Get the next conversation in your inbox

One signal-dense note when a new episode lands. No noise.

Join the list
Media
The Road to UNBOUNDEpisode 3

Reading the Signs

Hosts: Chris Carolan, George B. Thomas, Kyle Jepson, Casey Hawkins, Rob Jones

May 13, 2026

SharePost on X (opens in a new tab)Share on LinkedIn (opens in a new tab)

The crew reads the road signs on the way to UNBOUND 2026 — decoding how HubSpot chooses its headliners, what the Loop looks like five years in, and why the AI-era marketing playbook is being rewritten. Chris, George, Kyle, Casey, and Rob riff on speaker-selection strategy, change-management reality, and the provocative idea of a non-human headliner by 2027, all the way to Boston.

Chapters

  1. 00:01Cold Open and Show Welcome
  2. 00:53George's Household Reacts to Tom Brady
  3. 02:40Brady as Surprising Conference Headliner
  4. 03:24Celebrity Speakers: Insight or Entertainment?
  5. 04:41Mel Robbins, Yamini, and the Full Lineup
  6. 05:34The Marketing Power of Unexpected Speakers
  7. 07:40Dreamforce Detour and Mel Robbins Overlap
  8. 08:28Six Years of Themes: Reading the Signs
  9. 11:16Hindsight Confirms the Thematic Architecture
  10. 14:51Mel Robbins and the Let Them Theory
  11. 16:27Runway, Glean, and AI Tools at Unbound
  12. 22:07TBPN: Speed from Idea to Headliner
  13. 25:13Icebergs and the Loop Marketing Conspiracy
  14. 27:39Hubspot Culture Creates Its Own Luck
  15. 03:02Kyle on Eleven Years of Speaker Selection
  16. 06:45Over Under: When Does an AI Give the Keynote?

Transcript

This transcript was generated by AI and may contain errors. It is provided to help you skim and search the conversation.

Keep learning

You just watched the work. Now build it.

The next step is doing it yourself — live, with people on the same path.

See what is liveWhat it means to build here
Get the next conversation in your inbox

One signal-dense note when a new episode lands. No noise.

Join the list