WEBVTT

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72 % beat. That's the number that kept me up

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last night. If you have a digital vault, a crypto

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smart contract, or really any secure digital

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asset, as of this week, there's a new AI agent

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that can break into it and drain it of all funds

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72 % of the time. And to be clear, that isn't

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a theoretical figure from a sci -fi novel. That

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is the actual benchmark result from the latest

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coding agent released just days ago. We have

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crossed a threshold where the digital offense

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is statistically superior to the digital defense.

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Welcome back to The Deep Dive. It is Friday,

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February 20th, 2026. I'm your host, and I'm here

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with our resident expert to make sense of a week

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that... honestly feels like a year. It really

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does. It's great to be here. You know, usually

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we talk about AI explicitly building things,

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generating art, writing code, solving protein

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folding. But this week, the narrative shifted.

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It's about AI taking things. And it's about the

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massive economic machinery being built to support

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that power. Right. So let's map out where we're

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going today for you listening. We have a heavy

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stack of reports to get through. First, Google

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is hitting back hard in the model wars. Gemini

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3 .1 Pro is here. And the headline isn't speed.

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It's reasoning. We need to unpack what that actually

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means. Exactly. Then we're going to follow the

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money. And I mean serious money. OpenAI is looking

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at an $850 billion valuation. We'll look at why

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that number is so high and the controversial

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shift toward advertising that's coming with it.

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And finally, we are going to do a deep dive into

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that cold open statistic. We need to talk about

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why offense is currently beating defense and

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cybersecurity. And what happens when an AI can

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execute a flash loan attack all on its own? That

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is the part that's going to scare some people,

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but it's crucial to understand. Okay, let's start

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with the tools. It feels like we just finished

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analyzing Gemini 3 .0. That was what, November?

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Yeah, three months ago. Three months. And now

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we have Gemini 3 .1 Pro. Usually in software,

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a .1 update is a snooze. It's bug fixes. Maybe

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a new font. But looking at these specs, this

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seems entirely different. It's completely different.

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Google has rolled this out with a very specific

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focus, reasoning. And I think we need to pause

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on that word because it gets horribly abused

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in marketing. Please do. Because to me, reasoning

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implies consciousness, or at least human -like

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thought. Is Google claiming their chatbot is

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actually thinking? Not thinking in the biological

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sense, but think of it this way. Previous models,

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the ones we used in 2024 or 2025, were largely

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system one thinkers. If you know Daniel Kahneman's

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work, it's fast, instinctive, automatic. You

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ask for a poem, it predicts the next word immediately.

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It is reflexive. Okay, like a reflex. Exactly.

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Gemini 3 .1 is moving towards System 2. It's

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deliberate. It's slow. It's logical. When you

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ask it a complex question, it doesn't just spit

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out the statistically probable next word. It

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holds the problem in its mind, breaks it down

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into steps, critiques its own plan, and then

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executes. It is spending compute on inference

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time, literally taking time to think before it

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speaks. So it's the difference between a student

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blurting out an answer in class versus a student

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sitting down to work through a... a math -proof

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step -by -step. Perfect analogy. And the results

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are stark. According to the preview, Gemini 3

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.1 Pro has doubled its reasoning performance

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compared to 3 .0. Doubled in three months. Doubled.

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I am always skeptical of internal benchmarks.

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Companies love to grade their own homework. Did

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they test this against anything we'd recognize?

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They did. They used a test called Humanities

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Last Exam. Okay, that is a terrifying name for

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a test. Is that real? It is. It was designed

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to be the absolute ceiling of difficulty. Questions

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that require multidisciplinary knowledge to solve.

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It's the stuff that completely stumped the models

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from 2025. Gemini 3 .1 outperformed its predecessor

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there significantly. But the one that really

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matters to me is the APEX agent's leaderboard.

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I'm not familiar with APEX. APEX measures real

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professional past performance. It's not right

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a haiku. It's messy. It's take this scattered

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data set of CSV files, analyze the trends, cross

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-reference it with this PDF report on climate

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change, and give me a strategic insight. So actual

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knowledge work. Actual work. Gemini 3 .1 hit

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the top spot. It is designed for agentic workflows.

