Billboards in Times Square often represent a misguided marketing approach. Many startups spend large sums—around $50,000—on flashy ads, only to find they’ve made little impact. The key takeaway is that traditional billboard advertising doesn’t resonate with the people passing by. Instead, the true value lies in social media shares. If someone posts a photo of the billboard online, it can reach a much larger audience, especially if the content features relatable individuals rather than generic branding. Companies like Loops and Muzz have successfully utilized this strategy by showcasing their customers on the billboards. Loops ran a campaign asking startups to submit their logos for a chance to be featured, generating enthusiasm and leads without waiting for organic shares. Muzz’s clever use of a real user's face on their billboard sparked viral attention. The strategy is straightforward: instead of promoting themselves, brands should focus on celebrating their customers. This creates a sense of personal victory for those featured, prompting them to share the experience widely. The concept of "billboard arbitrage" emerges from taking advantage of the price disparity between outdoor advertising and the potential social media reach. A short billboard rental in Times Square can cost between $2,000 and $5,000, but the return in social impressions can far exceed that cost. To execute this effectively, brands should identify individuals likely to share their billboard feature, design the ad to highlight them, and capture the moment with professional photography. This approach can transform a standard billboard into a powerful marketing tool, turning customers into enthusiastic brand advocates.