The Impossible First

by Colin O'Brady

  * * *

  OUR CONVERSATION, and the unlikely wonder of it, was still replaying in my head the next morning over my oatmeal and my chores in breaking down camp, and as I got out onto the ice. A whiteout had thickened during the night, and as I rolled up my tent, I looked down at my boots, dusted white with snow, and another of Simon’s lyrics came to mind, from a song played on the stereo over and over in my house growing up.

  “Ta na na na na!” I croaked out into the emptiness in my terrible singing voice as I cinched the straps of the sled. “She’s got diamonds on the soles of her shoes!”

  Simon’s vision, that making art is a process and a journey, and that you should push toward it in hope, even if you’re not sure where you might end up, felt suddenly somehow even truer than his lyrics. My journey into Antarctica was itself a work in progress—a block of stone that might become a sculpture if I could complete the goal, or might never be completed despite all my efforts at chipping away, and I wouldn’t know until the end.

  I’d glimpsed that place of wonder before, and as I pulled into the harness, I thought of the morning just before sunrise at Burning Man, the annual gathering of nearly seventy thousand people who, for a week in August every year, build a temporary city in the middle of the blazing Nevada desert in celebration of community and unbound, radical self-expression.

  Light and darkness are intertwined at Burning Man, as days of dazzling, hard desert sun give way to star-strewn nights of deepest black. And the sunrises and sunsets—the great transitional moments of the day—seemed to me most magical of all in illuminating or casting into shadow the whole, mystically created city of giant art installations, music, and dance. The playa, as Burners call it, is more than two miles across. It rises from an ancient salt-pan lake bed, explodes into life for a single week, and then is packed away and cleaned up, down to the last scrap of paper. Stewardship of the land, like the rule that bars the buying or selling of anything at Burning Man, is baked into the culture.

  Jenna and I, after our first day at the festival, had danced all night, then jumped on our bikes somewhere around 4 a.m. We were riding out toward the playa’s edge, through a world of swirling dust and pulsing music and light—from brilliantly lit two-story-tall art installations, to fur-and-feather-wrapped bikes and naked people out walking with their headlamps—when something in the distance caught my eye and I felt compelled toward it.

  It was a tree. The Tree of Ténéré. In a place where there were no trees for as far as the eye could see, artists had created a huge, stunningly lifelike tree with shade and branches that could be climbed. And then as we stood there, our eyes wide with wonder, we saw that the tree itself seemed to be almost dancing. Thousands of tiny LED lights on the tree’s leaves flickered and fluttered with the music that was being performed down below.

  “They’re climbing the tree,” I whispered to Jenna.

  She glanced up at me, looking puzzled, cloaked in her Burner costume of faux fur, fishnet stockings, and dark-tinted goggles.

  I thought for a few moments about what I was really trying to say, and as I did I pulled off the formal but tattered top hat I was wearing as part of my own Burner costume, and ran a hand through my hair, which was thick with fine playa dust.

  “The artists who built this tree knew people would climb it. They didn’t just create it to sit in the middle of the desert by itself. They made it with a greater purpose. The tree is a vehicle for the real art. The people in the tree, under the tree, the two of us here, dancing, being inspired by it—that experience is the real masterpiece.”

  I stopped and fell even deeper into the spell as the pulsing echo of music from one of our favorite DJs, Tycho, rippled through the tree’s electric leaves. The great glow of the desert sunrise was exploding from over our shoulders, too, lighting up the tree in a new way.

  “Our adventure projects… they’re a vehicle, too. Our expeditions are like the tree. I love sharing them with the world—not so people can passively observe them as entertainment, but so they can experience them alongside us and be inspired to act on their dreams. I’m certain that everyone has a masterpiece inside them. Inspiring even one person to unlock their potential creates a ripple effect of positivity.”

  Jenna turned sharply to face me, beaming. “Yes, our projects aren’t about world records or athletic feats, they’re about the ripple effect.” She turned back toward the tree for a moment, then looked at me. “From the whiteboard into reality,” she said.

