Season 2 · on the road since Oct 7, 2026
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.
A new stop every Wednesday · Season 2
Season 2, Fourth Stop
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 set the context.
This stop’s cover is being made. Until it lands, the video plays on its episode page.
Chris
Rob
George
Casey
KyleStart
The first ride
Mile 1
“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. ThomasChrisRobGeorgeCaseyKyleMile 2
“But it's never been easier to get thoughts out of your head and turn them into value for others”
— Chris CarolanChrisRobGeorgeCaseyMile 3
“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 JepsonChrisRobGeorgeCaseyKyleMile 4
“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 JepsonRobGeorgeCaseyKylePit Stop
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.”
ChrisRobMile 5
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 JonesChrisRobGeorgeThis 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. ThomasChrisRobGeorgeCaseyKyleCommerce 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 JepsonChrisRobGeorgeKyle“There is no experiential substitute for proximity.”
— Rob JonesChrisRobCaseyKyleThe ROI Question
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. ThomasChrisGeorgeCaseyKyleSeven Weeks Out
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 JepsonChrisRobGeorgeKyleFive Weeks Out
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 JonesChrisRobCaseyOffice Hours
The first Office Hours on the road to Boston, and it belonged to the guest.
Passenger
“This feeling is unbound for me now.”
ChrisRobGeorgeCaseyFour Weeks Out
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.”
ChrisGeorgeOffice Hours
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.”
ChrisRobGeorgeCaseyThree Weeks Out
The plan for this one was reservations.
Passenger
“It's so basic, but just do it.”
ChrisRobGeorgeCaseyOffice Hours
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.”
ChrisRobGeorgeCaseyRegistration Day
“There is a natural aggregation. You don't actually need an algorithm. It can actually drive itself.”
— Nico LafakisChrisTwo Weeks Out
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.”
ChrisRobGeorgeKyleOffice Hours
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.”
ChrisRobGeorgeOne Week Out
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.”
ChrisRobGeorgeCaseyKyleOffice Hours
Office Hours is the informal half of The Road to UNBOUND.
Passenger
“Progress is not comfortable.”
ChrisGeorgeCaseyA stop, not the end
Boston
UNBOUND 2026 · September 16-18, 2026
Boston Convention & Exhibition Center
The bus got there.
UNBOUND 2026 Reflections
“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 JonesChrisRobGeorgeCaseyKyleThe 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.
The Road to UNBOUND
It starts here, on Wednesday, October 7, 2026.
A new stop every Wednesday.
Season 2, First Stop
ChrisRobCaseyKyleSeason 2, Second Stop
ChrisGeorgeCaseyKyleSeason 2, Third Stop
This stop’s cover is being made. Until it lands, the video plays on its episode page.
ChrisRobGeorgeCaseyKyleSeason 2, Fourth Stop
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 set the context.
This stop’s cover is being made. Until it lands, the video plays on its episode page.
ChrisRobGeorgeCaseyKyle
