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Ep 1. AI Edge: Where AI Meets Pop Culture, featuring guest Krish Raja10 Nov 202500:32:43

Welcome to Episode 1 of The AI Edge Podcast! Hosts Shiv Gupta and Myles Younger kick off the show with guest Krish Raja, AI expert and founder of AI Literacy, to break down the biggest AI stories shaking up marketing and advertising right now. This week: Coca-Cola doubles down on their controversial AI-generated holiday ad (yes, the one with the sloths), Sam Altman hints (again) that ChatGPT ads are inevitable, and Amazon and Shopify reveal drastically different strategies for AI in e-commerce, with huge implications for how we'll all shop and advertise in the future. The conversation gets real about job security, the risks of making big AI bets too early, and why marketers need to think critically about their relationship with AI tools. (Spoiler: if you're not improving yourself with AI, you're just improving AI.) Whether you're trying to keep up with the AI revolution or just want to cut through the hype, this episode gives you the clarity you need to navigate what's next. New episodes every Monday. Let's get you your AI edge.

Ep 26. AI Bias Is a Business Problem — Not Just an Ethics One, with Stefanie Beach & Nadia Koski18 May 202600:52:08

Amazon just killed Rufus. The upfronts just tried to sell data like it was primetime inventory. And every streaming platform announced an AI tool that sounds exactly like every other streaming platform's AI tool. Meanwhile, the industry is barreling toward agentic commerce built on data that excludes half the world — and most marketers haven't noticed yet.

This week, Shiv and Miles welcome two guests who are doing something about it. Stefanie Beach is the founder and CEO of The Marketeer Group and host of the Digital Marketeer Podcast. Nadia Koski is a 15-year ad tech and publishing veteran, American expat living in Florence, and the founder of a new podcast launching this week. Together, they're producing a panel at Cannes Lions focused on AI bias, inclusive data, and what the industry needs to do before it's too late.

They break down why Amazon sunsetting Rufus in favor of Alexa is actually a smart long game — and why agentic commerce will cannibalize commerce media in the process. They also get into why the upfronts are in their awkward teenage years, why selling data on an upfront timeline is a structural contradiction, and why every streamer announcing an "AI personalization tool" this week needs to actually show who's buying it and why.

Then the conversation gets more serious. Only 52% of the world's data is represented in today's AI systems. An AI crop app built for African farmers failed female farmers entirely because the training photos were all taken by men. Roughly 1 in 4 women feel that using AI at work is cheating — men simply don't carry that hesitation. And if agentic commerce gets built on this foundation, brands risk alienating Gen Z and Gen Alpha — the largest spending generation of the next decade — before they ever get a chance to reach them.

🎙 Check out Stefanie's podcast: The Digital Marketeer Podcast https://bit.ly/4uhs5oj

🎙 Nadia's new podcast launches Tuesday, May 19th — Still Human: Real Talk in the Age of AI Listen to the trailer here: https://bit.ly/3RMqCrJ

Ep 25. The MarTech Chrysalis: Why Marketing Is in a Messy Middle — and What Comes Next, with Scott Brinker, Chief MarTech11 May 202600:48:47

The MarTech landscape just flatlined for the first time in 15 years. Not because AI killed it — but because the companies that were always going to lose finally ran out of time. Meanwhile, marketers are building software without knowing they're building software, SaaS platforms are going headless, and the new constraint isn't data or budget or creative. It's context.

This week, Shiv and Miles sit down with Scott Brinker — aka Chief MarTech, founder of the Chief MarTech blog, former HubSpot ecosystem lead, and the person who has been tracking the MarTech landscape since it had 150 companies on it. Scott just dropped his annual State of MarTech report — 125 pages, a decade and a half of pattern recognition, and one central thesis: we are in the chrysalis stage. Things have dissolved. The butterfly hasn't formed yet. And anyone who tells you they've figured it all out is lying.

Scott breaks down why peak MarTech finally arrived — and why the companies exiting aren't the AI wrappers everyone expected but the legacy 2010s players that never won their categories and have been on life support for years. He also explains why the build-versus-buy question has exploded into build-and-buy-and-build-some-more, why marketers are creating software without realizing it, and why the entire order of operations most marketing teams are using with AI is exactly backwards.

They also get into why context is the new constraint — and what it means that human bridges between company context and customer context are disappearing as agents start talking to agents, why SaaS platforms that go headless are making the smartest long-term bet in the industry, and why the data layer players like Snowflake and Databricks are quietly racing up the stack.

Ready to level up your AI skills? Join the U of Digital AI Accelerator. Use code EARLYBIRDSLEARNAI for 20% off https://uof.digital/ai/accelerator/ Sponsored by Hightouch

New episodes every Monday. Get your AI Edge here.