  * * *

  IN MANY WAYS, the real floodgates of possibility—what might be or could be—had opened with our engagement on the summit of Cayambe. A new chapter had begun for me and for Jenna, just waiting to be written, and in late 2014, a month after my proposal, I flew to Chicago to see Mr. Gelber, the commodities firm owner who for years had supported my dream to race as a pro triathlete and maybe one day make the Olympics. I was terrified, mainly because of the debt of gratitude and respect I felt I owed him, which had grown like compound interest ever since he’d changed my life at that backyard barbecue just after I’d won the Chicago Triathlon five years earlier. Now I had to tell him that I was walking away from the very thing he’d been so supportive of for so long, my triathlon career, and ask him instead to sponsor me for the Explorers Grand Slam project, a commitment of several hundred thousand dollars.

  He met me in his downtown office, and after a few minutes of exchanging news about our families, I confessed my ambition to start a new chapter, leave the triathlon world and break the speed record for the Explorers Grand Slam. Then I paused, afraid to take the next step and mention the cost, even though Jenna and I had mapped it out exactly. So I described our goal of building a platform that would inspire kids and the passion we felt. But finally I couldn’t drag my feet any longer. Jenna’s and my grand vision, I said, would cost $500,000.

  “Wow, that’s a lot of money,” Mr. Gelber said. He was silent for a few seconds. “But it sounds like you’re becoming an entrepreneur, and I respect that, of course. That’s where I come from, too. I have to say, though, that I’m a little disappointed that you’re leaving triathlon and your dreams of the Olympics. I’ve supported you for a long time in those dreams, Colin.”

  “I know that, and I hope you know how grateful I am,” I said instantly. I could feel my heart pounding in my chest as a long bead of sweat ran down my neck into my shirt. The last thing I wanted was to disappoint this man sitting across from me, who’d been so generous and believed in me.

  “As you know, this year I’ve had my career-best results racing triathlon on the world stage. But the truth is that the Olympic dream”—I paused, looking for the right words—“I don’t think it’s going to happen, and this world-record project can be just as meaningful as the Olympics. Jenna and I have a vision for something we can build that can have more impact than any success or failure on a triathlon race course. Mr. Gelber, I always imagined you being there for that moment at the Olympics—you and your family in the stands cheering me on. But it would be just as meaningful to have you as part of our new dream.”

  I stopped and let that sit for a second. “So would you be interested in coming in as a title sponsor now, for this new venture?”

  He paused for a long time, and I felt I saw his expression harden.

  “Here’s the thing on this new venture, Colin,” he said, his eyes boring into me. “I’m not going to be your bank. I’m not going to just write you a check.”

  I lurched forward instinctively with my mouth open, afraid I’d pushed too far, afraid I appeared ungrateful.

  “I didn’t expect that, Mr. Gelber—”

  “My point is this. Entrepreneurship is hard. The hardest thing. Mostly it fails.” He stopped and looked kindly at me across his desk. “Show me something. Colin. Don’t talk plans and dreams. Come back to me with some poured concrete, something real, money committed from legitimate corporate sponsors, your own skin in the game, and maybe then I’ll match whatever money you’re able to raise.
”

  And when I got home to Portland, we wrote another item on the whiteboard and underlined it: “The Gelber Match.”

  * * *

  A FEW WEEKS LATER, on a gloomy Pacific Northwest winter Sunday, Jenna and I decided to go for a hike in Forest Park, the great greenbelt across Portland’s northwest corner, partly just to escape for a while the deeper gloom that we were falling into in our apartment. The Explorers Grand Slam project had taken vivid shape by then, but only in our own minds and no place else. We’d made no progress at all toward the “poured concrete” that Mr. Gelber expected.

  As we headed into the park, the drizzle turned into a cold rain, and we pulled up our rain jacket hoods. Drips rolled down off the top in front of my face.

  “Okay,” Jenna said out of nowhere. With her face covered up by a big green hood, she was just a voice. I couldn’t see her expression. “We’ve got some money saved, right?” she said.

