Season 2, Fourth Stop
Hosting
Season 2 · on the road since Oct 7, 2026
The Road to UNBOUND
Every episode is a stop on one road. Season one rode from the first ride in April to UNBOUND in Boston, and Season 2 drives on from there, with a new stop every Wednesday. Pick it up anywhere: scroll to drive it, or tap anyone to see their card.
Latest stop
Next stop: Oct 28, 10 AM Central · Season 2
Season 2, Third Stop
Why Don't People Ask for Help: Trust, a Witness, and Where Your Worth Comes From
This stop’s cover is being made. Until it lands, the video plays on its episode page.
On the bus
Chris
Rob
George
Casey
Kyle
ChrisRobGeorgeCaseyKyleStart
The first ride
Mile 1
First Ride
“And I think everybody needs to realize, like, that's what that event is kind of made for, is the heartfelt moments, the ability to transition and pivot and just be in the moment.”
— George B. ThomasOn the busChrisRobGeorgeCaseyKyleMile 2
Reading the Map
“But it's never been easier to get thoughts out of your head and turn them into value for others”
— Chris CarolanOn the busChrisRobGeorgeCaseyMile 3
Reading the Signs
“I suspect what has happened is the the event has established itself in such a way and the team has built the required connections that they don't have to rely on the intuitions of frontline employees at the company anymore, right?”
— Kyle JepsonOn the busChrisRobGeorgeCaseyKyleMile 4
Finding Your Lane
“I think what does make a difference though is if you have a speaker video that shows you giving a real talk to a real audience, that's going to make it so much easier for the person evaluating your application to know what you're actually offering than if it's just like you in your bedroom, uh, talking about how great you're going to do.”
— Kyle JepsonOn the busRobGeorgeCaseyKylePit Stop
The Next Five Years Won't Reward the Smartest People
The Road to UNBOUND pulls into South Florida for a conversation with marketing's most quotable headliner, Jay Schwedelson.
Passenger
“Stupider people have done it.”
— Jay Schwedelson On the busChrisRobMile 5
Surviving Boston
Before you set foot in the MCEC, the bus pulls over for the stuff nobody preps you for.
“And so now when I think of the conference, when I think of HubSpot, it's that much more fond because of the things that happened surrounding it.”
— Rob JonesOn the busChrisRobGeorgeFailure, Grit, and the Stories Behind the Hosts
This week the Road to UNBOUND pulls off the highway and gets personal.
“Look for those moments where people are willing to be vulnerable because they're teaching you real stuff at that moment, like they're legit.”
— George B. ThomasOn the busChrisRobGeorgeCaseyKyleRevenue Hub Lands, the Agenda Drops, and Why Philosophy Beats Tactics
Commerce Hub is gone — say hello to Revenue Hub.
“We don't have a way of looking at an individual person and understanding what is in their heart and mind and what they intend to do.”
— Kyle JepsonOn the busChrisRobGeorgeKyleThe Road to UNBOUND rolls on.
“There is no experiential substitute for proximity.”
— Rob JonesOn the busChrisRobCaseyKyleThe ROI Question
Boston Tickets, Breeze Credits, and the Dashboard That Can't Exist
Rob is in Oklahoma, so Chris Carolan, George B. Thomas and Kyle Jepson take the question everyone has been asking this week and ask it twice.
“Or I could sit back and I could let, even as a boss, let go of control and let serendipity win the day.”
— George B. ThomasOn the busChrisGeorgeCaseyKyleSeven Weeks Out
Show Us Your AI Build, and Why the Real One Is Invisible
Seven weeks out from Boston, the ride goes four-up: Rob Jones driving, George B. Thomas broadcasting from a half-unpacked new headquarters, Kyle Jepson on the eve of a month away, and Chris Carolan.
“If you're the sort of person who tends to speak up, you should you should make space for other people. But if you're the sort of person who tends to hold back, speak up.”
— Kyle JepsonOn the busChrisRobGeorgeKyleFive Weeks Out
They Named Twenty-Five Rooms, and Sessions Are One Fifth of It
Five weeks to Boston, and this week the show reads the page instead of talking around it.
“It should go without saying. It doesn't go without saying anymore. So I'm saying it. The people do matter that are building it.”
— Rob JonesOn the busChrisRobCaseyOffice Hours
Build Your Own Harness, or Outsource Your Understanding?
The first Office Hours on the road to Boston, and it belonged to the guest.
Passenger
“This feeling is unbound for me now.”
— Shubham Nigam On the busChrisRobGeorgeCaseyFour Weeks Out
Two First-Timers, and the Mathematics of One
Four weeks out, and for the first time on a Wednesday the guests let themselves in.
Passengers
“The underlying thread of all content creation is human connection. So in the world of AI, we are thirsty for connection and for stories.”