Ep 16. Is AI Advertising Ready for Prime Time? Trust, Slop, and the Commerce Media Land Grab, with Tameka Kee, U of Digital09 Mar 202600:41:49

Meta wants to turn its AI chatbot into a shopping engine — but what happens when a chunk of the catalog is fake? OpenAI just partnered with Criteo to inject ads into ChatGPT, and agencies are vibe-coding their own GEO platforms while unicorns raise $100 million to do the same thing. The commerce media land grab is on, and nobody's quite sure who wins.

This week, hosts Shiv Gupta and Myles Younger bring the conversation inside the house. Their guest is Tameka Kee, U of Digital's new Head of AI Enablement and Strategy — a 20-year ad tech veteran with stints at Rubicon Project, Magnite, and CIMM, who spent her first two weeks on the job going through the AI Accelerator herself.

Tameka breaks down why Meta's AI shopping tool could supercharge the drop-shipper problem and usher in a new era of AI product slop, why OpenAI partnering with Criteo is smarter than it looks (hint: it's as much a data play as a monetization play), and why Google's ecosystem — Maps, Wallet, Chrome, Translate, YouTube, Gmail — is still the greatest monetization machine ever built and ChatGPT has a long way to go. They also get into whether agency AI platforms will survive to 2029, what Stagwell's GEO build is really signaling, and why throwing money at AI adoption without understanding your team almost never works.

Ready to level up your AI skills? Join the U of Digital AI Accelerator. Starts March 9, 2026 | Use code PROCRASTINATOR for 25% off https://uof.digital/ai/accelerator/ Sponsored by Yahoo DSP

New episodes every Monday. Get your AI Edge here.

Ep 15. From the Digital Shelf to the AI Shelf — What CMOs Need to Do Now, with Linda Bethea, Danone02 Mar 202600:37:35

Everyone thought AI would kill the consultancies. Instead, OpenAI just partnered with Accenture, McKinsey, and BCG to form the Frontier Alliance — bringing enterprise AI to the brands that need help figuring out where to start. Turns out, the awkward phase of a new technology wave is exactly when consultancies earn their keep.

This week, hosts Shiv Gupta and Myles Younger sit down with Linda Bethea, Chief Marketing Officer at Danone North America, to talk about what brands are actually doing with AI, why efficiency isn't the same as effectiveness, and what happens when you send your entire C-suite to Seattle to learn about AI from Microsoft.

Linda breaks down how Danone built an AI task force before most companies understood what was coming, why the physical shelf gave way to the digital shelf — and why marketers now need to think about the AI shelf, and the three things every CMO should tackle first when getting started with AI (spoiler: always start with people). They also get into Profound's $96 million raise and unicorn status, a $20 million bet on injecting ads into LLMs, and why Anthropic is pushing back hard on government demands for access to its models and data.

Ready to level up your AI skills? Join the U of Digital AI Accelerator. Starts March 9, 2026 | Use code PROCRASTINATOR for 25% off https://uof.digital/ai/accelerator/

New episodes every Monday. Get your AI Edge here.

Ep 14. Are ChatGPT Ads Making AI Worse? The Engagement Problem, with Ken Rona, JWX23 Feb 202600:49:12

ChatGPT ads are live, and the real danger isn't ad load—it's the business model. When platforms get paid for engagement instead of answers, everything changes. Facebook proved that. Now OpenAI is walking the same path, and marketers need to understand what happens when AI stops prioritizing truth and starts optimizing for clicks.

This week, hosts Shiv Gupta and Myles Younger sit down with Ken Rona, Chief AI Officer at JWX (formerly JW Player), to talk about what's actually happening with ChatGPT ads, why Meta and Apple's AI wearables might finally matter, and how AI traffic is converting at rates that should terrify traditional search.

Ken breaks down why ChatGPT might intentionally get worse once ads take over, whether AI wearables will replace your phone or just clutter your desk, and what happens when AI-driven shoppers convert 3x higher than search traffic. They also discuss OpenClaw's billion-dollar one-person acquisition, vibe coding that isn't vibes anymore, and how Ken's team built a programmatic bidder in an afternoon that would normally take months.

Ready to level up your AI skills? Join the U of Digital AI Accelerator Bootcamp Starts March 9, 2026 | 20% off with code at checkout https://uof.digital/ai/accelerator/ Sponsored by Yahoo DSP

New episodes every Monday. Get your AI Edge here.

