The Acquisition Checklist Trailhead's CEO Built From 46 Billboard Deals
The practical diligence process John Murrow built from evaluating every deal, 46 times over.
TRAILHEAD MEDIA · CEO PERSPECTIVE
Trailhead Media has closed 46 acquisitions in under five years, growing from zero to a nine-state billboard network. Along the way, CEO John Murrow built a practical diligence process for evaluating every new deal — one he’s since written about in detail for other operators considering the same path.
Walk the Inventory, Meet the Team
The process starts well before closing: reviewing trailing financials, physically walking a meaningful sample of the inventory, and meeting the operators, bookkeepers, and installers who actually run the business day to day. Murrow has been direct about why that matters.
“Sellers who hide their team are usually hiding something about the team.”
The diligence continues through close, confirming lease portfolios against what’s on paper, understanding customer concentration, and having honest conversations with the seller about what’s realistic going forward — not just what the model assumes.
Integration Starts on Day One
Trailhead’s team commits to being on-site within 14 days of every closing — the same standard behind Trailhead’s own acquisition process for sellers — and to communicating directly with every customer in the business within the first 30 days. It’s a pattern the team has refined over more than 40 deals, and one Murrow credits with keeping every acquisition Trailhead has made a success.
For the lessons that came out of applying this checklist 46 times, read Lessons From 46 Billboard Acquisitions in Five Years.
Read the CEO’s full acquisition checklist: “The Acquisition Checklist I Wish I Had Read in 2020” on johnmurrow.com.