Lessons From 46 Billboard Acquisitions in Five Years
CEO John Murrow on the lessons that came from the integrations, not the deals themselves.
TRAILHEAD MEDIA · CEO PERSPECTIVE
Trailhead Media’s growth story is often told in numbers — 46 acquisitions, nine states, more than 3,300 billboard faces in under five years. CEO John Murrow has been candid that the harder, less quotable lessons came from the integrations, not the deals themselves.
The Team Is the Asset
One lesson Murrow returns to often: the value of an acquisition isn’t just the inventory, it’s the local operators who know the market. Deals where Trailhead retained and invested in the existing team consistently outperformed the ones where the team wasn’t the focus.
“The CEO has to stay in the deals. Not in the spreadsheet. In the deals… The seller is buying the future of the business. They want to look the future leadership in the eye.”
That’s meant Murrow staying personally involved in relationship-building through all 46 deals, rather than delegating that work to a transaction team — a discipline he credits with why every acquisition Trailhead has made is still part of the network today.
Measuring the Right Things
Rather than tracking deal count, Trailhead’s team measures success by billboard performance, team retention, and customer retention well after a deal closes — a longer view that Murrow says made the whole program more disciplined over time.
The diligence process behind those 46 deals is laid out in Trailhead’s Acquisition Diligence Checklist.
Read the CEO’s full reflection: “What I Learned From 46 Acquisitions in Five Years” on johnmurrow.com.