Ep 22. AI Is Eating the Ad Industry — Who Wins and Who Gets Squeezed? with David Berkowitz, AI Marketers Guild

Ep 29. Agentic Marketing Is Here — But Can AI Actually Stay On Brand? with Kashish Gupta, Hightouch

Amazon just launched Alexa Plus Agentic Ads — native checkout through voice, shoppable ads across third-party publishers, and a monetization machine that just keeps accelerating. WPP and Horizon are building agent-to-agent infrastructure. Databricks announced an agentic CDP. And Hightouch made a public offer for LiveRamp's identity spine while simultaneously raising at a $2.75 billion valuation. This week, Shiv and Myles sit down with Kashish Gupta, co-founder and co-CEO of Hightouch, to make sense of all of it. Hightouch works with some of the largest B2C brands in the world — Domino's, Spotify, and others — helping them do their marketing end-to-end in an AI native way. And Kashish has a clearer view than almost anyone of where the technology actually is versus where the hype says it is. Kashish breaks down the number one complaint he hears from CMOs right now — AI still can't reliably stay on brand, no matter which foundation model you use — and why getting from 80% to 99.9% accuracy is the hard engineering problem nobody is talking about. He also explains why AI probably shouldn't own media buying yet — you can't fire your AI, and having a throat to choke for the metric still matters — and why the right model is a proactive insights engine with human discretion at the center, not autonomous agents running everything unchecked. They also get into why agentic voice advertising isn't ready yet — the AI still can't think fast enough while you're talking — why Databricks building audiencing capabilities is actually good news for Hightouch, and why Hightouch's offer for LiveRamp's identity spine is less about competition and more about keeping identity neutral and accessible for the brands that need it most. Learn more about the AI Literacy Alliance at uof.digital/alliance New episodes every two weeks. Get your AI Edge here.

Ep 28. Apple Finally Showed Up to AI — And the Ad Industry Should Be Paying Attention, with Chris Kelly, Upwave

Apple announced its long-awaited Siri overhaul — and the reviews are basically "welcome to 2023." It's built on Gemini under the hood, while Apple simultaneously runs a privacy campaign aimed squarely at Google. Meanwhile, SpaceX went public at a two-trillion-dollar valuation, Anthropic and OpenAI both filed for IPOs with wildly different burn rates, and Anthropic dropped a new model called Mythos that's apparently too dangerous for the public to touch. This week, Shiv flies solo with Chris Kelly — founder and CEO of Upwave, his neighbor and friend — for a conversation that ranges from Apple's AI catch-up to the economics of the AI arms race to what real, concrete AI transformation looks like inside a measurement company. Chris breaks down why nobody should hold a year-old AI opinion against a current AI model — a year is "light years" in this space — and why Apple's massive iPhone distribution and head start on voice could let it make up ground faster than its brand reputation suggests. He also makes the case that AI conversations reveal far richer upper-funnel context than search ever could, opening up entirely new categories of ad units that don't exist today. And he pushes back on one of the most common AI marketing claims out there: that AI collapses the consumer journey. Some purchases still take three years, AI or not. They also get into why Anthropic going public might eventually mean an ads business — Super Bowl irony and all — why Google's AI strategy is really about embedding AI into every surface it owns rather than building a destination app, and why predictive brand lift could triple how much of the industry's advertising actually gets measured. Learn more about the AI Literacy Alliance at uof.digital/alliance New episodes every two weeks. Get your AI Edge here.

Ep 27. The Platforms Know Your Brand Strategy Better Than You Do — And That's a Problem, with Dr. Cecilia Dones, 3 Standard Deviations

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. Learn more about the AI Literacy Alliance at uof.digital/alliance New episodes every two weeks. Get your AI Edge here.

Ep 26. AI Bias Is a Business Problem — Not Just an Ethics One, with Stefanie Beach & Nadia Koski

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 [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 [https://bit.ly/3RMqCrJ]

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

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/ [https://uof.digital/ai/accelerator/] Sponsored by Hightouch New episodes every Monday. Get your AI Edge here.