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It isn't just a chatbot anymore. It's a research

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partner. I see. This explains the integration

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they announced with Notebook LM. I've been using

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Notebook LM for research, basically dumping PDFs

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in and chatting with them. But you're saying

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3 .1 Pro changes the nature of that interaction.

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Completely. Notebook LM was a retrieval tool.

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Find me the quote about interest rates. With

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3 .1 Pro, it becomes an analyst. You can say,

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look the interest rates in document A, compare

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them to the housing trends in document B, and

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predict the impact on this third variable. Whoa,

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imagine connecting scattered data into full picture

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insights like that at scale. It's stacking Lego

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blocks of data into a skyscraper. That is a significant

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shift. But I have to ask, if the cycle is down

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to three months, are we even learning the old

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tools before the new ones replace them? Barely.

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We're really just adapting to the speed of the

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upgrade, not the tool itself. We are becoming

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experts in adaptation rather than experts in

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software. Barely adapting to the upgrade speed,

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not the tool itself. Got it. That's a heavy thought.

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It might be the only skill that matters in 2026.

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All right, let's pivot. Because building these

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System 2 thinkers, these reasoning engines, is

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expensive. The compute costs are astronomical.

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Massive. The energy bills alone are enough to

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bankrupt small nations. Which brings us to the

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business side. We're seeing reports that OpenAI

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is finalizing a 100 % billion dollar raise. Yes.

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Which puts their valuation at over 850 billion

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dollars. It is staggering. To put that in perspective,

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that's approaching the territory of companies

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like Meta or Tesla. But OpenAI is a fraction

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of the age. It's nearly a trillion dollar valuation

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for a company that didn't exist a decade ago.

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And the backers are the usual titans. Amazon,

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SoftBank, Nvidia, Microsoft. It feels like the

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entire tech economy is consolidating around this

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one entity. It's becoming the too big to fail

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of the AI era. It is, but here's the tension.

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To justify an $850 billion valuation, you need

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massive revenue. You can't just have $20 subscriptions.

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You need something way more pervasive. And that

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brings us to the A word. Ads. Ads. OpenAI is

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beginning to test them. They are. And this is

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where the market is starting to fracture philosophically.

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You have open AI needing to monetize that massive

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valuation, testing ads and chat GPT. But then

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look at the competitors. Perplexity, which has

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been very aggressive, is actually stepping back

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from in -chat ads. Really? I thought they were

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leaning into that model. They were, but they

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issued a warning this week saying that ads can

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erode user trust. They are pivoting to preserve

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the integrity of the answer. And then you have

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Anthropic, who has publicly committed to staying

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completely ad -free. It's interesting. It's almost

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like the business model is becoming part of the

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product identity, like organic food versus processed

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food. It absolutely is. Think about it. If you're

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using an AI for serious research, medical advice,

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legal strategy, complex coding, do you want an

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answer that is interesting? influenced by the

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highest bidder? Or do you want the raw truth?

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I want the truth. Oh. But I also know the history

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of the internet. Free with ads usually wins against

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paid and private. That's the trillion dollar

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gamble. OpenAI is betting that their model is

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so smart you'll tolerate the commercial. Anthropic

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is betting that you'll pay a premium for silence

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and neutrality. Speaking of commercial, OpenAI

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isn't just looking at ads. They're looking at

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Hollywood. They poached Charles Porch from Instagram.

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Yes, the Hollywood connector. And after that

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$1 billion Disney deal, he's going on a listening

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tour to win over creators. Which is smart because

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creators are skeptical. Actually, skeptical is

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polite. They are furious. They see AI as the

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thing that scrapes their work to replace them.

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OpenAI knows they need to bridge that gap if

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they want to be the platform for media as well

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as text. They need to convince Hollywood that

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they come in peace. It's a battle for hearts

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and minds. So let me put you on the spot. With

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perplexity pulling back on ads and OpenAI leaning

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in, who actually wins the user's trust in the

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long run? The one that gives the best answer

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without selling me a toaster? In the short term,

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OpenAI wins on scale. But for the power user

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economy, I think anthropic or perplexity has

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the edge on trust. So the winner is the one giving

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the best answer without selling a toaster. I

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don't need my AI selling me appliances while

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I'm trying to debug code. Not yet, anyway. Okay,

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let's move to the story that launched the deep

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dive. The heist. The heist. We have discussed

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reasoning. We have discussed money. Now we see

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what happens when reasoning agents decide to

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take the money. This comes from a new study involving

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OpenAI's new coding agent, GPT -5 .3 Codex. 5

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.3. They are iterating fast. Very fast. The study

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used a benchmark called EVM Bench built with

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the crypto firm Paradigm. They set up vulnerable

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smart contracts, digital vaults, essentially,

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and unleashed the AI to see if it could break

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in. And this is where that 72 % come from. Correct.