Ep 13. Is AI Advertising Backfiring? Post-Super Bowl Reality Check, with Jeremy Bloom & Sam Khoury, Marketecture Media18 Feb 202600:38:38

The Super Bowl ads are still being dissected, and the backlash is real. AI fatigue is hitting advertising, brands are questioning whether anyone cares about their AI-powered campaigns, and marketers are caught between innovation theater and what consumers actually want.

This week, host Myles Younger sits down with Jeremy Bloom and Sam Khoury from Marketecture Media to unpack what went wrong with Super Bowl advertising, why AI hype is backfiring, and what happens when brands forget the basic rule: give consumers control, not spectacle.

Jeremy and Sam break down where AI fits (and doesn't fit) in entertainment, why authenticity beats automation, and why consumer control is the most underrated strategy in marketing. They also explain what Marketecture Live is building—a space where marketers can actually talk about what's working instead of what's being sold (with incredible food!).

Marketecture Live NYC | March 10-11, 2026 https://2026.marketecturelive.com/ Use code UOFD30 for 30% off

Ready to level up your AI skills? Join the U of Digital AI Accelerator Bootcamp https://uof.digital/ai/accelerator/

New episodes every Monday. Get your AI Edge here.

Ep 12. The Super Bowl Becomes the AI Bowl, with Babs Rangaiah09 Feb 202600:39:39

The Super Bowl LX became the AI Bowl. Anthropic ran ads calling out OpenAI for putting ads in ChatGPT, Sam Altman fired back on Twitter, and the marketing world had a meltdown about whether any of this even matters. Not to mention Svedka's fully AI-generated Super Bowl spot that took 300+ iterations, OpenAI asking brands for $200K to test ChatGPT ads, and AI agents autonomously creating their own religion called the Church of Molt.

This week is a big one. Hosts Shiv Gupta and Myles Younger sit down with Babs Rangaiah, industry thought leader and former marketing exec at Unilever, IBM, and Paramount+, now CEO of cc:babs, to talk through what just happened and what marketers should actually be doing about AI right now.

Babs breaks down why Anthropic's controversial Super Bowl play was actually genius, whether brands should test OpenAI's $200K ad program, and what he's seeing as he coaches Fortune 500 CMOs navigating AI. They also talk about AI agents creating their own religions, why some marketing teams still aren't discussing AI in 2026 planning meetings, and when we'll finally see the breakthrough AI case studies that force everyone to pay attention.

Plus, thoughts on AI-generated Super Bowl creative, why peer pressure drives adoption faster than anything else, and whether Meta will end up creating most of your ads for you.

New episodes every Monday. Get your AI Edge here.

Ep 11. Should AI Ads Require Labels? IAB's Transparency Framework Explained, with Caroline Giegerich02 Feb 202600:46:21

YouTube just overtook Reddit as the most-cited source in AI search results. Meta's ad revenue is funding a $135 billion AI spending spree. And marketers are about to see a wave of AI ads during the Super Bowl. But here's the question nobody's answering: should advertisers have to disclose when they use AI?

This week, hosts Shiv Gupta and Myles Younger sit down with Caroline Giegerich, VP of AI & Marketing Innovation at the IAB, to discuss the AI Transparency and Disclosure Framework: the industry's first attempt to answer when, how, and why marketers should label AI-generated advertising.

Caroline breaks down the core questions: Do we disclose AI use in advertising? In what circumstances? Who's responsible: the brand, agency, or platform? What's the threshold for requiring a label? 

Caroline walks through what the IAB is building, why it matters, and shares some surprising research: turns out advertisers think consumers love AI ads way more than they actually do. They also dig into Meta's massive earnings, why YouTube citations are changing content strategy overnight, and what marketers should be watching during the Super Bowl.

New episodes every Monday. Get your AI Edge here.

Links to IAB's research and framework discussed in this episode: 

Research: https://www.iab.com/insights/the-ai-gap-widens/ Framework: https://www.iab.com/guidelines/ai-transparency-and-disclosure-framework/

Ep 10. ChatGPT Ads Explained, with Patrick O'Shea & Kevin O'Malley, AdDaptive Intelligence26 Jan 202600:39:54

It finally happened. OpenAI announced ads are coming to ChatGPT in February at $60 CPMs with under-$1M spending commitments. The entire advertising industry is about to change overnight.

Hosts Shiv Gupta and Myles Younger sit down with Patrick O'Shea and Kevin O'Malley, co-founders of AdDaptive Intelligence, to break down what this means for marketers. Patrick and Kevin have been business partners for 20 years, deep in B2B marketing automation since the programmatic days, and they're here to cut through the noise.

