:

MICROSOFT WAS SKEPTICAL OF OPENAI, FEARED AMAZON RIVAL

AI DESK1 MIN READ
FRI, MAY 8, 2026

■ AI-SUMMARIZED FROM 5 SOURCES ▸ TIMELINE

Internal Microsoft emails from 2018 reveal the company harbored doubts about OpenAI's viability, yet hesitated to distance itself for fear of pushing the startup toward Amazon.

Court documents from Elon Musk's lawsuit against OpenAI co-founder Sam Altman expose Microsoft's complicated relationship with the AI company before its eventual partnership. Microsoft executives questioned OpenAI's technical capabilities and business model in communications spanning years. However, the tech giant remained cautious about openly criticizing the startup, worried that doing so might drive OpenAI into Amazon's orbit. The emails demonstrate a strategic calculation: Microsoft valued maintaining influence over OpenAI's direction more than expressing its concerns publicly. This defensive posture ultimately positioned Microsoft to become OpenAI's largest investor when the partnership materialized. The evidence underscores the competitive tensions in AI development, where tech giants balance skepticism with the need to maintain strategic relationships in a rapidly evolving sector.

■ MORE FROM THE BIG TECH DESK

Apple is reportedly redesigning the iPhone interface around a redesigned Siri. The overhaul marks a significant shift in how the voice assistant integrates with iOS.

22H AGOIndustry Desk

Tencent is shifting strategy toward smaller AI models to compete with Chinese rivals. Executive Vice President Dowson Tong revealed that AI now accounts for over 20% of the company's revenue and generates 95%+ of new internal code.

22H AGOAI Desk

Dell reported Q1 revenue of $43.84B, up 88% year-over-year and significantly above the $35.43B analyst estimate. The company also issued FY 2027 guidance above expectations, sending shares up 15% in after-hours trading.

22H AGOIndustry Desk

Anthropic, the company behind Claude, has raised $65 billion in funding to reach a $965 billion valuation, surpassing OpenAI as the most valuable AI startup. The massive funding round reflects continued investor appetite for artificial intelligence companies.

22H AGOAI Desk

■ SUBSCRIBE TO THE DAILY BRIEF

ONE EMAIL, 5 STORIES, 06:00 UTC. UNSUBSCRIBE ANYTIME.