Eyes on the Chaos
Thursday, May 28, 2026

Archived edition

Thursday, May 28, 2026

11 stories curated from 16 sources

In today's issue

DesignEthicsProduct
  1. 01
    Illinois Lawmakers Just Passed America's Strongest AI Safety Bill

    Illinois passes landmark AI safety bill requiring third-party safety audits.

  2. 02
    AI coding startup Cognition raises $1B at $25B pre-money valuation

    Cognition more than doubles valuation to $25B with $492M revenue run rate.

  3. 03
    Robinhood will let your AI agent trade stocks and make (or lose) lots of money

    Robinhood opens trading platform to AI agents with dedicated accounts.

  4. 04
    YouTube is putting AI labels where you'll actually see them

    YouTube moves AI disclosure labels to prominent positions and adds automatic detection.

  5. 05
    Payroll startup Remote says it grew revenue 50% per employee without adding headcount

    Remote achieves 50% revenue per employee growth through AI adoption alone.

  6. 06
    Figma Agent: a first look

    First hands-on review of Figma's new integrated AI tool.

  7. 07
    The trust gap between AI and humans

    Designers must fix AI onboarding before brilliant AI products fail.

  8. 08
    You are no longer the user. You are the principal.

    AI agents fundamentally change the user-product relationship into principal-agent dynamics.

  9. 09
    Your SEO strategy is optimized for a search engine that no longer exists.

    Google's AI-first search fundamentally breaks traditional SEO strategies.

  10. 10
    Tech CEOs are apparently suffering from AI psychosis

    Box CEO calls out unrealistic CEO beliefs about AI productivity gains.

  11. 11
    The AI fight brewing inside The New York Times

    NYT union gears up for battle over AI use in newsrooms.

AI Research & News

Illinois Lawmakers Just Passed America's Strongest AI Safety Bill

Wired

EthicsProduct

Illinois passes landmark AI safety bill requiring third-party safety audits.

  • What it requires: Companies like OpenAI, Anthropic, and Google must have third parties confirm they're following safety standards.
  • Political momentum: Governor JB Pritzker says he'll sign it, making it the strongest AI safety legislation in America.
  • Industry impact: Sets precedent for other states and creates compliance burden for major AI companies.

For product

Product teams should start documenting safety practices now — similar regulations will likely spread to other states and could affect product development timelines.

AI coding startup Cognition raises $1B at $25B pre-money valuation

TechCrunch

Product

Cognition more than doubles valuation to $25B with $492M revenue run rate.

  • Massive growth: The AI coding startup more than doubled its valuation in just eight months.
  • Revenue traction: Reached $492 million in annualized revenue run rate, showing real market demand.
  • Market signal: Validates that AI coding tools are becoming essential enterprise infrastructure, not just novelties.

For product

Time to evaluate AI coding tools for your engineering teams — the revenue numbers suggest these tools are delivering measurable productivity gains.

Robinhood will let your AI agent trade stocks and make (or lose) lots of money

The Verge

EthicsProduct

Robinhood opens trading platform to AI agents with dedicated accounts.

  • How it works: Traders can create separate accounts for AI agents with specific funding amounts to automate investment decisions.
  • Use cases: Agents can monitor industries, make trades, or rebalance portfolios automatically.
  • Big warning: Robinhood emphasizes significant risks as agents could make rapid, large-scale trading decisions.
YouTube is putting AI labels where you'll actually see them

The Verge

EthicsDesign

YouTube moves AI disclosure labels to prominent positions and adds automatic detection.

  • Better visibility: Labels now appear prominently and actually say 'AI' instead of being buried in descriptions.
  • Automatic detection: YouTube will start automatically identifying and labeling AI-generated content, not just relying on creator disclosure.
  • Platform shift: Follows Google's broader AI verification efforts from I/O, signaling industry-wide transparency push.

For design

Consider how your team will handle AI disclosure in product features — the trend toward prominent, automatic labeling suggests regulatory pressure is building.

Payroll startup Remote says it grew revenue 50% per employee without adding headcount

TechCrunch

Product

Remote achieves 50% revenue per employee growth through AI adoption alone.

  • Impressive metrics: Surpassed $300M ARR and became cash-flow positive with dramatic productivity gains.
  • AI-driven efficiency: Achieved 50% increase in revenue per employee specifically through AI adoption without hiring.
  • Concrete proof: Provides real-world evidence that AI can deliver measurable business outcomes beyond hype.

Product & UX

Figma Agent: a first look

Sidebar.io

DesignProduct

First hands-on review of Figma's new integrated AI tool.

  • Deep integration: AI tool is built directly into Figma with permission to make changes across the canvas.
  • Early testing: First real-world testing shows potential but also reveals current limitations.
  • Design workflow impact: Could fundamentally change how designers interact with their primary tool.

For design

Start planning how your design systems and processes might need to adapt — Figma Agent could change designer workflows faster than expected.

The trust gap between AI and humans

UX Collective

DesignProduct

Designers must fix AI onboarding before brilliant AI products fail.

  • Trust crisis: Even excellent AI products are failing because users don't trust them enough to get started.
  • Onboarding critical: The gap between AI capability and user adoption is widening due to poor initial experiences.
  • Designer role: UX designers need to focus on building trust and reducing friction in AI product onboarding.
You are no longer the user. You are the principal.

Sidebar.io

DesignProduct

AI agents fundamentally change the user-product relationship into principal-agent dynamics.

  • Mental model shift: Users become 'principals' who direct AI 'agents' rather than directly operating interfaces.
  • Design implications: Product architecture must account for this new three-way relationship between human, agent, and system.
  • UX transformation: Traditional user experience design patterns may need complete rethinking for agent-mediated interactions.

Business & Strategy

Your SEO strategy is optimized for a search engine that no longer exists.

TechCrunch

Product

Google's AI-first search fundamentally breaks traditional SEO strategies.

  • Rules changed: Google I/O made AI-generated answers front and center, replacing the traditional 10 blue links model.
  • Visibility crisis: Most brands have almost no insight into how AI describes them to customers.
  • Strategic shift needed: Years of SEO strategy building around traditional search ranking is now largely obsolete.
Tech CEOs are apparently suffering from AI psychosis

TechCrunch

Box CEO calls out unrealistic CEO beliefs about AI productivity gains.

  • Reality check: Box CEO Aaron Levie says 'CEOs are uniquely prone to AI psychosis' regarding productivity expectations.
  • Religious fervor: Points to almost religious belief in AI gains that may not match real-world implementation.
  • Leadership blindspot: Suggests executives are making strategic decisions based on AI hype rather than measured results.
The AI fight brewing inside The New York Times

The Verge

Ethics

NYT union gears up for battle over AI use in newsrooms.

  • Union tensions: Unionized staff at The New York Times are preparing to fight over how AI should be used in journalism.
  • Industry trend: Rules about AI in newsrooms are increasingly being decided at bargaining tables between unions and publishers.
  • Broader implications: Shows how AI adoption debates are moving from tech teams to collective bargaining across industries.