by Will Dean
Jenn had come up with her idea for Rent the Runway at almost the same time as I had first thought about Tough Mudder, so we spent a lot of time scouring the curriculum for ideas that might be helpful and refining our business plans. Her heretical mission was to democratize high fashion by creating a service that rented haute couture fashion to women. Jenn is an honorary Tough Mudder in that she showed resilience and faith in her idea in the face of skepticism and obstacles. I think she and I were the only two graduates in our year to launch our own businesses upon graduating.
Rent the Runway began in 2009 with twenty-eight designer brands and no warehouse. They stored their dresses at a dry cleaner’s four blocks from the office. As with Tough Mudder, Jenn hit the ground running. An article in the New York Times led to a hundred thousand members signing up in her first week of business, and she had a million members just over a year after launch. Today, Jenn employs 850 people and has a 160,000 square-foot warehouse in New Jersey that houses the largest dry cleaners in the United States; she works with 340 of the world’s top designers. A recent article in Cosmopolitan suggested, without irony, that she had, in a few short years, achieved the not inconsiderable task of “changing the way women shop forever.” Throughout that journey since Harvard, Jenn and I have met up and swapped experiences and challenged each other regarding what we could be doing differently or better.
One of the things all these entrepreneurs share, I think, is a sense that, looking back, they hardly had a choice in what they did. The business they wanted to create effectively chose them. They just enthusiastically embraced their fate.
That’s also true of me and Tough Mudder. The motivation to be an entrepreneur is often boiled down to the cliché that you must above all follow your passion. I don’t think that phrase quite gets what I am describing. If I hear people say things like “I want to set up a ski company because skiing is my passion,” I can’t help feeling they are likely to be disappointed. If they run a ski company, they are going to spend an awful lot of time in an office, talking about skis. They would probably be better off, if they really wanted to follow their passion, to get a job where they have lots of spare time and can live near a mountain.
When Jenn Hyman or Neil Blumenthal or James Reinhart describe their respective passion, it is not often about the product or even the environment they have created (though they are proud of those things). It is about the way their business has proved that their original idea about making the world a slightly more enjoyable and efficient place was right all along. The products themselves were just a vehicle for delivering that idea.
When I think of my own early efforts at commercial enterprises, I could certainly convince myself there was a pattern in what I was trying to prove. That I was being led to the problems I think I eventually tried to address with Tough Mudder. I set up three businesses at school and university. The first was when I was fourteen and part of what was called a “Young Enterprise scheme,” an initiative to encourage entrepreneurial thinking in schools. Most people made biscuits or cushions and sold them at school events, making about a hundred pounds. The team I led managed to get the concession for a nail polish that changed color under UV light from a company in the States by creating a Web page—this was 1997—that suggested we were older than we were. The earliest leadership decision of my business career was to maneuver the teacher who was supervising us out of the decision-making process. And we sold about four thousand pounds’ worth of this nail polish around town (with the aid of a UV lamp borrowed from the science labs). For a few months among the teenagers of Kettering, it was the must-have accessory. Everyone wanted to be a member of that nail-polish tribe.
The second business came about after I persuaded my headmaster to let me send out a letter to all the parents at school, suggesting that their sons and daughters needed a sports bag branded with the Oundle school emblem and name. The letter, which I still have, wasn’t perfectly written, but it was well worded enough to suggest that while the bags were not mandatory, kids might feel a bit left out if they did not have one. I mentioned as a further incentive that students at a rival school had branded bags. After a bit of legwork and bargaining I found a supplier in Hull, in the north of England, who could supply these bags for three pounds, and I sold them to parents at a still reasonable twenty pounds. When I came back to school early for preseason rugby training, I went to the headmaster’s office and asked, “Did anyone order the bags?” He came out with a huge box stuffed full of letters, and I remember sitting on my bed going through all the orders. Basically, every boy in the school had bought one. I made ten thousand pounds.
At university in Bristol—when I wasn’t writing overlong essays for my economics class—I started a similar business. I had an idea for a T-shirt that had course subjects printed on the back and the names of all the people majoring in that discipline listed underneath in small type. These T-shirts are quite common now, but at the time, no one had seen them before and they sold extremely well. I expanded to other campuses and colleges around the country. People could never work out how I got all the names of the people majoring in the discipline, but it was pretty simple. I’d take a high-res picture of the bulletin board outside a lecture hall, which routinely listed the names of students studying a particular subject. I’d then e-mail the photos to an outsourcing company and someone in the Philippines printed up the shirts for me.
These little businesses were just hobbies, though I took them seriously—and at one point thought about making the T-shirt enterprise a full-time occupation. Somewhere underneath I think I wanted to prove that despite all the academic complexities of my economics course—which I loved—a business boiled down to a few basic equations: you think about what people might want to buy, you make a product, you figure out how much it costs to make it, you figure out how much you can sell it for, and then you sell it. Then you look at how much time you spent on all that and you decide whether that was a good use of your time.
