Jason Calacanis

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.