I don't think I took a single vacation the first 12 years of my career as an entrepreneur.
After all, I'd started my fourth software company at 21 years old and in just a few years we'd added thousands of customers who were paying us millions in revenue. My goal to build a great software company and retire by age 30 was coming to life.
That software company also became my life.
Ironically, when my first real vacation finally came in 2009 it was brought on by chasing another goal, to stand with my friends at the base of Mt. Everest.
This goal wouldn't allow me to remain connected to my growing company, because on the high slopes of the mountain town of Lobuche, Nepal just a few miles from the highest point on earth, Internet connectively costs $5.00 per megabyte. We intentionally carried only the cash we needed for basic survival and rescue, and the thought of even one additional ounce of weight - let alone a laptop - in my pack was enough to stop me in my tracks.
Instead of worrying about daily user adds and competitor announcements one May evening in Nepal in 2009 I was more absorbed with trying to figure out where the cook - at the teahut we were staying - was going to get the chicken we'd just ordered for our chicken curry dinner.
Of concern was the fact there was no refrigeration in the building. But there were a few stray chickens running around the dirt trail that brought us into town earlier that day. Then, there was one less stray chicken... and our meal was served.
At dinner our team of four sat around the edge of the large open room on padded benches, backs slumped from the strain of the day's climb, faces in our food as the last rays of light reflected off the surrounding peaks and the warm light of the yak dung fire stove attracted our gaze.
Daily living at elevations higher than trees are willing to survive means you use anything that burns to stoke a fire, despite the fact it might have just gone through a yak. The yak dung fires put thick brown smoke in the air that taxed our lungs beyond the strain they were already enduring from the thin air at 14,000 feet above sea level.
By dung-fire light I read the last few pages of a paperback my teammate Scott had lent me the day before, a collection of four F. Scott Fitzgerald short stories, Diamond as Big as the Ritz being the finale. My mind was engulfed by the tale of a college break hometown visit turned airstrike firestorm.
As I fell asleep that evening on a half inch foam pad on a wood bench in a chamber of plywood walls, my digital life back home was the last thing on my mind.
It may have been the concern, wonder, and exhaustion brought on by walking and eating and sleeping where the atmosphere contains just 45% of the oxygen of sea level. Or it may have been the escape from nonstop emails, social alerts, and office walk-ins. Over those three weeks I experienced joy like a child again.
For 21 days the happy distraction continued. With one comical exception.
At Gorak Shep - the most remote village on the trek route and just a two hour slog by foot to Everest Base Camp on the Khumbu Glacier - I got a glimpse of my former life. Upon arriving at the teahouse our Sherpa, Lalit Tamang, had conducted his normal check-in routine starting with a conversation with the proprietor, a quick tour of our sleeping quarters, then sanitary inspection of the kitchen that would prepare our food.
But this evening was different. As we sat down in the public room - our legs and lungs still burning from the afternoon acclimatization hike - the proprietor and our sherpa made a beeline to my side, holding in their hands a 2008 MacBook Pro laptop computer.
Overhead was the sound of rescue helicopters completing their last evacuations just uphill, in the back of the room a big pot of liquid steamed over a yak dung fire, and to my right a Norwegian climber and his doctor tried to administer a few spoonfuls of soup to the mouth of the injured man who we learned had fallen into a 90 meter crevasse that morning and had broken his spine.
As our host and our sherpa sat down, Lalit explained he had shared my expertise with technology to our host. Then acting as our translator, he explained that the Microsoft Windows installation was failing to boot correctly in his Parallels environment.
In a bit of a daze about, well everything, I made some attempts to find some errors in the console, gave the computer a few stern thumps by hand then did my best to explain my expertise was more in the area of the software that runs on computers than in computers themselves.
My apologies were relayed back to our host who took the computer back into his possession and disappeared into the kitchen. My heart sunk as I thought about how long it might be until someone sitting in that teahouse common room would be able to fix that guy's laptop.
Then my mind shifted back to the burning in my lungs and the pain in my legs.
I was so tired that evening the six stairs to the second floor took the last of my energy. I laid on the plywood floor in the fetal position outside my bedroom for several hours, eventually gaining the strength to open the door and fall inside.
Despite the physical struggle, or perhaps because of it, something powerful came out of my time in that remote landscape in Nepal. I began to feel a level of focus and relaxation I hadn't experienced up until that point in my working career.
After all, I was the guy who wasn't willing to let anyone outwork him. In my mind, leisure time was for people who didn't want to succeed.
As a teenager while my friends played video games I taught myself HTML and built a website for a fictitious shopping mall.
In high school while my teammates were out smoking weed and raiding their parents' liquor cabinets I sold my basketball coach a website for his bed and breakfast property for $95.00.
On a beach in the Bahamas during my honeymoon - cocktail in hand and my bride by my side - I plowed through Marcus Buckingham's First Break all the Rules and took notes about how to achieve more and lead smarter.
You see, it wasn't that I didn't enjoy leisure time, it was just that the thought of future achievement brought with it an addicting mental reward, similar to driving home in a brand new car. I could keep that feeling going every day by working harder than the day before.
Over time I became addicted to that feeling. And it pulled me deeper and deeper into my work. Occasional days out of the office were permitted but only with fast Internet and plenty of downtime in which I could get shit done.
Later that year I was diagnosed with Thyroid cancer that had spread to the lymphnodes on both sides of my neck. I got the news via phone while sitting at my desk, called my business partner into my office, broke into tears while trying to explain it, then marched out of the office to begin treatment.
Over the next two months I endured a 10 hour surgery, weeks of physical and psychological rehab followed by radiation, and more scans and hospital visits than I can count.
