Do You Know Your 100 Miles? (Not Running Related)

In light of the recent CEO announcement for Contegix, I decided it was to resurrect this draft blog post. The post is surprisingly not about Leadville, ultramarathons, or even running despite the question. It is about knowing oneself and what one wants for a life well prioritized and planned.

Of all the questions around the Contegix equity investment, the most common was around why I stepped away as CEO of Contegix. It was asked by my team when we took the investment and has been asked by numerous friends and entrepreneurs since then.

It was asked in straightforward ways, “Hey, so why aren’t you CEO anymore?”

It was asked with innocence and timidness, “Everything good, man?”

It was asked with declarations and poor assumptions, “Dude, what the f* happened?”

Before getting to how I made this decision, it’s important to understand the context and a conversation with my mentor that happened almost two decades ago.

The conversation with my mentor about entrepreneurs started innocently and light-hearted. At this point in my life, I knew my path was one of entrepreneurship. I did not know precisely what that meant or how it would play out. Craig and I were about to start what eventually became Contegix after a few iterations. I had not yet learned a fundamental truth. The path of entrepreneurship is inevitably a path of risk and leadership.

I was yet again confronted with a question for an answer in response to mine. I had asked about entrepreneurs and their impact. I wanted to know how to be an entrepreneur that built a great company by facilitating and helping build incredible talent, even if the company ended up being an exporter of talent. Sensing the requirement of time to accomplish this truly, he pivoted to the core.

He repeated the question as I stared at him, “Do you know why Steve Jobs and Larry Ellison are so well known?”

I vaguely remember giving some remotely intelligent answer about how they had impacted the world and their stakeholders.

He repeated the question a third time, and this time he included an answer.

“Do you know why Steve Jobs and Larry Ellison are so well known? It is because their respective 100 miles is much longer than almost anyone else’s. Others have a 100 mile distance that sets up the next phase.”

He went on to explain what he meant by the cryptic statement.

The Mississippi River was filled with steamboat traffic not too long ago. While the traffic may have faded some, rivers remain vital to our country and economy. These boats have been and continue to be the heart of commerce and military transportation. Traversing these waterway has never been easy though. Rivers are like living, breathing organisms. Even today, the risk is inevitable and often unexpected because change is constant.

At this historic time, vessels lacked the current protections of GPS, sonar, and radar that help detect the changes in currents, debris, sandbanks, and many other factors. They lacked radio to communicate with other water-faring vessels about real-time changes in the river or to send a request for help. It was dangerous for the men who worked on these boats. It still is in many ways.

In lieu of the modern equipment, there were experts, specifically men who knew the most treacherous and dangerous sections of the river. These experts traveled up and down the river. Each would often focus on a specific segment, say 100 miles (or so). They would learn, re-learn, and memorize every change in the river with brain cells filled with the minute details.

Captains were generalists with a mission to traverse the entirety of the river. These men were specialists whose livelihood was based upon knowing a specific segment. No one knew it better, except for maybe another expert with more tenure or proficiency.

The captain, a man (unfortunately, it was almost always a male) appointed such by employment, tenure, rank, or direct ownership, is the last line of responsibility and authority for the boat during its voyage. When a ship would approach a treacherous or unknown section, the captain had a decision whether to hire the specialist who knew the next 100 miles better than he did or attempt the passage under his command. If the decision were made to hire one, the captain would hand over control of the boat and its precious cargo of souls and merchandise to the designated captain. The ship was his to command and his to relinquish when the 100 miles was over. He was the designated captain for that 100 miles.

Up and down the river, each designated captain went being hired and navigating the precarious waterways he knew. He stayed in the boundaries of those 100 miles.

Almost two decades later, I have yet to verify if the history is accurate. It perhaps may only be an analogy for which I could relate growing up in Saint Louis and living alongside the majestic Mississippi. Yet, I told this story to a friend a year ago who remarked he saw this in action on a European riverboat cruise in 2017.

Regardless, the insight for me was immediate. Jobs, Ellison, and many others since this conversation are known because they have a long 100 miles. They have had a long period to make an impact on their stakeholders and communities. They have gone from founders to tech icons, and they have evolved along the way. In the case of Jobs, it could be said that he had 2 sections at Apple and, perhaps, learned the second course during his time away from Apple navigating other waters. The cost of this is considerable sacrifices and prioritization of the essential mission.

This conversation left a mental mark with me that I carry to this day and have relied upon numerous times, including our transaction.

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Craig and I decided to take an investment for numerous reasons. The most significant was our core value of Rapid Accelerated Growth. It was odd that most people never read the description of this core value. The growth was not in reference to the financials – the top or bottom line. It was in reference to our stakeholders, especially our talent, our team, and customers. We fundamentally believe that if these grow, the growth of the financials was a drag-along effect. It was a core reason we implemented the 20% pre-tax profit sharing.

We knew that the competitive landscape was shifting for both cloud and managed cloud services. An investment was the fastest path to be either fail or be prepared for the market shifts. It was contingent upon the right equity partner. We found that in Strattam Capital and its team. It was a relationship developed over years and one built on honest, regular discussions around expectations. These still continue to this day.

I flashbacked to the mentor conversation a few weeks ahead of completing the Contegix transaction in 2016. I realized that my 100 miles was coming to an end as CEO of Contegix if we went through with the transaction. I had navigated Contegix from an idea with the first servers in my basement. The transaction would mean Contegix would now by the combination of three companies and cultures.

Contegix’s CEO needed to be an expert at navigating the delicate waters of integrating these companies and their respective cultures. The CEO would need to spend more time with customers in this competitive landscape and time with our private equity partner.

I would need to expand my 100 miles if I wanted this journey whether through this transaction or another method. As the then-current CEO, my responsibility was to ensure the best talent for the journey ahead.

In the midst of this, I also realized there was a new role for me. I may have been relinquishing the role of captain. I was still on the boat and would continue the role I loved most – being the voice of our customer on the Board and the technology liaison between the business and the Board. For service companies, there should always be someone on the Board who loves the customer first and foremost (rather than the service, product, sales cycle, or anything else). For the executive team, that role is often the CEO.

As the new captain takes the next 100 miles, I relish in the fact that any change does not diminish the work and effort done by predecessors. These were absolutely foundational to get to this point. One cannot hire the designated captain if the boat fails to make it to the rendezvous point.

As a passenger on the boat, I appreciate that more than most.

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