  “Sure, we’ve got about $10,000 between us,” I said.

  “I’m thinking we should put it all on the line, every dime,” she said firmly.

  I paused. I’d heard that tone in Jenna’s voice before, that firm resolve. She’d been thinking a long time about this, I could tell, before ever opening her mouth.

  “What are you saying, Jenna?”

  She pulled aside her hood with a swift motion, getting a face full of rain. It ran down over her eyelashes onto her cheeks.

  “We gotta go all in,” she said. “If we’re really going to do this project, we need a website and a cohesive message…. If you’re really going to change the world, you have to look the part. We have to look the part, and have a fully built-out brand and a one-sentence idea that a sponsor can instantly grasp—something that says what the Explorers Grand Slam is, and what larger impact we will have, and why it’s something the world should care about.”

  “It’s pretty much our life savings…. Are you sure?”

  “I’m sure,” she said, then smiled up at me. “And if in the end our idea doesn’t come to life, well at least we’ll have a cool website.”

  * * *

  THE SCARIEST THING about creating a website that says you’re going to do something is that then it becomes real. And Jenna’s website, built over the next few months with our savings, not only declared to the world that I’d go climb some of the world’s tallest mountains and trek to the North and South Poles, but do it faster than anyone in history—and begin it all in December of that year, 2015, only six months after the website’s launch. I’d certainly climbed some mountains growing up, and I was strong and fit from my years of triathlon racing, but I’d never been to the Himalayas, never been on any mountain above twenty-one thousand feet.

  What was even scarier was we still had no real support or funding to make it actually happen. We’d spent our last penny on the website, not knowing how the vision would become a reality.

  So then desperation really set in. The faintest whiff of a lead on someone who might know someone who might possibly be able to help us became the stuff of instant obsession. There’s a cocktail party and someone who worked a few years at Intel’s Oregon office might be there? Great, who do we call? She retired five years ago from Intel? So what? You never know.

  The doors slammed over and over in our faces, and the message—sometimes veiled, sometimes flatly stated—became a drumbeat that however enthusiastic and earnest we were, we were still young and naïve.

  I became acquainted with every possible variation of the word “no,” and learned to hear the cues as well for false, veiled enthusiasm, and all the horrible variations of the word “maybe,” which were so often just polite ways of saying no while keeping false hopes alive. But the dismissal that never lost its power was “good luck, kid,” which conveyed both rejection and doubt at the same time. It said no, and then suggested that everyone else with a lick of sense would say the same.

  We made cold calls and left messages and wrote fawning, suck-up emails to corporations and high-net-worth individuals, month after month, often with no reply in return. We rehearsed, over and over, what we’d say if and when we could get our foot in the door of a big sponsor. Jenna had calculated costs and logistics, researched potential sponsors, and established a partnership between our new nonprofit, Beyond 7/2, and the Alliance for a Healthier Generation, an organization that was at the time impacting more than 20 million American schoolkids in twenty-nine thousand schools nationwide, working to combat childhood obesity and encourage lifelong healthy habits.

  We became hyperaware of any potential opportunity to bring our idea to life, no matter how slim the chances. We talked to everyone. Whether through a chance encounter, a random introduction, or a meeting with someone we already knew, every conversation was like another bread crumb on the trail.

  But the estimated $500,000 of bare-bones costs—the tab for getting around the world to the Seven Summits and two poles with an expedition at each location—seemed completely beyond reach. Chartering helicopters to and from remote locations, and rushed last-minute changes in getting flights, permits, and supplies would make for soaring logistical costs. We’d make no money doing it even if we could pull it off, but that didn’t matter. Blinded and fueled by our passion and the impact we dreamed of creating, the whiteboard filled up, got erased, and filled up again.

  And then one day I ran into a friend who mentioned that a friend of his worked at Columbia Sportswear, the big Oregon-based outdoor clothing and gear company. Jenna and I immediately took the unsuspecting Columbia employee to coffee, cornering him in a booth in downtown Portland as we poured out our dreams and plied him with lattes. Might the company be enlisted as a sponsor? Who would we need to pitch to? He promised to talk to a colleague higher up in the company’s leadership, and then we cornered her with caffeine and enthusiasm until she said she’d talk to someone else. We bought a lot of coffee. We were desperate.

