The character arc of Jason Calacanis

A life drawn by Character Arc from the public record

Born on 28 November 1970 in Brooklyn. Between then and now sit Xaverian High School in 1988, Fordham University, the Silicon Alley Reporter from 1996, Weblogs Inc. co-founded on 24 September 2003 and sold to AOL in October 2005, Sequoia Capital in December 2006, the Open Angel Forum in 2009, This Week in Startups announced on 16 March 2009 and premiered on 1 May 2009, Mahalo profitable in 2011 and closed in 2014, and the book Angel in 2017. The line below draws the story so far, in order.

Tap the line to pluck it. Hover or tap any mark for its card. Drawn from the public record of his life; the sources are at the foot of the page.

Who is Jason Calacanis?

An algorithm closed it.

He graduated from Xaverian High School in 1988 and took a Bachelor of Arts at Fordham University. During the dot-com boom he was part of New York's Silicon Alley community, and in 1996 he began producing the Silicon Alley Reporter, a magazine about the industry growing up around him. That is the pattern of the whole line: he reports on a thing, and then builds one.

On 24 September 2003 he co-founded Weblogs, Inc. with Brian Alvey, supported by an angel investment from Mark Cuban. It was a publishing company built on the growth of blogs, and AOL bought it in October 2005 for twenty five to thirty million dollars. He resigned as its chief executive on 16 November 2006 and joined Sequoia Capital as an entrepreneur in action in December 2006, a position he held until May 2007.

Mahalo, his search company, reached fifteen million unique visitors a month and became profitable in 2011. In the same year its traffic fell sharply after Google's Panda search algorithm update, and it shut down in 2014. Somebody else changed a ranking and the company went with it. What he did afterwards is the part worth drawing: he had announced This Week in Startups on 16 March 2009 and premiered it on 1 May 2009, and it is still running; he founded the Open Angel Forum in 2009 to connect early companies with investors; he invested in an early ride hailing company that was worth roughly a hundred million dollars by 2017 and in the meditation company Calm in 2018; and he published Angel with HarperCollins in 2017.

The moments

Jason Calacanis's timeline.

The 1980s

Jun 1988

Xaverian, then Fordham

Milestone. A Brooklyn high school, and a university in the Bronx.

The 1990s

Jun 1996

The Silicon Alley Reporter

Milestone, and it changed everything. He reported on the industry before he was part of it.

The 2000s

24 Sep 2003

Weblogs, Inc.

Milestone, and it changed everything. A publishing company built on blogs, backed by Mark Cuban.

6 Oct 2005

AOL bought it

Milestone, and it changed everything. Two years from founding to a sale.

16 Nov 2006

He resigned from Weblogs

Milestone, and it changed his direction. Out of the company a year after selling it.

Dec 2006

Sequoia, briefly

Milestone. Six months inside a venture firm, which is a short education.

1 Mar 2009

Start a weekly show

Crossroads, decided.

The paths laid out: commit to every week, taken, or keep writing instead. The programme premiered on 1 May 2009 and he was still co-hosting podcasts as of 2022.

16 Mar 2009

A podcast announced

Milestone, and it changed his direction. Announced first, which is one way to make yourself do it.

1 May 2009

This Week in Startups

Milestone, and it changed everything. Sixty minutes a week, kept up since 2009.

Jun 2009

The Open Angel Forum

Milestone, and it changed his direction. A room where founders meet investors without paying to be there.

The 2010s

Jun 2011

Panda, and Mahalo

Setback, and it changed everything. Profitable and fifteen million visitors, and then somebody changed a ranking.

18 Jul 2017

Angel

Milestone, and it changed his direction. A book on how to do the thing, written by somebody who had.

Jun 2018

He invested in Calm

Milestone. A meditation company, from an investor known for volume.

The line reaches today still adding to itself, which is why it is drawn now rather than at the end. What it has set moving is a habit rather than a company: he shows up weekly, has done since 2009, and the compounding is in the showing up rather than in any one bet.

What he wrote

Books by Jason Calacanis

2017
Angel
How to invest in technology startups, published by HarperCollins. Written by somebody who had been on both sides of the table, having sold a company to AOL and then spent a decade backing other people's.

Your turn

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His had a company closed by somebody else's algorithm and kept going for another decade. Yours is already further along than you think, and drawing it takes about five minutes.

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Jason Calacanis: frequently asked questions

What people ask about his line.

What is Jason Calacanis's character arc?

He reported on the New York internet scene from 1996, then built in it: a blog network co-founded in September 2003 and sold to AOL in October 2005. His search company was profitable in 2011 and closed in 2014 after a Google algorithm change.

What happened to Jason Calacanis's company Mahalo?

It reached fifteen million unique visitors a month and became profitable in 2011. In the same year its traffic fell sharply after Google's Panda search algorithm update, and it shut down in 2014. Somebody else changed a ranking and the company went with it.

What did Jason Calacanis sell to AOL?

Weblogs, Inc., a publishing company he co-founded with Brian Alvey on 24 September 2003 with angel backing from Mark Cuban. AOL acquired it in October 2005 for twenty five to thirty million dollars, and he resigned as chief executive on 16 November 2006.

When did Jason Calacanis start his podcast?

He announced This Week in Startups on 16 March 2009 in a blog post and premiered the sixty minute programme on 1 May 2009, with Brian Alvey as its first guest. Announcing it before making it is one way of having to make it.

What book did Jason Calacanis write?

Angel, on how to invest in technology startups, published by HarperCollins in 2017. He had founded the Open Angel Forum in 2009 to connect early stage companies with investors, and by 2017 one of his own investments was worth roughly a hundred million dollars.

Was Jason Calacanis at Sequoia Capital?

Briefly. He joined as an entrepreneur in action in December 2006, the month after resigning from Weblogs, Inc., and held the position until May 2007. Six months inside a venture capital firm is a short and concentrated education.

Where did Jason Calacanis grow up?

Brooklyn, New York, where he was born on 28 November 1970. He graduated from Xaverian High School in 1988 and took a Bachelor of Arts at Fordham University, then spent the dot-com boom inside New York's Silicon Alley community.

Where does this timeline of Jason Calacanis's life come from?

From the public record. Character Arc drew every moment on this line from the sources listed at the foot of the page, and the kind and weight of each moment are our editorial reading. Jason Calacanis isn't a Member of Character Arc and has no connection with it, and no feeling is attributed to him.

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Sources

Jason Calacanis, English Wikipedia biography, filed under living people.
AOL acquisition of Weblogs, Inc., October 2005, and the TechCrunch report of 16 November 2006.
HarperCollins publication record for Angel, 2017.