— Sheri Otto On the busChrisGeorgeOffice Hours
Return on Involvement, and Where the Serendipity Actually Happens
Office Hours, four weeks out, and the two guests are at opposite ends of the same road.
Passengers
“By the time you can articulate the question, that's not the problem that you're trying to solve anymore.”
— Joshua Oakes On the busChrisRobGeorgeCaseyThree Weeks Out
The Word, Not the Event
The plan for this one was reservations.
Passenger
“It's so basic, but just do it.”
— Will DePeri On the busChrisRobGeorgeCaseyOffice Hours
Crossing an Ocean for the Part Nobody Schedules
Office Hours, twenty days out, two guests and no script.
Passengers
“There's not enough like real stories from just customers that don't feel like it's like a sales pitch.”
— Matthew Ruxton On the busChrisRobGeorgeCaseyRegistration Day
Picking My Sessions Live
“There is a natural aggregation. You don't actually need an algorithm. It can actually drive itself.”
— Nico LafakisOn the busChrisTwo Weeks Out
An Orange Suit, an Inflatable Alien, and What a Personal Brand Actually Is
Session reservations opened to the rest of the ticket holders on Tuesday, and the first stretch of this one is the table comparing notes on what happened when they clicked.
Passenger
“You have a human to human connection and then we start a serious discussion.”
— Klemen Hrovat On the busChrisRobGeorgeKyleOffice Hours
The Decision Engine and the Scaffolding Nobody Took Down
Office Hours is the informal half of The Road to UNBOUND.
Passengers
“It's done like that because that's the way it's always been done like that rather than kind of standing still and reflecting on whether that's still working.”
— Hannah Fisher On the busChrisRobGeorgeOne Week Out
Rob Tries to Start an Argument About Whether the Humans Still Matter
One week out, all five hosts are in the room, and the show never gets to the schedule.
Passenger
“What AI and you know, technology has yet to replace is heart.”
— Caroline Prettyman On the busChrisRobGeorgeCaseyKyleOffice Hours
The Last One Before Boston: Know Thyself, Then Find the Human Who Slowed Down
Office Hours is the informal half of The Road to UNBOUND.
Passenger
“Progress is not comfortable.”
— Sarah Lane-Hawn On the busChrisGeorgeCaseyA stop, not the end
Boston
UNBOUND 2026 · September 16-18, 2026
Boston Convention & Exhibition CenterThe bus got there.
UNBOUND 2026 Reflections
Already on the Road to Next Year, and the Gems Are in the Rejects
“Every field in the CRM is a decision about what to forget. And if you take a customer apart, you damn well better be able to put them back together.”
— Rob JonesOn the busChrisRobGeorgeCaseyKyleThe first show after Boston opened by calling the road finished.
“Welcome back again to the road to unbound not sure if we can still call it that because the road has officially ended as of about three o'clock eastern last friday”
Rob JonesUNBOUND 2026 Reflections · Sep 23, 2026 · 00:01Then Kyle disagreed.
“But yeah, Rob, the one thing I will disagree with you on is I am already on the road to Unbound. I'm feeling pretty good about things I want to do next year. And I'm delighted I have twelve months to figure out how to do them.”
Kyle JepsonUNBOUND 2026 Reflections · Sep 23, 2026 · 06:49And Rob closed the hour by agreeing.
“It continues. It is not over. We are on to the next.”
Rob JonesUNBOUND 2026 Reflections · Sep 23, 2026 · 52:51George had already said what the word means, back on Aug 13, 2026.
“But an unbinding or a human being unbound from the things that they once couldn't do is a very interesting concept to think about when you think about the event and the connections and the tech and the everything that we're talking about.”
George B. ThomasOffice Hours · Aug 13, 2026The Road To UNBOUND is not just about getting you to the event. It is about getting you to the mindset.
Chris CarolanDriver The Road to UNBOUND
Season 2
It starts here, on Wednesday, October 7, 2026.
A new stop every Wednesday.Season 2, First Stop
AI Taking the Joy Out of the Work: Passing Plates or Cooking, and Don't Delegate the Things You Love
On the busChrisRobCaseyKyleSeason 2, Second Stop
AI-Native Teaching and Learning: Ask for an Immersive Experience, Not a PowerPoint Deck
On the busChrisGeorgeCaseyKyleSeason 2, Third Stop
Why Don't People Ask for Help: Trust, a Witness, and Where Your Worth Comes From
This stop’s cover is being made. Until it lands, the video plays on its episode page.
On the busChrisRobGeorgeCaseyKyleSeason 2
The road ahead
A new stop every Wednesday.
Next stop: Season 2, Fourth Stop, Wednesday, October 28, 2026.
