The Bell Board Podcast Transistor (https://transistor.fm) https://feeds.transistor.fm/the-bell-board-podcast The Bell Board Podcast is the outdoor advertising industry's go-to show for candid conversations, hard-won insights, and straight talk from the people building, buying, and selling billboards. Hosted by Neil Bell — operator, developer, and guy who still can't drive past a billboard without doing math in his head — each episode goes beyond the numbers to explore the deals, the decisions, and the lessons that define a life in OOH. Neil Bell 00c23450-97f3-5fce-8d69-ee46ef78918c yes af3b0c65-aa68-4474-97c2-3ae561434d24 en Tue, 08 Sep 2026 09:00:12 +0000 Tue, 08 Sep 2026 09:04:12 +0000 https://podcasters.spotify.com/pod/show/neilage22 https://img.transistorcdn.com/d-Lwz506JLZ12rzt7VghHW10yrNliCGL1H3yG1Hw2_0/rs:fill:0:0:1/w:1400/h:1400/q:60/mb:500000/aHR0cHM6Ly9pbWct/dXBsb2FkLXByb2R1/Y3Rpb24udHJhbnNp/c3Rvci5mbS9hYWNj/MWMyMjA2MjFiNmZl/NDYxODQ2Y2JkZTZl/ZTc4My5qcGc.jpg The Bell Board Podcast https://podcasters.spotify.com/pod/show/neilage22 episodic Neil Bell The Bell Board Podcast is the outdoor advertising industry's go-to show for candid conversations, hard-won insights, and straight talk from the people building, buying, and selling billboards. Hosted by Neil Bell — operator, developer, and guy who still can't drive past a billboard without doing math in his head — each episode goes beyond the numbers to explore the deals, the decisions, and the lessons that define a life in OOH. The Bell Board Podcast is the outdoor advertising industry's go-to show for candid conversations, hard-won insights, and straight talk from the people building, buying, and selling billboards. Neil Bell No No Building a Billboard Business That Lasts | Hal & Diana Stevenson 8 8 Building a Billboard Business That Lasts | Hal & Diana Stevenson full 0dd742bc-d59b-48c2-a93f-50800d50a2a2 https://share.transistor.fm/s/23292384 How do you build an independent billboard company that can grow without depending on one person to run everything? Diana Stevenson (CEO) and Hal Stevenson (Chief Development Officer) of Grace Outdoor Advertising join Neil Bell to share the lessons behind building, operating, and preparing their outdoor advertising business for the next generation.


Hal and Diana trace their path through billboard leasing and development in Oklahoma, Texas, and Southern California, an early and costly bet on digital billboards years before the ad industry was ready for them, and the recession that brought them back to South Carolina to rebuild Grace Outdoor from the ground up. Diana explains how she came back to run the company on one condition — she'd be in charge — and then rebuilt its systems, its team, and its client base from scratch.


They also dig into some of the biggest challenges facing independent OOH operators today: multi-year permitting fights, managing thousands of digital-billboard contracts a year, servicing national advertisers, and training the next generation to run the business without them.


For independent billboard owners and outdoor advertising professionals, this is a firsthand look at what it takes to turn decades of industry knowledge into a company that can run beyond its founders.


LINKS


Grace Outdoor Advertising: https://graceoutdoor.com

LinkedIn: https://www.linkedin.com/company/graceoutdooradvertising/

Facebook: https://www.facebook.com/pages/Grace-Outdoor/109527645755004

Instagram: https://www.instagram.com/graceoutdooradvertising/


KEY TAKEAWAYS


• Grace Outdoor Advertising manages billboard inventory for roughly 30 different entities — family LLCs, longtime partners, and small companies whose owners live nowhere near the signs

• Diana Stevenson came back to run the company on one condition — that she'd be in charge — then rebuilt its systems from scratch, starting by learning who their clients were and how they paid

• A single digital billboard face can generate thousands of contracts a year, versus about 24 for a static sign — software like Apparatix, integrated with their accounting system, is what makes that volume manageable

