Career Lessons Learned on the World's Most Grueling Bike Race

Career Lessons Learned on the World's Most Grueling Bike Race
Source: Patrick Sweeney

A torrent of sweat is running off your nose, the humidity and triple digit temperatures make it a struggle to just take in a breath. As you get off your mud-caked mountain bike to fill up your water bottle for the 10th time today you notice a cute, very brightly colored little frog on the ground. Curiosity gets the best of you so you bend over to look closer. The little monster torpedoes a poisonous dart that pierces your neck, tapping right into your jugular and the next thing you see is a pure bright light and Saint Peter.

Poisonous dart frogs, dengue fever, rabid howler monkeys, miles of mud and the icing on the cake: a 6.6 magnitude earthquake.

These are a few of the dangers awaiting five successful CEOs who are about to embark upon an epic mountain bike race.

These five (chose your adjective: studly, crazy, overcompensating, exemplary, suicidal, introspective) CEO/Entrepreneurs have been training all of 2012 for this race.

Five guys who are part of a team racing across Central America. The race is La Ruta de Los Conquistadors and it is widely known as the world's toughest mountain bike race. 250 people will start it and no one knows how many will finish, or live to tell about it. Our team is CoreCo/dwinQ.

Meet the Team

Career Lessons Learned on the World's Most Grueling Bike Race
Source: Patrick Sweeney

I'm one of the CEOs.

Over the course of the next ten days I'll tell the story of why we are doing it, give an update midway through the race, and then share the lessons we learned in and how it affected us.

First meet the team:

Patrick Sweeney (Me): I run dwinQ, one of the hottest social media companies in the world. We are the first company to build brand champions at events and venues by capturing and posting precious social memories to social media without guests lifting a finger.

Sami Inkinen: An entrepreneur who co-founded Trulia which just went public. Its real estate analysis and recommendations helps consumers make better home buying and selling decisions.

Will Mueke: He was a top performer at Goldman Sachs. He left to start CoreCo Holdings, a private equity fund focused on helping Central American companies grow (especially in the "green" sector) and bring investment into the region.

John Stimpson: A former college tennis player who is running an international lumber company and logistics provider doing business throughout the Americas.

Nat Grew: The team's inspiration is a native Costa Rican whose business is a land trust and stewardship company creating a watershed scale, mix-use international model for sustainable development and environmental education.

We are five different guys who came together for the same challenge: Survive three days of torture while following the route the brave conquerors blazed in the 1560s.

Why leave the corner office for the tropical jungle?

Our reasons for taking on this formidable contest are as diverse as the group, but the common thread stitching us together is the desire to push ourselves to be better, to learn more about ourselves, to appreciate despair and look for fleeting moments of jubilation.

In the process we will forge new relationships and experience an amazing environment but that's secondary to the effort.

This is Nat's fifth time racing at La Ruta and he suggests that:

"The race is a complete journey and an analogy to life itself. You know where it starts and where it finishes, and everything in-between is filled with continuous adventures and circumstances where one is challenged to the highest level physically and mentally in order to reach your purpose and follow your intention. Sometimes there are moments when you think that things can't get any worse yet you stick with it and persevere. Before you know it your entire internal and external environment has transformed and you are overwhelmed by a sense of inspiration, energy and simple joy for life. And inevitably before you know it the cycle repeats itself, many times during each stage."

I'm nervous.

Career Lessons Learned on the World's Most Grueling Bike Race
Source: Patrick Sweeney

The race is way longer than anything I've ever done. I was second in the Olympic trials in 1996 in Rowing - that was a seven minute race - this is my first La Ruta, a three day race, and despite having done Leadville Trail 100 MTB for the past two years, this ranks ten times harder in my mind to any endurance event I've ever done.

For me, the training required painful discipline to squeeze 12 hours of riding into a typical week filled with steering a rocketing start-up, enjoying an active family, flying 150,000 miles, and keeping season tickets to the Red Sox (thankfully they didn't provide a compelling reason to be off the bike - proving yet again everything has a purpose). But if I can do it, I believe anyone reading this blog could as well.

Days One and Two: A Test of Endurance

Career Lessons Learned on the World's Most Grueling Bike Race
Source: Patrick Sweeney

There are two very different kinds of endurance – physical and mental. It is when you are pushing the limits of both simultaneously that you learn the most about yourself.

The team CoreCo/dwinQ members at this year's La Ruta de los Conquistadores ("The toughest mountain bike race on the planet") had plenty of time for introspection on a first day that was 95 degrees and had high humidity. Of the 500 people who started day one only 350 finished.

Day two we climbed up over 10,000 feet to the top of an active volcano. The mud, blood, sweat and determination mixed together to blend a potent cocktail of grit that brought all five of the CEOs on our team to the finish line on both days.

This year is the 20th anniversary of La Ruta and it began with a typically mellow Costa Rican send off – the saying "Pura Vida."

We left the soft sandy beach of Jaco and rode 10 kilometers on easy roads. Then the climbing began. The first climb was a three mile test of leg strength and mental discipline. The long pitch topped out at 30% grade in several sections. Many people walked, some that rode regretted it six or seven hours later when they needed strength reserves. It's easy for the inexperienced to start out too hard and too fast, with the adrenaline of a big race.

Career Lessons Learned on the World's Most Grueling Bike Race
Source: Patrick Sweeney

By far the toughest mental challenge came in the middle of day one when we penetrated the Carara jungle.

