Podcast Description:

How do you complete 44 billboard acquisitions while building a scalable outdoor advertising company? Trailhead Media CEO John Murrow shares the strategies, mistakes, systems, and leadership lessons behind the company’s rapid growth.

John explains how Trailhead Media launched during COVID, completed multiple acquisitions within its first few months, and grew to approximately 3,300 billboard faces across the Southeast.

The conversation covers billboard lease negotiations, acquisition due diligence, remote operations, digital billboard investments, programmatic advertising, private equity, company culture, and the challenges of integrating billboard assets quickly.

This episode is for billboard operators, outdoor advertising professionals, independent media owners, sales leaders, and anyone interested in scaling an out-of-home advertising company.

Guest Website: https://trailheadmedia.com/

Time Stamps / Chapters:

00:00 Meet John Murrow of Trailhead Media

00:57 Launching Trailhead Media during COVID

03:07 John’s career in billboard real estate

03:47 Reducing billboard lease costs

06:11 Relationships and landowner negotiations

08:12 Moving from operations into the CEO role

11:20 Completing 44 billboard acquisitions

13:39 Acquisition mistakes and due diligence lessons

15:58 Trailhead’s more strategic acquisition approach

17:28 Building a remote billboard operating model

20:57 Growing outdoor advertising’s share of media

23:01 Billboard attribution and the 95-5 rule

27:48 Digital billboards and programmatic advertising

36:09 Building culture through acquisitions

42:20 What private equity misunderstands about billboards

46:28 John’s biggest leadership lesson

50:24 Why John loves the billboard industry

53:02 Final advice for building great teams

Tags:

billboard acquisitions, outdoor advertising, billboard industry, Trailhead Media, John Murrow, out of home advertising, OOH advertising, billboard company growth, billboard operations, digital billboards, programmatic advertising, billboard lease negotiations, billboard sales, outdoor media acquisitions, billboard business, remote operations, private equity billboard companies, billboard leadership

Hashtags:

#OutdoorAdvertising #BillboardIndustry #OOHAdvertising

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