• National advertisers make up an estimated 25-35% of Grace Outdoor's business; they pay reliably but slowly (often around four months), which rewards operators with strong back-office systems

• One billboard permit took 3.5 years and only came through after Grace Outdoor won an appeal to the Board of Zoning Appeals 4-1, after planning staff had recommended denial with no clear legal reason

• Hal's approach to difficult zoning fights is persistence over litigation — suing a municipality tends to end the relationship for every permit after it

• Every excavation carries real risk: Grace Outdoor has hit a pressurized sewer line and a 36-inch water main on separate builds, with the water-main repair costing roughly half that project's profit

• Grace Outdoor grows only at the edges of its existing South Carolina/North Carolina footprint, since a single sign in a distant market is hard to sell without a local presence

• The company's name, "Grace," came from Hal's brother Danny, half-jokingly, after a territorial conflict with Lamar Advertising split their earlier business venture


SUMMARY


Hal and Diana Stevenson met while he was a fill-in bank branch manager and she was a part-time teller in Columbia, South Carolina. Hal's billboard career started through a mentor's company, Omni Outdoor Advertising, and took the couple through leasing and permitting jobs in Oklahoma City, San Antonio, and Southern California — including an early, expensive bet on digital billboards on LA's 405 freeway (roughly $800,000 for one face) that the advertising industry wasn't yet equipped to buy into. When the recession hit and the bank pressure on the business mounted, Hal asked Diana to come back and run things. She agreed, on one condition: she'd be in charge.


From there, Diana rebuilt the company from the ground up — literally starting by getting the mail and learning how every client paid — and used that ground-level knowledge to redesign the company's systems, team, and client relationships. The company took the name "Grace" at the suggestion of Hal's brother Danny, after a territorial dispute with Lamar Advertising split an earlier venture the brothers were both involved in. Today, Grace Outdoor manages billboard inventory for around 30 different entities, from family LLCs to small companies whose owners have no local presence, and does an estimated 25-35% of its business with national advertisers — relationships that pay reliably but slowly, and that reward operators with strong back-office systems like Apparatix, integrated with their accounting software, to keep thousands of digital-billboard contracts a year organized.


The conversation also covers the operational realities of running an independent OOH company: permitting and zoning fights that can take years and hinge on persistence rather than litigation (including a 3.5-year, 4-1 board-appeal win), the real risk of hitting utilities during installation, and the ongoing project of moving decades of Hal's institutional knowledge out of his head and into a team — including son-in-law Josh, now the company's CEO — so Grace Outdoor can keep running without depending on any one person. The episode ends earlier than planned after a technical issue cut the recording short; Neil promises to have Hal and Diana back for a second conversation.


TIMESTAMPS


00:00 Meet Diana and Hal Stevenson of Grace Outdoor
01:19 Hal's Start in the Billboard Business
05:37 Building the Business One Sign at a Time
06:20 Becoming an Early Digital Billboard Adopter
07:59 Diana Returns and Takes Charge
12:49 Rebuilding Grace Outdoor From the Ground Up
15:16 Managing Signs for Multiple Owners and Entities
17:12 How Grace Outdoor Chooses Where to Grow
24:13 Preparing the Business for the Next Generation
28:27 The Risks of Building New Billboards
31:30 Persistence, Permitting, and Zoning Challenges
35:27 How Digital Billboards Serve Local Communities
37:20 Building Systems for Digital Billboard Operations
39:54 Working With National Advertisers and Payment Terms
~44:20 Sponsor Message: Drachman M&A Co. & SignDash (est.)
~46:00 Wrap-Up & What's Next (est.)


