My Week: Will Dean of Tough Mudder

The man behind 'the toughest event on the planet' on keeping busy, attracting talent and why entrepreneurs are like celebrities.

by Rebecca Burn-Callander
Last Updated: 09 Oct 2013
I’m on the road a lot. At least ten days of every month are spent travelling. I have meetings with sponsors and partners, I speak at entrepreneur forums, and I attend events run by Tough Mudder, the Iron Man event I founded. It’s an incredibly fast-paced lifestyle.

Like most CEOs, there is no typical week for me. But, if I’m in New York - where Tough Mudder is headquartered - I usually start work at 6am. Most of my work has to be done by 9am. That’s when my meetings begin. My first catch-up of the day is always with my COO and co-founder Guy Livingstone. He handles the day-to-day running of the business - I try and stay out of the fire-fighting. At these meetings I hear about the parking guy in Arizona who kicked up a fuss at an event or the lawyer who’s suing us for a mystery client who allegedly broke a leg at one of our events. When you’re running a start-up business, it’s easy to feel as though – at times – the whole world is against you.

Then there’s a series of meetings with team leaders and department heads. Over the past four months, headcount has doubled to nearly 50. When there was just 25 staff, I could communicate with everybody pretty effectively. Suddenly, with all these people, things can be misinterpreted so easily. Our team is pretty young – the average age is around 26. Trying to communicate complicated strategic goals that are really important to kids straight out of university, who maybe aren’t so business savvy, is a real challenge. But we’ve cracked it. We’re creating a company brochure, more of a comic book really, to lay out our goals and plans for the future.

Tough Mudder is still growing. I spend around four to six hours interviewing new people every week. Guy and I have a policy that we interview every new starter. But with 14,000 resumes flooding in this year alone, it can be time-consuming!

There’s a reason so many people want to work for us. First, there’s the Tough Mudder University. I went to Harvard Business School, so every month I pull out a company case study – something relevant to the challenges we might face as a business – and sit down with the team to discuss it. I also make sure that every person in the business is focussed on developing at least one professional skill at all times.  It’s not 100% altruistic. Not only does it help my staff to think more strategically about the firm, it also helps keep them engaged.

Tough Mudder is packed with high achievers. Some only want to work here two or three years and then launch their own ventures. Guy and I are actually in the process of starting a fund to help these budding entrepreneurs get started. After all, you don’t invest in an idea, you invest in a person, and we have nothing but faith in our lot. We’re looking forward to becoming venture capitalists!

Around 20% of my week is spent doing those mundane tasks that you feel anyone could do, but that ultimately need to be done by the CEO. Approving plans, chairing meetings, being seen at events and – no offence intended – regurgitating quotes for journalists on what Tough Mudder is and how I got started. It helps that I now have an excellent PA. She’s ruthless with my diary, making sure I spend no more than four or five hours a day in meetings.

The days are always hectic but I do try and finish work at sensible time. My fiancée is a corporate lawyer; we’re two busy people struggling to maintain a work/life balance. We usually manage to be home by 8 o’clock so that we can have dinner together before collapsing into bed. I suppose that’s the irony of running a company that encourages people to create fitness goals and push themselves, Guy and I struggle to find time to do it ourselves now.

Not that it’s all bad of course. The funny thing about the US is that entrepreneurs are like celebrities: the American dream is to start a business and get rich. Let me tell you about a little encounter I had earlier this week. I look quite a lot like Matt Stafford, the quarterback for Detroit Lions. I was on the subway and some guy winks at me and says, ‘Hi Matt!’. I said he’d got the wrong guy. I suppose my English accent made him feel a bit silly. But then this other man turns around, looks at me and says, ‘No! It’s that Tough Mudders guy.’ And a third guy pipes up, ‘Yeah! It’s that Will Dean.’ It was one of the most surreal moments of my life.

- Tough Mudder is based in New York. Check out our all-new Comment section on Monday 14th November to read Will Dean’s ‘Englishman in New York’ diary for Global Entrepreneurship Week.  

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