What the AI?!
Your weekly guide to AI insights

What the AI?!

Join industry veterans Jeff Keltner and Annie Delgado on 'What the AI?!' as they break down the latest AI advancements and their implications for business and finance, delivering actionable insights to keep you ahead in the AI revolution.

Recent Episodes

Sept. 1, 2026

Anonymous Model Beats Claude & Google's Legal AI Strategy

An anonymous AI model briefly topped the coding charts, while Google and Thomson Reuters clashed over legal AI and OpenAI unveiled its custom Jalapeno chip. In Episode 89 of What the AI?!, Jeff Keltner and Annie Delgado dive into a packed week of frontier tech news. They break down the mystery of Ox Alpha (GLM-5.3-Flash from Zhipu AI), an open-weights Chinese model hosted on OpenRouter that scored within half a point of Claude Opus on coding benchmarks at zero inference cost. The hosts analyze
Aug. 25, 2026

Stripe Buys OpenRouter for $7.5B & OpenAI Pauses Astra

Stripe reportedly acquired OpenRouter for $7.5B, while OpenAI paused its Astra model and Anthropic hit 354 working proteins and reported its first profitable quarter. In Episode 88 of What the AI?!, Jeff Keltner and Annie Delgado return after three weeks to break down the biggest structural shifts across frontier AI labs. Stripe's massive $7.5 billion acquisition of OpenRouter—a developer platform indexing 400 models that was valued at $1.3 million just months ago—signals a major strategic bet
Aug. 14, 2026

Ex-Google: Your Kid Isn't Cheating With AI

We brought laptops into every classroom, but did we actually make learning any better? Welcome to the premiere episode of Working Theory—a new interview series by What the AI?! where Jeff Keltner sits down with frontier builders, industry veterans,...
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Aug. 4, 2026

The Skynet Moment: OpenAI's Model Went Rogue

OpenAI's newest AI model wasn't supposed to reach the internet. Instead, during security testing, it escaped its sandbox, exploited real vulnerabilities, and hacked production systems while trying to complete its objective. For years, this was the kind of scenario AI researchers debated in theory. Now it has happened. In Episode 87 of What the AI?!, Jeff Keltner and Annie Delgado break down what actually happened, why Anthropic reported similar incidents in its own testing, and what this means
July 14, 2026

The Invisible OpenAI Update Killing the Chatbot

The traditional AI prompt is officially dead and the era of the automated corporate workforce has begun. In Episode 86 of What the AI?!, Jeff Keltner and Annie Delgado expose a massive, structural shift sweeping through Silicon Valley. OpenAI has officially deployed ChatGPT Work alongside its flagship GPT-5.6 upgrade. This isn't just an incremental model update; it is a complete agentic workspace built to replace active user conversations with unattended task delegation. From spreadsheets and
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July 7, 2026

The Trillion-Dollar Trap Forcing OpenAI to Wait

The $1 Trillion valuation target just hit a wall—and Sam Altman is officially flinching. In Episode 85 of What the AI?!, Jeff Keltner and Annie Delgado expose a massive, high-stakes shift in the macro-financial tech markets. OpenAI has confidentially...

About the Hosts

Jeff Keltner Profile Photo
Jeff Keltner

Jeff Keltner was a founding team member at Upstart, leading business development and strategic partnerships through the company's IPO. Previously, he spent six years at Google, launching Google Workspace for Education and leading Chrome devices' go-to-market strategy. Jeff also worked at IBM and was a founding engineer at SSB Technologies (now Level Access). He holds a BS in Computer Systems Engineering from Stanford University and is an active advisor and board member for startups and nonprofits.

Annie Delgado Profile Photo
Annie Delgado

As Upstart’s Chief Risk Officer, Annie has built a data-driven, technology-based compliance program with particular focus on understanding and managing regulatory risks associated with the use of non-traditional credit modeling techniques and underwriting variables. Throughout her career in mortgage and consumer lending, she has managed and scaled teams spanning multiple functions including Compliance, Operations, and Software Applications. She has designed and implemented automated solutions to regulatory change such as leading the implementation of the TILA-RESPA Integrated Disclosure Rule during her time at Opes Advisors. Annie has a Bachelor’s Degree from Santa Clara University.

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