They discuss why this isn't just search ads 2.0, OpenAI's 4% commerce fee (while Google and Microsoft charge nothing), Google's "we'll never do ads in Gemini" response, and why B2B marketers are uniquely positioned for this shift. Plus, the new cottage industry of AI ad services about to explode, and why the best advice is simple: start testing now.

Every other LLM will rush to launch ads. Budgets are being carved out. The AI ad ecosystem is emerging overnight. Let's dig into it. New episodes every Monday. Get your AI Edge here.

Ep 9. Welcome to Zero-Click Commerce, with Akaash Ramakrishnan, AdSkate22 Jan 202600:32:42

We're entering the age of zero-click commerce, where shopping happens entirely inside an LLM. If your creative isn't machine-readable, you're already behind.

In this special bonus episode, hosts Shiv Gupta and Myles Younger sit down with Akaash Ramakrishnan, Co-Founder at AdSkate Inc, to talk about what happens when AI agents start doing the shopping for us. Apple just picked Google over OpenAI to power Siri, and Google launched Universal Commerce Protocol with major retailers like Walmart and Target: signs that AI Shopping is actually happening

Akaash explains why creative needs to change when AI is looking at your ads instead of humans; it's not just about making something that looks good anymore, your ads need to be readable by machines. They dig into what creative metadata actually means, how AI selects the right creative for the right moment (instead of just blasting ads at everyone), and why we're finally getting real personalization instead of just making 40 versions of the same thing. 

Plus, what Google's new ad formats mean for marketers, why retailers partnering with Google might be repeating history, and what happens to traditional advertising when people stop browsing websites.

New episodes every Monday. Get your AI Edge here.

Ep 8. Diageo's AI Playbook for 2026, with Mike Ditter20 Jan 202600:16:36

Diageo has one of the most iconic brand portfolios in the world: Guinness, Don Julio, Crown Royal, Bulleit. So what does AI implementation actually look like at a company this big? Mike Ditter, Director of AI Strategy and Emerging Technology, Diageo, breaks down exactly how they're doing it.

Recorded live from CES 2026, hosts Shiv Gupta and Myles Younger sit down with Mike to talk about what he's seeing on the show floor, how voice is changing the human-AI interface, and why 2026 is all about building capability, not chasing tools.

Mike breaks down his work at Diageo across three areas: AI-powered content creation (with style and agency, not robots replacing humans), enabling enterprise AI adoption (because refusing to use AI in 2026 is like refusing to use email), and specific use cases that unlock value from Diageo's massive portfolio of brands, from Guinness to Don Julio.

He drops his pro tips for AI adoption, unpacks why the gap between imagination and implementation has completely collapsed, and how Mike (a molecular biology major with no CS degree) won a hackathon against 200 hardcore coders.

Oh, and Mike used Deep Research to figure out how much dinosaur pee is in a water bottle for his 5-year-old. The answer is 1%. And yes, there's math to prove it.

This is a great, quick episode for you to get your AI Edge right from the frontlines of CES. New episodes every Monday. 

Ep 7. Live from CES: Meta, Manus, and the Ad Tech Shake-Up, with guest Sarah Caputo12 Jan 202600:21:20

Meta spent $2 billion on a company most people have never heard of, and it might be their smartest move since Instagram.

A special episode recorded live from CES 2026, hosts Shiv Gupta and Myle Younger sit down with Sarah Caputo, independent consultant and former CDO, to figure out what Meta's really up to with this acquisition. Sarah's got theories: protecting their small business revenue, making a play for wearables as the next big ad platform, and maybe finally figuring out what people actually want AI to do.

They also talk about why every ad platform now has basically the same "AI does everything" product with a slightly different name, why being operationally efficient isn't special anymore, and Sarah's take on how OpenAI should actually make money (spoiler: not by copying Google's playbook). Plus, why these new autonomous tools might shake things up for DSPs and what agencies better start doing if they don't want to become irrelevant.

You don't want to miss this one. Straight from the CES floor with perspectives you won't get anywhere else: practical, honest, and built for marketers. New episodes every Monday. Get your AI Edge here.

Ep 24. AI Is Making Ads Better — But Where Is All That Money Actually Going? with David Danziger, Dstillery04 May 202600:52:30

The New York Times says AI is making digital advertising boring. Meta just posted its biggest earnings quarter ever. Google's CapEx story is looking smarter by the day. And OpenAI is quietly building toward a $100 billion ad business while the three-headed AI monster — Gemini, Claude, and ChatGPT — keeps getting more tangled by the week.

This week, Shiv and Miles sit down with David Danziger, SVP of Partnerships at Dstillery, one of the leading independent targeting companies in advertising. David has spent his career at the intersection of data, partnerships, and the open internet — with stints at LiveRamp, The Trade Desk, and Yahoo — and he brings a practitioner's eye to a week full of big numbers and bigger questions.

