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

Keywords:

billboard acquisitions

outdoor advertising growth

billboard company operations

Trailhead Media CEO

John Morrow interview

billboard lease negotiations

digital billboard investment

programmatic billboard advertising

remote billboard operations

outdoor advertising leadership

billboard acquisition strategy

out-of-home advertising

billboard company culture

billboard due diligence

private equity billboards

Building a successful billboard company takes far more than finding a good location. In this episode of The Bell Board Podcast, Neil Bell sits down with Matt Schulze of Selective Structures to talk billboard construction, digital billboard strategy, and the lessons of a 30+ year career in out-of-home (OOH) advertising.

Matt shares the wild story of how a bear costume unexpectedly launched his career, wood-pole vs. steel-monopole construction, why billboard maintenance gets overlooked, what makes a billboard truly "digital-ready," building stadium scoreboards and major sign projects, and what he believes the next generation of OOH operators needs to focus on.

Guest: Matt Schulze — Selective Structures (selectivestructures.com)
Host: Neil Bell — New South Outdoor (newsouthoutdoor.com)

0:00 Introduction & meet Matt Schulze (Selective Structures)
1:03 The bear costume story that started a billboard career
4:24 Leaving radio for the billboard business
7:31 Tommy Teepell's influence & finding success in billboards
9:21 Why billboard companies should work together
11:10 How the billboard industry has changed over 30 years
14:55 Why every billboard should be built digital-ready
17:30 Wood pole vs. steel monopole billboards
20:04 Common mistakes new billboard owners make
27:29 Billboard maintenance: paint, head bolts & longevity
32:04 Billboard safety & protecting installation crews
39:57 Wind frames vs. panels for hurricane-prone markets
41:27 Rising steel costs & how to compare billboard structures
45:00 Building stadium scoreboards & major sign projects
47:32 Digital billboard strategy & buying the right equipment
55:10 Billboard advertising around the world
59:23 Creative billboard permitting & using AI responsibly
1:02:24 Economic cycles in the billboard industry
1:04:08 Billboard investing & return on investment (ROI)
1:05:43 Matt's biggest career lesson
1:08:02 Advice for the next generation of billboard operators
1:10:36 Closing thoughts

This episode is supported by:
Drachman M&A Co. — the outdoor advertising industry's M&A advisory firm. drachmanco.com
SignDash — billboard sales & inventory management software for independent OOH operators. signdash.com

#Billboards #OutdoorAdvertising #OOH #DigitalBillboards #BillboardConstruction

AI is rapidly changing billboard sales, but technology alone isn't enough. In this conversation, Kevin Gephart shares why successful out-of-home advertising starts with better sales thinking, stronger client relationships, and selling ideas instead of inventory.

Whether you're an independent billboard operator, sales manager, media executive, or advertising professional, this episode explores practical strategies for improving sales performance, leveraging AI, building better compensation plans, and helping advertisers achieve stronger marketing results.

Kevin also explains why local advertising remains one of the biggest untapped opportunities in out-of-home advertising and why operators should focus on growing the overall advertising pie—not just competing with other billboard companies.

Guest: Kevin Gephart - https://oohsalesfaster.com/

Sponsors:

Stark Capital - https://starkcapitalsolutions.com/

Selective - https://www.selective.com/

Time Stamps / Chapters:

00:00 AI Is Changing Billboard Sales

01:00 Kevin Gephart's Background

05:14 Selling Ideas Instead of Billboard Space

10:20 Why Cold Calling Still Works

11:47 Using AI as a Sales Assistant

14:08 Why Short Advertising Campaigns Fail

18:19 Winning in Smaller Local Markets

23:22 Vendor Partnerships & Digital Opportunities

27:30 Stop Competing Only With Other Billboards

37:35 Sales Compensation & Incentives

46:06 Explaining Digital Billboards to Advertisers

53:17 Working With Advertising Agencies

01:00:08 What Has Become Harder About Selling Advertising

01:05:05 The One Mindset Shift Every Billboard Operator Needs

YouTube Tags:

billboard advertising, billboard sales, out of home advertising, OOH advertising, billboard marketing, AI in sales, AI for advertising, digital billboards, advertising sales, sales training, Kevin Gephart, OOH Sales Faster, local advertising, media sales, billboard operator, advertising strategy, cold calling, sales management

Hashtags:

#BillboardAdvertising #OutOfHome #SalesTraining

Keywords:

billboard sales strategy

out of home advertising

OOH advertising sales

AI for sales teams

billboard sales training

digital billboard marketing

local advertising strategy

media sales coaching

cold calling techniques

advertising sales management

billboard operator tips

creative billboard advertising

sales compensation plans

AI for prospecting

Kevin Gephart interview