Mile 1 — First Ride
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The Road to UNBOUNDEpisode 1
First Ride
Hosts: Chris Carolan, Rob Jones, George B. Thomas
April 29, 2026 · 45:35
The first ride. Rob Jones takes the wheel as tour guide, Chris Carolan drives, and George B. Thomas climbs aboard for the inaugural Road to UNBOUND. The Mayor of Inbound earns his title, AI in the HubSpot ecosystem gets the first hot take of the season, and the Inbound slip counter starts at zero—for now.
Chapters
- 00:01Welcome Aboard: Hosts Introduce the Show
- 00:54What Is Unbound? Defining the Conference
- 01:53Rob's Orange Suit Origin Story
- 03:44Chris Finds His People at Inbound 2023
- 07:50The Show's Purpose: More Than a Conference
- 10:47First Stop: George B. Thomas Boards in NC
- 13:14George's 14 Years and a HubSpot Academy Moment
- 17:42Driving North: Casey Hawkins Joins the Bus
- 19:50Casey's First Conference and Internet Friends Made Real
- 21:27Advice for the FOMO-Struck and Conference-Skeptical
- 23:50Kyle Jepson's Stop: Boston Already
- 25:09Naming the Thing: Inbound vs. Unbound Ruling
- 26:45Kyle's Admin Session That Changed Everything
- 28:40Unbound's Expanding TAM and the Generalist Era
- 33:32Grow Better: Detaching Identity to Keep Growing
- 44:33Arrived at Boston — Road Trip Wraps
Transcript
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On the bus
Chris Carolan
Driver
Rob Jones
Tour Guide
George B. Thomas
Hallway Philosopher