Mike Underdown of Crosstown Fiber: Five Things I Wish Someone Told Me Before I Became A CEO

An Interview With Doug Noll

It’s not all on you: I used to think that the CEO had to be the best at everything. Meeting a leader like Bob Jones, who communicated effectively despite not having the conventional credentials, taught me that leadership is about making others feel valued, not being the smartest person in the room.

As a part of our series called ‘Five Things I Wish Someone Told Me Before I Became A CEO’ we had the pleasure of interviewing Mike Underdown.

Mike Underdown serves as the President & CEO of Crosstown Fiber, where he leverages his extensive experience in the DataCenter and telecommunications sectors. His background spans various domains, including sales, operations engineering, and new market development, along with real estate, financial consulting, and venture capital. Interested in innovation, Mike actively seeks opportunities in both early-stage startups and companies “on the bubble.”

Thank you so much for joining us in this interview series! Before we dig in, our readers would like to get to know you a bit more. Can you tell us a bit about your “backstory”? What led you to this particular career path?

The path to telecommunications was paved for me by my father-in-law’s pioneering work as an executive at Illinois Bell. He was at the forefront of competitive telecommunications, orchestrating the design of infrastructure within Chicago’s freight tunnels. His dedication and innovative spirit caught my attention, leading me to explore and eventually immerse myself in the world of telephone communications. His legacy continues to resonate with me, shaping my career and fueling my passion for the industry.

Can you share the most interesting story that happened to you since you began leading your company?

What has struck me most since leading my company is the realization of how interconnected our industry truly is. As I’ve traveled and spoken about our platform to various communities, I’ve been amazed by the number of people I’ve either met before or who know of me. The connections I’ve discovered have been incredible, revealing just how small and tightly-knit our industry is. It’s a testament to the power of relationships and the impact they can have on our professional lives.

Can you share a story about the funniest mistake you made when you were first starting? Can you tell us what lesson you learned from that?

In the early stages of my career, I was part of a company that filed for bankruptcy. Frustrated and feeling defeated, I quit the industry in a sort of “temper tantrum,” only to realize that the frozen pizza industry was far more corrupt than the telecom industry! This realization brought me back to telecom, where I acquired assets from the bankrupt company I had just left to start anew. Looking back, my dramatic exit and brief flirtation with the pizza industry seem rather humorous. The experience taught me valuable lessons about resilience, the importance of choosing the right field, and the ability to see humor in our mistakes. It was a reminder that setbacks can lead to new beginnings, and sometimes, a change in perspective can turn a failure into a funny story.

None of us are able to achieve success without some help along the way. Is there a particular person who you are grateful towards who helped get you to where you are? Can you share a story about that?

I’ve been fortunate to have several mentors throughout my career, each contributing to different aspects of my growth. Early in my career, I had a mentor who taught me valuable HR skills and people management techniques, helping me identify ways to manage people both inside and outside the business. I’ve also had financial mentors who have greatly influenced my understanding of capital and debt markets, as well as leadership development. Recently, I faced a challenge with individuals outside of my firm that were damaging a project. A mentor suggested I meet with an executive coach, and I started courses that have become one of the most success-based and influential things I’ve done. These mentors have shaped my career and continue to guide me.

Leadership often entails making difficult decisions or hard choices between two apparently good paths. Can you share a story with us about a hard decision or choice you had to make as a leader?

In leadership, I tend to avoid forcing hard decisions and instead allow them to find their natural resolution. I believe that hard choices often present themselves as either both good or both bad, and reflecting and echoing the way the world works is often more effective than trying to force a direction. This approach recognizes the complexity of decision-making and the fact that choices are rarely black and white. By allowing decisions to unfold naturally, I’ve found that the right path often reveals itself.

Ok, thank you for that. Let’s now jump to the primary focus of our interview. Most of our readers — in fact, most people — think they have a pretty good idea of what a CEO or executive does. But in just a few words can you explain what an executive does that is different from the responsibilities of the other leaders?

As a CEO, I see myself as a servant to the team. My role is to ensure that the playing field is laid out so that the team can go in and play hard and do their thing. Unlike other leadership positions, the CEO’s responsibility is not just about making decisions or having all the answers. It’s about creating an environment where the team can thrive, removing obstacles, and finding solutions to challenges. It’s a role that requires a unique blend of humility, vision, and support.

What are the “myths” that you would like to dispel about being a CEO or executive? Can you explain what you mean?

One common myth about leadership is that the CEO must be the hardest working, all-knowing individual in the room. In my perspective, the true role of a leader is to serve the team by removing blockages or finding solutions to make them go away. The CEO is not there to have all the answers or do all the work, but to ensure that the playing field is ready for the team to play hard and do what they were brought in to do. It’s about facilitating success rather than dictating it.

