Insiders React: Cloudflare Makes AI Pay + Figma Files For IPO, Grammarly Buys Superhuman

Jul 3, 2025

The podcast dives into Cloudflare's innovative AI pay-per-crawl feature, raising questions about web monetization. Grammarly's strategic acquisition of Superhuman aims to elevate its AI offerings. Figma's upcoming IPO could signal a resurgence in public tech, yet carries its own risks. The potential for automation to disrupt jobs is discussed, with founder Vinod Khosla predicting significant changes in the workforce. Plus, the conversation turns to how China may leverage free AI tools for global influence, illustrating the interplay of technology and geopolitics.

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INSIGHT

Grammarly's Bold Data Strategy

Grammarly acquires Superhuman and Coda to secure proprietary data and distribution for AI stickiness.
They aim to stay relevant as grammar checking becomes commoditized by large language models.

ADVICE

Don't Underestimate Browser Extensions

Browser extensions remain one of the best ways to deliver AI across workflows.
Avoid underestimating their stickiness and potential despite perceived installation frictions.

INSIGHT

Cloudflare's Pay-Per-Crawl Innovation

Cloudflare repurposes HTTP 402 status code to enable pay-per-crawl for websites.
This protocol-level payment enforcement could revolutionize AI data scraping monetization and internet decentralization.

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What happens when the internet starts charging AI to crawl its content?

And can legacy tools like Figma or Grammarly survive the AI age, or will they be replaced by smarter, faster upstarts?

In this episode, Yaniv Bernstein and Chris Saad break down some of the most important shifts in tech and business right now. From Cloudflare’s launch of AI pay-per-crawl to Grammarly’s bold acquisitions and Figma’s high-stakes IPO, this is an unfiltered look at how the AI boom is reshaping product strategy, startup success, and even the global order. Plus, they react to legendary VC Vinod Khosla’s explosive predictions about automation, abundance, and the role of China in AI soft power.

In this episode, you will:

Discover why Cloudflare’s 402 status code could transform AI data scraping and web monetization
Understand Grammarly’s plan to stay relevant with the acquisitions of Superhuman and Coda
Explore how Figma’s IPO could signal the return of the public tech market—and why it’s risky
Evaluate the threat of vibe coding tools to traditional design workflows
Hear Vinod Khosla’s take on why 80% of jobs could be automated within 5 years
Unpack how China might use free AI tools to gain soft power and global influence
Learn why a high-risk, high-reward mindset defines the best founders and VCs in Silicon Valley

Whether you’re building your first startup or thinking about your AI strategy, this episode offers critical insights from people who’ve seen these cycles before and know where the puck is heading.

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