Let’s start with the obvious: Raj Chauhan has been around the block. And I don’t mean the block you stroll around on your morning jog. No, Raj’s block is more like an endless digital loop, filled with broken banner ads, DSPs, SSPs, and a short but intense detour into cannabis—because why stick with one volatile industry when you can juggle two? He's been playing in the digital advertising sandbox since 1995, back when we still believed AOL chat rooms were the height of innovation and “you’ve got mail” was a daily thrill.

Raj’s career is the stuff of ad tech legend—if your idea of a legend is someone who went from building ad networks in the '90s, back when digital ads were the Wild West, to dipping into the green pastures (pun intended) of cannabis, and finally resurrecting himself as the man to watch in the future of retail media. In short, Raj’s story is the “phoenix rising” of ad tech, only with fewer ashes and more regulatory nightmares.

The Wild West Days of Digital: Raj's Early Start

Rewind to 1995: the internet was in its awkward teenage years, and digital advertising was barely crawling. Banner ads were the new kid in town, and Raj was part of the crew that built the first ad networks. If you ask him what it was like back then, he’ll tell you it was more like a flea market than the data-driven juggernaut we know today. “There was a lot more kind of hand-to-hand combat,” Raj says, reminiscing about those days when deals were closed with a handshake, and you could actually get to know the people you were working with. It was personal. It was messy. And it worked.

But it wasn’t just the relationships that made those days different—it was the lack of noise. No algorithms feeding you data points until your head spins, no real-time bidding that takes human judgment out of the equation. “Back then, there was no concept of marketplaces,” Raj explains. “We were just serving up ads. There wasn’t a lot of data.” Imagine that: ads without data. It’s like trying to sell a car without mentioning the horsepower.

This was the golden era of banner ads—well, if by "golden" you mean clunky, inefficient, and completely devoid of targeting. Raj, like every pioneer in a new industry, was figuring it out on the fly. “We’d cobble together a hundred sports websites or cooking sites, and then we’d go to a brand and say, ‘Hey, buy across this whole ecosystem!’” he says. And surprisingly, it worked. This was the precursor to the sophisticated audience matching we have today—only it was done with a lot more guesswork and a lot less AI.

The Shift to Platforms: Ad Tech Gets "Efficient"

As ad networks grew, so did the industry’s appetite for efficiency—read: platforms. Suddenly, it wasn’t enough to just cobble together a bunch of websites and call it a day. Enter SSPs (Supply-Side Platforms) and DSPs (Demand-Side Platforms), which promised to turn digital advertising into a sleek, data-driven, real-time affair. If the early days were the flea market, the platform world was more like Amazon: streamlined, impersonal, and designed to remove human interaction entirely.

“The big change was the transition from the network world to the platform world,” Raj says. “You suddenly had data. You could target immediately, transact immediately, and have always-on campaigns.” Sounds great, right? Who wouldn’t want more data, more targeting, more precision?

But here’s the thing about Raj: he’s a relationship guy. Always has been. So while the rest of the industry was jumping into data pools headfirst, Raj couldn’t help but miss the days when deals were made over lunch instead of dashboards. “I kind of liked the interpersonal dealings of campaigns and business in the past,” he admits. There’s something very human in that—a yearning for the chaos and connection that defined the early days of ad tech, long before we started overengineering the whole damn thing.

Raj’s Detour into Cannabis: Weed, Compliance, and Sticker Nightmares

At this point, you’re probably thinking, “Okay, so Raj built ad networks. Big deal. Everyone did that in the '90s.” And yeah, sure, plenty of people were slapping together ad networks back then. But how many of them took a hard left into cannabis in 2017? Not many.

Why cannabis? Well, why not? Raj saw an industry that was on the verge of explosion—much like digital advertising had been in the late '90s—and figured, “Why not get in on the ground floor?” Spoiler alert: the cannabis industry was nothing like digital ads. It was, as Raj puts it, “the hardest thing I’ve ever done in my life.” And this is a guy who once built a $2 million ad network while driving a U-Haul from Malibu to San Jose.

The cannabis world, it turns out, is a bureaucratic hellscape. Raj describes it as a game with constantly changing rules. “Every quarter, every year, cannabis laws were changing, and that meant label changes,” he says. Imagine running a business where you’re constantly chasing new regulations, slapping compliance stickers on products that were already shipped from China, and praying the state doesn’t decide to rewrite the rules again next month. It’s a nightmare that makes ad tech look like a picnic.

But Raj isn’t one to back down from a challenge, and for seven years, he hustled his way through the cannabis industry, learning the hard way that no amount of innovation can solve a regulatory quagmire. “Retail and delivery businesses in cannabis are incredibly challenging,” he says, with the same weariness you’d expect from someone who’s seen some serious shit. And while the cannabis business didn’t make Raj a billionaire, it did teach him one thing: sometimes, the old adage of “what doesn’t kill you makes you stronger” is more true than you’d like it to be.

The Return: Retail Media, Connected TV, and the Voodoo Magic

After seven years in the weed trenches, Raj did what any seasoned tech veteran would do: he came back to ad tech, but this time with a twist. Enter Voodoo, his new venture that’s combining the magic of retail media with the endless potential of connected TV. If you’ve been paying attention, you know that retail media is the hot new thing—brands are desperate to turn passive TV viewers into active shoppers, and Raj sees a massive opportunity.

“The whole instant gratification mindset is changing the game,” Raj says, eyes gleaming like a kid with a brand new toy. He’s not talking about QR codes either (which, let’s face it, are about as clunky as the banner ads of old). Raj envisions a future where shoppable moments are baked right into your TV show. Watching the latest Netflix series? See a jacket you like? Click once and it’s on its way to your doorstep. “One-click shopping is coming,” he declares with the confidence of someone who’s been in the trenches long enough to know when a revolution is about to happen.

But don’t get it twisted: Raj doesn’t buy into every shiny new thing the industry throws at him. When I ask him if we’re going to see a future where people pause their TV shows to buy products, he just laughs. “I don’t think people are going to stop their shows to shop,” he says, like it’s the most ridiculous thing he’s ever heard. Instead, the future is about seamless integration—ads that fit naturally into the content, products that are a click away without disrupting the experience.

What Keeps Him Going: Innovation, Grit, and an Endless Curiosity

For a guy who’s been in the game as long as Raj, you’d think he’d be burnt out by now. But no—Raj is more energized than ever. “I haven’t been this excited about the space since 2008,” he says, referring to the early days of SSPs when the entire industry was still figuring out what the hell was happening. For Raj, it’s the innovation that keeps him going. Retail media, connected TV, shoppable moments—they’re all part of the next wave, and Raj is ready to ride it.

And if you think it’s all about the money, think again. Raj is more interested in the grind, the challenge, the thrill of building something from nothing. “You have to grind,” he says, almost like a mantra. “The devil’s in the details.” He’s not one to shy away from the hard work, and that’s what separates him from the thousands of others who came and went in the digital advertising space.

Raj may not be the loudest guy in the room, but he’s the one who knows how to play the long game. Whether it’s building ad networks, navigating the nightmare of cannabis regulations, or leading the charge in retail media, Raj is the guy who’s always thinking two steps ahead.

And if you’re wondering what advice he’d give to his younger self, the guy slinging banner ads in the ‘90s? Simple: “I would’ve started focusing on creative and measurement much earlier,” he says. Because at the end of the day, even in a world where data reigns supreme, it’s the creative that connects with people—and Raj Chauhan, the relationship guy, knows that better than anyone.

So here he is, Raj Chauhan: the ad tech survivor, the weed warrior, and the retail media wizard. Still grinding, still innovating, and still loving the game.

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