AI to ROI · 2026-05-19 · 39 min
OpenAI built $25 billion in annualized revenue and 910 million weekly active users in three and a half years. It also has 33% gross margins, a projected $14 billion loss, a CFO who was reportedly demoted for saying the company is not ready to go public, and an investor presentation that told its software partners it plans to replace them. In this episode, Ray and Peter work through six documented challenges facing OpenAI, six specific actions that could right the ship, and what enterprise leaders should actually do with their AI strategy given all of it. What we covered in this episode: The model is not the moat, and ChatGPT's market share is eroding Analyst Benedict Evans has noted that the six leading large language model companies are now roughly equivalent in capability, with no proprietary data advantage or network effect allowing any one to pull decisively ahead. ChatGPT's share of enterprise and developer usage has fallen from roughly 80% two and a half years ago to around 60% today, growing at just 4% while Claude grew 14% and Gemini 12%.
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