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Jason Calacanis

Jason Calacanis is a startup investor, author and podcaster who hosts This Week in Startups and co-hosts All-In, sharing conversations with founders and investors.

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Jason’s happenings, collected from public sources, plus their backstory and Starbook, where fans write.

Known for

Overview

From: Brooklyn, New York
Work: Podcaster, entrepreneur, angel investor and author
Early chapter: Founded Silicon Alley Reporter in 1996
Breakout: Co-founded Weblogs, Inc. with Brian Alvey in 2003; later sold it to AOL
On the mic: This Week in Startups, All-In and This Week in AI

Mini bio

A publisher first.

Jason grew up in Brooklyn and built a career around the people making new technology. In 1996, Jason founded Silicon Alley Reporter to cover New York’s emerging tech community. Before the podcasts, there were magazines, conferences and a lot of conversations with founders.

Building a network.

In 2003, Jason and Brian Alvey formed Weblogs, Inc., turning specialist blogs into a publishing business. Its later sale to AOL became a defining early milestone. Jason also founded Mahalo, a search service with manually edited results, in May 2007.

From publishing to podcasting.

This Week in Startups has documented builders and their companies since 2009. Jason’s work now spans founder interviews, startup news and investor discussions, including All-In, where Jason is a co-host and executive producer. In March 2026, Jason announced another roundtable show, This Week in AI.

Backing the builders.

A former Sequoia Capital scout, Jason became an early investor in companies including Uber, Robinhood, Calm and Thumbtack. The 2017 book Angel shares lessons from that work. Jason also runs Founder University, helping founders at the beginning of their startup journey.

Creditschronological, newest first

2026This Week in AIHost; announced the new roundtable podcast in March
2017Angel: How to Invest in Technology StartupsAuthor
2009This Week in StartupsHost
2003Weblogs, Inc.Co-founder with Brian Alvey
1996Silicon Alley ReporterFounder and editor

Quotes

Podcasts are my way of committing to lifelong learning, networking with driven people, and sharing with like-minded folks.Jason Calacanis, “NEW PODCAST: This Week in AI”

March 11, 2026. https://calacanis.substack.com/p/new-podcast-this-week-in-ai

Trivia

Jason signs newsletter posts “JCal,” a nickname fans will also see around the podcasts.
Mahalo, the search service Jason founded, takes its name from the Hawaiian word for “thank you.”
Jason says LAUNCH Festival grew out of wanting founders to have an event they could afford to attend and demo at.