This Week in Startups

Jason Calacanis has been covering the startup world since 2009, making This Week in Startups one of the longest-running shows in its category. Jason is an angel investor with early bets in Uber, Robinhood, and Calm on his resume, and he brings that deal-flow perspective to every episode. The show covers startups, technology, markets, media, and whatever else Jason finds interesting that week, which turns out to be a lot. The format splits between solo commentary episodes where Jason breaks down the week's biggest startup and tech stories, and interview episodes where he sits down with founders, investors, and operators. Jason's interview style is direct and sometimes confrontational -- he'll push back on founders who dodge questions or pitch vague ideas. That bluntness can be polarizing, but it consistently produces more honest conversations than the typical softball podcast interview. Recent 2026 episodes have covered the intersection of SpaceX and xAI, AI agent security risks, and practical advice for early-stage founders on saving cash and prioritizing distribution. Jason and his co-host Alex bring a mix of macro-level analysis and ground-level founder advice that keeps the show relevant for both investors and operators. The show publishes multiple episodes per week, which means it functions almost like a news source for the startup ecosystem. If something big happens in tech on Tuesday, Jason is talking about it by Thursday. That timeliness, combined with Jason's extensive network and willingness to say things other podcast hosts won't, makes TWiST a staple for anyone who wants to stay current on what's actually happening in the startup world rather than reading about it a week later.