How Trailhead Media Was Built to Buy the Billboards No One Else Wanted
The founding thesis behind Trailhead: buy what nobody else wanted to spend the time on.
TRAILHEAD MEDIA · CEO PERSPECTIVE
When Trailhead Media co-founder and CEO John Murrow looks back at 2020, the opportunity he saw wasn’t glamorous. It was thousands of static, rural billboard faces sitting on long-term ground leases, owned by independent operators with no clear succession plan and no interest from the big national platforms chasing metro digital.
Fragmentation as the Opportunity
That overlooked corner of the out-of-home industry became the founding thesis at Trailhead: buy the operators nobody else wanted to spend the time on, bring them onto one platform, and run them well. Murrow co-founded Trailhead in 2020 and led its operations and real estate through the company’s rapid run of acquisitions, stepping into the CEO role himself in 2025 as the company moved into its next stage of growth. In under five years, that thesis became 46 acquisitions across nine states, making Trailhead the 10th largest out-of-home company in the country with more than 3,300 billboard faces.
The Seller Is the Deal
Murrow has written about what he learned along the way, including a lesson that shaped how Trailhead approaches every acquisition: in a fragmented industry, you’re not just buying a business, you’re stepping into a relationship the seller spent decades building.
“Your real job in the deal is not the model. It is making sure the seller feels seen and respected, and making sure they are walking away whole.”
That approach — respecting the local team, understanding the market before changing anything, and staying focused on the people behind every deal — is part of why Trailhead has been able to grow the way it has: one relationship, one market, and one billboard operator at a time. It’s the same philosophy behind Trailhead’s Sell Your Billboards program today.
For more on how that plays out deal by deal, read Trailhead’s Acquisition Diligence Checklist.
Read the full story from Trailhead’s CEO: “Buying the Billboard Business Nobody Wanted” on johnmurrow.com.