# Jason Calacanis

> Jason Calacanis is a Brooklyn-born angel investor, serial entrepreneur, and podcaster who turned a $25,000 check into Uber into a roughly $100 million windfall. He hosts This Week in Startups, co-hosts the chart-topping All-In podcast, runs the LAUNCH accelerator and Founder University, and invests in roughly 100 startups a year. A former dot-com journalist who founded Silicon Alley Reporter and sold Weblogs, Inc. to AOL, he wrote the bestselling playbook 'Angel' and is one of the most visible bridges between scrappy founders and the venture world.

- **Role:** Host of This Week in Startups & co-host of All-In; Founder of LAUNCH
- **Organizations:** This Week in Startups (TWiSt), All-In Podcast, LAUNCH / Launch Accelerator, Founder University, Inside.com, Weblogs, Inc. (former), Mahalo.com (former), Silicon Alley Reporter (former), Sequoia Capital (former EIR)
- **From:** Bay Ridge, Brooklyn, New York, USA
- **Nationality:** American
- **Education:** High School Diploma, Xaverian High School, B.A. in Psychology, Fordham University
- **Known for:** Turned a $25,000 angel investment in Uber into a stake worth roughly $100 million, Hit three billion-dollar unicorns within his first 50 angel investments, Sold Weblogs, Inc. to AOL for a reported $25-30 million

## Career timeline

- **1996** — Founded Silicon Alley Reporter, a 16-page newsletter chronicling New York's internet scene
- **2003** — Co-founded Weblogs, Inc. with Brian Alvey
- **2005** — Sold Weblogs, Inc. to AOL for a reported $25-30 million
- **2006** — Joined Sequoia Capital as an Entrepreneur-in-Action; invested $25K in Uber's predecessor
- **2007** — Left Sequoia and launched the Mahalo web directory; coined the 'fatblogging' trend
- **2009** — Launched This Week in Startups podcast (May 1) and founded the Open Angel Forum
- **2013** — Raised a $10 million venture fund for LAUNCH
- **2017** — Published 'Angel' with HarperCollins
- **2018** — Joined the All-In podcast as a co-host
- **2022** — Hosted the first All-In Summit in Miami; advised on Twitter's transition after Elon Musk's acquisition

## Achievements

- Turned a $25,000 angel investment in Uber into a stake worth roughly $100 million
- Hit three billion-dollar unicorns within his first 50 angel investments
- Sold Weblogs, Inc. to AOL for a reported $25-30 million
- Built This Week in Startups into a 5,000+ episode startup media franchise
- Co-host of the chart-topping All-In podcast
- Authored the bestselling angel investing book 'Angel' (HarperCollins, 2017)
- Backed Robinhood, Calm, Trello, Superhuman, Thumbtack, Wealthfront and more before they were household names

## Latest updates

- **2026-01** — Continues hosting This Week in Startups (5,000+ episodes) and co-hosting the All-In podcast.
- **2025-06** — Running LAUNCH Accelerator cohorts and Founder University, investing in roughly 100 startups per year.

## Links

- Website: https://calacanis.com
- LinkedIn: https://www.linkedin.com/in/jasoncalacanis/
- Twitter/X: https://x.com/Jason
- YouTube: https://www.youtube.com/@thisweekin
- Instagram: https://www.instagram.com/jason/

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Profile page: https://yespress.io/jason-calacanis
Published by YesPress — https://yespress.io
Last updated: 2026-06-03