This Week in Startups

Jason Calacanis has been doing This Week in Startups since 2009, making it one of the longest-running shows in the startup podcast space. Calacanis is a serial entrepreneur and angel investor -- he was an early backer of Uber, Calm, and Robinhood, among others -- and he brings a founder-first perspective that's more scrappy than polished. The show runs daily, blending news analysis episodes with founder interviews and live pitch sessions where entrepreneurs present their startups for real-time feedback. The pitch episodes are where TWIST really shines. Founders get a few minutes to make their case, and Calacanis doesn't hold back. He'll tell someone their market is too small, their pricing is wrong, or that they should pivot entirely. It's direct in a way that most podcast hosts won't be, and listeners consistently point to these segments as the most valuable part of the show. Occasionally, Calacanis will actually invest on air, which adds genuine stakes to the format. With 1,400-plus episodes, the archive is enormous. Recent content has shifted heavily toward AI agents and their impact on startups, reflecting Calacanis's own investments in the space. The show's energy is high and unapologetic -- Calacanis has strong opinions and shares them freely, which some listeners love and others find grating. He also promotes his own ventures more frequently than you might expect. But here's the thing: if you're actually building a startup or thinking about angel investing, TWIST provides a practical, street-level view of the startup ecosystem that more institutional VC podcasts simply don't offer. The 4.2 rating from over 1,200 reviews reflects a loyal audience that keeps coming back.