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

What happens after the billboard sale is often where the real work begins. In this episode, we sit down with Behind The Board founder Becky Smith, a billboard operations specialist who helps independent operators streamline their businesses and reclaim their time. Becky has spent years managing the day-to-day operations of multi-market billboard companies, working directly with advertisers, installers, printers, and owners to keep campaigns running smoothly.

We discuss the operational challenges that can slow growth, including campaign scheduling, advertiser communication, proof-of-performance reporting, billing, documentation, and digital billboard management. Becky shares why many operators don't need more sales—they need better systems and support behind the scenes to handle everything that happens after a contract is signed.

The conversation also explores delegation, scaling an out-of-home advertising business, building efficient workflows, and creating processes that allow owners to focus on growth rather than getting buried in daily administrative tasks.

Whether you're an independent billboard operator, out-of-home advertising professional, or entrepreneur looking to build a more efficient business, this episode is packed with practical insights on operations, organization, and sustainable growth.

Learn more about Becky and Behind The Board:
behindtheboard.io

00:14:32 IBO Growth and Bigger Industry Events

00:18:29 Why Panels Deliver the Most Value

00:20:53 Learning Through Industry Networking

00:23:05 What Successful Billboard Operators Do Well

00:26:16 Bootstrapping vs Private Equity in Billboard Advertising

00:28:20 Why Billboard Businesses Aren't Traditional Real Estate

00:30:08 Growth Challenges and Delegation

00:35:27 Digital Billboards and Industry Change

00:37:13 Consolidation and the Future of Independent Operators

00:40:19 Attribution, Metrics and Advertiser Expectations

00:42:21 The Challenge of Measuring Out-of-Home Advertising

00:45:15 Launching a New Business Venture

00:48:20 Helping Billboard Operators Scale

00:53:02 Entrepreneurial Advice and Taking the Leap

Tags:

billboard advertising, billboard business, out of home advertising, OOH advertising, digital billboards, independent billboard operators, billboard industry, outdoor advertising, billboard sales, business growth, entrepreneurship, private equity, attribution marketing, advertising metrics, billboard conferences, IBO, out of home media

Hashtags:

#BillboardAdvertising

#OutOfHomeAdvertising

#Entrepreneurship

Time Stamps / Chapters:

Want to build a billboard business? In this episode, Justin of Vital Outdoor shares what he's learned after more than two decades in the out-of-home advertising industry, including finding billboard locations, financing growth, digital billboard adoption, and navigating legal battles.

From launching one of Oklahoma's first digital billboards to fighting a four-year lawsuit over a permit, this conversation is packed with real-world lessons for billboard operators, entrepreneurs, and anyone interested in out-of-home advertising.

Whether you're new to the billboard industry or already own signs, you'll hear practical insights on site selection, sales, permitting, financing, and the realities of growing an outdoor advertising company.

Time Stamps / Chapters:

00:00 Introduction & Sponsor Message (Stark Capital)
00:02:55 Meet Justin of Vital Outdoor
00:03:38 From Sign Company to Billboard Operator
00:05:37 Building the First Billboards in 2004
00:09:02 Launching One of Oklahoma's First Digital Billboards
00:16:28 Extreme Sports, Paragliding & Skydiving
00:19:45 Running a Family Billboard Business
00:23:16 Sponsor Message (Selective Structures)
00:26:08 The Four-Year Billboard Lawsuit
00:35:33 The Billboard Construction Disaster Story
00:40:52 Growing to 15 Digital Billboards
00:44:34 Lightning Strikes a Digital Billboard
00:49:25 Why Some Billboard Locations Surprise You
00:53:03 The Value of the IBO Community
01:00:23 Advice for Young Billboard Entrepreneurs

YouTube Tags:

billboard business, billboard advertising, out of home advertising, OOH advertising, digital billboards, billboard investing, billboard permits, billboard financing, outdoor advertising, billboard entrepreneur, Vital Outdoor, Justin Vital Outdoor, IBO, independent billboard operators, digital billboard business, billboard site selection, billboard sales, out of home media

Hashtags:

#BillboardBusiness
#OutOfHomeAdvertising
#Entrepreneurship

Keywords:

billboard business

digital billboard advertising

out of home advertising

outdoor advertising company

billboard investing

billboard permits

billboard financing

billboard site selection

digital billboard business

billboard entrepreneur

billboard sales strategies

independent billboard operators

billboard legal challenges

billboard acquisition strategy

outdoor advertising industry

Grey Vick built one of the Carolinas' largest independent billboard companies from the ground up — 770+ faces, 50+ digitals — starting in 2007 with used utility poles, renegotiated loans, and bigger companies telling him he wouldn't make it. Neil and Grey trade war stories from the financial crisis, debate the real economics of easements vs. leases, and get into why long-term branding on a billboard works the way compound interest does. A builder who never sold out and a serial developer who's flipped seven companies talk straight about what this business actually takes — and why neither of them can quit the rush of watching a pole go in the ground.

From commercial banker to billboard lender,operator, and publisher — Dave Westburg has built a three-legged career at the center of the out-of-home industry.

In this debut episode, Neil and Dave cover how Dave discovered OOH, why he calls it the best returns for the least risk of any media sector, what makes Billboard Insider tick, and the real talk on financing, entrepreneurship, and when to make your move.