Sam vs. Tucker | Larry vs. AI | NPM vs. Hackers | Cluely vs. Memes

On the Gregory and Paul Show, we break down the latest in startups, SaaS, AI, and whatever the internet is debating this week.

This episode covers Tucker Carlson’s tense interview with Sam Altman, Oracle’s $300B cloud deal with OpenAI, Apple’s thin new iPhone and AirPods with live translation, the largest npm hack in history, and why Perplexity is backing away from AI ads. The guys finish with a dive into Cluey’s viral marketing engine and an update on their upcoming TechCrunch Disrupt mixer.

️ Episode 014 – Highlights

Tucker vs. Sam Altman (0:07)
Tucker Carlson presses OpenAI’s CEO on tough topics, from employee scandals to AI risks. Gregory and Paul debate whether CEOs can survive this level of scrutiny in today’s media environment.

☁️ Oracle’s $300B AI Cloud Bet (9:41)
Oracle lands OpenAI as a customer. Larry Ellison re-enters the spotlight as Oracle’s stock spikes, showing why a “neutral cloud” alternative matters.

The Thinnest iPhone + AirPods Translate (15:24)
Apple drops a thinner iPhone 17 Pro in pumpkin spice orange—and AirPods that can live-translate languages. Cool or meh?

⚠️ npm’s Supply Chain Hack (20:47)
A phishing attack compromises millions of packages. Paul explains how one maintainer’s mistake created mayhem across the software world. Gregory wonders why attackers aren’t better at monetizing hacks.

Perplexity Pauses AI Ads (33:42)
Once seen as the future of search monetization, Perplexity walks away from LLM-based ads. Gregory argues AI ads are still “Google Adwords x10”—the only question is who will scale them.

Cluey as a Meme Stock for AI Tools (42:14)
The viral note-taking app has mediocre product reviews but world-class marketing. Paul breaks down their UGC machine. Gregory compares it to Tesla and luxury branding.

SF Founder + Investor Mixer at Disrupt (57:03)
Gregory’s October 28th mixer hits capacity, with investors, founders, and Stifel as marquee sponsor. Waitlist now open.