A few years back, a peer saw a copy of a Board of Directors report I submitted as CEO of a company. A Powerpoint presentation accompanied the report, but the report itself had piqued her interest. She specifically wanted to know the reasoning behind the order of topics.

Clarity and precision are paramount when communicating with the Board. The Board is responsible for guiding an organization’s strategic direction, and its decisions are rooted in the information presented. Consequently, the format and order of the reports provided to them should not be an afterthought. Instead, it should narrate a compelling, holistic story of the organization, moving from the future to the present and then reflecting on the past.

The following order seemed obvious to me. I wanted to tell a story with the primary focus on our future. Here are the five points I focused on:

(Note: I am leaving this somewhat generic due to protect the confidentiality of the organization.)

1. Culture: The Bedrock of the Future

Culture is the cornerstone upon which any organization is built. It shapes the vision, values, and long-term aspirations. By beginning a report with culture, we are essentially starting with the future. Culture informs where a company wants to go and what it hopes to achieve. It outlines the north star that guides decisions and actions. By understanding and cultivating the right culture, organizations set themselves up for future success, making it a natural starting point for any narrative.

2. Talent: Present Assets Crafting Tomorrow’s Success

Every company’s future hinges on its talent. The people who come in every day bring the culture to life, innovate, and drive success. Presenting talent next positions them as the present-day architects of tomorrow’s achievements. Talent provides a bridge between the aspirational elements of culture and the concrete aspects of operations. They represent the organization’s commitment to the future and indicate the steps being taken in the present to ensure that the future is bright.

Every time I am asked about the future of an organization, I point to talent – who we have building that future and who we are missing. People are the heart of innovation.

3. Operations: The Engine Running Today

Moving into the operational aspect brings the narrative solidly into the present. This is the heartbeat of the day-to-day, where plans meet execution. By understanding operations, the Board can see how effectively the company is running right now. It answers the question, “How are we currently executing our strategies, and are we set up for success?”

4. Sales: Indicators of Current Market Position

Sales, as a reflection of the organization’s current market position, continues the story of the present. It provides real-time data on how products or services are being received, how well the company is competing, and where there might be opportunities or challenges. In many ways, sales are the culmination of the efforts of culture, talent, and operations.

5. Finances: Reflecting on the Past to Inform the Future

Finances close the report by grounding the narrative in reflecting past decisions and their outcomes. The general financial health, liabilities, and cash flow give a comprehensive view of where the company stands as a result of previous actions. It offers both a look back and a basis for future forecasting.

In essence, this five-point report format tells a cohesive story: We begin by setting the scene with our future aspirations (culture), introduce our main characters and their actions in the present (talent, operations, and sales), and then reflect on how past decisions have shaped the current state (finances). This narrative not only provides a comprehensive view of the organization but also ensures that the Board remains future-focused while being grounded in the realities of the present and lessons from the past.

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.

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.

I am a (doting, loving) father. I am a (faithful, nightly cuddling, giddy) husband. I am an (intensely loyal) friend. I am an entrepreneur. I am a (math and computer) geek. I am a mentor and a mentee. I am an ultra marathoner. Oh, and I have multiple sclerosis.

Three years ago today, Courtney and I walked into a doctor’s office. We left with what we knew was the outcome. I was diagnosed with multiple sclerosis, specifically relapsing recurring multiple sclerosis. It started with an MRI to check some neck and spinal issues. It was followed by Courtney ordering a full with and without contrast MRI. It culminated with the official diagnosis that day.

This will come as a surprise to many, including some very close friends and family. Please know that is a reflection of the situation rather than my love for you. We told very few people in order to limit the exposure. We wanted to protect our family and our children. We wanted to ensure we had the answers to our questions which would be their question. We wanted them to see how it has not stopped our family. We wanted them to all be old enough to know rather than have 1 or 2 hold the secret. We wanted to be able to prepare them for what others may say, think, and whisper. Time gave us that breathing room and allowed us to not live on the margins. We only recently told our incredible kiddos.

Graciously share, and help people be the best they can be.
– Bob Cancalosi

Why am I talking about this now? Because I am tired and angry. And neither of those are symptoms caused by MS.

When I was first diagnosed, I researched everything I could about MS. It painted a picture of a very difficult life. It was a life spinal taps, canes, wheelchairs, hospital beds, MRIs, pain, etc. Many of these were covered by the phenomenal organizations working hard to cure MS. I understand why. These stories and images create emotion, and emotion drives people to open their wallets and purses. They are working to ensure this disease is cured.

This is a noble goal, and I commend everyone working on it. I have already benefitted from their relentless commitment and will hopefully benefit from a cure. These stories are also the realities for many with MS. That can never be forgotten. I repeat – these stories are the realities for many with MS and that can never be forgotten.

Yet, these stories were scary for me. These are all I found when I searched online. They might be driving energy and money to find a cure. This will create tomorrows for those with MS and their families. Yet, they were destroying my todays.

I am tired of only these stories, and I am angry at only these stories. These cannot be the only stories and experiences. I believe they are having another impact, and it’s not positive.

I have been blessed to meet and talk with numerous people with MS. Too many have given up their dreams, goals, and lives to this disease. Some of it was because of the symptoms and realities of the disease. Some of it was because the disease emotionally and mentally stole it. I met a woman who decided against having children because of her MS. She has not had a relapse in nearly a decade. My nurse coordinator gave up cycling months after being diagnosed. She still had the strength and balance to ride. She told me her fear of the disease paralyzed her.

Bow our heads and pray to the lord
Til I die I’m a fuckin’ ball
– Who Gon Stop Me by Kanye West  & Jay-Z

Since my diagnosis, I have completed the Contegix investment by our private equity firm. (Small side note – our PE firm was extremely supportive of my decision to become public. I can not rave enough about the team and their character.) I took an 87-mile jaunt through Leadville that was cut short by a torn hamstring (not my MS). I have given a dozen speeches on tech, entrepreneurship, and the future of Saint Louis. I have become scuba certified and completed over a dozen dives. I have logged thousands of miles running. I have made coffee for my wife nearly 1000 times. I have hugged my children too many times to count.

I have bad days. The most common issue is pain, especially something known as the “MS Hug”. I had one a few weeks back on a Sunday. Courtney asked me how my day was as we settled into bed for the night. I shared I had been in pain most of the day. She seemed very surprised and ticked off a list of things I had done that day. From picking up donuts for the kids and a sleepover guest to running 15 miles to taking the kids to lunch, I was in pain.

She then asked why I didn’t just relax and take it easy. I told her that I was going to be in pain most of the day regardless of what I did or what happened. That day, like every single day, is a gift. I was not going to waste a gift. Pain was going to be there, and I had enough strength to push.

I strive to live my life with integrity, authenticity, and grit. I am going to continue living my life the same. Every second is a gift to make the world better for myself, my family, my community, and the world. I believe this is only achievable by going after impossible goals and helping others do the same. My MS is merely part my journey.

Thus, I am going to share more in the hope it helps those struggling with achieving their goals, including those with MS. I am going after Leadville Trail 100 in 325 days. I am working on my next venture to fix a century-old problem. I will walk my daughter down the aisle one day in the far-off future. I have huge goals for myself and my family. I am going to set sights on the impossible. Oh, and I have multiple sclerosis.