Note: CNBC published an article titled “6 Lessons One CEO Learned from Biking with Richard Branson”. This blog post gives more detail on Virgin Strive and the overall experience.
Below are eight entrepreneurial lessons gained by cycling three-hundred miles in four days with 20,000 feet of vertical climbing (the equivalent of the largest peak in the United States, Mount Denali of Alaska) having no previous cycling experience, other than on beach cruisers, with a total of four weeks of training and preparation. The lessons learned are remarkably similar to a lifetime of entrepreneurial experiences, just intensified into a few weeks of preparation and a handful of riding days. By way of background, I was invited to Virgin Strive by Sir Richard Branson in July 2016, specifically to leg 2 of the cycling, which kicked off on September 15, 2016 in Magliano, Italy. Virgin Strive is operated by the Branson family, most notably Sam and Holly in close cooperation with the Big Change, a youth charity organization. Previously committed personal travel two weeks prior to Strive meant I would have a total of four weeks to learn the basics of cycling, acquire gear, arrange travel logistics and train to ride up to 100 miles per day through the mountains of Italy. How often is Richard Branson going to invite you to cycle with his family, closest friends and colleagues ? Not often I suspected — so I accepted the invitation.
The mission and values of Virgin Strive resonate, it gave purpose to the hard work and persistence that it would take. ‘Strive’ aims to fill the gap that our school systems fail to cover in promoting a growth-oriented and hopeful mindset in our young people. Having founded Next Generation Entrepreneurs with the Pinellas Education Foundation and Shane Whitlatch, Strive would provide the opportunity to exchange ideas with like-minded people. Strive is led by remarkably positive and supportive people, so not only would we be generating money for a great idea, I would be stretching my physical and mental limits, and have an opportunity to learn from some of the very best.
Fortunately, FairWarning’s Leadership Team is incredibly strong and we were all on the same page about what needed to be done in the weeks of my absence. The team was supportive and up for expanded leadership. To participate in Virgin Strive, I would be coming from a kitesurfing family vacation in Fiji, hitting the cycling and mountains of Italy within 72 hours of arriving from Pacific waves and wind. It was important to me that FairWarning leadership meet together during my stopover back home to ensure we remain synched up on our healthcare customer initiatives and preparation for Dreamforce in October. Kitesurfing is something I learned at 52 years of age and is the travel-adventure sport of a lifetime — but that is another story.
As cycling leg 2 of Strive completed, I reached goals that 45 days prior I never thought would be possible. It became obvious that the experiences of Virgin Strive were lessons about entrepreneurship and life that resonate deeply with my own experiences, the summary of which is “Persist, Collaborate, Grow and Thrive”. Some of the specifics are below: 1) Know and Trust Yourself. Unrelenting optimism is a must to any worthwhile endeavor, but knowing your actual current capabilities and how to get leverage from your strengths is a key to success. I am accustomed to persisting through long periods of physically, mentally and stressful conditions to reach goals. It might be the biggest skill I have. There was no chance of getting through three hundred miles with athleticism and power. I had to be realistic. Grinding it out over time was the best plan based on my strengths. When other riders are cruising past you up a hill, or blowing past you down a hill, when it feels like you are really doing something
wrong, you have to trust your own instincts about the right plan for you. Self-awareness is a strength in entrepreneurship and in cycling.
2) Set Big Goals and Work Backwards to the Moment. Entrepreneurs have big goals and dreams but the day comes when it’s time to roll up your sleeves and execute. The key is to keep the ultimate goals in the back of your mind at all times, but have a plan for every day and even every moment as to how you will get incremental progress. Like most things entrepreneurial you have to embrace massive conflicts, in this case keeping in mind finishing 300 miles but turning the pedals over in every moment according to a tactical plan.
For cycling this means understanding the roadmap for the day including elevations, distance and expected conditions, then arriving at a strategy for managing yourself through the course. As expected there is always the unexpected from rain to winds, accidents, blowouts, helping a teammate on the roadside and equipment failure, so you adjust and keep moving. This is identical to business, you dream big then decompose the steps into a plan that can be executed every day adjusting quickly when conditions arise.
