Jason Calacanis: Startups, Angel Investing, Capitalism, and Friendship | Lex Fridman Podcast #161

The following is a conversation with Jason Calacanis, who's an entrepreneur, investor, author of Angel: How to Invest in Technology Startups, and as many people may know, he's a fun, brilliant, long-time podcast host of This Week In Startups and co-host of the All-In Podcast with Chamath Palihapitiya, David Sacks, and David Friedberg, who all happen to be poker buddies and self-proclaimed besties. The result is always a great listen due to both the love and the heated disagreements. Quick mention of our sponsors: Brave Browser, Linode Linux Virtual Machines, Four Sigmatic Mushroom Coffee, and Rev Speech-to-Text Service. Click the sponsor links to get a discount and to support this podcast. As a side note, let me say that I've been learning a lot about real world finance in the past few months. To give you a bit of context, on the side I've studied trading from an algorithmic trading perspective as a machine learning and game theory problem off and on for a few years in undergrad and grad school. I found the distributed complex system aspect of finance and economics in general fascinating. But now, I find even more fascinating the human side of the whole thing, ideas of greed, power, freedom, and truth. WallStreetBets, Robinhood, and the whole beautiful mess around this topic allows us to have great conversations about human nature and the systems that underlie the rise and fall of civilizations. If you enjoy this thing, subscribe on YouTube, review it on Apple Podcasts, follow on Spotify, support on Patreon, connect with me on Twitter @lexfridman. And now, here's my conversation with Jason Calacanis. I have a million things to talk to you about-

Yeah.

... but we do happen to be living through what I would think of as a historic event in, in terms of its impact, in terms of like almost philosophically thinking about the role of people and how they can fight power with this whole WallStreetBets and GameStop situation.

Yeah.

I was wondering, you've covered in your, uh, amazing All-In Podcast, you guys have been having fascinating battles over this whole situation.

(laughs)

I was wondering if you could tell maybe from your perspective, as it's unrolling, uh, the, the saga of WallStreetBets and GameStop, what are some interesting insights-

Yeah.

... uh, that, uh, you have about this whole set of events?

In full disclosure, I was an angel investor in Robinhood before they launched, and when I met the founder Vlad and his partner, you know, they pitched me at a, a, a bar not too far from where we are right now in Palo Alto called Antonio's Nut House.

(laughs)

And my friend Adeo ... It's a (laughs) really good story. My friend Adeo had asked me to speak at his founder's institute, which is kinda like an accelerator for people who are thinking about starting a company.

Yes.

And so I gave a talk and then he said, "Hey, let's go to Antonio's Nut House and, um, we'll meet Elon for a drink." Uh, and so Elon met us for a drink there. And it's the, it's the divest of dive bars.