I was scared for my life and I was scared about what would be left of my company if I survived my treatment plan. After all, I had created the company from nothing seven years earlier, and without me I figured it was at risk of becoming nothing again.
Then, as the new year arrived something amazing happened. The board of directors I chaired made important decisions, my business partner worked his butt off every single day, our executive team put out fires as needed, and our team of 150 employees remained engaged.
We ended 2009 with over $25 million in revenue, up 80% from the previous year.
I had missed three months of work that year, one for my trek to Mt. Everest in Nepal in May, and two for my surgery and recovery period in November and December.
And in result, I learned one of the most powerful lessons of my professional life. My frenetic and endless emails, meetings, and conference calls might have been important, but they certainly weren't critical to my company's success.
What I realized was that a company that needed me to work as hard as I had worked up until that point would actually have been a shitty company. It would have been a company where everyone is waiting on me, and hiring a new employee just means one more person needs some of my tine.
If my goal was really what I said it was - to sell my company and enjoy the resulting freedom I so desired - then I actually needed to build a company that didn't need me at all. Otherwise, no one would want to buy it.
By overworking before, I was laying the groundwork for overworking later. And that wasn't going to help me hit my goal of selling the company and retiring by age 30.
Upon returning to work after my medical leave I was very careful not to pick things back up that weren't absolutely critical to our success.
I didn't rejoin our executive committee and I changed my title from executive chairman to chairman to allow me to focus on leading our board of directors where we made decisions about market strategy, capital partners, and managing levels of technology and people as we prepared for a future IPO.
Three years later, in February 2012, I sold the company for over $100 million and I wasn't required to work a single day for the acquirer. I was officially no longer necessary. And it was amazing.
The day we announced the deal I packed my desk items into a box and walked to my car.
In retrospect, in addition to the changes I made after my vacation and medical crisis in 2009, I had done a few things correctly before that time that turned out to be critical in enabling my team to make 2009 such an incredible year for the business.
Removed Myself from Our Technology Team
I wrote the entire first version of our application in 2002 when I was a sophomore at the University of North Carolina. Just two years later our first leadership-level hire was a software developer with incredible ability who later became our chief technology officer. He became responsible for our entire application and hired a technology team to support him.
Handing my codebase and full responsibility for our entire infrastructure off to a new person was scary at first, and he didn't do a perfect job, but it was the right decision for so many reasons.
It removed me as the single bottleneck for all software changes and it allowed my business partner who was acting as our product manager - making decisions about which features we should build next - to work directly with the person who could make changes the fastest.
It also allowed me to assist with other parts of the business where we had fewer resources like customer service and partnerships.
Hired an Experienced Chief Financial Officer
A professor at UNC and early investor introduced us to a very talented software company CFO who had just relocated to our area from Atlanta. We couldn't even come close to affording his salary but we knew we needed his expertise so we hired him one day a week until our revenue grew enough that we could bring him on full time.
We eventually raised $65 million in equity and debt capital because our CFO knew exactly how and when to do it. He made promises to investors he knew he could keep and his reputation afforded him immediate trust with all of the most important financial partners we didn't yet know we needed when we hired him.
Built a Professional Management Team
Like any fast growing company our original heads of customer service, technology, and marketing just happened to be the people on our team who first had these underlying abilities.
Heck, myself and my business partner were the Chairman and CEO only because we founded the company, not because of any qualifications we had for those roles.
So, as our team passed 150 full time employees we were mindful of making sure our top leaders were people who had previously lead teams of similar size. Our senior directors were mentored by their peers at a nearby software company that was about two years ahead of us in terms of revenue growth. Through incredible acts of humility and awareness most leaders asked for new talent to replace or complement their leadership with their teams.
By our sixth year in business we had an incredible team of professional managers reporting to my business partner and they were responsible for all day-to-day operations of the business.
Added Outside Investors to Our Board of Directors
Most people think that outside investors are only worth the money they invest in the business. And it some ways its true, because the best investors will trust your intuition and knowledge to make most important decisions about your business.
But in times of trial, outside investors can be incredibly helpful because they are the only people with any reason to care as much as you about fixing your problems. Since they purchased ownership in your company with the dollars they invested, they are now owners like you, and they may be the only people who think the way you do when something critical needs to change.
They also sit on a lot of boards and see a lot of companies and leaders, so they already know the answers to a lot of questions you're just encountering for the first time. Our investors were supportive of my month-long trip to Nepal and never questioned my time out of the office for medical treatment after that. Maybe they knew it would be an experience that would help me grow as a person and as an entrepreneurial leader too.
Raised More Capital Than We Needed
It's worth mentioning the global economy went through the worst recession in nearly a hundred years in 2008, and the next year my team grew revenue 80% while many of our competitors pulled back marketing spend and hunkered down expecting the worst.
One of the biggest reasons for our success throughout the global recession was the fact that we had raised a lot of capital from investors in 2006 and 2007 when honestly we didn't need the money. We were growing quickly and were flush with cash and outside investors seemed like a distraction.
From the sage advise of friendly entrepreneurs and our chief financial officer we decided to raise $5 million to supercharge our investments in marketing and technology, and prepare for the uncertainty of the future.
When that future came in the form of a global recession just a couple of years later, all our competitors reduced their marketing budgets which made advertising our business significantly cheaper.
We then turned up our marketing spend to take advantage of the cheaper unit costs and we accelerated into the third position in the industry within a year.
In summary, without the challenges of 2009 I may have never realized how strong my company and my team really were.
It's possible to think that without these experiences I might have tried to force myself deeper into our operations in an attempt to achieve some unreasonable level of perfection, instead of letting go of the wheel and watching the rocket ship take off.