TOPICS COVERED


• Independent billboard ownership

• Billboard leasing & development

• Digital billboard advertising

• Billboard permitting & zoning appeals

• Billboard business succession

• National advertiser relationships

• Billboard management software (Apparatix)

• Family-owned business systems

• Utility strikes & installation risk

• IBO / independent operator community


SPONSOR BLOCK


This episode is supported by:


Drachman M&A Co. — the outdoor advertising industry's M&A advisory firm; Neil's own M&A advisor for New South Outdoor. drachmanco.com


SignDash — billboard sales & inventory management software for independent OOH operators. signdash.com


HASHTAGS


#BellBoardPodcast #OutdoorAdvertising #BillboardBusiness #OOHAdvertising


]]> How do you build an independent billboard company that can grow without depending on one person to run everything? Diana Stevenson (CEO) and Hal Stevenson (Chief Development Officer) of Grace Outdoor Advertising join Neil Bell to share the lessons behind building, operating, and preparing their outdoor advertising business for the next generation.


Hal and Diana trace their path through billboard leasing and development in Oklahoma, Texas, and Southern California, an early and costly bet on digital billboards years before the ad industry was ready for them, and the recession that brought them back to South Carolina to rebuild Grace Outdoor from the ground up. Diana explains how she came back to run the company on one condition — she'd be in charge — and then rebuilt its systems, its team, and its client base from scratch.


They also dig into some of the biggest challenges facing independent OOH operators today: multi-year permitting fights, managing thousands of digital-billboard contracts a year, servicing national advertisers, and training the next generation to run the business without them.


For independent billboard owners and outdoor advertising professionals, this is a firsthand look at what it takes to turn decades of industry knowledge into a company that can run beyond its founders.


LINKS


Grace Outdoor Advertising: https://graceoutdoor.com

LinkedIn: https://www.linkedin.com/company/graceoutdooradvertising/

Facebook: https://www.facebook.com/pages/Grace-Outdoor/109527645755004

Instagram: https://www.instagram.com/graceoutdooradvertising/


KEY TAKEAWAYS


• Grace Outdoor Advertising manages billboard inventory for roughly 30 different entities — family LLCs, longtime partners, and small companies whose owners live nowhere near the signs

• Diana Stevenson came back to run the company on one condition — that she'd be in charge — then rebuilt its systems from scratch, starting by learning who their clients were and how they paid

• A single digital billboard face can generate thousands of contracts a year, versus about 24 for a static sign — software like Apparatix, integrated with their accounting system, is what makes that volume manageable

• National advertisers make up an estimated 25-35% of Grace Outdoor's business; they pay reliably but slowly (often around four months), which rewards operators with strong back-office systems

• One billboard permit took 3.5 years and only came through after Grace Outdoor won an appeal to the Board of Zoning Appeals 4-1, after planning staff had recommended denial with no clear legal reason

• Hal's approach to difficult zoning fights is persistence over litigation — suing a municipality tends to end the relationship for every permit after it

• Every excavation carries real risk: Grace Outdoor has hit a pressurized sewer line and a 36-inch water main on separate builds, with the water-main repair costing roughly half that project's profit

• Grace Outdoor grows only at the edges of its existing South Carolina/North Carolina footprint, since a single sign in a distant market is hard to sell without a local presence

• The company's name, "Grace," came from Hal's brother Danny, half-jokingly, after a territorial conflict with Lamar Advertising split their earlier business venture


SUMMARY


Hal and Diana Stevenson met while he was a fill-in bank branch manager and she was a part-time teller in Columbia, South Carolina. Hal's billboard career started through a mentor's company, Omni Outdoor Advertising, and took the couple through leasing and permitting jobs in Oklahoma City, San Antonio, and Southern California — including an early, expensive bet on digital billboards on LA's 405 freeway (roughly $800,000 for one face) that the advertising industry wasn't yet equipped to buy into. When the recession hit and the bank pressure on the business mounted, Hal asked Diana to come back and run things. She agreed, on one condition: she'd be in charge.


