Weekly(ish) AI Digest
There’s no podcast for the week because of the Canadian and American national holidays. Instead, enjoy a few of the best things I listened to in AI.
Vinod Khosla on Uncapped
Uncapped has quickly become one of my favourite podcasts. Jack is on our board but I’m not just being a brown noser - I promise. The guests are top tier and Jack is a natural podcaster given his deep curiosity.
They talk about:
AI replacing most jobs
The post-work world
The OpenAI investment story (Khosla was the first big venture money in)
Founder driven innovation
Sander Schulhoff (Learn Prompting, HackAPrompt) on Lenny’s Podcast
AI prompt engineering in 2025: What works and what doesn’t. Sander is one of the best prompt engineering resources in the world. Lenny’s summary here.
Andrew Wilkinson on Lenny’s Podcast
Andrew Wilkinson shares how he used AI to replace his assistant, why boring businesses beat sexy ideas, why you need to fish where the fish are, and how he lost $10m.
The Compound and Friends podcast on the impact of AI on markets
This is a pretty different perspective on AI. Joe Davis is Vanguard’s Global Chief Economist and Global Head of the Investment Strategy Group and this podcast talks about the longterm impacts of AI on public financial markets. You’re not going to learn anything about implementing AI in your business but I thought it was really fascinating.
The Laffont Brothers on the AI Supercycle
Another more macro conversation about AI. As I said in my podcast with Collin Cadmus, I think revenue leaders MUST understand venture to succeed in their role and this is a great breakdown. Highly recommend.
Also, holy shit - Elon is a wild man!
