Jason Calacanis

Jason Calacanis began his entrepreneurial journey in the late 1990s by launching a print newsletter that he photocopied and sold at parties, securing hundreds of $100 subscriptions and generating tens of thousands in revenue, allowing him to operate independently. He later founded a search engine leveraging crowd-sourced results (SERPs), which scaled to $10 million in revenue before Google de-indexed it, dropping revenue to $500,000; this experience shaped his views on competition in tech. Transitioning to angel investing, Calacanis joined Sequoia's first scout program and became one of Uber's earliest backers (claiming 3rd or 4th investor), alongside investments in Robinhood and Calm, building a portfolio fueled by his media network and estimated net worth of around $120 million. His podcast 'This Week in Startups' emerged as a key platform, amassing 150 million+ cumulative views and providing inbound access to top founders. In recent years, Calacanis co-founded the All-In Podcast during COVID-19 with Chamath Palihapitiya, covering topics from tech origins to high-profile events like the Twitter buyout and 2024 US election influences. He continues hosting 'This Week in Startups,' interviewing founders on growth, markets, and innovations, with episodes as recent as December 2025 discussing iRobot's bankruptcy and OpenAI deals.