The Bulwark Podcast Jason Calacanis: Anarcho Capitalism
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Aug 13, 2025 
Jason Calacanis, an entrepreneur and angel investor, shares intriguing perspectives alongside Tim Miller. They dive into the complex relationship between Silicon Valley and politics, highlighting the influence of figures like Elon Musk. The duo critiques the impact of recent economic policies and discusses the pitfalls of anarcho-capitalism. They also explore immigration policy tensions and the societal implications of AI, questioning how automation will affect the workforce. The conversation is a vibrant mix of humor and thought-provoking analysis.
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Regulatory Tone Drives Startup Markets
- Business leaders view the current administration as far more pro-growth and pro-M&A than the prior one.
- Removing aggressive antitrust enforcement revived IPOs, M&A, and market optimism for startups.
Tariffs As A Political Revenue Tool
- The administration uses tariffs as a political and fiscal tool they call 'shock and bore.'
- Tariffs can generate large revenue while creating negotiation space with trading partners.
Measure Policy By Midterm Data
- Watch near-term political outcomes to judge policy success; midterms will test economic claims.
- Use incoming macro data like inflation, unemployment, and tariff receipts to evaluate impact.