Sierra CEO and OpenAI Chair on Rising AI Costs, GPT-5, and AI Data Wars

If there’s one thing the artificial intelligence industry hasn’t been lacking in recently, it’s news. So on Wednesday’s episode of TITV, our editor-in-chief Jessica Lessin asked Bret Taylor, CEO of customer-support agent firm Sierra, and Winston Weinberg, CEO of legal agent startup Harvey, for their thoughts on recent developments ranging from OpenAI’s rocky GPT-5 release to the rising costs that businesses face when purchasing agents and other advanced AI.

Taylor has an interesting perspective as both the CEO of an AI startup that has raised nearly $300 million in funding and the chair of OpenAI’s board of directors. 

Here are four takeaways from the conversation: