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There are risky marketing stunts, and then there’s getting the United Nations involved. That’s exactly what happened when Ken Robertson, former Head of Mischief at Paddy Power, launched a PR campaign so bold it put the notorious Irish bookmaker in the crosshairs of global scrutiny—and cost him more than a few sleepless nights.

In this week’s episode of Embracing Marketing Mistakes, Will and I had the pleasure of chatting with Ken, now CEO at The Tenth Man, about the time he found himself in the middle of one of Paddy Power’s most controversial stunts. And let me tell you, it’s a story worth hearing.

It all started with a wild plan: sponsor a basketball game in North Korea with Dennis Rodman. Yes, that Dennis Rodman. As Ken explained, “Kim Jong-un wasn’t impressed with the Harlem Globetrotters, so we came up with the idea to bring a US team to play North Korea on Kim’s 30th birthday. Paddy Power would sponsor it, of course.”

Sounds like typical Paddy Power, right? But then the situation took a darker turn. Just before the event, Kim Jong-un went on a purge, executing half his government, which suddenly put the spotlight on Paddy Power for supporting such a regime. “Big questions were asked. The UN got involved. We came under massive pressure,” Ken told us.

I had to ask, “Is there a moment where you think, ‘this has gone too far’?”

Ken’s answer? “Yeah, that was one of the few times I lost a lot of sleep over it.”

This episode is packed with lessons for any marketing professional willing to walk the tightrope of risk and reward. If you’re looking for insight into how to push creative boundaries—and when to step back—this one is a must-listen.

Listen to the full episode here

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