3) Listen to People Who Have Done It. John Houston an avid cyclist was the right person at the right time to provide insights and guidance. For whatever reason John’s mindset resonated and I took notes for forty-five minutes in a crash course on long distance cycling. John is a long-time customer at the University of Pittsburgh Medical Center who knows a thing or two about excellence. John’s insights about knowing your capabilities, keeping your own pace, nutrition and using the proper gear was invaluable to completing the goals of leg 2. There were many others who contributed bits and pieces of critical information.
Embarrassingly, even the idea of padded cycling shorts was news to me. That insight really answered some early questions plaguing me about how someone’s rear-end could survive eight hours on a bike seat. Listening to people who have “done it,” and letting that resonate with your own values and beliefs is a lesson for all seasons, and most certainly entrepreneurship.
4) Surround Yourself with Positive and Supportive People. A big part of your ability to improve and grow by making new distinctions comes down to the company you keep. What is the saying ? “You are the sum total of the five people you spend the most time with.” This holds true in entrepreneurship and in cycling. Make sure you have support on all fronts from people that have something to offer even if it is simple encouragement and a positive attitude. And it has to be a two-way street, be an active cheerleader, ready to support others when they need it. The Virgin Strive group was the most positive and supportive group I have ever been around. This is a winning culture in cycling, entrepreneurship and life.
5) Roll Forward at All Times. Roll the bike forward, keep your bearing on the course and keep moving forward all the time. Go as fast as the terrain, conditions and your body will give you in the moment, but keep moving. Looking over your shoulder or dwelling on the past doesn’t get you anywhere. When you persist in moving forward over a long period of time, eventually you show up at the finish line every day and in the grand scheme.
6) Avoid Big Crashes, Injury and Don’t Die. Cycling is inherently dangerous not necessarily in any given instant but over the course of long rides things are bound to happen unless you
actively manage risk. Riding through traffic in cities, around blind corners in villages, up hills with sharp drops when you are tired or speeding downhill along a mountain edge in the rain with oncoming traffic all present risks.
So I established a rule early, “don’t die”. Yes we all want to gain time after grinding up a hill, but if it is raining or the road has light gravel, is it really worth going top speed downhill to pick up a minute or two when the downside is serious injury or loss of life ? The same applies in entrepreneurship, we all want to go fast especially after long periods of planning, investment and waiting, but remember some basic rules, don’t run out of cash and go bankrupt or injure the company so badly you can never recover. Go fast but develop your intuition and skills in risk management.
7) Recovery is Mandatory. Recovery isn’t optional, recovery is mandatory. As soon as you step off of the cycle at the end of a long, tiring day, there are specific steps that have to happen in order that you repeat your performance the next day. Surprisingly, if you pay attention to recovery, you actually can improve your performances even when riding long daily distances. To accomplish really big goals in cycling and entrepreneurship, recovery time is a must.
8) Smile, Laugh, Celebrate. During the most difficult moments of cycling when my rear-end hurt so badly I had to stand and peddle or my legs felt done while riding up a never ending hill, I would instinctively smile at the Strive support teams watching us pass by, and distinctly remember them saying ‘keep smiling’. For whatever reason, just smiling and having a sense of humor about an outrageous endeavor works. Your body responds to positive input even when it is just your own outlook and smile. Strive also did a fabulous job of making every day fun with little celebrations along the way, and a big celebration on the last night. This matches FairWarning’s values that it took over twenty years for me to live – “Care, Compete, Innovate, Celebrate and Change Lives”.
It is time for much deserved champagne with my wife Teresa who is beyond supportive, we are always in it together. She couldn’t be physically with Strive in Italy as she was giving a speech on behalf of her late Father Larry to the Indiana High School Basketball Hall of Fame Election Committee. Larry was nominated by former teammates but was passed by the committee last year. Fingers crossed Teresa’s speech to the Election Committee tips the scales, knowing her, he will get in this year. Teresa and I both have a much deserved reputation for drinking champagne, or wine for the smallest of occasions, and the big ones.
By Kurt Long, CEO and Founder of FairWarning