A 22-year-old AI creator made an ExpressVPN ad. Now it’s going to Times Square

After more than 20,000 registrations, Max Kaplan’s winning AI-made ad is heading to ExpressVPN’s Times Square Digital Takeover ahead of the FIFA World Cup 2026™ Final.

Max Kaplan had only been making AI videos full-time for a few months when he entered ExpressVPN’s Big Ad Contest. Now his winning ad is set to appear in Times Square, and he’s heading to the FIFA World Cup 2026™ Final.

For Kaplan, a freelance AI creator from Colorado, the win still feels surreal.

ExpressVPN launched the contest to put its own ad space in creators’ hands. People were invited to make short videos with AI around the ExpressVPN brief, with the winning entry earning World Cup Final tickets and a place in ExpressVPN’s Times Square Digital Takeover.

More than 20,000 people registered across the campaign window, with the contest promoted through ExpressVPN’s own channels and partners including Artlist and Nas Daily.

In the week leading up to the FIFA World Cup 2026™ Final, ExpressVPN will run the takeover in partnership with Clear Channel Outdoor. Kaplan’s ad will appear alongside ExpressVPN’s campaign work across digital displays in one of the world’s most recognizable advertising locations.

Max Kaplan, winner of the ExpressVPN Big Ad Contest

From medicine to AI video

Kaplan didn’t come into the contest through the traditional advertising world. He was originally premed, working full-time in dermatology and planning to go to PA school. Then he started seeing people experiment with AI video online.

“I started making AI videos when Google Veo 3 came out, and people were doing those Bigfoot vlogs,” he said. “I thought, this seems fun. I want to learn it.”

About two months ago, he left his job and began making AI videos full-time. “I have no background in directing,” Kaplan said. “I love seeing what other people make. Some of it is astonishing. I get inspired by these people every day.”

That was part of what made the contest exciting for ExpressVPN. It brought in people who might not have had access to a traditional ad production route, but who had ideas, taste, timing, and the tools to make something people would actually watch.

The idea behind the winning ad

Kaplan’s winning entry started with a lot of ideas he didn’t like. “I put the three briefs into an LLM and used it to explore a bunch of possible hooks,” he said. “Most of them didn’t feel quite right, but one idea involved a tiny robot on your phone that protects you. That got me thinking: what if the robot wasn’t tiny, and what if it was actually fighting off scammers?”

Before he generated anything, Kaplan spent time getting the script right. “I spent a few hours really making sure the script was solid before I even generated anything,” he said.

The final video was made with AI, but Kaplan’s process was still recognizably creative. He had to find the idea, shape the story, build the rhythm, and keep refining it until it worked.

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What the judges saw

The judges watched entries that ranged from surreal to cinematic, with creators using AI to take the ExpressVPN brief in directions the team hadn’t expected.

“I spent the last few days watching all of the videos, and honestly, I was blown away,” said Nuseir Yassin, founder of Nas Daily. “The creativity, the storytelling, and the imagination that creators put into these submissions made choosing a winner super difficult.”

“AI is changing who gets to create, and this challenge proved it,” he added. “Huge congrats to our winners. And thank you to everyone who joined the challenge. Keep creating. We’re just getting started.”

Erez Strauss, Creative Director at ExpressVPN, said the contest was about finding creators who could use AI to bring unexpected ideas to life.

“We all know that AI ads will be the future of paid advertising, but the Big Ad Contest was all about finding the creators who know how to use AI to bring their ideas to life in the most creative ways,” he said.

“We received lots of amazing ads, from a duck saving a penalty kick all the way to aliens trying to take over the human species. Unfortunately, we could only pick five winners, but I truly believe each one of them managed to convey the importance of surfing the internet securely with ExpressVPN in a way I could never have imagined.”

Adva Navon Banai, Video Partnerships Manager at Google, said reviewing the submissions showed how far creators are already pushing the format.

“Reviewing the submissions was an incredible experience,” she said. “The AI artists showcased an impressive ability to push creative boundaries, making the well-deserved winning selections stand out far above our expectations.”

Giving creators the big stage

Winning the contest doesn’t only mean a prize. ExpressVPN is sharing the creators’ videos in full on its social channels in collaboration with the creators themselves. That means the creators appear alongside ExpressVPN as authors of the work, giving them visible credit and introducing them to a larger audience.

The FIFA World Cup prize helped give the contest its scale. As an official tournament supporter, ExpressVPN wanted the Big Ad Contest to feel bigger than a standard tech brand giveaway. Final tickets and a Times Square placement gave creators a shot at something genuinely memorable.

From a contest entry to Times Square

For Kaplan, the prize brings together two things he never expected: seeing his work in Times Square and going to the FIFA World Cup Final. “I grew up an American football fan, but I got really into the last World Cup, and I’ve been loving this one,” he said. “It’s the best sporting event in the world. The culture, everything. It’s insane.”

When he told a friend he had won, the reaction matched his own. “He was just in shock, so excited for me,” Kaplan said. “I couldn't even believe it.”

The Big Ad Contest was a bet on what happens when a brand hands over the brief, the tools, and the stage. Kaplan’s winning ad may have been made with AI, but the story behind it is very human. A young creator took a chance, followed a strange idea, and made something big enough to appear in one of the most famous advertising spaces in the world.