  Finally, the fourth or fifth person in the chain of connections we’d made inside Columbia called and said he’d gotten us a meeting with the CEO himself, Tim Boyle.

  “After that you’re on your own,” our connection said, sounding happy to be finally rid of us.

  So then we started really studying the company—not just its historical successes and mistakes, but also its advertising and marketing strategies. Jenna read everything she could get her hands on about the Boyle family—refugees from Nazi Germany who’d come to America, bought a little hat company in Portland in 1938, and renamed it for the great river of the Pacific Northwest. She learned that Mr. Boyle favored casual button-downs over formal work attire, and she also learned about the legend of Tim’s mom Gert Boyle—the daughter of the company’s founder and still, in her nineties, Columbia’s hard-charging chairwoman. Gert’s blunt, “get things done” approach ran deep in the corporate culture. And as we drove to the suburban office park where the company had its headquarters, we felt ready.

  Jenna had intended to wear her politics clothes that morning but changed her mind at the last minute and opted for Portland casual, a simple top and slacks. I put on a sport jacket. I’d considered getting even more dressed up until Jenna said my image, as the athlete who’d be out on mountaintops and polar caps doing the project, should be a little scruffier. “Clean but rugged,” she said. “That’s the Columbia sweet spot.” For good measure, I added to my not-so-scruffy ensemble a Columbia shirt and pair of shoes. We couldn’t know what little touch might turn the decision in our favor.

  We parked, found our way into the office building, and an assistant took us down the hall into a windowless executive boardroom. Mr. Boyle was already there, sitting at the head of a long wooden table that was lined with water pitchers and glasses from a previous meeting. We’d expected a group of marketing, advertising, or sponsorship people, but he was it. For better or worse we’d be pitching in the major leagues, trying to sell our idea to one of the wealthiest and most powerful businessmen in the state. We glanced at each other and I felt my jaw tighten. My heart poun
ded in my chest as we took seats adjacent to Mr. Boyle at the table’s end.

  Jenna had prepared for weeks what she’d say and went through it flawlessly, how Columbia’s image around the nation and the world was tied to the outdoor spirit of the Pacific Northwest, and how our project was in many ways trying to tell that same inspiring story, about a local Oregon boy heading out to some of the world’s most challenging places, living the Oregon dream.

  “Your current campaign is ‘Tested Tough.’ What better way to test Columbia’s gear and showcase it than to have Colin wearing it in some of the world’s harshest places?”

  Then, on her laptop, we pulled up our project’s launch video from the life savings–funded website we were so proud of, watching every muscle on Mr. Boyle’s face for a reaction.

  Unfortunately, the expression we saw wasn’t good. He looked ready to yawn as the video played. Then he glanced at his watch and stood up, clearly already gone, thinking about his next, more important meeting. After barely five minutes, the pitch meeting we’d agonized over for weeks was sputtering to a close.

  “Nice meeting you both,” he said cordially. “Good luck with this.”

  I kept talking as we scrambled to our feet, trying to spark something, anything, that could keep us all in the room, but Mr. Boyle shut me down with a stern glance and a little downward tilt of his head. “Good luck, Mr. O’Brady,” he said, emphasizing the word “luck” in a way that sounded like a thousand slamming doors.

  Then Jenna charged. It was the same stiffening of posture I’d seen in the car driving back that day into Portland. She’d resolved something.

  “I think you’re missing something here,” she said, taking a half step closer to Mr. Boyle and looking him in the eyes. “This isn’t just a feat, or a stunt—we’re building toward something larger.” For the next minute she talked about how the Explorers Grand Slam project would be a brick in the wall of a much bigger vision, how we wanted to use it and projects like it to inspire people, especially kids. She stressed how Columbia Sportswear would be a great partner with us, that there’d be “mission alignment.”