Ep 23. AI Native or Dead: What It Really Takes to Transform a Business, with Mark Josephson, Executive Coach

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.

Ep 24. AI Is Making Ads Better — But Where Is All That Money Actually Going? with David Danziger, Dstillery

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