Popular guests

Economic historian and Free Press columnist. Known for his expertise in economic history and international affairs.

Head of Product at Linear. He is responsible for product strategy, AI workflows, and Linear's AI agents.

British-American philosopher and speaker known for interpreting and popularizing Eastern philosophies (Buddhism, Taoism, Hinduism) for Western audiences; noted for his poetic, accessible lectures and radio talks on mindfulness, ego, and the nature of self.

Stand-up comedian, actor, podcaster, and author. He co-hosts two podcasts: “Your Mom’s House” with his wife, comedian Christina Pazsitzky, and “Two Bears, One Cave” with Bert Kreischer.

Former head of strategy at Microsoft and a prolific angel investor. Has invested in nearly 500 companies throughout his career.

Co-founder and CEO of Substack, a platform for independent writers and creators. Previously the CTO and co-founder of Kik Interactive.

Entrepreneur who makes millions from local side hustles. He shares his business insights and philosophy of embracing multiple ventures.

Former Head of Strategy at 37signals (makers of Basecamp) and author of "Shape Up: Stop Running in Circles and Ship Work that Matters."

One of the creators of Cursor, a code editor specializing in AI-assisted programming.

Personal finance expert and bestselling author known for The Automatic Millionaire, who provides practical advice on saving, investing, debt management, and building wealth.