Chris Carolan
Driver
A weekly ensemble show · Wednesdays 10 AM Central
The Road to UNBOUND
Five hosts. One bus. Wednesdays between now and Boston. Talking around HubSpot, not about it. Entertaining first. Educational second. Humanity at all costs.
Wednesdays to Boston
Show type
Weekly ensemble
Cast
Five hosts
Run
Now → Sept 2026
Destination
Boston, MA
02 / Latest
From the Last Stop
The most recent episode that's already aired. Everything else lives in the archive.
Mile 4 — Finding Your Lane 
Finding Your Lane
Rob takes the wheel for a sports-radio "hot takes" round on the question every would-be speaker is asking: how do you actually get selected for the UNBOUND stage? George B. Thomas and Kyle Jepson — both confirmed 2026 speakers — agree and disagree their way through speaker reels as proof of stage presence, submitting multiple topics, and the cardinal sin of pitching your business instead of serving the audience. Plus the surprise reveal of two new co-host speakers and George's pivot from a rejected AI talk to filling a gap the UNBOUND team needed filled.
May 20, 2026
01 / Cast
Five Hosts, One Frame
Five voices, one bus, one shared road. Click through for the full bio.
03 / Clips
Recent Cuts
Highlights from the road, vertical-cut for the feed.
Featured
Find Your Unique Event Fit
Featured
Focus on Audience, Not Business
Featured
Speaker Selection: Not Easy at All
Balancing Breadth and Depth at a Conference
Casey and Rob on Unique Speaking Topics
Crafting Compelling Event Proposals
04 / Countdown
Boston, In…
September 16, 2026. Boston Convention & Exhibition Center. The bus arrives.
Boston · UNBOUND
99Days
07Hours
50Minutes
03Seconds