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GPT -5 .3 codex exploited the vulnerabilities

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72 % of the time. Now for context, compare that

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to just six months ago. GPT -5 scored 31 .9 %

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on the exact same tasks. That is more than doubling

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in capability in half a year. That curve is vertical.

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It is exponential. And it's not just finding

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a bug. A GPT -5 .2 agent was able to execute

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a full flash loan attack on its own. Can we pause

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there? Because flash loan attack is one of those

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crypto terms that sounds exciting but makes no

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sense to most people. Break that down for us.

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Okay. Imagine a bank vault. You walk in and say,

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I want to borrow $100 million, but I have no

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collateral. In the real world, the bank laughs

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at you and calls security. Right. In crypto,

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the bank says, sure, take the hundred million,

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but you have to pay it back within the exact

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same transaction. It's like freezing time. You

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borrow the money, you run around the market,

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you buy and sell assets to manipulate the price.

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You make a profit and you return the original

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loan all before the clock starts ticking again.

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So it all happens in a single split second block

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of code. Exactly. If you fail to pay it back,

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the whole thing reverses like it never happened.

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But if you succeed, you keep the profit. It requires

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incredibly. complex coding and timing to pull

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off. And the AI did this autonomously. Autonomously.

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No human steering the wheel. That is unnerving.

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So the offense is elite. What about the defense?

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Surely if the AI can break it, the AI can fix

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it. That's the problem. The defense is lagging.

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The same study showed that bug detection, the

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AI trying to fix the code, tops out around 46%.

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So it's almost twice as good at breaking in as

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it is at fixing the lock. Why? It comes down

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to the nature of the task. Breaking things is

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often about finding one weak point. Fixing things

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requires understanding the entire system so you

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don't break something else. Patch success sits

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at only 39%. 39%. Beat. That's barely better

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than guessing. Unless, and this is the key, unless

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you give the model a small hint. A hint. If you

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give the AI a nudge, literally telling it roughly

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where the problem is, patch success jumps to

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94%. That is a huge gap. It tells us that the

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bottleneck isn't intelligence. The AI is smart

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enough to fix it. The bottleneck is search. It

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doesn't know where to look for the solution without

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guidance. It's like searching for a needle in

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a haystack versus being told the needle is in

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the top left corner. That feels incredibly human.

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I could fix the leak if you just tell me. me

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which pipe is bursting. Exactly. But in cybersecurity,

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you don't get hints from the attackers. You know,

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I have to admit, I still wrestle with prompt

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drift myself. I am just trying to get the model

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to write a coherent email sometimes, and it goes

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completely off the rails. Yeah. The idea of trusting

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it to patch a smart contract holding millions

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of dollars, that feels like a massive leap of

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faith. It is. But OpenAI sees this gap. They

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don't want their tools to be super weapons for

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hackers. They're launching Aardvark, which is

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their AI security research agent, and they've

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put up a $10 million fund for cybersecurity researchers.

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They know that if AI can break systems this fast,

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defenders need AI just as powerful. Because in

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crypto, there is no undo button. Once it's gone,

00:12:15.679 --> 00:12:18.000
it's gone. So if offense is twice as good as

00:12:18.000 --> 00:12:20.460
defense right now, is any digital vault actually

00:12:20.460 --> 00:12:23.419
safe? Not really, unless you have an AI guard

00:12:23.419 --> 00:12:25.700
dog that's smarter than the AI burglar. And right

00:12:25.700 --> 00:12:28.460
now, the burglars are winning. So no vaults are

00:12:28.460 --> 00:12:32.080
safe unless your AI guard dog outsmarts the burglar.