David breaks down why the NYT's "boring" framing is ironic at best and wrong at worst, why Meta's CapEx story looks very different from Google's when you factor in the infrastructure play underneath it, and why the open internet is going to see real AI benefits too — not just the walled gardens. He also explains why a wrapper on an LLM isn't enough anymore, why ChatGPT ads are essentially search ads with more granular intent signals, and why the companies with real data assets underneath them are the ones that will win.

They also get into how MCP is replacing what APIs used to do — faster, easier, and already happening in production at Dstillery — why multimodal AI means any input can produce any output and what that actually unlocks for targeting, and how a workflow that used to take two days of back-and-forth emails now takes fifteen minutes inside Dstillery's agentic tools.

Ready to level up your AI skills? Join the U of Digital AI Accelerator. Starts May 12th | Use code EARLYBIRDSLEARNAI for 20% off https://uof.digital/ai/accelerator/ Sponsored by Hightouch

New episodes every Monday. Get your AI Edge here.

Ep 6. AMA Episode: Agency Jobs, Sycophant AI, and Data Snake Oil05 Jan 202600:24:06

No guest this week, just Shiv and Myles answering listener questions in their first-ever mailbag episode. And the questions got deep.

  • Will agency jobs disappear or are we headed back to a Mad Men era?
  • What does a fully AI-enabled agency actually look like (and which ones are about to fail)?
  • How do you trust AI to build client profiles when ChatGPT is basically a sycophant telling you everything's brilliant?

Your hosts unpack this and so much more.

Then things get existential: How can we tell if AI is speeding up good judgment or slowly eroding it? And what AI workflows do Shiv and Myles actually trust enough to use every day at U of Digital?

Shiv confesses his secret Claude projects, Myles admits his "workflow" is just opening another browser tab, and they both tackle whether we should be measuring the quality of human judgment before worrying about AI making it worse.

Plus: synthetic audiences, B2B data garbage, and why anti-sycophancy technology might be the thing nobody's talking about.

New episodes every Monday. Get your AI Edge here. 

Ep 5. The AI Platform Wars Are Over, featuring Simon Poulton of Tinuiti22 Dec 202500:46:25

Simon Poulton searched for toilets in Google's AI Mode and saw his first AI-generated ad. That moment confirmed what he's been saying for months: Google's already won the AI platform wars, and OpenAI has 12 months to prove otherwise.

This week, hosts Shiv Gupta and Myles Younger sit down with Simon Poulton, EVP of Innovation & Growth at Tinuiti, to break down the AI platform wars and what's actually happening behind the hype.

They dig into why Google's distribution advantage beats model quality, what happens when ChatGPT remembers your furniture preferences from six months ago, whether agentic advertising is real or just a stunt, and why brands keep building AI tools they don't actually need.

Plus: Simon's take on vibe coding, the rise of "agentic deference," and what marketers should actually be doing right now instead of chasing every shiny AI object.

Link to Tinuiti's 2026 AI Trends report we referenced in this episode is available here.

New episodes every Monday. Get your AI Edge here. 

Ep 4. The Great Agentic Commerce Discussion, featuring Andrew Lipsman15 Dec 202500:38:34

Myles wrote a piece saying agentic commerce is coming fast. Andrew Lipsman rebutted, calling it a "collective hallucination." The discussion got interesting, so we brought it to the podcast.

This week, hosts Shiv Gupta and Myles Younger sit down with Andrew Lipsman, Independent Analyst & Consultant in Retail Media, to hash out whether AI agents shopping on our behalf is real, or just another overhyped trend like Facebook Shops and Google Shopping.

They also dig into Disney's $1B OpenAI bet (licensing Mickey Mouse to Sora), Criteo piping commerce data into LLMs, Google bringing ads to Gemini in 2026, and the big question: if agentic commerce takes off, does retail media collapse?

The episode ends with "Convince Me," where each gets 60 seconds to sell the other. Good stuff. You don't want to miss it. 

New episodes every Monday.

Ep 3. The AdTech and MarTech Divide Is Dead, featuring Heather Macaulay, President, MadConnect08 Dec 202500:35:21

Black Friday 2025 was the inflection point: AI shoppers converted at double the rate, AI traffic surged 805%, and brands finally learned that if AI can't see you, you don't exist.

This week, hosts Shiv Gupta and Myles Younger are joined by Heather Macaulay, President of MadConnect, to break down what the Black Friday data actually means, unpack Scott Brinker's massive 2026 Martech Report, and tackle the elephant in the room: the decade-old divide between AdTech and MarTech is finally collapsing...and most marketing teams aren't ready.