The single track sliced through miles and miles of dense green jungle. Wet cement would have been easier riding than the red clay we fought through for hours on end. With no traction because of mud caked onto uselessly thin tires, we spent much of the time carrying bikes both up and down hills. Seven river crossings (those populated by poisonous snakes and fresh water crocodiles) gave us the occasional opportunity to rinse of the dead weight of red clay from our bikes and bodies. After the first day was done we had climbed more than 12,000 vertical feet.

Career Lessons Learned on the World's Most Grueling Bike Race
Source: Patrick Sweeney

The second day was much more straightforward but equally challenging.

It was a straight climb starting just above sea level to the top of the still active Irazu volcano. The climb up was a mix of trails, cart paths and paved roads - sometimes out in the blistering sun, sometimes in the mist and chill of high altitude but seemingly endlessly straight up. The descent for some was as challenging as the climb. Many people who are not technically astute on fast mountain bike descents over rocky terrain made the decision to walk places where others flew down.

At dinner tonight I asked the other entrepreneurs on my team what they were thinking. Several experienced riders talked about the change in quality of the race from previous years – noting a higher level of professionalism in the logistics and execution. Some mentioned what a nice job the La Ruta de los Conquistadores team did marketing the race and selling the experience. This has accounted for the biggest turn out ever. All of us agreed that the unexpected extra 10 kilometers at the end of day two was the race organizers' way of keeping riders guessing – like the Conquistadores who first crossed the country must have done.

At many points during the race we all reflected on our motivation for racing La Ruta. We knew, as entrepreneurs must believe, that we would succeed. No one thought about quitting despite mechanical issues, missed feeding stations or other mishaps. We knew to expect the unexpected and brace ourselves against the challenges we were given. We all knew that the physical endurance is ever present – these days in the middle of the race it is a simple test of will.

Huge white grins jumped out from faces caked with mud, dirt and sweat. Our battered bikes were cast off in the sand after three hard days of crossing Costa Rica's most challenging terrain during the 20th annual La Ruta de Los Conquistadores mountain bike race. We finally made it to the Limon's Caribbean beaches.

The five entrepreneurs that made up my team exchanged adrenaline-fueled high fives and warm hugs. We each felt the proud weight of our finisher's medal tugging at our necks.

After three days of punishment in the jungle, on a volcano, along sandy beaches and over Class IV rapids (in biking gear) what lessons did we take away and can bring to life, businesses and those we lead?

Career Lessons Learned on the World's Most Grueling Bike Race
Photo by: Patrick Sweeney

Never stop moving –There were times when we were in the remotest areas of Costa Rica, not a soul in sight - and then we would come to a fork in the road. We picked a path and rode it for as long as we needed to in order to get enough information to keep moving in that direction or change course. Most of the time, as in business, our first instincts were right, but even if we were not right the first time we gained valuable information and made adjustments.

Think of everything that could go wrong and prepare with Plan A, B, and C – Even though we had two of everything, creativity played a big role in staying positive and keeping the machine of team CoreCo/dwinQ running. From one of the CEOs borrowing a pair of shoes two sizes too big, to broken bike parts fixed in the field and carrying an extra water bottle, each CEO at one point had to adopt strategies to be ready when Murphy's Law decided to fight the team. When one of the guys lost his brakes on a treacherous downhill he improvised and stayed safe. Creativity kept him positive, and performing when crashing and burning seemed imminent.

Know when to be aggressive and when to be patient – Day one started out with a very, very (did I mention very?) steep 12,000 foot climb. Many people cooked their legs after just 3,000 feet. On day three, many people started out too slow and when we came to the first railroad bridge, they had to wait 20 to 25 minute standing impatiently in a queue before they could cross, one foot at a time balancing their bike on their shoulders. Being more aggressive would have saved 20 minutes. Looking out at the bigger picture and deciding what action it calls for now is crucial to long-term success.

Exercise your courage and it becomes stronger – Everyone has courage equal to the greatest explorers, but 99% of the population never taps into it. It's easy to find a reason not to face something you are scared of – like snakes or flying or crashing your bike on a downhill. Translated to the business world, maybe this means you don't want to leave a steady job or try a new way of doing things when one particular method has worked well for years. Acting courageous perpetuates courageous behavior and provides great rewards. This axiom should stay clearly in the cross hairs of your behavioral scope so that you can be different from the 99% of other people who never take a risk and exercise that courage.

Sometimes for the team to finish first you have to finish last – Team CoreCo/dwinQ actually consisted of five CEO entrepreneur sponsors (myself and four colleagues) and a total of 19 riders, many of them up and coming Costa Rican kids who could not afford to do the race without our help. Our goal was to get everyone to the finish line as fast – and as safely – as possible. We had a couple of injuries, and one technical disqualification, but otherwise going into day three we were on track to get everyone to the other side of Costa Rica. Suddenly one of the younger women began to struggle on the last day. One of the fastest CEOs (who was having a personally strong race) chose to ride the last day at his slowest pace to stay with this woman. He finished fourth to last that day, but as he came in with the woman, he realized he had created a big positive for Costa Rican cycling and mountain biking. He relentlessly put the team ahead himself and all of us benefitted from it.

Now, as I'm sitting on the plane flying home, happy to be away from the bike for a week or two, I look around the cabin and believe that everyone should pick their own La Ruta each year. Sitting on the beach or watching "Dancing with the Stars" might be relaxing, perhaps pleasurable, but it does nothing for long term happiness or personal growth. Picking your own challenging La Ruta, be it physical or mental, that requires courage, discipline, creativity and planning or training will make you a better person, better parent and better leader no matter what your position.

PS – Feel free to share the toughest thing you've ever done in the Comments section and how it made you better as person or a leader

Patrick Sweeney is President and CEO of dwinQ, a social media marketing company.

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