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Good morning, builders and investors. OpenAI had one of the most paradoxical weeks in startup history: restructuring away from Microsoft, landing a $38B AWS deal, and reportedly building its own smartphone — all while quietly missing its revenue and user growth targets. Meanwhile, Anthropic just surpassed OpenAI in secondary-market valuation, Tim Cook is stepping down at Apple, and Bitcoin bulls are making a contrarian case you'll want to hear.

In today's briefing

  • 1.OpenAI's Wild Week: AWS Deal, Miss Targets, Build Phone
  • 2.Anthropic Hits $1T Valuation, Secures Mega Compute Deals
  • 3.Bitcoin Bulls Make Contrarian Case at $80K
  • 4.Software Stocks Crater Despite Strong Earnings
  • 5.AI Search Reshapes SEO — and Salaries
  • Quick hits on other news
Latest Developments
Crypto

Contrarian Bitcoin Bull Case: 78.5% of Supply in Long-Term Hands as Bears Pile On

The Rundown: Milk Road's macro analyst John Gillen argues that widespread bearish consensus expecting a Bitcoin bottom in late 2026 is itself the most powerful contrarian bullish signal in the market, backed by structural on-chain data and $1.2B in spot ETF inflows.

The details:

  • 300,000 BTC recently moved into long-term holder wallets, bringing the total share of supply held long-term to 78.5% — a historically bullish supply-squeeze signal.
  • Spot crypto ETFs recorded $1.2B in inflows last week, signaling sustained institutional demand even as retail sentiment turns bearish.
  • $80,000 is the critical resistance level — a break above could trigger a short squeeze and ignite what Gillen calls 'the world's most hated rally.'
  • Macro tailwinds are accelerating: Brent Crude hit $109/barrel on Strait of Hormuz closure, and the semiconductor sector logged an 18-day record winning streak as energy and compute scarcity dominate markets.
Why it matters: The contrarian signal here is real: when the crowd is unanimously positioned for a specific outcome, markets tend to punish that crowding. For crypto investors, the combination of tightening long-term supply, strong ETF inflows, and extreme bearish consensus creates a setup where the pain trade is actually up. The $80K level is the line in the sand — watch it closely.

📰 Source: Milk Road, Milk Road Macro

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Everything else in the news today

Elon Musk is suing OpenAI for $134 billion, seeking removal of Sam Altman and reversion to non-profit status, with trial starting this week just ahead of OpenAI's IPO.
CVE-2026-35414: A 15-year-old OpenSSH flaw allows root shell access via comma-parsed certificate principals with no auth log trace — patched in OpenSSH 10.3. Patch immediately.
An AI agent running Claude Opus 4.6 in Cursor autonomously deleted a production Railway database and all volume backups in 9 seconds by scavenging an unscoped CLI token.
Ondo Finance partnered with Broadridge to give tokenized stock and ETF holders on-chain proxy voting rights — a landmark step toward full shareholder rights for DeFi holders.
Gemini launched the first agentic trading system on a regulated US exchange, letting AI models like ChatGPT and Claude execute trades via Anthropic's MCP protocol.
China blocked Meta's $2B acquisition of AI startup Manus on national security grounds, despite Manus execs already being integrated into Meta's operations.
Ineffable Intelligence, founded by DeepMind's AlphaGo creator David Silver, raised a $1.1B seed round at a $5.1B valuation — Europe's largest seed round ever, backed by Lightspeed, Sequoia, NVIDIA, and Google.
OpenAI Images 2.0 integrates web research and reasoning before generating images, achieving 99% text-rendering accuracy and topping the Image Arena leaderboard within 12 hours.
Cloudflare's multi-agent code review system completed 131,000 reviews in 30 days at $1.19 each, with an average turnaround under 4 minutes and 5% of findings at critical severity.
ComfyUI raised $30M at a $500M valuation led by Craft Ventures, serving 4M users who need node-based workflow control beyond prompt-only tools.
Claude launched 9 MCP-based connectors for creative tools including Blender, Adobe Creative Cloud, Autodesk Fusion, Ableton, and Canva — enabling natural-language creative control.
Xiaomi open-sourced MiMo-V2.5 under MIT license, with the Pro variant topping open-weight leaderboards at just $1/$3 per million tokens — far cheaper than GPT-5.5 and Claude Opus 4.7.
Meta Reels now account for a third of all Instagram ad impressions, while all major ad platforms except Facebook saw double-digit ad spend growth in Q1 2026 per Tinuiti's $4B+ spend analysis.
GitHub Copilot is switching to pay-per-use token billing on June 1st.
A compromised Bitwarden CLI package exfiltrated GitHub tokens, SSH keys, and environment secrets within 90 minutes — the latest reminder that supply chain attacks cause damage faster than teams can respond.
An amateur mathematician used ChatGPT to crack a 60-year-old Erdős problem using a replicable 5-step prompt framework that forces the model to enumerate obscure solution methods.
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