00:12:33.639 --> 00:12:35.860
We are going to take a quick break. When we come

00:12:35.860 --> 00:12:37.820
back, we're going to step away from the destruction

00:12:37.820 --> 00:12:40.279
and look at the builders, including a legend

00:12:40.279 --> 00:12:42.740
in the field who is building 3D worlds from scratch.

00:12:43.620 --> 00:12:47.299
Stay with us. Monroe's sponsor, Reed Placeholder.

00:12:47.880 --> 00:12:50.159
Welcome back to the Deep Dive. We've talked about

00:12:50.159 --> 00:12:52.740
the big models and the big money, but I want

00:12:52.740 --> 00:12:55.120
to zoom in on the builders for a minute. The

00:12:55.120 --> 00:12:57.600
people making the utilities we use every day.

00:12:57.679 --> 00:13:00.000
The tool belt. Exactly. And there's one name

00:13:00.000 --> 00:13:01.360
that popped up this week that everyone should

00:13:01.360 --> 00:13:05.580
know. Fae Fae Lit. The godmother of AI. She is

00:13:05.580 --> 00:13:08.559
responsible for ImageNet, which basically kickstarted

00:13:08.559 --> 00:13:10.639
the deep learning revolution over a decade ago.

00:13:10.779 --> 00:13:12.899
She has a new company, World Labs, and they just

00:13:12.899 --> 00:13:15.500
raised $1 billion. Which is huge for a startup,

00:13:15.620 --> 00:13:18.159
but it's the product. Morble, that's interesting.

00:13:18.299 --> 00:13:21.460
It turns text into editable 3D worlds. 3D worlds.

00:13:21.539 --> 00:13:23.240
So we aren't just generating images anymore.

00:13:23.460 --> 00:13:26.600
No. This is about spatial intelligence. We are

00:13:26.600 --> 00:13:29.639
entering design pipelines. Imagine typing a description

00:13:29.639 --> 00:13:32.679
of a medieval city, the cobblestones, the lighting,

00:13:32.820 --> 00:13:35.840
the physics of the fog, and having a fully editable

00:13:35.840 --> 00:13:38.220
3D model generated that you can drop straight

00:13:38.220 --> 00:13:40.659
into a video game or a movie. That feels like

00:13:40.659 --> 00:13:43.200
the next frontier. We conquered text. We conquered

00:13:43.200 --> 00:13:46.840
static images. Now we are conquering space. Spatial

00:13:46.840 --> 00:13:49.659
computing needs content. Think about the metaverse

00:13:49.659 --> 00:13:52.919
or Apple's Vision Pro. It's empty right now because

00:13:52.919 --> 00:13:55.809
building 3D assets takes humans... Hundreds of

00:13:55.809 --> 00:13:58.669
hours. If AI can do it in seconds, that changes

00:13:58.669 --> 00:14:00.509
the entertainment industry forever. It lowers

00:14:00.509 --> 00:14:03.409
the barrier to entry to near zero. Speaking of

00:14:03.409 --> 00:14:05.289
which, there were a few other rapid -fire tools

00:14:05.289 --> 00:14:07.690
that caught my eye this week. Did you see origami

00:14:07.690 --> 00:14:11.250
.chat? I did. It is a data enrichment tool. Connects

00:14:11.250 --> 00:14:13.990
over 100 sources. You can use it to find customers,

00:14:14.210 --> 00:14:16.929
enrich a CSV file. It's highly practical. It's

00:14:16.929 --> 00:14:20.049
unsexy, but it saves hours of grunt work. And

00:14:20.049 --> 00:14:23.389
chloe .ai. Open claw in the cloud. Zero setup.

00:14:23.759 --> 00:14:25.840
It's basically an autonomous assistant you can

00:14:25.840 --> 00:14:27.799
spin up in five minutes to browse the web and

00:14:27.799 --> 00:14:30.340
do tedious tasks for you. It seems like we are

00:14:30.340 --> 00:14:33.159
moving from chat with a bot to assign a bot a

00:14:33.159 --> 00:14:36.700
job. That is the defining theme of 2026. Don't

00:14:36.700 --> 00:14:38.720
talk to me, do it for me, even for content creation.

