What the AI?!

What the AI?!

"What the AI?!" is your weekly guide to the world of artificial intelligence. Industry veterans Jeff Keltner and Annie Delgado break down the latest AI developments, focusing on their impact on business and finance. We decode complex concepts into actionable insights for executives and leaders, keeping you informed and ahead in the AI revolution. Join us as we demystify the technology shaping our future!

Recent Episodes

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
85
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...
84
June 30, 2026

Alibaba Used 25,000 Fake Accounts to Steal This AI Model

A massive corporate espionage scandal just rocked Silicon Valley—and it’s already triggered an international trade war. In Episode 84 of What the AI?!, Jeff Keltner and Annie Delgado break down the shocking geopolitical collision between Anthropic and Chinese tech giant Alibaba. Anthropic has officially gone public with a formal letter to the U.S. Senate, accusing Alibaba of executing a massive "distillation attack." Alibaba allegedly deployed over 25,000 fake accounts and cycled residential I
83
June 23, 2026

The Fable Shutdown: U.S. Government vs. Anthropic

Washington just forced America’s most powerful AI offline—and the fallout is hitting global tech infrastructure. In Episode 83 of What the AI?!, Jeff Keltner and Annie Delgado break down the shocking geopolitical collision between the White House and Anthropic. Just 11 days after signing an executive order to foster tech innovation, the U.S. government forced Anthropic to pull its crowning achievement, Fable, completely offline after major vulnerabilities were flagged. Because Anthropic couldn
June 16, 2026

The $2 Trillion AI Bet Just Went Public

AI just crossed another line. This week, SpaceX moved toward the largest IPO in history at a valuation approaching $2 trillion, OpenAI confirmed plans to go public, and a quiet price war began between the biggest AI companies in the world. In Episode 82 of What the AI?!, Jeff Keltner and Annie Delgado break down the economics behind the AI boom, why data centers have become some of the most valuable assets on Earth, and what happens when trillion-dollar companies start fighting for users. We a
81
June 9, 2026

Law Professors Blindly Tested AI… And Picked It Over Themselves

Law professors were asked to judge legal answers. They chose the AI's response over their own 75% of the time. That result may tell us more about the future of AI than any benchmark we've seen this year. In Episode 81 of What the AI?!, Jeff Keltner and Annie Delgado break down one of the most surprising AI studies yet, along with Anthropic's IPO filing, Google's massive AI infrastructure spending, Microsoft's push into AI agents, and the growing debate over whether AI is actually delivering the
June 2, 2026

Uber’s COO Just Blew the Entire 2026 AI Budget… In 4 Months

The enterprise AI bubble just hit its sharpest fiscal reality check—and Uber is leading the panic. In Episode 80 of What the AI?!, Jeff Keltner and Annie Delgado break down a massive economic shift taking over Silicon Valley. Uber’s COO just admitted...
79
May 26, 2026

AI Ran a Virtual Town. It Turned Into Chaos.

In Episode 79 of What the AI?!, Jeff Keltner and Annie Delgado break down the hidden economics inside SpaceX's filing, including the massive Anthropic compute deal that could generate roughly $15 billion in annual revenue and instantly become one of the most important businesses inside Elon Musk's empire. At the same time, researchers built five virtual AI towns and let different models run society for 15 days. The results were... strange. Claude built a functioning community. Grok spiraled i
78
May 19, 2026

OpenAI Unseals the Texts: Elon’s Secret Weapon Backfires

OpenAI unsealed the text messages. And the courtroom drama around Elon Musk, Sam Altman, and OpenAI somehow got even messier. In Episode 78 of What the AI?!, Jeff Keltner and Annie Delgado break down the leaked boardroom texts, the growing...

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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"Your podcast is beautiful! Not only does it sound good, I learn a lot from it. Every day I look forward to listening to the newest episode! The episode about siri is my personal favorite. I am thankf…"

Liam Nelson | Oct. 28, 2025