The Billboard at the End of the World: How I Accidentally Built the Future of an Industry Nobody Thought Had One

There is a billboard on the 405 in Los Angeles that nobody remembers seeing but everyone has definitely seen. It sits above the concrete like a bored god: enormous, patient, completely indifferent to whether you're late for a meeting or crying in your car or eating a burrito with one hand while merging into traffic that has no business moving at this speed. The billboard just is. It has always been there. It will always be there. And for most of my adult life, I believed, along with approximately everyone else who worked in digital marketing, that it was dying.

I was wrong about that. I am often wrong about the things I am most confident about, which is maybe the only genuinely interesting thing about me.

Let me tell you something about growth marketing that nobody in growth marketing will tell you: most of it is a controlled hallucination. You build dashboards. You run A/B tests. You optimize conversion funnels with the kind of ritualistic devotion that medieval monks reserved for illuminated manuscripts, except the monks were at least making something beautiful. You get very good at measuring things, and then you confuse measuring things with understanding things, and then, if you're not careful, you confuse understanding things with controlling things. The whole enterprise is a series of category errors dressed up in the language of science.

I came up in that world. I was good at it. I could look at a CAC-to-LTV ratio and feel something close to what I feel when I hear a chord resolve in a song. There was a rightness to it. A cleanness. And then I joined AdQuick and spent the next several years trying to apply that framework to an industry that predates the internet by about a century and a half, and the cognitive dissonance of that experience, the friction between the measurable and the immovable, taught me more about marketing, business, and the nature of human attention than any growth playbook ever did.

This is the story of that friction. Or at least my version of it.

I want to make an argument that will sound insane on its surface but which I believe is actually correct: out-of-home advertising is the most honest form of advertising that exists.

Bear with me.

Every other ad format is, at its core, an act of intrusion. The pre-roll YouTube ad arrives uninvited. The sponsored post on Instagram disguises itself as content your friends made. The search ad positions itself as organic information. These are fundamentally deceptive architectures; they pretend to be something they are not. A billboard, on the other hand, makes no such pretense. It stands in the world and says: I am an advertisement. I am large. I am here. What are you going to do about it? There is a dignity in that honesty that the digital world abandoned sometime around 2009 and has been quietly mourning ever since without admitting it.

This is what I understood, intellectually, when I first started thinking seriously about AdQuick. What I did not understand, what took years of actual work to internalize, is that the billboard's honesty was also its perceived weakness. Because you can't click on a billboard. You couldn't pixel-track a billboard. You couldn't retarget someone who drove past a billboard at 67 miles per hour while singing along to a Tame Impala song at uncomfortable volume. The advertising industry had spent a decade training itself to believe that what cannot be measured does not exist, and by that logic, the billboard was basically a ghost.

My job, in a sense, was to convince the industry it was haunted.

Here is something I think about more than is probably healthy: the moment in a technology company's life when it stops being weird and starts being inevitable.

Every company that ends up mattering has this period of maximum weirdness, a stretch of time when the core idea is genuinely strange and the people pursuing it are operating on a kind of faith that cannot be fully articulated to outsiders. The idea sounds like a joke when you describe it at a dinner party. "We're building software that makes it easy to buy outdoor advertising the way you'd buy a Google ad." The person across from you nods in a way that is clearly not nodding and says something like, "Oh, interesting," and then pivots to asking about your girlfriend.

I lived in that dinner-party-pivot zone for a long time.

What I didn't fully appreciate during those years is that the weirdness wasn't a bug. It was actually the primary competitive advantage. The out-of-home industry, for all its longevity and all its genuine cultural power, was still being largely bought and sold through methods that would have been familiar to a Mad Men era account exec. Relationships, phone calls, faxes in some cases, a thousand fragmented local vendors with a thousand slightly different rate cards and availabilities and specs. The category was enormous, billions of dollars annually, but the infrastructure was held together with something close to institutional memory and personal trust. There was no operating system.

We were building the operating system for an industry that didn't know it needed one. That's the weird thing to pitch. That's the thing that gets you the polite nod. But it's also, if you are right about the timing and right about the execution, the kind of thing that compounds into something genuinely significant.

I should be honest about something, which is that growth marketing as a discipline has a pathological obsession with velocity that is not always healthy. The loop must tighten. The funnel must fill faster. The number on the dashboard must be larger this week than it was last week or something has gone wrong, someone is to blame, an optimization must be found. This is a useful mental model when you are trying to scale a DTC brand selling skincare products. It is a somewhat less useful mental model when you are trying to change the purchasing behavior of an industry with decades of entrenched habits and relationships that predate the smartphone.

The thing I learned, slowly, in the way that you learn things that conflict with your priors, is that some important processes are not growth curves. Some important processes are more like tectonic shifts: nothing moves for a long time, and then everything moves at once, and the whole landscape is different and you either positioned yourself correctly during the quiet years or you did not.

AdQuick was positioning during the quiet years. The company was building the supply network, thousands of operators, dozens of formats, a marketplace with real depth and real data, while the broader advertising market was still mostly ignoring the category. And then the pandemic happened, which you might think would be devastating for an industry predicated on people being outside and moving around, and in the short term it was, but in the longer term it accelerated a transformation that was already underway. Brands that had been skeptical of out-of-home, or simply ignorant of its capabilities, suddenly found themselves in a world where digital advertising was more saturated and more expensive than ever, where consumers were exhausted by screens, where the physical world was, paradoxically given everything, more meaningful and more noticed.

The billboard at the end of the 405 had been waiting patiently. Suddenly everyone wanted to talk to it.

I want to tell you about a conversation I had early in my time at AdQuick that I have turned over in my head many times since.