From there, Diana rebuilt the company from the ground up — literally starting by getting the mail and learning how every client paid — and used that ground-level knowledge to redesign the company's systems, team, and client relationships. The company took the name "Grace" at the suggestion of Hal's brother Danny, after a territorial dispute with Lamar Advertising split an earlier venture the brothers were both involved in. Today, Grace Outdoor manages billboard inventory for around 30 different entities, from family LLCs to small companies whose owners have no local presence, and does an estimated 25-35% of its business with national advertisers — relationships that pay reliably but slowly, and that reward operators with strong back-office systems like Apparatix, integrated with their accounting software, to keep thousands of digital-billboard contracts a year organized.


The conversation also covers the operational realities of running an independent OOH company: permitting and zoning fights that can take years and hinge on persistence rather than litigation (including a 3.5-year, 4-1 board-appeal win), the real risk of hitting utilities during installation, and the ongoing project of moving decades of Hal's institutional knowledge out of his head and into a team — including son-in-law Josh, now the company's CEO — so Grace Outdoor can keep running without depending on any one person. The episode ends earlier than planned after a technical issue cut the recording short; Neil promises to have Hal and Diana back for a second conversation.


TIMESTAMPS


00:00 Meet Diana and Hal Stevenson of Grace Outdoor
01:19 Hal's Start in the Billboard Business
05:37 Building the Business One Sign at a Time
06:20 Becoming an Early Digital Billboard Adopter
07:59 Diana Returns and Takes Charge
12:49 Rebuilding Grace Outdoor From the Ground Up
15:16 Managing Signs for Multiple Owners and Entities
17:12 How Grace Outdoor Chooses Where to Grow
24:13 Preparing the Business for the Next Generation
28:27 The Risks of Building New Billboards
31:30 Persistence, Permitting, and Zoning Challenges
35:27 How Digital Billboards Serve Local Communities
37:20 Building Systems for Digital Billboard Operations
39:54 Working With National Advertisers and Payment Terms
~44:20 Sponsor Message: Drachman M&A Co. & SignDash (est.)
~46:00 Wrap-Up & What's Next (est.)


TOPICS COVERED


• Independent billboard ownership

• Billboard leasing & development

• Digital billboard advertising

• Billboard permitting & zoning appeals

• Billboard business succession

• National advertiser relationships

• Billboard management software (Apparatix)

• Family-owned business systems

• Utility strikes & installation risk

• IBO / independent operator community


SPONSOR BLOCK


This episode is supported by:


Drachman M&A Co. — the outdoor advertising industry's M&A advisory firm; Neil's own M&A advisor for New South Outdoor. drachmanco.com


SignDash — billboard sales & inventory management software for independent OOH operators. signdash.com


HASHTAGS


#BellBoardPodcast #OutdoorAdvertising #BillboardBusiness #OOHAdvertising


]]> Tue, 08 Sep 2026 09:00:00 +0000 Neil Bell Neil Bell 2803 How do you build an independent billboard company that can grow without depending on one person to run everything? Diana Stevenson (CEO) and Hal Stevenson (Chief Development Officer) of Grace Outdoor Advertising join Neil Bell to share the lessons behind building, operating, and preparing their outdoor advertising business for the next generation.


Hal and Diana trace their path through billboard leasing and development in Oklahoma, Texas, and Southern California, an early and costly bet on digital billboards years before the ad industry was ready for them, and the recession that brought them back to South Carolina to rebuild Grace Outdoor from the ground up. Diana explains how she came back to run the company on one condition — she'd be in charge — and then rebuilt its systems, its team, and its client base from scratch.


They also dig into some of the biggest challenges facing independent OOH operators today: multi-year permitting fights, managing thousands of digital-billboard contracts a year, servicing national advertisers, and training the next generation to run the business without them.


For independent billboard owners and outdoor advertising professionals, this is a firsthand look at what it takes to turn decades of industry knowledge into a company that can run beyond its founders.


