June 2026 Random Ramblings

SpaceX is buying Cursor for ~$60B, and one of the early backers was SBF. So was a convicted fraudster also the greatest VC of all time? That's where June's random ramblings start. From there: why I've flipped from AI doom toward AI as a force multiplier, whether deep subject-matter expertise gets MORE valuable as the world fills with AI slop, why legacy brands (KPMG, CBS, People) might actually gain power in an AI world, why "my edge is a long time horizon" is usually a tell for underperformance, and the cracks showing up in Polymarket and prediction markets. This episode is sponsored by my upcoming AI webinar with AlphaSense. The AI landscape has never been more crowded — or more confusing. Everyone's telling you to adopt AI, but almost nobody's asking the harder question: which tools actually give you an edge? I'm sitting down with Dave Wang of Wall Street Prompt and Ben Collins of AlphaSense to break down the modern AI stack for investors — from horizontal platforms like OpenAI and Claude to agentic workflows and finance-specific intelligence tools — and where each one actually fits in a real research process. If you're trying to build an AI-enabled workflow that sharpens your judgment rather than replacing it, you won't want to miss this. Join us on June 25th - register now: https://www.alpha-sense.com/resources... Chapters: 00:00 What's on the menu this month 02:05 Sponsor: my AI webinar with AlphaSense 03:22 Was SBF the greatest VC of all time? (Cursor, SpaceX, Anthropic) 09:48 Do any frauds or blowups hide assets this valuable? (GGP, Enron, EOG) 11:42 Why I flipped from AI doom toward AI as a force multiplier 13:41 Why AI rewards the creative, and the top 0.1% problem 16:18 AI slop and the rising return on deep expertise (Knicks, ABVX) 20:12 KPMG's hallucinated AI report and secondhand hallucinations 21:57 Does brand get MORE valuable in an AI world? (CBS, People, TMZ, ChatGPT licensing) 25:14 Why "my edge is a long time horizon" is usually a lie 28:50 Forced selling, diamond hands, and the seven-years-of-underperformance letter 32:02 My three-year rule 32:53 Polymarket, MicroStrategy, and the limits of the rulebook 35:00 Prediction markets are reflexive: why nobody's waging "Polymarket wars" yet 37:36 Wrap Links: Yet Another Value Blog - https://www.yetanothervalueblog.com See our legal disclaimer here: https://www.yetanothervalueblog.com/p... Production and editing by The Podcast Consultant - https://thepodcastconsultant.com/