Jason Calacanis

Jason Calacanis (born 1970) is a Brooklyn-born angel investor and media entrepreneur who sold Weblogs Inc. to AOL, scouted for Sequoia, and turned early checks into Uber and Robinhood into one of angel investing’s most publicized track records. Through his LAUNCH accelerator, Founder University, and the This Week in Startups podcast — plus his co-host seat on All-In beside Chamath Palihapitiya — he invests in roughly a hundred startups a year and narrates the industry to millions.

Evangelist of the AI Roaring 20s

In a December 2023 essay he declared the next startup supercycle already underway, naming it “The AI Roaring 20s” and arguing that AI tools plus a global talent pool let three founders ship products to customers in under 30 days on a shoestring. He has backed the thesis with his portfolio — LAUNCH cohorts have skewed heavily toward AI companies since 2023 — and with new media: in 2025 he launched a dedicated This Week in AI podcast. In January 2026, after visiting Tesla’s Optimus studio, he predicted the robot would eclipse the cars entirely as a ten-trillion-dollar AI opportunity.

His boosterism comes with a street-smart edge. In 2026 he issued what he called a final warning to Y Combinator founders against taking free OpenAI tokens for equity, arguing the lab was studying naive startups to “incorporate it as free product into their platform,” and urging founders to move to open-source models and own their data. Critics find his hype cycles exhausting and his predictions scattershot; even they concede he has been directionally early on AI adoption, as he was on ride-sharing.