Heather also unpacks why integration is harder than it looks, what Amazon's walled garden strategy means for other retailers, and where most brands are getting AI readiness wrong. Plus the big hard truth: AI won't fix bad data; it amplifies it.

If your org chart still separates AdTech and MarTech, this episode is your wake-up call. New episodes every Monday.

Ep 2. Synthetic Audiences and the $50B Question, featuring Chad Reynolds, CEO Vurvey Labs17 Nov 202500:42:57

The big questions: Are we teaching AI to tell us what we want to hear? If AI only knows the past, who discovers the future? And what happens to the $50 billion market research industry?

This week, Shiv Gupta and Myles Younger dive into the biggest AI announcements shaking up advertising right now, including the Amazon vs. Google AI agent wars and what happens when ad platforms automate the work agencies used to do.

For the main event, Chad Reynolds, Founder & CEO of Vurvey Labs, talks synthetic audiences: what they are, how brands are using them to test ideas without recruiting real people, and why Vurvey's approach is different. Chad's building AI models powered by actual human data from 3 million people, not scraped internet content. He reveals where synthetic audiences work (and where they spectacularly fail), how to validate AI-generated insights against real behavior, and whether we're headed toward a world where market research happens entirely without humans.

The question isn't if synthetic audiences will replace traditional research, it's when. You don't want to miss this one.

New episodes every Monday.

Ep 23. AI Native or Dead: What It Really Takes to Transform a Business, with Mark Josephson, Executive Coach27 Apr 202600:51:02

OpenAI launched GPT-5.5 and called it a step toward a super app. Anthropic dropped Claude Design and quietly kept building what might be today's version of G Suite. Google launched a native agent builder in Gemini Enterprise. And Meta got caught secretly tracking employee keystrokes to train AI — then told the employees who objected: no.

This week, Shiv and Myles sit down with Mark Josephson — three-time CEO, former head of Bitly, and now an executive coach working with founders and senior leaders on how to actually transform their businesses with AI. Mark has a front-row seat to what's working, what isn't, and what separates companies that are going to make it from the ones that are quietly running out of time.

Mark breaks down why Anthropic has a clarity of purpose that OpenAI still hasn't found, why the real Google competitive battle isn't against Claude or ChatGPT but against AWS and Azure at the cloud layer, and why the future is simply binary — companies will either be AI native or they'll be dead, the same way print was always going to die once digital arrived. He also shares the story of a founder who cancelled every meeting on a Monday, handed his entire company Claude Code, and committed to two hours of daily AI training until they got there.

They also get into why Meta secretly tracking keystrokes is a warning sign that should make everyone think harder about who they're trusting with this technology, why smart regulation matters more than the performative policy theater coming out of OpenAI, and what it actually means to be an AI native leader — not the person doing all the building, but the person who understands what's possible.

Ready to level up your AI skills? Join the U of Digital AI Accelerator. Starts May 12th | Use code EARLYBIRDSLEARNAI for 20% off https://uof.digital/ai/accelerator/ Sponsored by Hightouch

New episodes every Monday. Get your AI Edge here.

Ep 22. AI Is Eating the Ad Industry — Who Wins and Who Gets Squeezed? with David Berkowitz, AI Marketers Guild20 Apr 202600:46:20

OpenAI wants to be a $100 billion ad business by 2030. Meta just overtook Google as the largest ad company in the world. Anthropic launched a new model, built a design studio, and is now worth more on the private market than OpenAI. And Allbirds — yes, the sneaker company — rebranded as an AI infrastructure company and watched their penny stock spike 600%.

This week, Shiv sits down with David Berkowitz, longtime marketing leader, community builder, and founder of the AI Marketers Guild at Marketecture, to make sense of a week where everything moved at once.

David breaks down why OpenAI's $100 billion ad ambition is a hell of a magic trick that requires nearly tripling their user base, why Meta's flood-the-feed strategy might not be as tenable as their revenue numbers suggest, and why Google — with nine billion-user-plus products and a 15-year head start building AI — is playing a much longer game than anyone is giving them credit for. He also explains why the seed and early-stage AI companies that felt safe six months ago should now be getting nervous, and why the "anti-AI" brand positioning trend is mostly companies talking out of both sides of their mouth.

They also get into what marketers should actually be doing with ChatGPT ads right now, why the organic vs. paid AI debate is just the Google search debate starting all over again, and how the industry has moved from Walmart calling a basic chatbot a "super agent" to an era where your audience is building their own agents and calling your bluff.

