From Voice Over IP to Hyperscale AI: Tony Rossabi on Two Decades of Industry Change

The digital infrastructure industry is moving faster than ever.

AI is reshaping demand, hyperscalers are racing for capacity, and data centers have become one of the most important pieces of the global technology ecosystem. But long before AI became the center of the conversation, Tony Rossabi was already building his career through the evolution of telecom, fiber, and digital infrastructure.

In this episode of The Route to Networking, Jamie Maher sits down with Tony Rossabi, Co-Founder of Ocolo and a long-time leader across telecoms, connectivity, and data centers. 

Tony has spent more than two decades in the industry, working across voice, fiber, and infrastructure before moving into executive leadership, investment, and advisory roles. Having seen multiple waves of transformation firsthand, he brings a unique perspective on where the industry has been, where it is now, and what comes next.

The conversation covers everything from the early days of Voice over IP to the explosion of AI infrastructure, the growing talent shortage across data centers, and why resilience may be the most important career skill in the industry today.

Along the way, Tony shares stories from the early telecom era, explains why speed-to-market has overtaken cost as the biggest priority for some companies, and gives honest advice for professionals trying to build long-term careers in digital infrastructure.

“This industry will never stop growing because people are always looking for more efficient ways to communicate.” 

An Unconventional Start in Telecom

Tony’s path into digital infrastructure was anything but traditional.

Before entering telecom, he worked as a government attorney in New York while bartending on weekends. He also spent time living abroad and driving ambulances in Mexico City before eventually making the jump into telecom in the late 1990s. 

“I’m actually an attorney by trade… part-time government attorney, full-time bartender on the weekends.” 

His entry into the industry came when friends invited him to California to help build a Voice over IP company during the early stages of the technology boom. At the time, VoIP was considered groundbreaking technology.

“That was revolutionary at the time, which obviously is not so revolutionary anymore.” 

Tony reflects on how different the industry looked back then. Telecom giants like AT&T, Verizon, and MCI were the companies leading innovation, while businesses like Google and Apple were nowhere near the powerhouses they are today. 

“We’ve seen a complete revolution within the space.” 

Following the Growth of Digital Infrastructure

One of the most interesting parts of the discussion is hearing how Tony’s career naturally evolved alongside the infrastructure itself.

He started in voice, transitioned into fiber, and eventually moved into data centers as the market developed.

“How did those minutes get passed? They’re done through transport, which is fiber… and then what does fiber connect to? It connects to data centers.”

That progression gave him a front-row seat to the way connectivity infrastructure expanded over the last twenty years.

Tony explains how every layer of modern communication now depends on interconnected infrastructure.

“Everything is passing through somebody’s fiber, somebody’s data center, and potentially somebody’s tower.” 

He also talks about how dramatically priorities have changed in recent years.

“What’s happening today has to be fast. You got to be fast, fast, fast.” 

According to Tony, some companies are now prioritizing speed-to-market over cost entirely, particularly as AI demand accelerates infrastructure growth.

Why AI is Changing Everything

AI becomes a major focus throughout the episode, especially around the impact it is having on data center demand and infrastructure development.

Tony describes the pace of growth over the last 18 months as unlike anything he has seen before.

“We’ve seen more growth in data center space in the last 18 months than we’ve seen in probably the last 15 years.” 

The discussion dives into the growing pressure around capacity, power, cooling, and deployment timelines as hyperscalers race to scale AI infrastructure.

“The biggest challenges that we have are finding reasonable space and finding reasonable power.” 

Tony also touches on emerging technologies like liquid cooling and explains why the industry is still learning how to adapt to the next generation of AI-driven infrastructure requirements.

“We moved from air cooled to liquid cooling… people are really learning about it.” 

At the same time, he believes the industry’s biggest problem may not be technology at all.

It is people.

The Talent Problem Facing Data Centers

One of the strongest themes throughout the conversation is the growing shortage of talent across digital infrastructure.

Tony explains that demand for skilled workers is growing faster than companies can hire or train them.

“We can’t find enough electricians, we can’t find enough people.” 

He points to several reasons behind the issue. Experienced professionals are retiring, infrastructure growth is accelerating, and new technologies are creating entirely new training requirements.

“We just can’t train people fast enough.” 

It is a challenge that affects every part of the market, from construction and operations through to engineering and leadership.

Tony believes the industry needs to invest far more heavily in developing the next generation of talent if growth is going to continue sustainably.

“We have to continue to cultivate people to come into this industry.” 

The Skills That Matter Most

Beyond the infrastructure discussion, the episode is packed with career advice for people building careers in networking and digital infrastructure.

Tony believes one of the biggest differentiators for long-term success is resilience.

“There’s going to be change. There’s going to be a problem. You’re going to have to get through it.” 

He explains that many people entered the industry during periods of growth, but not everyone stayed through the difficult moments.

“Some dropped out. They just said, ‘forget it, I’m done.’” 

Organization and discipline are also recurring themes throughout the conversation.

“I have daily lists and monthly lists. I got to get stuff done.” 

Tony also emphasizes the importance of networking, helping others, and taking initiative early in your career.

“Don’t wait to be told. Just go do it.” 

One particularly interesting part of the discussion focuses on confidence and leadership.

“You can be as confident as you want… you don’t want to be cocky.” 

Leadership, Boards, and Building Great Companies

Having spent years working both inside companies and at board level, Tony also shares his perspective on leadership and advisory roles.

He explains that great board members should act as guides and resources rather than trying to control day-to-day operations.

“You’re there to help, not to run the company.” 

The discussion explores the balance between being supportive, challenging leadership teams, and avoiding becoming too intrusive.

“You don’t want empty seats in the boardroom… but you also don’t want to be too intrusive.” 

Tony also shares one philosophy that has stayed with him throughout his career.

“We invest in people.” 

For him, successful businesses are ultimately built by strong teams, relationships, and leadership cultures.

Quick Fire Round

We wrap up with our quick-fire round, where Tony shares his thoughts on:

• The biggest challenge facing data centers 
• The future of AI infrastructure 
• Leadership and career growth 
• The importance of confidence in business 
• What younger professionals need to focus on most 

He also gives his honest thoughts on how fast the industry is moving, what companies are getting right, and why staying adaptable is more important than ever.

You will have to listen to the full episode to hear all of his answers.

Listen to the Full Episode

This episode offers an honest and insightful look into the evolution of telecoms, data centers, and digital infrastructure through the eyes of someone who has spent more than twenty years helping shape the industry.

From AI and hyperscale growth to talent shortages, leadership, and career advice, Tony Rossabi shares lessons that will resonate with anyone working in networking, fiber, telecoms, or digital infrastructure today.