Investor / Entrepreneur / Host

Jason Calacanis

Angel investor, founder of Inside.com, and co-host of the All-In Podcast. Early investor in Uber, Robinhood, and Calm. Host of This Week in Startups. Known for hustle-culture entrepreneurship and provocative takes.

Known For

All-In PodcastThis Week in StartupsEarly Uber investorAngel investing

Canon

Biographies as Substitute Mentors

Curious

Courage Is a Learnable Skill

Curious

Environment Shapes Behavior More Than Willpower

Canon

False Information Spreads Faster and Further Than Truth

Canon

The Hedonic Treadmill — Happiness Returns to Baseline

Canon

Meaning Comes from Responsibility, Not Happiness

Canon

Focus Only on What You Can Control

Canon

The True Self vs. False Self — Childhood Adaptations That Persist Into Adulthood

Canon

Episodes

#How AI Agents Will Change Banking ForeverMar 9, 2026 #E2258: Is Anthropic Making the Biggest Mistake in AI History?Mar 5, 2026 #E2252: When Will OpenClaw Go Mainstream?Feb 18, 2026 #E2244: Where Early-Stage Founders MUST FocusFeb 3, 2026 #E2243: SpaceX + xAI Gets Us One Step Closer to Musk IndustriesFeb 2, 2026 #E2242: AI Agents and Security RisksJan 30, 2026 #10 Predictions for 2026Dec 30, 2025 #Can AI Replace Executive Coaching?Dec 15, 2025 #The 2025 AI Startup PlaybookNov 25, 2025 #Lightmatter: Photonic Computing for AISep 15, 2025 #AI Wearables: The Next Platform or Another Flop?Sep 1, 2025 #State of Angel Investing 2025: What Has ChangedAug 20, 2025 #AI Is Coming for Entry-Level Jobs FirstJul 10, 2025 #Startup Post-Mortems: Why These Companies FailedJun 15, 2025 #The AI Fundraising Bubble: How Much Is Real?May 20, 2025 #Bootstrapping vs VC in the AI EraApr 10, 2025 #Is SaaS Dying? The AI Replacement TheoryMar 20, 2025 #Founder Mental Health: The Conversation We Need to HaveFeb 15, 2025 #The Remote Work Data Is In: What Actually WorksJan 20, 2025