Ready to level up your AI skills? Join the U of Digital AI Accelerator. Starts May 11th | Use code EARLYBIRDSLEARNAI for 20% off https://uof.digital/ai/accelerator/ Sponsored by Hightouch

New episodes every Monday. Get your AI Edge here.

Ep 21. The AI Ad Economy Is About to Explode — Are You Ready? with Debra Aho Williamson, Sonata Insights13 Apr 202600:50:50

Sam Altman is either a visionary genius, a pathological liar, or both. OpenAI wants to be a $100 billion ad business by 2030. Anthropic dropped a mysterious model called Mythos that's apparently too powerful for the public to use. And the AEO/GEO industry has officially jumped the shark.

This week, Shiv and Myles sit down with Debra Aho Williamson, founder and chief analyst of Sonata Insights and writer of the fast-growing Substack The AI Ad Economy. Debbie spent nearly two decades at eMarketer building and leading their social media research practice — she was one of the first analysts to identify social media as a force that advertisers needed to take seriously. Now she's doing the same thing with AI.

Debbie breaks down why the organic reach window in AI platforms is closing faster than most marketers realize — and why Facebook's playbook of giving brands free reach and then taking it away is about to repeat itself in AI. She also shares why she bought a product she'd never heard of after ChatGPT recommended it, what that means for brand discovery, and why the explosion of AEO and GEO vendors is a sign the space has already jumped the shark.

They also get into whether OpenAI's industrial policy paper is genuine concern or brilliant PR, why Trade Desk's new Performance Mode is starting to look a lot like the black box ad networks that came before it, and why Time Magazine pitching branded content as an AI visibility play is either genius or a harbinger of chaos — depending on who you ask.

Ready to level up your AI skills? Join the U of Digital AI Accelerator. Starts May 11th | Use code EARLYBIRDSLEARNAI for 20% off https://uof.digital/ai/accelerator/

New episodes every Monday. Get your AI Edge here.

Ep 20. Who Actually Controls the AI Ad Stack? with Joe Root, Permutive06 Apr 202600:51:28

OpenAI just raised $122 billion at an $852 billion valuation — and apparently that only gives them 18 to 24 months of runway. They bought a live streaming network for over $100 million. They're building conversational ads with Smartly. Amazon is quietly opting every search advertiser into sponsored prompts inside Rufus. And Walmart is going the opposite direction entirely, building a native app inside ChatGPT.

This week, Shiv and Miles sit down with Joe Root, co-founder and CEO of Permutive, a data collaboration platform that sits at the intersection of media companies, agencies, and advertisers. Joe has a front-row seat to how AI is actually reshaping the ad stack — not in theory, but in the workflows his customers run every day.

Joe breaks down why AI is a tailwind for Permutive by dismantling the old agency margin model, why over half of his customers are now letting agents run tasks on their behalf — up from just 5% eighteen months ago — and why the real shift isn't replacing software, it's changing how humans interact with it.

They also get into why live content is the one thing AI can't replicate and what that means for publishers, why the native ad format for conversational AI is still completely unsolved, and why Amazon's sponsored prompts in Rufus might just be a repackaged version of a search arbitrage play that never really worked the first time around.

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Ep 19. AI Won't Save Your Brand If Agents Don't Know Who You Are, with Melissa Grady Diaz, Measured Wellness30 Mar 202600:51:00

OpenAI killed Sora. Disney pulled its billion-dollar commitment. The headlines called it proof that AI video is dead. It isn't. But the breathless takes — in both directions — are a pretty good sign that marketers are still figuring out how to think about all of this clearly.

This week, Shiv and Tameka sit down with Melissa Grady Diaz, former CMO of Cadillac and now a senior leader at health-tech startup Measured Wellness, to talk about what's actually changing for brand marketers right now — and what most people aren't paying enough attention to yet.

Melissa breaks down why performance marketing is about to have a real problem as agents take over the discovery layer, why brand building outside of paid media is becoming more important than ever, and why you should never fully hand your marketing over to a platform that's optimizing for response instead of brand health. She also gets into what it was like to experiment with AI at the CMO level at Cadillac, why incremental AI adoption can actually make things worse, and the right way to think about building from scratch versus improving what already exists.

They also cover Apple's surprising decision to open Siri up to any AI model, what it means that ChatGPT has become the Kleenex of AI — and why that brand equity might be slipping away — and why agentic commerce is happening whether the skeptics like it or not.

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Ep 18. The Ad Tech Plumbing That Makes Agentic Advertising Actually Work, with Brian Tomasette23 Mar 202600:43:10

Mark Zuckerberg says just tell AI what you want to sell and it handles the rest. Brian Tomasette — 25-year ad tech veteran, former Amazon DSP product leader, and current PhD researcher — says that's high school physics without friction. The business rules, privacy constraints, and data ownership that make advertising actually work don't disappear because the model is powerful enough. They just need better tools to operate them.

