OpenAI's Multi-Billion Deal with AMD & Polymarket, Vercel and Supabase Raise Mega Rounds

Jason Lemkin and Rory O’Driscoll on 20VC argue OpenAI is running the same Windows-Intel power play as Microsoft did 30 years ago, this time with AMD and Nvidia as its chip stack.

• OpenAI secured penny warrants for up to 10% of AMD in exchange for buying AMD Instinct chips up to 6 GW; AMD stock rose ~30% on announcement.
• Rory frames OpenAI as the new Microsoft, Nvidia as Intel, AMD as AMD again, and Microsoft as the IBM that created the monster it can’t control.
• Nvidia alone is making money in AI; OpenAI’s leverage despite massive losses comes entirely from owning the users, not the revenue.
• Polymarket raised $2B at $9B from Intercontinental Exchange (NYSE owner); was effectively illegal under Biden — Trump Jr. joined the board, deregulation flipped it.
• SPAC terms now require stock to reach 1.5x before sponsor collects 30% promote, versus penny-share structures in 2021 that let sponsors profit while investors lost.
• Lemkin was underwhelmed by OpenAI Dev Day app integrations — called it Slack 2.0, noting Slack connectors exist everywhere but nobody uses them.
• Replit and Lovable both near $160–170M ARR; Lemkin says over $250M by year-end but sees traffic plateau and high churn from casual “lookie” users.
• Naveen Rao (ex-Databricks VP AI) raised $1B at $5B pre — Rory says compressed venture risk: proven founder, hard problem, hot sector justifies it despite brutal return math.

2025-10-09 · Watch on YouTube