LINKS


Grace Outdoor Advertising: https://graceoutdoor.com

LinkedIn: https://www.linkedin.com/company/graceoutdooradvertising/

Facebook: https://www.facebook.com/pages/Grace-Outdoor/109527645755004

Instagram: https://www.instagram.com/graceoutdooradvertising/


KEY TAKEAWAYS


• Grace Outdoor Advertising manages billboard inventory for roughly 30 different entities — family LLCs, longtime partners, and small companies whose owners live nowhere near the signs

• Diana Stevenson came back to run the company on one condition — that she'd be in charge — then rebuilt its systems from scratch, starting by learning who their clients were and how they paid

• A single digital billboard face can generate thousands of contracts a year, versus about 24 for a static sign — software like Apparatix, integrated with their accounting system, is what makes that volume manageable

• National advertisers make up an estimated 25-35% of Grace Outdoor's business; they pay reliably but slowly (often around four months), which rewards operators with strong back-office systems

• One billboard permit took 3.5 years and only came through after Grace Outdoor won an appeal to the Board of Zoning Appeals 4-1, after planning staff had recommended denial with no clear legal reason

• Hal's approach to difficult zoning fights is persistence over litigation — suing a municipality tends to end the relationship for every permit after it

• Every excavation carries real risk: Grace Outdoor has hit a pressurized sewer line and a 36-inch water main on separate builds, with the water-main repair costing roughly half that project's profit

• Grace Outdoor grows only at the edges of its existing South Carolina/North Carolina footprint, since a single sign in a distant market is hard to sell without a local presence

• The company's name, "Grace," came from Hal's brother Danny, half-jokingly, after a territorial conflict with Lamar Advertising split their earlier business venture


SUMMARY


Hal and Diana Stevenson met while he was a fill-in bank branch manager and she was a part-time teller in Columbia, South Carolina. Hal's billboard career started through a mentor's company, Omni Outdoor Advertising, and took the couple through leasing and permitting jobs in Oklahoma City, San Antonio, and Southern California — including an early, expensive bet on digital billboards on LA's 405 freeway (roughly $800,000 for one face) that the advertising industry wasn't yet equipped to buy into. When the recession hit and the bank pressure on the business mounted, Hal asked Diana to come back and run things. She agreed, on one condition: she'd be in charge.


From there, Diana rebuilt the company from the ground up — literally starting by getting the mail and learning how every client paid — and used that ground-level knowledge to redesign the company's systems, team, and client relationships. The company took the name "Grace" at the suggestion of Hal's brother Danny, after a territorial dispute with Lamar Advertising split an earlier venture the brothers were both involved in. Today, Grace Outdoor manages billboard inventory for around 30 different entities, from family LLCs to small companies whose owners have no local presence, and does an estimated 25-35% of its business with national advertisers — relationships that pay reliably but slowly, and that reward operators with strong back-office systems like Apparatix, integrated with their accounting software, to keep thousands of digital-billboard contracts a year organized.


The conversation also covers the operational realities of running an independent OOH company: permitting and zoning fights that can take years and hinge on persistence rather than litigation (including a 3.5-year, 4-1 board-appeal win), the real risk of hitting utilities during installation, and the ongoing project of moving decades of Hal's institutional knowledge out of his head and into a team — including son-in-law Josh, now the company's CEO — so Grace Outdoor can keep running without depending on any one person. The episode ends earlier than planned after a technical issue cut the recording short; Neil promises to have Hal and Diana back for a second conversation.


TIMESTAMPS


00:00 Meet Diana and Hal Stevenson of Grace Outdoor
01:19 Hal's Start in the Billboard Business
05:37 Building the Business One Sign at a Time
06:20 Becoming an Early Digital Billboard Adopter
07:59 Diana Returns and Takes Charge
12:49 Rebuilding Grace Outdoor From the Ground Up
15:16 Managing Signs for Multiple Owners and Entities
17:12 How Grace Outdoor Chooses Where to Grow
24:13 Preparing the Business for the Next Generation
28:27 The Risks of Building New Billboards
31:30 Persistence, Permitting, and Zoning Challenges
35:27 How Digital Billboards Serve Local Communities
37:20 Building Systems for Digital Billboard Operations
39:54 Working With National Advertisers and Payment Terms
~44:20 Sponsor Message: Drachman M&A Co. & SignDash (est.)
~46:00 Wrap-Up & What's Next (est.)


