The Side Hustle Show

How to Start a Billboard Business: $30k a Month Part-Time (Greatest Hits)

February 19, 2026

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  • Billboard ownership offers a unique combination of real estate asset appreciation and passive business income, with existing billboards being highly valuable due to regulated supply. 
  • Acquiring an existing billboard can be done by identifying distressed sellers or researching county records, with initial ROI potentially being realized within three years. 
  • Billboard advertising primarily builds long-term brand awareness and trust, rather than providing immediate direct response, making it suitable for businesses needing consistent visibility. 
  • Building wealth through a side hustle like the billboard business requires a long-term time horizon and consistency over many years. 
  • The guest's business, Signs of Good, incorporates a charity component where a portion from every sold ad goes to a nonprofit. 
  • When struggling, seek an outside perspective, like a mentor or coach, rather than just trying harder, as illustrated by the hummingbird analogy. 

Segments

Guest Motivation and First Billboard
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(00:00:10)
  • Key Takeaway: The guest was motivated to seek passive income after experiencing job insecurity while working as a pharmaceutical rep.
  • Summary: The guest sought side hustles to protect his family after facing potential layoffs at his job. He was inspired to pursue billboards after noticing an empty, run-down sign while driving. His first acquisition was secured post-recession from a distressed developer for $75,000, including the land and structure.
First Billboard Acquisition Details
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(00:04:28)
  • Key Takeaway: The first billboard, a four-sided static structure, cost $75,000 and generated $2,400 monthly revenue, leading to a three-year payback period.
  • Summary: The initial purchase price of $75,000 was based on the seller’s original cost, and the structure was located in a unique spot surrounded by three roads. The guest priced the four sign faces at $600 each by researching competitor rates, achieving positive cash flow immediately. This initial investment paid for itself in approximately three years based on the revenue generated.
Billboard Acquisition Strategies
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(00:09:54)
  • Key Takeaway: Beginners can start by acquiring distressed existing billboards or by building new ones, though finding distressed sellers is becoming increasingly difficult.
  • Summary: Both acquiring existing, distressed signs and building new ones on owned land are viable entry points. Awareness of billboards increases once one starts looking, a phenomenon related to the reticular activating system. Billboard sales are often facilitated by brokers, or owners can be contacted directly to inquire about selling.
Regulation and Asset Value
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(00:13:34)
  • Key Takeaway: Federal and state regulations limiting new billboard construction since 1972 restrict supply, significantly increasing the value of existing, grandfathered-in assets.
  • Summary: The industry is fragmented between large conglomerates (like Lamar) and independent operators, offering exit opportunities for smaller owners. New construction requires navigating federal, state, city, and county permits, which deters competition. The limited supply driven by regulation makes owned billboards a very valuable, regulated media property.
Leasing Land vs. Owning
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(00:23:47)
  • Key Takeaway: Landowners can sublease space for billboards, typically receiving 10% to 20% of the sign’s annual revenue, allowing billboard owners to operate without purchasing the underlying real estate.
  • Summary: The guest utilizes both owned land and leased property for his billboards, choosing the structure based on the specific deal. Lease payments are often negotiated as a percentage of the revenue generated by that specific sign face. Building strong relationships with local landowners is key to successful, fair leasing arrangements.
Billboard Valuation and Business Equity
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(00:25:23)
  • Key Takeaway: Billboard assets can be sold for a multiple of 7x to 12x their annual revenue, allowing owners to build equity separate from the underlying real estate.
  • Summary: The high sale multiple means billboard ownership provides both immediate cash flow and significant long-term equity potential. By systemizing operations (using accountants, installers), the asset becomes sellable as a business that does not require the owner’s daily presence. Owners can choose to sell the billboard operation while retaining the land, or sell both together.
Filling Ad Space and Contract Terms
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(00:28:09)
  • Key Takeaway: Advertisers are attracted by visibility, credibility, and the desire to see themselves advertised, leading to long-term contracts, typically 12 to 24 months for static signs.
  • Summary: Placing a large phone number on the sign is the first step to attracting inbound inquiries from interested local businesses. Static signs are preferred by the guest due to lower maintenance compared to digital screens, which require managing power and internet. Long-term contracts are preferred to amortize the cost of printing and installation for static vinyl advertisements.
Traffic Stats and Day-to-Day
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(00:36:29)
  • Key Takeaway: Highway traffic counts are publicly available via state census data, but billboard pricing is ultimately determined by location quality, competition, and recall factor, not just raw impressions.
  • Summary: State highway departments track traffic counts, providing a baseline for estimating impressions, though billboard operators often use proprietary metrics. A billboard in a low-competition area can command similar rates to one on a busier highway if it achieves higher recall due to its unique placement. The guest’s current involvement is minimal, requiring about five hours per week, managed by a small team.
Retirement and Future Plans
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(00:44:38)
  • Key Takeaway: The guest achieved financial freedom by ensuring his passive income (billboards) covered his expenses by a significant multiple before retiring from his W-2 job.
  • Summary: The guest maintained a conservative approach, waiting until his passive income comfortably exceeded his growing family expenses before retiring. He plans to double his billboard inventory within two years, viewing the business as a long-term asset that continues to grow in value. His next focus is teaching others how to build wealth through this model via his ‘Billboard Academy’.
Long-Term Wealth Building
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(00:49:13)
  • Key Takeaway: Wealth accumulation requires a big time horizon and consistency over time, not necessarily massive initial effort.
  • Summary: Building wealth is a long-term endeavor that relies on consistent effort rather than immediate large actions. Ten years, while seeming long, is a relatively short span in the grand scheme of life. Realizing the ability to build wealth over time is key to sustained success.
Guest Business Details & Charity
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(00:49:33)
  • Key Takeaway: Chris Brown’s billboard business includes a charitable component tied to every ad sold.
  • Summary: Chris Brown can be found online at wantmore.org and his business, Signs of Good, is on Facebook. A portion of every dollar from sold ad space is directed toward a charity component. This demonstrates integrating social good directly into the side hustle model.
Final Tip: Hummingbird Metaphor
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(00:49:52)
  • Key Takeaway: Escape from the ‘rat race’ often requires an outside perspective or guide rather than just trying harder.
  • Summary: The speaker uses the analogy of a trapped hummingbird needing a feeder lowered step-by-step to escape, illustrating that sometimes people are just flying harder against a barrier (like a window or a problem). Finding a mentor or guide provides the necessary external perspective to see the next best steps toward freedom.
Billboard Investment Value
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(00:52:28)
  • Key Takeaway: Billboards function as an alternative asset class offering hands-on control, cash flow, and equity appreciation.
  • Summary: The billboard business is presented as an alternative investment where the owner has proactive control over filling ad space and seeking better deals. This offers both monthly cash flow (e.g., $2,400 per face) and equity, as the asset can be sold for seven to twelve times that monthly income.
Show Notes & Bonus Offer
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(00:53:17)
  • Key Takeaway: Show notes, links, and a free bonus resource are available via a specific URL.
  • Summary: All show notes and links mentioned are located at sidehustlenation.com/billboards. Listeners can download a free bonus resource there: a list of 25 other unconventional rental ideas. Supporting the show’s advertisers is encouraged as it helps keep the content free.