This Week in Startups
Hosted by Jason McCabe Calacanis & Lon Harris · 44 decoded episodes · newest Oct 5, 2026
Jason Calacanis covers startups, tech, markets, media, and all the hottest topics in business and technology. He also interviews the world's greatest founders, operators, investors, and innovators.
Episodes 44
- Oct 5, 2026 · 1h 11mAI tutor turns productive struggle into personalized learningThe episode tests whether AI can expand one-on-one teaching without reducing education to instant answers.
- Oct 3, 2026 · 53 minUnrestricted AI tests the limits of safety and enterprise adoptionThe episode examines who should control safeguards for powerful AI as businesses, regulators, and model developers struggle to define responsible use.
- Sep 30, 2026 · 1h 18mTwitch and Airbnb turned rejection into a startup advantageThe episode tests whether founders can still afford the long experimentation and persistence that helped Web 2.0 companies find their markets.
- Sep 28, 2026 · 50 minApple’s next big bet could span AI, robots, and sunlightThe episode tests whether Apple should make larger strategic acquisitions while examining how personalized UV data could turn a wearable into a research platform.
- Sep 28, 2026 · 41 minA $5,000 bounty tests whether annotation can become infrastructureThe episode links a hands-on product contest to a larger question about whether web annotations could power fact-checking, context, and valuable data for AI systems.
- Sep 25, 2026 · 1h 26mAI agents test the limits of oversight and startup ambitionThe episode connects an Australian portal breach to a broader question about how much autonomy, access, and trust AI systems should receive.
- Sep 23, 2026 · 1h 27mInvestors question AI valuations as models enter a price warThe panel connects frontier-model economics, inflated private valuations, and tighter venture discipline to the returns founders and investors can realistically expect.
- Sep 18, 2026 · 1h 34mOpen robotics meets the fight over AI controlThe episode connects open-source robotics and local models to a larger question: how should societies manage powerful AI without stifling useful innovation?
- Sep 15, 2026 · 19 minAI prototypes need a production harness to surviveThe episode explains why impressive AI demos become unreliable business systems and what infrastructure makes long-running agent workflows dependable.
- Sep 14, 2026 · 1h 11mAI oversight meets meme coins and improvised data centersThe discussion tests where human responsibility, regulation, and infrastructure must catch up with increasingly capable AI systems.
- Sep 11, 2026 · 1h 13mPentagon weighs five billion dollar loan to AI startup FluidStackThe intersection of national security and venture capital is shifting as the federal government begins funding private AI infrastructure directly.
- Sep 10, 2026 · 23 minHow startup founders can protect their equity using vesting and term sheetsStructuring equity incorrectly in the early days can lead to devastating cap table disputes that derail a startup before it can scale.