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Startup Advertising Deal

Designing a Times Square Billboard Overnight

Reading Time: 6 minutes

When an offer sounds too good to be true, it probably is.

At least, that was Michael Kuznetsov’s first thought when he was hit up by an advertising salesperson with a “deal of a lifetime.”

That deal? The chance for his startup to advertise on one of the most visible billboards in the world for a fraction of what it normally costs.

But of course, there was just one catch:

They had to get the creative turned around in less than 24 hours.

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“I Have Great News and Bad News…”

Getting your logo on a flashy billboard in Times Square will set you back a few dollars. With costs in the range of <$1.1 million to $4 million a year, it’s the most expensive outdoor advertising placement in the world. But for that price tag, your ad will be placed in front of 26 million pairs of eyeballs a year. That’s over 70,000 people every single day.

And that’s just the people seeing your billboard in person. Ads in Time Square show up on TV news programs every morning and in thousands of social media photos every day. That kind of exposure doesn’t come cheap, which is why you won’t find too many startups buying up glitzy signs on 42nd Street.

Unless of course, you get one hell of a deal.

“The offer was the deal of a lifetime,” recalls Kuznetsov, Head of Marketing for TalkSpace, a New York City-based startup that offers online therapy for people seeking mental health counseling. “But of course, with one very big catch.”

There’s always a catch, right?

“The very big catch was that we would have to turn creative around for one of the biggest, most visible billboards in the world in the course of 24 hours.”

Want to see a room full of designers shoot fire out of their eyes? Try telling them you need creative for a massive video board in less than a day.

To complicate things further, this particular billboard has some quirks that had to be considered when designing the ad. The 8-storey video board is cylindrical, stretching around the corner of the Nasdaq Building, and features 25 square cutouts for windows where anything in the design would not be shown. This was no 14 x 48 foot rectangular highway sign.

For a lot of companies, that would be it: no deal, can’t do it.

But what startups lack in cash reserves, they make up for in agility and attitude.

“I sat down with our Creative Director and his team and I said, ‘Hey guys, I have great news and bad news,” explains Kuznetsov. “The great news is we have a Times Square billboard. The bad news is we’re all about to hustle our asses off.”


startup advertising deal all nighter

Brew another pot, team, it’s gonna be a long night.


Rather than groan, the team jumped into action. They immediately began breaking the job down into smaller tasks, assigning them to team members, and most importantly:

“Planning for what type of pizza to get delivered at 2:00 in the morning.”

For the design team, it was a chance to try something they’ve never done before and show off TalkSpace in a big way.

“Michael presented it to us as a surprise,” recalls Kris Mikkelsen, Creative Director at TalkSpace. “So we were like, ‘Oh my God, you just spent the entire afternoon not telling us about this, and now it’s halfway through the evening and we gotta do it?’ But we were mostly just excited.”

Excited, but keenly aware of the challenge the task presented. As a startup, TalkSpace’s design team had far more experience with product design than advertising. Not only was this uncharted territory for the company, it was an entirely new experience for individual team members.

“Big Risk That We Would Miss Our Deadline…”

The first step in the design process is deciding what actually should go on the billboard. Given the unique nature of the sign, this was a complex decision.

As a video board, the team could use motion graphics to add creative elements to their ad. There was also the question of the window cutouts. Should they find a creative way to incorporate them into the design?

“Depending on that decision, we were going to be on time with our creative because we made the right trade-off, or we could bite off more than we could chew,” says Kuznetsov. Tempting as it is to get wildly creative with the design, doing so could result in “a big risk that we would miss our deadline.”

In the end, they compromised with a design that stayed true to their brand, but was also realistic, given the limited time and resources they had to work with.

For more tips on marketing and design collaboration, check out this article.

“We started around 4:00 in the afternoon,” recalls Mikkelsen. “And we got this concept of a couch sitting in all these different scenarios, because you can do therapy with us from anywhere.”

Playing off the New York influence of Times Square, they placed the couch in footage of the subway, Central Park, Times Square, and more. Concepts in hand, the team set off working.

9 hours of copywriting, motion graphics, and editing later, they were wrapping up. Mikkelsen’s 2 designers went home around 3:00AM, while he stayed back to put on the finishing touches. He didn’t head home until after the sun was up, but they had pulled it off.

And about a day later, the billboard was live in Times Square.

Startup Billboard

With the billboard live, Kuznetsov took on the next big challenge:

“Figuring out which bar in Times Square was the best one to go to in order to be able to have a celebratory beer together and see our billboard on the side of the building.”

But celebrate they did, and the whole team got to bask in the glory of their hard work. Beers were toasted, and selfies were posted to Facebook and sent to parents. The small but mighty startup was shoulder-to-shoulder with corporate giants.

“A True Competitive Edge…”

While advertising at the Crossroads of the World may normally be reserved for the big guys, Kuznetsov thinks it was precisely the small size of his team that allowed them to act on this opportunity.

“Even though we don’t have an enormous design and creative team and marketing team, we can take advantage of opportunities that come up that would never even make it to the inbox of a decision maker at a large corporation,” Kuznetsov explains.

When the deal of a lifetime presented itself, TalkSpace didn’t have to wait for multiple levels of approval or requisition the budget from the accounting department. They saw an opportunity, analyzed it, made a decision, and acted on it.

“That’s a true competitive edge for a startup over a large corporation.”

It’s not impossible for large companies to achieve this kind of agility if they dedicate themselves to it. Team leaders have to be free to make big decisions (including costly ones), and team members at all levels must feel empowered to bring suggestions to the table.

Most importantly (and most challenging of all), failure must be an option. Kuznetsov didn’t know whether the billboard would work or not. It could very well have been an expensive failed experiment. But startups like TalkSpace thrive because of their willingness and ability to take risks and double down on the ones that pay off.

This doesn’t mean they’re reckless with their efforts. Kuznetsov says that central to his decision to purchase the billboard were the multiple ways they would measure its effectiveness.

“When we were considering this, we had to look not just at the price and the internal cost, but also what we thought we were going to get from it,” says Kuznetsov. “There are some very straightforward things we need to do there around purchase attribution, but then there is a point about taking a deep breath and sitting for a minute and just listening to the feedback you got.”

The effect of the billboard extended beyond basic impressions and sales; it was also a mile-marker for the entire TalkSpace team. A sign (literally) that they had arrived. And for a small startup, putting in long hours to build something bigger than themselves, those moments matter.

“These things are hard to quantify, and as important as it is to have a very rigorous, attribution-driven way of doing your marketing, it would be amiss not to listen for the other benefits that you got from doing something like this.”

When the deal of a lifetime comes along, you’d be wise to take it. After all, who hasn’t dreamed of seeing their names up in lights?

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