‘Kids were tougher in the 1990s’: what happens in Dan Pena’s £27,000 ‘tough love’ seminars?

Dan Pena has a picture of Adolf Hitler on his wall, but not any old picture. You know, not a simple portrait with Bavarian hills in the background, or a snap of the Führer doting on Helga Goebbels, Joseph’s daughter. No, Pena has a Hitler collage – Nazis marching through Nuremberg, a swastika blotting out the sky, hellfire on the horizon and, the final layer, a red and murderous photograph of the man himself superimposed on to the right-hand side.

‘Allegedly I used to hit my students in the 1990s. I will neither confirm nor deny that’

The collage hangs almost dead centre on Pena’s ‘wall of influencers’, a gallery of 91 men and women who inspired him to become the high-performance individual he is today: a businessman worth $500 million and an online celebrity with millions of followers. To the right of Hitler is Joseph Stalin and to the left is Jesus. To Jesus’s left is Vlad the Impaler, and above Vlad is Pena’s father Manny. ‘They’re not all good people,’ says Katherine, Pena’s PA. ‘Look, there’s Donald Trump.’

Katherine is showing me around Guthrie Castle, Pena’s 15th-century estate on the east coast of Scotland near Arbroath. We had seen Pena’s walled garden, his orchard, his nine-hole golf course and his corridor of newspaper clippings and certificates. We’d marvelled at his enormous collection of baseball caps and at a stuffed bear whose throat he’d slit hunting in America – and which for some reason now wore a Native American feathered headdress. Our tour ended in the ‘Pavilion’, observing the wall.

For 30 years Pena has delivered seminars to young men (and a small number of young women) about becoming ‘high performance’: not just obtaining wealth, but being an alpha male. Then 15 years ago the Trillion Dollar Man (that’s his nickname for himself, I’m afraid) started uploading clips of his seminars to YouTube, and they proved very popular.