Jason Calacanis

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.

Jason Calacanis, an angel investor and seasoned podcaster, shares his journey in the evolving podcast landscape. He dives into the emotional intimacy of daily podcasting and his obsession with media production. Calacanis reflects on how childhood poverty fueled his entrepreneurial spirit, and his knack for spotting startup winners. He also touches on the critical challenges tech faces post-Facebook and recalls how Elon Musk nearly lost everything in 2008. Their conversation reveals the delicate balance of fame and the risks of entrepreneurship.