What is the most striking difference between your actual job and how you thought the job would be?

The most striking difference between my actual job as a CEO and what I initially thought it would be, lies in the decision-making process. I used to believe that my role was to make definitive decisions, and that each decision was either right or wrong. However, I’ve learned that this is rarely the case. Decisions often fall into a gray area, and the success of a chosen path is determined by the team’s implementation and execution. It’s a nuanced understanding that has shifted my perspective on leadership and the nature of decision-making.

Do you think everyone is cut out to be an executive? In your opinion, which specific traits increase the likelihood that a person will be a successful executive and what type of person should avoid aspiring to be an executive? Can you explain what you mean?

I believe that not everyone is suited to be an executive, as it requires specific traits and a certain mindset. Patience, understanding, and the ability to be present in the moment are essential components of a successful executive. An executive must genuinely listen to others, reflect on their input, and ensure that they feel heard. People who struggle with hearing others or who are overly driven may find the role challenging. Being an executive is about more than ambition; it’s about empathy, awareness, and the ability to connect with and lead others.

What advice would you give to other business leaders to help create a fantastic work culture? Can you share a story or an example?

Creating a fantastic work culture requires walking the walk and talking the talk. It’s about establishing principles that foster communication and a positive attitude. For example, one of my principles is “see something, say something,” which encourages honesty and open communication. I believe that culture grows from reflecting on what you like and facilitating its growth while shrinking what you don’t like. Open lines of communication with as many people as possible create a culture where everyone feels heard and valued. It’s about building a community where honesty and sharing are rewarded, and relationships are nurtured.

How have you used your success to make the world a better place?

I’ve used my success to contribute to social causes, particularly in the Midwest. We’ve worked with greenhouses and utilized our subsurface Utility Contractors to provide electricity to areas that wouldn’t otherwise have access to gardens, especially during winter. Projects like our Angel Project in Chicago aim to promote digital equity and make a tangible difference in communities. These initiatives reflect my belief in using success to create positive change and contribute to the greater good.

Fantastic. Here is the primary question of our interview. What are your “Five Things I Wish Someone Told Me Before I Became A CEO” and why? (Please share a story or example for each.)

1 . It’s not all on you: I used to think that the CEO had to be the best at everything. Meeting a leader like Bob Jones, who communicated effectively despite not having the conventional credentials, taught me that leadership is about making others feel valued, not being the smartest person in the room.

2 . Delegation is not a sin: Early on, I felt that the business was mine alone to build, but I quickly learned that this approach leads to drowning in workload. Delegating is essential; it’s why you have employees. Sharing the load is vital to growth.

3 . Mentorship is the key to growth: Both being a mentor and having one has been invaluable. I’ve learned from senior outside counsels and mentored young people within my company. The value creation of mentoring has made me a better listener and a more aware and present leader.

4 . Far more connected to people than you’ll ever know: I never considered myself super connected, but as I traveled more, I realized that people I thought I knew had a much higher regard for me than I knew. It’s a powerful realization of how connections matter.

5 . CEO is a leader of people, not just the business: I’ve come to understand that the role of a CEO extends beyond merely overseeing the business operations. It’s about leading and taking care of the people within the organization. By ensuring that they have the tools, support, and opportunities they need, the business naturally thrives. It’s a lesson in prioritizing human connections and understanding that if you take care of your people, they will take care of the business.

You are a person of great influence. If you could inspire a movement that would bring the most amount of good for the greatest number of people, what would that be? You never know what your idea can trigger.

I believe I’m at the forefront of the fiber movement, and I see fiber optic cable as the road that will support future economies, education, and the advancement of society. By pushing fiber optic systems into schools and housing, especially in socioeconomically disparate communities, we can create a more connected and equitable world. It’s a movement that aligns with my passion and what I believe we’re starting to achieve.

Can you please give us your favorite “Life Lesson Quote”? Can you share how that was relevant to you in your life?

My favorite life lesson quote is, “Absent information, the human mind will go negative.” This has taught me the importance of over-informing rather than under-informing. In leadership, clear communication prevents misunderstandings and negative assumptions. It’s a principle that has guided my approach to relationships and decision-making.

We are very blessed that some very prominent names in Business, VC funding, Sports, and Entertainment read this column. Is there a person in the world, or in the US with whom you would love to have a private breakfast or lunch with, and why? He or she might just see this if we tag them.

I would love to have a private meal with Bill Belichick, the General Manager of the New England Patriots. I’m a big fan of his approach to organization and human resources. His leadership style, strategic thinking, and ability to build successful teams resonate with my own beliefs about effective leadership. It would be an honor to learn from someone who has achieved such success in his field.

Thank you for these fantastic insights. We greatly appreciate the time you spent on this.