Jason Calacanis

Jason McCabe Calacanis (born November 28, 1970) is an American Internet entrepreneur, angel investor, and author. He is best known for his work in the technology industry, including founding Weblogs, Inc., an influential early blogging network, and for his role as a serial entrepreneur and investor in numerous startup companies. He is a prominent figure in the world of angel investing and has been involved in the early stages of several successful tech companies, including Uber and Robinhood.

Early Life and Education

Calacanis was born and raised in the Bay Ridge neighborhood of Brooklyn, New York City. He graduated from Xaverian High School and later attended Fordham University, where he earned a Bachelor of Arts in psychology.

Career

Weblogs, Inc.

In 2003, Calacanis co-founded Weblogs, Inc. with Brian Alvey. The network, which included popular sites like Engadget, was sold to AOL in 2005 for an estimated $25–30 million. This marked one of the earliest high-profile acquisitions in the blogosphere and solidified Calacanis's reputation as a successful entrepreneur.

Angel Investing

Calacanis is a notable angel investor with a track record of investing in high-profile companies. He was an early backer of Uber, a ride-sharing company, and Robinhood, a financial services platform. Through his angel investing syndicate, he has supported numerous other startups.

Podcasting and Media

Calacanis hosts the popular podcast "This Week in Startups," where he interviews entrepreneurs and provides insights into the tech industry. He is also a frequent guest and commentator on various media platforms discussing technology and entrepreneurship.

Other Ventures

Besides Weblogs, Inc., Calacanis has been involved in various other technology startups and projects, including Mahalo, an internet-based knowledge exchange, and Inside.com, a news aggregation and mobile news app.

Controversies

Calacanis's outspoken nature and aggressive investing style have led to controversies within the tech community. He has been both praised and criticized for his direct approach to business and investment.

Publications

Calacanis authored the book "Angel: How to Invest in Technology Startups" (2017), where he shares insights and strategies for angel investing based on his experience in the field.

Personal Life

Calacanis resides in the San Francisco Bay Area and is known for his active presence on social media platforms, where he engages with the tech community and discusses current trends and issues.

This concise reference captures essential information about Jason Calacanis, highlighting his contributions to technology, investment strategies, and media presence.


Written by OpenAI's gpt-4o. Generated at Dave Winer's request for use in his blog. Published Tuesday, June 16, 2026, 5:52 PM EDT.

The prompt we use: "Build a short, balanced reference page about Jason Calacanis. Follow the structure of a Wikipedia article but keep it brief -- an outline of the basic facts, not a long detailed treatment. Cover who or what it is, why it matters, and the essential history. Stay neutral; where there is controversy, note the main sides briefly rather than taking one. Include links to authoritative web sources so the reader can follow the original work. Return the page as Markdown, starting with a top-level heading for the name."