Jason Calacanis
Born 1970 · Age 55
American Internet entrepreneur, angel investor, podcaster and author. Co‑founder of Weblogs, Inc., founder of Silicon Alley Reporter and Mahalo, host of This Week in Startups, founder of LAUNCH/Launch Festival and active angel investor (notably an early Uber investor).
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Life & Career Timeline
Born in Bay Ridge, Brooklyn, NY
Born Jason McCabe Calacanis in Bay Ridge, Brooklyn. Son of a bar owner and a nurse; grew up in a working-class household of Greek and Irish descent.
Early entrepreneurship — sold customized T-shirts
As a child/teen, launched a small local venture selling customized T-shirts in his neighborhood (first early entrepreneurial experiment).
Graduated Xaverian High School
Completed secondary education at Xaverian High School in Brooklyn.
Graduated Fordham University (B.A., Psychology)
Earned a Bachelor of Arts in psychology from Fordham University (date not explicitly stated; estimated based on HS grad year).
Founded Silicon Alley Reporter / Rising Tide Studios
Started the Silicon Alley Reporter (originally a 16‑page photocopied newsletter) and media company Rising Tide Studios, covering the New York internet scene.
Silicon Alley Reporter expands to full magazine and conferences
Publication grew from a photocopied newsletter into a ~300‑page magazine; company also organized Internet/web/new media conferences in NY, LA, SF.
Company peak before dot‑com crash — ~100 employees, ~$12M revenue
Silicon Alley enterprise reached roughly 100 employees and approximately $12–12.5M in revenue at peak prior to the dot‑com crash.
Turned down a $20M buyout offer
Reportedly refused an approximately $20M buyout offer for Silicon Alley Reporter prior to the dot‑com crash.
Dot‑com crash — company collapses; major layoffs
After the dot‑com crash revenue fell dramatically (reported fall from ~$12M to ~$500k); laid off ~80 people; near‑bankruptcy.
Co‑founded Weblogs, Inc. with Brian Alvey
Launched Weblogs, Inc., a blog network that eventually incubated multiple popular niche blogs; early angel support from Mark Cuban.
Mark Cuban provided angel support for Weblogs, Inc.
Weblogs, Inc. received angel backing from Mark Cuban during its early growth phase.
Weblogs, Inc. generating ~$1,000/day from AdSense
About two years after founding, the Weblogs, Inc. blogs were reportedly generating roughly $1,000 per day from Google AdSense advertising.
Joined AOL/Netscape leadership (post‑acquisition)
Following the Weblogs acquisition, Calacanis took roles including general manager of Netscape as part of AOL's reorganization.
AOL agreed to acquire Weblogs, Inc.
Time Warner's AOL agreed to buy Weblogs, Inc. in Oct 2005 in a deal reported at roughly $25–30 million.
Resigned from AOL / Netscape
TechCrunch reported Calacanis resigned from his CEO role at Weblogs, Inc. and as GM of Netscape on Nov 16, 2006; he later confirmed it publicly.
Joined Sequoia Capital as an 'Entrepreneur In Action' (EIA)
Accepted an EIA/entrepreneur role at Sequoia Capital starting December 2006; position lasted into May 2007.
Launched LAUNCH (Launch Festival) and Launch Universe
Started the LAUNCH Festival (initially free in 2007) to showcase early‑stage startups; later built LAUNCH Accelerator and associated programs.
Founded Mahalo (human‑powered web directory / search)
Launched Mahalo, a human‑edited web directory and search/answer site based in Los Angeles.
Credited with starting 'fatblogging' trend
Popularized 'fatblogging'—posting weight loss updates on blogs as an accountability tactic.
Left Sequoia EIA program
End of his EIA role at Sequoia Capital (held Dec 2006 through May 2007).
Mahalo raised approximately $20M venture capital
Mahalo raised roughly $20 million from investors including Sequoia Capital, News Corp, CBS, Mark Cuban, and Elon Musk (reported timing ~2007–2008).
Seed investment in Uber (reported $25K)
Calacanis made an early angel/seed investment in Travis Kalanick's ride‑sharing company (reported seed check $25,000). Timing commonly cited as early Uber seed period (c.2009).
Announced 'This Week in Startups' podcast (TWiST)
Announced plans for a new show (This Week in Startups) on March 16, 2009 via blog post; conception of TWiST.
Premiered 'This Week in Startups' (TWiST)
TWiST premiered on May 1, 2009 (60‑minute program). First guest: Brian Alvey. TWiST grew into a long‑running influential startup podcast/video series.
Founded Open Angel Forum
Launched the Open Angel Forum to connect early‑stage startups with angel investors; promoted an anti 'pay‑to‑pitch' stance (criticized fees of $1k–$8k for founders).