This week, Miles sits down with Brian to get into the real plumbing behind agentic advertising — what's actually being built today, how far off the utopian vision really is, and why the tools aren't going away anytime soon. Brian is currently researching neuro-symbolic AI at Drexel University and contributing to the IAB Tech Lab's AAMP framework, which is building the buyer and seller agent infrastructure that could eventually reshape how media gets bought and sold.

They break down why AI agents will use DSPs more optimally rather than replace them, what the IAB Tech Lab's buyer and seller agent SDKs actually do, and why Andrej Karpathy is right that it's not the year of agents — it's the decade. Brian also introduces the "AI vampire" phenomenon — the way vibe coding becomes as addictive as TikTok and drains you faster than actual genius work ever could — and why the right move is sometimes just closing the laptop and going for a hike.

Links from this episode:

AAMP — Agentic Advertising Management Protocol https://iabtechlab.com/standards/aamp-agentic-advertising-management-protocols/

IAB Tech Lab Buyer Agent Documentation https://iabtechlab.github.io/buyer-agent/

IAB Tech Lab Seller Agent Documentation https://iabtechlab.github.io/seller-agent/

Andrej Karpathy: "It's Not the Year of Agents, It's the Decade of Agents" https://www.youtube.com/watch?v=BlVnGXEzFow

The AI Vampire — Steve Yegge https://steve-yegge.medium.com/the-ai-vampire-eda6e4f07163

Beads — Steve Yegge's Claude Code library https://github.com/steveyegge/beads

Neuro-Symbolic AI Research Paper https://arxiv.org/abs/2510.05486

HAZ Lab at Drexel — Brian's Research Lab https://zharry29.github.io/hazlab/

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Ep 17. Is Agentic Commerce Dead or Just Delayed? Mailbag Edition with Shiv Gupta & Myles Younger16 Mar 202600:37:12

ChatGPT just paused its buy button. The agentic commerce skeptics are doing a victory lap. Shiv and Myles aren't buying it.

This week it's just the two of them — no guest, no guardrails — working through the biggest story of the week and a mailbag full of questions from the smartest people in the industry. They break down why ChatGPT backing off instant checkout is a strategic pause, not a retreat, why Amazon's real moat has nothing to do with software, and why the iOS App Store is the most useful analogy for understanding where AI commerce is actually headed.

They also get into Amazon's new sponsored prompts inside Rufus, a wave of AI product launches with increasingly questionable names, and why the utopian promise of the open internet is a pretty good warning sign for what's about to happen to AI.

Plus the mailbag: who's best positioned to build the standard for agentic buying, whether walled gardens will eventually swallow AI the way they swallowed the web, and the hair care products powering the AI Edge podcast.

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Ep 27. The Platforms Know Your Brand Strategy Better Than You Do — And That's a Problem, with Dr. Cecilia Dones, 3 Standard Deviations01 Jun 202600:52:10

Google just announced the biggest overhaul to search in 25 years. The blue links aren't going away — they're just being buried. AI mode is now the default. Agents can be dispatched from the search bar. Native checkout is live. And five new ad formats launched alongside all of it. Meanwhile, OpenAI is quietly moving toward a CPA pricing model for ChatGPT ads, Anthropic just hit $47 billion in ARR and may turn a profit this quarter, and Meta wants you to pay a subscription fee to escape the attention economy it built. Make that make sense.

This week, Shiv and Myles sit down with Dr. Cecilia Dones, founder of Three Standard Deviations and professor of AI and strategic communications at Columbia University and NYU. Dr. Dones helps organizations move from AI adoption to AI advantage — and she brings an academic rigor to the conversation that reframes some of the biggest stories in the industry in ways most people haven't considered.

Dr. Dones breaks down why Google's AI overhaul isn't just an ad product story — it's a governance story. As more brand strategy, planning, and creative decisions migrate inside platform walls, the algorithms will eventually know a brand's identity better than the brand does. She also explains why ChatGPT's pixel is a fundamentally different data asset than anything Google has ever had — because it doesn't capture what people searched for, it captures how people actually think. And she delivers the most actionable advice in the episode in one sentence: audit your brand in AI today, because it looks nothing like your SEO did.

They also get into why Meta charging a subscription fee to avoid ads is an oxymoron and a trust problem wrapped in one, why the measurement industry is quietly shifting back toward econometric modeling as platform attribution gets more opaque, and why "set it and forget it" always creates a PR disaster eventually.

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