Beyond that equation, with the bags and the T-shirts in particular, I was increasingly interested in the way you could sell the idea of communality, how you could create a business out of shared identities—even just the must-have factor of nail varnish or a bag or a T-shirt—and how you could quickly make that tribal, viral idea spread. They were all little test cases for a more grown-up business based on that universal need: belonging.
Many definitions of social enterprises would not include for-profit organizations like Tough Mudder, which sell ideas of community along with their product. I believe that is a false opposition. Businesses can deliver values and happiness and well-being just as surely as charities or government agencies. Entrepreneurs should apply their problem-solving talents to social questions as well as markets. Clearly Tough Mudder is not in the business of curing cancer or bringing peace to the Middle East. But I believe that it has found one way of aligning its commercial success with some real human and societal needs. On one level we are in the events business, selling weekend obstacle courses. On another we are part of a trend that makes health and vivid experiences the new luxury goods. But I think at the core what we are offering are those hard-to-find and much-in-demand qualities: community and self-belief.
At Harvard, I played around with a few of these thoughts. Quite early on, and by accident, I introduced a new sport to the university. The sport was a version of the ancient Indian game of kabaddi, which involves capturing territory and raiding parties and, curiously, not taking a breath while in the opposition’s part of the field. It was said to have been the sport of Lord Krishna himself. I’d learned to play kabaddi while I was stationed in India with the Foreign Office. I mentioned the game at one point in a seminar at Harvard and was met by the alpha males in my section with a bit of predictable mocking and derision. “What’s Will railing about now?” To me that response sounded something like a challenge, so I invited my classmates outside for a kabaddi lesson. I’m not sure how well this story reflects on
me, but when I mentioned this chapter about heretical—Tough Mudder—leadership to Jenn Hyman she insisted I include it. I’ll tell it, in that case, mostly as she remembers it.
Jenn recalls how I led the section out on the field and divided it into teams and had them chanting “KABADDI! KABADDI!” in low and high voices. She explains how I instructed them in the game’s unfamiliar, aggressive poses and karate kicks, performed with shirts off, facing each other. At this point her memory captures more details than mine. “Basically, you took a bunch of thirty-year-old men and quickly made them act like five-year-olds,” she claims. “They seemed to love it. That wasn’t the end of it though. You told them, ‘We are going to do this once a week and we are going to attract more people.’ This built up to a crescendo to the point—and I have photos—when all of the men in our entire year were gathered outside the prestigious Baker Library to play a kabaddi tournament. Chanting. Squaring up to each other. Doing the weird martial arts. All the women had been invited and were just laughing and wondering what the heck was going on. I thought it was one of the most hilarious things I had ever seen. These guys were all taking it immensely seriously. You were roaming the field, urging them on: ‘Kabaddi! Kabaddi!’”
Jenn recalls, too, another moment that I don’t remember. She watched me, she claims, looking out over a field containing at least four hundred shirtless men acting like idiots, many of whom thought they were (measured in zeros) the smartest males in the world. She swears she whispered to me, “Will, what is this?” Apparently, I looked back at her with a raised eyebrow and said, “Jenn, it’s alpha males.” Jenn is in touch with more of those kabaddi players than I am. By all accounts they remember the kabaddi season fondly to this day.
Jenn further insists that Tough Mudder could never have come about if it hadn’t been for my version of kabaddi at Harvard. I’m not at all sure about that, but I would go as far as to say it was another, jokey test of my interest in the seductive power of tribes. Mostly I was having a bit of fun with the high seriousness of many of those guys, their sense that everything was a competition and an opportunity to display their manly prowess. But it also revealed something else: something that made me think. I’d managed to create this weekly event with just a silly challenge and a partly made up set of rituals and rules. What if you used those principles more in earnest, challenged people to believe in something as passionately as you believed in it; what might be possible then?
Heretics tend, Seth Godin claims, to use the language of faith: “Challenging the status quo requires a commitment, both public and private,” he writes. “It involves reaching out to others and putting your ideas on the line. Heretics must believe. More than anyone else in an organization, it’s the person who’s challenging the status quo who must have confidence in her beliefs.”
That sense of unshakable belief in the viability of your idea is crucial because it feeds the resilience that gets any new project or businesses off the ground and encourages the grit that sees it start to thrive. The idea of making money is not in itself sustaining. There has to be the stronger motivation that you are doing something worthwhile and interesting with your life and spreading those qualities to the lives of others. Without that core belief you would never keep going.
Neil Blumenthal at Warby Parker did not believe in a new kind of eyeglasses; he believed he could make a difference in the world with a new kind of business model. Jenn Hyman does not see Rent the Runway as a shop or a service but as a “life mission,” which is “to make women feel beautiful and self-confident every day and by nature of doing that to be empowered to change their lives, to ask for the promotion and get the guy and achieve what they want to achieve.”
