On this week’s Bell Board Podcast Trailhead Media CEO John Murrow talks about the pros and cons of having an equity fund as a business partner. Trailhead Media is backed by Viking Global Investors. What’s Viking like as a partner? Having Viking is a partner has been really good for […]
Tag: trailhead media
John Murrow on converting statics to digital billboards
On this week’s Bell Board podcast Trailhead CEO John Murrow talked about digital billboards. Digital billboards account for 305 of Trailhead’s 3,300 faces. How do you decide when to upgrade from a static to digital So for us to convert a static to a digital, we want it to […]
John Murrow on managing lease costs
Neil Bell of the Bell Board Podcast released a podcast interview with Trailhead CEO John Murrow this week. We will run excerpts from the podcast. Today Murrow talks about managing lease costs.. Getting started in out of home. I started with Adams Outdoor as a real estate rep. Soon moved […]
Trailhead Media’s Carl Hutchinson Says Be Wary of Lease Inflators
A few weeks ago out of home leasing and development expert told our readers to be cautious about billboard lease escalator clauses. Trailhead Media Assistant Director of Real Estate agrees: From my experience, this is exactly where many OOH deals quietly go wrong. I’ve seen leases that looked completely reasonable […]
John Murrow New CEO at Trailhead
Randy Otto is stepping down as CEO at Trailhead Outdoor effective May 1. Otto had been the company’s CEO since 2022. Trailhead’s Chief Operating Officer John Murrow will become CEO. An email was sent to Trailhead employees announcing the transition. About Trailhead Media Trailhead Media is is a private out […]
Trailhead for sale?
Billboard Insider hears from multiple sources that Trailhead Media is testing the waters on a sale. Trailhead’s lead investor Viking Global has been in the investment since 2020 and we assume they will be calling the shots. Trailhead has approximately 3,500 faces including 260 digital faces, clustered in the North […]
Trailhead Media Acquires See Rock City Structures in TN, GA, AL & NC
For Immediate Release June 8, 2023 See Rock City is pleased to announce the sale of its 77 out of home advertising faces in Tennessee, Georgia, Alabama, and North Carolina to Trailhead Media. Williamson & Associates acted as exclusive broker and advisor to the seller. This transaction is a special […]
Randy Otto on Trailhead Media’s Latest Acquisition
Last month Trailhead Media purchased 18 total billboard faces including 12 digital billboard faces from Billboards for Education, a Tennessee out of home operator owned by Matt Richman. The acquisitions gives Trailhead approximately 3,306 total faces including 236 digital faces. Billboard Insider talked to Trailhead CEO Randy Otto about the […]
Short Versus Multi-Year Ad Contracts. What Do You Do?
In our company of the day feature today Brad Sourbeer of Parker Outdoor talks about his push for long-term ad contracts. Many presenters at the fall 2022 IBO show talked about long term ad contracts: Huntington Outdoor CEO Justin Powell says long term contracts are recession prep. The best time […]
Robert MacMillan Out as CEO of Trailhead Media
Billboard Insider confirmed, through multiple sources that Viking Global the owner of Trailhead Media and CEO Robert MacMillan have agreed that MacMillan will step down from his role as CEO of the rapidly growing Out of Home company. The separation from his CEO role was effective February 22nd and employees […]



