Earliest YouTube TWiST episode recorded publicly (archive)
TWiST episodes began appearing on YouTube (earliest archived YouTube episode dated June 3, 2010).
Mahalo reached profitability then hit Google Panda disruption
Mahalo achieved profitability in 2011 and reportedly peaked at ~15 million unique monthly visitors; later in 2011 traffic declined sharply due to Google's Panda update.
ThisWeekIn.com network shut down (TWiST continued)
The broader ThisWeekIn.com podcast/network shut down in 2012 but the This Week in Startups show continued as a weekly podcast and video series.
Began/accelerated active angel investing across many startups
Over the 2010s he expanded angel investments via LAUNCH syndicates and his fund — noted portfolio companies include Robinhood, Wealthfront, Uber, Desktop Metal, DataStax, Thumbtack, Superhuman, Trello and Calm.
Raised a $10M venture fund for Launch investments
Calacanis raised a $10 million fund to invest in startups emerging from the LAUNCH conference; limited partners included David Sacks.
Announced investment check size strategy for Launch fund
Declared plan to invest roughly $25k–$100k in 5–10 startups per year from Launch events/syndicates.
Mahalo shut down
After years of decline in search traffic and relevance following algorithm changes, Mahalo was shut down in 2014.
Listed in Jeffrey Epstein's 'little black book' (public reporting)
Calacanis was listed as a contact in Jeffrey Epstein's 'little black book'; the connection drew attention after public release of related documents.
Banned from Y Combinator Demo Day
Calacanis was excluded from attending Y Combinator's Demo Day in 2016 following feedback from YC founders about interactions with him.
Estimated value of his early Uber stake ~ $100M
By 2017 media reports estimated Calacanis's early $25k Uber investment had appreciated to roughly $100M.
Profiled for rebounding after nearly losing everything
Media profiles (e.g., Business Insider) chronicled his fall from dot‑com peak to near bankruptcy and subsequent recovery as an angel investor and entrepreneur.
Published book 'Angel: How to Invest in Technology Startups'
Published Angel: How to Invest in Technology Startups—Timeless Advice from an Angel Investor Who Turned $100,000 into $100,000,000 (HarperCollins, 2017).
Sold all Facebook stock and publicly criticized Mark Zuckerberg
Publicly announced he had sold all of his Facebook stock in 2018 and criticized CEO Mark Zuckerberg for business/ethical practices.
Invested in Calm (meditation app)
Reported to have invested in Calm in 2018; Calm later raised $88M in Feb 2019 valuing it at ~$1B.
Founded / Relaunched Inside.com (theme newsletters)
Founded/ran Inside.com, a news & newsletters product; the company raised $2.6M (reported) and grew to hundreds of thousands of subscribers.
Calm raised $88M, valued at $1B
Calm completed an $88M funding round in Feb 2019 that reportedly valued the company at ~$1 billion (Calacanis was an investor).
Partnered with NSW Government — Sydney Launch Festival
Partnered with the New South Wales (NSW) Government to create the Sydney Launch Festival for startups (June 2019).
Acclaimed podcast appearances and profile features (Acquired special, etc.)
Featured on major podcasts and long‑form interviews (e.g., Acquired special episode Apr 28, 2020) chronicling his entrepreneurial and investing career.
Molly Wood became co‑host of This Week in Startups
From 2021 Calacanis co‑hosted This Week in Startups along with Molly Wood (Wood co‑hosted through 2023).
Supported & helped lead SF DA Chesa Boudin recall effort
Was an early supporter and organizer for the successful 2022 recall of San Francisco District Attorney Chesa Boudin.
Helped run Twitter during Elon Musk’s 2022 reorganization (advisory/operational role)
Following Elon Musk's acquisition and management changes at Twitter in 2022, reports say Calacanis assisted in running aspects of the company along with David Sacks.
Co‑hosted All‑In podcast; All‑In Summit in Miami
Calacanis is a co‑host of the All‑In podcast alongside Chamath Palihapitiya, David Sacks and David Friedberg; May 2022 the team hosted the first All‑In Summit in Miami.
Molly Wood left This Week in Startups
Molly Wood departed as co‑host of This Week in Startups in 2023; Calacanis continued hosting the show.
Net worth estimated in public sources
Multiple public profiles estimate Calacanis's net worth in the range of roughly $60M–$100M as of the early‑to‑mid 2020s (commonly cited ~$100M).
Continues to host TWiST and co‑host All‑In; active investor
Maintains regular podcasting activities (This Week in Startups, All‑In) and remains active in angel investments, LAUNCH events and media projects.
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