Jason Calacanis

Angel investor, podcast host, author.

Since the dot-com era, Jason Calacanis has been at the forefront of Internet entrepreneurship. And while many business insiders keep their secrets close to their chest, Jason remains committed to sharing his invaluable insights. Whether as a podcast host, commentator, or author, he is unquestionably one of the leading voices in bringing complex economic theory to the public.

At the start of the COVID-19 pandemic, Jason started the All-In podcast with fellow venture capitalists and angel investors Chamath Palihapitiya (Social Capital), David Sacks (PayPal), and David Friedberg (The Climate Corporation). It quickly emerged as one of the world’s leading business podcasts, enjoying hundreds of thousands of views a week on YouTube and welcoming such guests as Mark Cuban, Vivek Ramaswamy, Sam Altman, Elon Musk and Donald Trump.

Since then, Jason (with All-In co-host David Sacks) has helped Elon run and re-structure Twitter, playing a fundamental role in reshaping the platform into its current image.

So why did we want to talk to him?

Jason describes himself as a moderate but has historically voted Democrat. At the precipice of the closest (and yet most divisive) election in recent memory, we wanted to hear what a typically Democratic voter had to say about it.

We got that, and we got more.