The Road to UNBOUND
Arrived in Boston
Five hosts talking around HubSpot, not about it. A weekly ensemble show riding from now through UNBOUND 2026, entertaining first, educational second.
This show has its own home.
The Road to UNBOUND runs its own site at theroadtounbound.com — the full schedule, the hosts, and how to be part of it live there. Studios is where it connects to the rest of the work.
Episodes
The Road to UNBOUND
Reading the Map
The crew breaks down the UNBOUND 2026 agenda for the first time on the show — what to make of the session tracks, which keynotes hint at the bigger story, and…
Watch the episodeThe Road to UNBOUNDOctober 28, 2026
The Road to UNBOUND - Season 2, Fourth Stop: Is This Cheating? A Lullaby, Guilt, and Where You Put the Effort
Rob Jones drove the fourth stop of the second season with Chris Carolan, Casey Hawkins, George B. Thomas and Kyle Jepson, and he left to get a prop while Chris…
Open the episodeThe Road to UNBOUNDOctober 21, 2026
The Road to UNBOUND - Season 2, Third Stop: Why Don't People Ask for Help: Trust, a Witness, and Where Your Worth Comes From
Rob Jones drove the third stop of the second season with Kyle Jepson, George B. Thomas, Chris Carolan and Casey Hawkins, and he brought a question out of the…
Open the episodeThe Road to UNBOUNDOctober 14, 2026
The Road to UNBOUND - Season 2, Second Stop: AI-Native Teaching and Learning: Ask for an Immersive Experience, Not a PowerPoint Deck
Chris Carolan drives Season 2's second stop with Kyle Jepson, George B. Thomas and Casey Hawkins: what teaching and learning look like when we can all create…
Open the episodeThe Road to UNBOUNDOctober 7, 2026
The Road to UNBOUND - Season 2, First Stop: AI Taking the Joy Out of the Work: Passing Plates or Cooking, and Don't Delegate the Things You Love
Kyle Jepson gave the first stop of Season 2 the question the hour kept returning to: "…when we're working with AI, are we just passing plates or are we…
Open the episodeThe Road to UNBOUNDSeptember 23, 2026
The Road to UNBOUND - UNBOUND 2026 Reflections: Already on the Road to Next Year, and the Gems Are in the Rejects
Kyle Jepson's take on the week after UNBOUND 2026 is a disagreement: "I am already on the road to Unbound." He is answering Rob Jones, who opened the show by…
Open the episodeThe Road to UNBOUNDSeptember 1, 2026
The Road to UNBOUND - Registration Day: Picking My Sessions Live
Registration opens and Chris builds his UNBOUND schedule live and unplanned — picking, in his own words, "based on the who. And not necessarily the what." Four…
Open the episodeThe Road to UNBOUNDJuly 29, 2026
The Road to UNBOUND - Seven Weeks Out: Show Us Your AI Build, and Why the Real One Is Invisible
Four hosts, seven weeks from Boston. Session signup dates and Kyle's 21 pre-built videos for his month away — then an unplanned hour on feeling behind, asking…
Open the episodeThe Road to UNBOUNDJuly 22, 2026
The Road to UNBOUND - The ROI Question: Boston Tickets, Breeze Credits, and the Dashboard That Can't Exist
Rob is on vacation, so Chris, George and Kyle ask the ROI question twice: is a trip to UNBOUND defensible on a spreadsheet, and can you prove what an AI credit…
Open the episodeThe Road to UNBOUNDMay 13, 2026
Reading the Signs
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…
Open the episodeClips
240 short cuts from The Road to UNBOUND — most under a minute, straight into the conversation.
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