 26, 2018). "This meditation app is now worth $250 million and has Trump-related stress to thank". CNBC. Retrieved June 11, 2019.
  39. ^ LaVito, Angelica (February 6, 2019). "Relaxation app Calm raises $88 million, valuing it $1 billion". CNBC. Retrieved July 30, 2019.
  40. ^ Hernbroth, Megan. "A famous startup investor had a DM fail and accidentally revealed his clever strategy for getting into super competitive funding rounds". Business Insider. Retrieved August 23, 2019.
  41. ^ Cecilie Rohwedder (November 17, 2013). "Careers: Learning the Art of the American Pitch --- Coaches Teach International Entrepreneurs to Deliver Persuasive Presentations to Investors, Clients". The Wall Street Journal. p. B6.
  42. ^ "Podcasts Business Leaders in Philadelphia". Philly Mag. February 12, 2018.
  43. ^ "The Ultimate Guide to the Best Business Podcasts". Fortune. Retrieved August 23, 2019.
  44. ^ "Chamath Palihapitiya is 'Not Even Sure That China is a Dictatorship'". January 18, 2022.
  45. ^ "Golden State Warriors Co-Owner: "Nobody Cares About What's Happening to the Uyghurs" in China". January 17, 2022.
  46. ^ Jones, Dustin (January 17, 2022). "Co-owner of NBA's Warriors slammed after saying 'nobody cares about the Uyghurs'". NPR.
  47. ^ "All-In Summit". Aedea Partners LLC — Strategy Consulting and Training with Aneta Key. May 15, 2022. Retrieved July 16, 2022.
  48. ^ "Revenge of the Dotcom Poster Boy". Wired. ISSN 1059-1028. Retrieved June 11, 2021.
  49. ^ "Jade's first show! Invitation to OUT THERE Exhibit, June 12". Jason Calacanis. May 29, 2009. Archived from the original on December 20, 2022. Retrieved November 21, 2021.
  50. ^ Akela, Lacy (June 3, 2022). "What's Stopping Chesa Boudin?". The Intercept. First Look Institute. Retrieved November 3, 2022.
  51. ^ Akela, Lacy (January 26, 2021). "A Tech Investor Is Raising Funds to Investigate San Francisco Prosecutor's Decarceral Approach". The Intercept. First Look Institute. Retrieved November 3, 2022.
General
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