I was talking with someone who had spent thirty years in the traditional OOH business, a guy who knew every operator in the country by first name, who had sold campaigns to brands that were now museum pieces, who had seen the industry survive the arrival of television and then cable and then the internet and then mobile and then social media and was still standing. I was trying to explain the platform we were building, the way it could surface inventory and automate the buying process and attach measurement to campaigns that had historically operated in a data vacuum.

He listened carefully. He was smart and experienced and knew things I would never know. And then he said something that landed with me: "The problem with making this easy is that the relationship is the product."

He wasn't wrong. He was just describing the world as it was, in a way that inadvertently described exactly why it would change. Because the world where the relationship is the product is also the world where access is unequal, where small brands can't compete with large ones for premium inventory, where efficiency is sacrificed on the altar of familiarity, where the industry grows as slowly as the relationships that underpin it. The democratization of access, making it so that a startup in San Francisco could plan and buy a national OOH campaign with the same ease as a Fortune 500 company, wasn't just a business opportunity. It was a structural correction.

I respected his perspective. I still do. He was right that something valuable existed in those relationships. He was also right, without meaning to be, that something had to change.

One of the genuine intellectual pleasures of this work is the measurement problem, which is a problem I probably talk about at parties more than is advisable but which I find legitimately fascinating.

Here is the core tension: digital advertising became dominant in part because it promised measurement. You could track exactly how many people saw your ad, how many clicked, how many converted, down to fractions of a percentage point. This created an industry-wide assumption that measurement was the point, that the value of an ad was coterminous with its measurability. And this assumption, which seemed so obviously correct in 2012, has become increasingly questionable in the decade since.

The problems are numerous. Click fraud. Attribution that doesn't account for the fact that you were already going to buy those shoes before you saw the ad. View-through conversions that would make a fortune-teller blush. The "last click" fallacy, which is like crediting the doorman for the sale because he opened the door after you already decided to buy. The entire digital measurement apparatus is built on a set of agreements about what counts as evidence that, examined closely, turn out to be somewhat philosophical in nature.

Out-of-home advertising, which for decades was dinged for being unmeasurable, has paradoxically become more rigorous in its measurement approach than some of its digital counterparts, not because it's easier to measure a billboard than a banner ad, but because the industry had to develop honest measurement methodologies rather than rely on the convenient self-reporting of platforms with skin in the game. When you measure OOH campaign effectiveness, you're typically measuring it the way a scientist would: through controlled exposure groups, through actual consumer behavior, through data that didn't originate from the entity selling you the advertising.

This is not a small thing. This is actually a very large thing that the industry hasn't fully articulated to the outside world.

I have been the CEO of AdQuick for long enough now to have developed a few firm convictions and a much larger set of revised opinions, which I think is probably the correct ratio for anyone in this position.

Firm conviction: the out-of-home industry is not declining. It is transforming, which is a different thing entirely and which produces similar-looking short-term symptoms, disruption, consolidation, hand-wringing, think-pieces, but which ends in a completely different place. Industries that are declining run out of customers. Industries that are transforming find new ones, build new infrastructure, develop new capabilities, and often emerge stronger and more durable than they were before the transformation began. OOH is in the second category.

Firm conviction: software companies that serve industries rather than disrupt them have a more interesting and often more defensible competitive position than software companies that attempt pure disruption. This sounds conservative and maybe it is, but it reflects something real about the way entrenched industries work. The operators who own the physical inventory, the billboards, the transit shelters, the airport displays, are not going away. They own real assets with real audiences. The opportunity is to make those assets infinitely more valuable through software, data, and connectivity, not to route around them. We are the operating system. We are not trying to replace the hardware.

Revised opinion: I used to think the primary barrier to OOH growth was measurement. I now think it is imagination. The brands that have unlocked OOH as a channel tend to have a different relationship to physical space, to the idea that advertising can exist in the world rather than just on a screen, to the understanding that attention is not a single thing and that the attention you get from someone who looked up from their phone and saw something unexpected and vivid on the side of a building is qualitatively different from the attention you get from someone who was served an ad while scrolling. You can't buy that qualitative difference at any price in digital. In OOH, it is structurally built in.

There is a version of this story in which my teammates and I are heroic disruptors who saw what others could not and bent an industry to his will through sheer force of intelligence and determination. That is not this story. That version exists mainly in pitch decks and LinkedIn posts and the kind of flattering profiles that publications run when a company is raising money.

The actual version is messier and more interesting. It involves a lot of being wrong and updating. It involves learning that growth marketing instincts, while useful, are not universal solvers. It involves developing genuine respect for an industry that was deeply weird and deeply old and, it turned out, deeply underestimated. It involves the specific education that comes from trying to change something and discovering, in the process, that the thing you are trying to change has more integrity than you initially appreciated.

The billboard on the 405 was never dying. It was just waiting for someone to figure out how to talk to it in a language that the rest of the advertising world could understand. That translation project, building the systems and the data infrastructure and the marketplace that lets brands and agencies treat out-of-home like a modern media channel, is what AdQuick is. That's what the last nine years have been.

I am not finished with it. I'm not sure I'll ever be finished with it in the way that growth marketers think about finishing things, because the category is genuinely large and the transformation is genuinely ongoing and there is a difference between building something and optimizing something and I have, to my considerable surprise, found that I am much more interested in building.

The billboard on the 405 is still there. It will be there tomorrow. It will be there when all the apps I used in my twenties are museum pieces and the dashboard metrics I once found beautiful are as quaint as a Nielsen rating.

I used to find that permanence slightly unsettling, the idea that this pre-digital, pre-algorithmic artifact of commerce could just stand there, indifferent to everything the tech industry was doing to the advertising world. Now I find it clarifying.

Some things are large enough and physical enough and honest enough about what they are that they simply endure. The question is never whether the billboard survives. The question is whether you build something worthy of standing next to it.

I'm working on it.