In the latest episode of Let’s Get Digital, Carrie Charles, host of the show and CEO of tech staffing firm Broadstaff, sits down with Mike Underdown, founder and CEO of Crosstown Fiber, to talk about his journey through the telecom world, the lessons he’s carried into building Crosstown, and his approach to expanding fiber in Chicago and beyond.

Mike’s career started in the early days of competitive local exchange carriers, working at Teleport Communications Group. There, he learned from industry pioneers who helped shape the modern fiber landscape. After AT&T acquired TCG, Mike realized the corporate environment wasn’t the right fit and went on to hold leadership roles at Adelphia Business Solutions and other network providers, gaining deep experience in construction, infrastructure design, and network development.

His path wasn’t without detours. When Adelphia collapsed, Mike left telecom for a time, starting a frozen pizza distribution business. That venture taught him the realities of running a small business and sparked his drive to work for himself. He returned to the industry, launching Chicago Fiber Systems and later founding an engineering and construction management firm. Along the way, he faced his most personal challenge—battling stage four cancer. That experience shaped his leadership philosophy, reinforcing values like doing the right thing simply because it’s right, staying curious, and focusing on process over outcome.

Crosstown Fiber was born in 2019 from a Chicago Public Schools network build that Mike helped design. Seeing the potential to create unique, underground fiber routes where none existed, he founded the company with an emphasis on diversity of paths and long-term capacity. Today, Crosstown’s network is entirely underground, with high-count fiber builds designed to serve data centers, schools, and enterprises. Mike is clear about the importance of connectivity between data centers, noting that without interconnection, “a data center is just a warehouse.”

In the conversation, Mike highlights common mistakes in data center planning—such as waiting until after construction to think about network connectivity. He explains that early investment in communication infrastructure can save significant cost and complexity later, and can help communities avoid repeated street cuts and disruptions.

Crosstown’s growth is focused on Chicagoland and surrounding states, with an eye on building routes that avoid risky infrastructure corridors like rail lines and fuel pipelines. Mike’s approach is to design with resilience in mind, steering clear of hazards that could cause long outages.

Company culture is another theme. Mike describes his team as a close-knit group of long-time partners and employees who work collaboratively to solve complex construction challenges. Many have worked together for decades, and he credits this trust and experience with enabling Crosstown to build nearly 400 route miles of network in a challenging market.

Looking ahead, Crosstown plans to expand into neighboring markets such as Milwaukee, South Bend, and Grand Rapids, often in partnership with large technology companies. For Mike, the goal is simple: build infrastructure that sets a high standard for quality and reliability.

Tune in to the full episode of Let’s Get Digital featuring Mike Underdown’s episode here.