ChatGPT Ads: The New Arbitrage for 2026

Steal our winning strategy to optimize your content for AI discovery: https://clickhubspot.com/hdo Attend Kieran's free Webinar on Reclaiming Strategic Time in the AI Era: https://hubs.la/Q040m6fn0 Shownotes Kipp and Kieran dive into the massive opportunity for marketers as ChatGPT and AI platforms launch new ad products. 0:00 Introduction - ChatGPT is Getting Into the Ads Game 1:00 The Opportunity - 900 Million Weekly Active Users 4:00 First Look at ChatGPT Ad Mockups 5:00 Transaction-Based Model vs Auction Model Rumors 6:00 OpenAI's Ad Principles - User Choice and Control 7:00 The Google AdWords Gold Rush Story 8:00 Simon Nixon - From Accountant to Billionaire on Google Ads 10:00 The AdSense Model and Jason Calacanis 12:00 Three Gold Rush Opportunities with ChatGPT Ads 13:00 Opportunity 1 - The Conversion Rate Arbitrage 14:00 Why ChatGPT Traffic Converts 10-13x Better 15:00 Intent-Based Ads vs Keyword-Based Ads 16:00 Opportunity 2 - Vibe Code Apps and Advertise Them 17:00 Using AEO Tools to Find Demand 19:00 Opportunity 3 - Citation Sites and Affiliate Plays 20:00 The Modern AdSense Model - Selling Citations 21:00 Why Paying for Citations is Hard to Enforce 22:00 How to Prepare Before the Ads Launch 24:00 Why OpenAI Needs to Give Us Targeting Data Ep. 396 Mentions ChatGPT ⁠https://chatgpt.com MoneySuperMarket ⁠https://www.moneysupermarket.com Host Links: 📲Kipp Bodnar,   / kippbodnar   📲Kieran Flanagan,   / searchbrat   ‘Marketing Against The Grain’ is a HubSpot Original Podcast // Brought to you by The HubSpot Podcast Network // Produced by Darren Clarke. About the Show Kipp Bodnar, HubSpot’s CMO and Kieran Flanagan Hubspot's SVP of Marketing, lead you down the rabbit hole of marketing trends, growth tactics and innovation. On the way you’ll pick up undiscovered strategies to give you that slight edge for success. These are not your typical twitter thread regurgitated marketing tactics that everyone is doing. These are new methods, with unfiltered examination of successful fresh ideas.