TOPICS COVERED


• Independent billboard ownership

• Billboard leasing & development

• Digital billboard advertising

• Billboard permitting & zoning appeals

• Billboard business succession

• National advertiser relationships

• Billboard management software (Apparatix)

• Family-owned business systems

• Utility strikes & installation risk

• IBO / independent operator community


SPONSOR BLOCK


This episode is supported by:


Drachman M&A Co. — the outdoor advertising industry's M&A advisory firm; Neil's own M&A advisor for New South Outdoor. drachmanco.com


SignDash — billboard sales & inventory management software for independent OOH operators. signdash.com


HASHTAGS


#BellBoardPodcast #OutdoorAdvertising #BillboardBusiness #OOHAdvertising


]]> No How Trailhead Media Scaled Through 44 Billboard Acquisitions | John Murrow 7 7 How Trailhead Media Scaled Through 44 Billboard Acquisitions | John Murrow full b1c36006-263e-42a0-aa00-f33cd7dc2e3d https://share.transistor.fm/s/80c04b83
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

]]>
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

]]> Tue, 11 Aug 2026 09:00:00 +0000 Neil Bell Neil Bell 3463
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

]]> No From Bear Suit to Billboard Vet: Matt Schulze's 30+ Years in OOH 6 6 From Bear Suit to Billboard Vet: Matt Schulze's 30+ Years in OOH full 769b7621-185e-40e5-9023-417e92970d23 https://share.transistor.fm/s/d7e3505d 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

]]> 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

]]> Tue, 28 Jul 2026 09:00:00 +0000 Neil Bell Neil Bell 4274 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

]]> No Stop Selling Billboards. Start Selling Ideas. | Kevin Gephart 5 5 Stop Selling Billboards. Start Selling Ideas. | Kevin Gephart full 86e6fa06-3b4b-4b8d-bfa7-61ddc25cb112 https://share.transistor.fm/s/f0b202b7 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


]]> 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


]]> Tue, 14 Jul 2026 13:10:17 +0000 Neil Bell Neil Bell 3995 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


]]> No From Operator to Owner: Scaling a Billboard Business Without Losing Control | Becky Smith - Behind The Board 4 4 From Operator to Owner: Scaling a Billboard Business Without Losing Control | Becky Smith - Behind The Board full ffdb63f6-0b18-4eee-b89b-db8a89fa2629 https://share.transistor.fm/s/99123bef 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: 

]]> 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: 

]]> Tue, 30 Jun 2026 10:00:00 +0000 Neil Bell Neil Bell 3390 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:  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 th No Want to build a billboard business? w/Justin Booher - Vital Outdoor 3 3 Want to build a billboard business? w/Justin Booher - Vital Outdoor full 93a29594-d270-4885-8496-ff14c9985efe https://share.transistor.fm/s/677c7c91 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


]]> 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


]]> Tue, 16 Jun 2026 13:00:00 +0000 Neil Bell Neil Bell 3848 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 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, No Episode 2 | Grey Vick | Grey Outdoor 2 2 Episode 2 | Grey Vick | Grey Outdoor full ac2a64bb-1c23-4c1c-bdab-269b45637f80 https://share.transistor.fm/s/15b607e8 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.


]]> 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.


]]> Mon, 18 May 2026 13:00:51 +0000 Neil Bell Neil Bell 4788 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. 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 No Episode 1 | Dave Westburg, Billboard Insider 1 1 Episode 1 | Dave Westburg, Billboard Insider full 60f978fe-a7f3-4ccd-8bc9-c8a3267dcf63 https://share.transistor.fm/s/011ad945 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.

]]> 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.

]]> Mon, 20 Apr 2026 16:00:43 +0000 Neil Bell Neil Bell 3911 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. 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 retu No