Markets in the midst of technological change tend to have two camps. One is the legacy incumbents that have strengths in their brands and the other in upstarts that are nimbler. In digital media, it turned out brand won. At Possible, The Rebooting held TRB Conversations, a series of podcast discussions with media leaders on what they’re betting on. The connective tissue that emerged is that publishers are leaning more heavily on the value of their brands as they reorient their businesses to focus less on scale and more on depth. This episode features conversations with Shachar Oren, CMO/CRO of EX.CO; Brendan Spain, vp of advertising for the Americas, The Financial Times; Rachael Savage, svp of ad revenue operations, Hearst Magazines; and Avi Zimack, chief growth officer, Bustle Digital Group. Chapters: 00:00 Welcome 00:57 EX.CO 01:20 CTV Meets Digital Lessons 02:45 Closing the CTV Budget Gap 06:49 All Screens Advertising Future 09:10 Measurement and Agentic Shift 11:32 FT Brand Safety Reality 14:29 FT Video and Paywall Growth 16:39 Global Brand Advantage 22:20 Hearst Brands Need Playbooks 25:34 Scale vs Niche Monetization 28:16 Hearst AI and Data Backbone 33:06 BDG Pivot to Activations 37:50 Influencers and Brand Seals 43:57 Events Plus Data Flywheel