Missions are essential to entrepreneurs. I was affected as I was setting out on the journey to Tough Mudder by reading former presidential candidate Ross Perot’s extraordinary account of his extraordinary life. Perot’s singular obsession with problem solving had seen him become both the “fastest, richest Texan” and the biggest loser in the history of the New York Stock Exchange in a single day. Later in life he invested both in Steve Jobs and in hostage release—to prove his point that there were always solutions—and never stopped trying to remake the world a little more efficiently. “Failures,” he wrote, “are like skinned knees—painful but superficial.” Even so, the things he remembered of his career, and the things you remember from his account of it, were not the successes but the number of times people said no to him—seventy-seven—before he got his first sale and how often he literally risked everything to prove his belief in his business ideas—to the extent that his wife threatened to divorce him and his family disowned him.
Perot was an extreme case. But I recognized from his story the sense that any entrepreneurial mission is nonnegotiable. The best test of any idea is the realization that you will never be happy in your life until you have at least given it your best shot. The moment you are struck with that realization is the moment when you understand you are perhaps wired slightly differently than most people. Confirmation of that comes when you have to explain for the fiftieth time why you are not doing the easy thing, like using your talent and experience to get a salaried job, but instead are obsessed with this strange thing that is not even a thing except in your head: mud runs, in 2009, in America, in my case.
All entrepreneurs probably know that feeling—and the slightly pitying look on the faces of people who don’t quite get it. At the very start of Tough Mudder, when I was mostly working on my own, I would go for drinks with friends from Harvard. They would listen to me talk about my heretical and muddy mission with a slightly disbelieving look—“What’s Will talking about now?”—and when it came to paying the check they would say, “I’ll get this,” as if I had become a no-hope charity case. “It’s not that bad!” I would insist. “I can afford to buy a round.”
That sense of disbelief, the idea that I might come to my senses and go work for a consultancy, persisted long after Tough Mudder launched. When I met up with friends, they would tell me about their frustrations with their boss or a tough presentation they had to give or whatever, and I would explain how I was in a standoff with New Jersey contractors who were holding our equipment hostage in their van until we paid them. Or how I had discovered that the people who had offered us a deal on renting portable toilets were actually mobsters who had no portable toilets but wanted payment anyway.
One of the things that often came up when we were discussing business ethics at Harvard was the “Nigeria question.” That is the one that asks, “What would happen to your company values of decency and transparency if, say, you were in Lagos and you needed to get a bridge built quickly?” The answer is always, “Well, things are a bit different in Nigeria.” But in my daily experience things were a bit different if you went four miles through the Holland Tunnel. The high-level problems that you think you are solving with your business are not the problems that overwhelm you day by day.
It is not the major setbacks that get to you; it is the accumulation of small ones. I didn’t cry often when we set up Tough Mudder (after all, as the pledge says, “I do not whine—kids whine”) but the closest I came was just before the second event when we had been hit by Mr. Mouse’s writ and were coming to terms with the full logistical nightmare of what we had committed to.
I was at a post office in New York, and it was imperative that we mail some large parcels of equipment for the California team that night. We got to the post office with the parcels with ten minutes to spare but were informed that when you send a package, it can’t have any writing on it other than the address. So we had to buy brown paper to rewrap and readdress the packages, and by the time we had done that the woman pulled down the shutter and said we were too late. It was after five p.m., and we had missed the next-day delivery. We were tired. There had been, it seemed, a thousand things conspiring against us that week. And I felt tears welling up. It wasn’t the worst thing that happened. But it was t
he last thing that happened.
During despairing moments, and all entrepreneurs have plenty of them, it is your sense of mission that keeps you going. In the difficult transition from founding a company to the day-to-day dramas of leading it, it is essential to keep that founding principle in mind. To a large degree that means falling back on your core values. I tried to always be clear and consistently principled when it came to some of the tougher situations regarding contracts and negotiation. I tried to behave at all times like a Tough Mudder.
A couple of days before our first event of the second year, for example, our contractor put down his tools and refused to carry on until we paid him for materials he said he had paid for out of pocket. The contract we had signed stated we would pay him twenty thousand dollars up front, as we had done, and the balance twenty-eight days after completion. He wanted the balance—eighty thousand dollars, I think—then and there, or, he said, the course would not get built. If he had come to me and asked to renegotiate or said he had a specific cash problem, I would have listened and maybe would have compromised. As the contractor knew, however, we had ten thousand people arriving in two days’ time to run a course that had not been built. He gambled on me doing the easy thing and paying up. But I don’t like to be threatened. It sets bad precedents. To his surprise, I told him on the spot that his demands were out of line and his services were no longer needed. After a slightly panicky search, we managed to find another contractor, the Policelli family, who could build the course on short notice and who have become a crucial and trusted part of our story.