00:14:39.000 --> 00:14:42.100
There's Reloop, avatars, cloned voices, video

00:14:42.100 --> 00:14:44.929
editing all in one spot. You just chat with it

00:14:44.929 --> 00:14:47.570
to make a full video. It's moving so fast. I

00:14:47.570 --> 00:14:49.750
saw that a Wharton professor released the eighth

00:14:49.750 --> 00:14:52.289
edition of his AI guide this week. The eighth

00:14:52.289 --> 00:14:54.549
edition. It just highlights that textbooks are

00:14:54.549 --> 00:14:57.129
obsolete the absolute moment they're printed.

00:14:57.230 --> 00:14:59.049
Absolutely. If you're reading a printed book

00:14:59.049 --> 00:15:01.590
on how to use AI, you're studying history. You

00:15:01.590 --> 00:15:04.200
are looking at fossils. So, faithfully focusing

00:15:04.200 --> 00:15:07.039
on 3D worlds, is that the next frontier after

00:15:07.039 --> 00:15:09.320
text and video? Absolutely. Spatial computing

00:15:09.320 --> 00:15:12.019
needs content, and only AI can build it fast

00:15:12.019 --> 00:15:14.440
enough. Spatial computing needs content, and

00:15:14.440 --> 00:15:17.740
only AI can build it fast. I love that. Let's

00:15:17.740 --> 00:15:19.059
try to pull this all together. We've covered

00:15:19.059 --> 00:15:21.799
a lot of ground today. What is the big idea here

00:15:21.799 --> 00:15:24.259
for the listener? I think if we weave these threads

00:15:24.259 --> 00:15:27.500
together, we see a clear picture of 2026. First

00:15:27.500 --> 00:15:30.799
is capability. Gemini 3 .1 proves that models

00:15:30.799 --> 00:15:33.419
are learning to reason, not just predict. They

00:15:33.419 --> 00:15:36.539
are becoming methodical thinkers. Second is risk.

00:15:37.039 --> 00:15:39.840
That reasoning power allows for autonomous offense.

00:15:40.220 --> 00:15:43.179
The tools are becoming weaponized much faster

00:15:43.179 --> 00:15:46.019
than they are being secured. And third? The economy.

00:15:46.460 --> 00:15:49.139
The market values this power at nearly a trillion

00:15:49.139 --> 00:15:51.980
dollars, but the business model is still totally

00:15:51.980 --> 00:15:55.220
fractured. We're seeing a split between the ads

00:15:55.220 --> 00:15:57.639
model where you are the product and the subscription

00:15:57.639 --> 00:16:00.419
model where you pay for privacy and neutrality.

00:16:00.580 --> 00:16:02.500
It's a pivotal moment. You know, I keep thinking

00:16:02.500 --> 00:16:05.700
about that gap, the offense versus defense gap

00:16:05.700 --> 00:16:07.860
in cogeneration. It is the most critical metric

00:16:07.860 --> 00:16:09.980
right now. It isn't just a crypto problem, is

00:16:09.980 --> 00:16:12.769
it? No. It's everything. Banking, healthcare,

00:16:13.110 --> 00:16:15.990
power grids. It's a preview of all cybersecurity.

00:16:16.929 --> 00:16:20.330
Two sec silence. If the AI can pick the locks

00:16:20.330 --> 00:16:22.990
72 % of the time, it doesn't matter how strong

00:16:22.990 --> 00:16:25.490
the door is. We need better locks and we need

00:16:25.490 --> 00:16:28.370
them fast. We do. And we likely need AI to build

00:16:28.370 --> 00:16:31.570
them. That is the reality of February 2026. It

00:16:31.570 --> 00:16:33.690
is a world of incredible speed, high stakes,

00:16:33.850 --> 00:16:36.009
and brilliant machines that are learning to think.

00:16:36.210 --> 00:16:38.230
Thank you for diving in with us today. Thanks

00:16:38.230 --> 00:16:41.029
for having me. And to you listening. Stay curious,

00:16:41.250 --> 00:16:43.629
stay vigilant, and maybe double -check your digital

00:16:43.629 --> 00:16:46.049
locks today. We will catch you in the next deep

00:16:46.049 --> 00:16:47.629
dive. OGAU Music.
