Ops Caruso

In this episode of The Bear Roars, Dan Caruso sits down with Colby Synesael—former top-ranked telecom analyst turned investment banker—to trace the evolution of digital infrastructure and its collision course with AI.

Colby shares how a chance job at a collapsing telecom company launched a decades-long career covering the industry’s most pivotal transformations. From the post-dot-com rebuild to the emergence of communications infrastructure as a standalone sector, his vantage point has offered rare insight into the companies, strategies, and capital shifts that defined the space.

Their conversation explores the powerful impact of AI on data centers, fiber networks, and power infrastructure—revealing why energy availability, transmission, and next-gen technologies like small modular reactors are becoming central to the future of connectivity. They also examine the growing investor appetite for infrastructure-like assets and what the shift from AI training to inferencing means for metro fiber and edge deployments.

Colby and Dan look back on the critical moments that shaped the sector, while also unpacking the trends and technologies that will define its next chapter. From early industry conferences to the rise of private capital, this episode offers an insider’s view into how digital infrastructure became one of the most consequential—and investable—industries of our time.

This episode is packed with real history, sharp perspective, and a clear-eyed look at what comes next.

Order Dan’s Book – Bandwidth: The Untold Story of Ambition, Deception, and Innovation that Shaped the Internet Age and Dot-Com Boom: dan-caruso.com/book

To nominate a founder or yourself as a future guest speaker, email: contact@loudbearproductions.com

In this episode of The Bear Roars, Dan Caruso sits down with Dave Schaeffer, founder and CEO of Cogent Communications, to unpack one of the most fascinating and unorthodox careers in telecom.

Before launching Cogent, Schaeffer ran the second-largest taxicab company in Washington, D.C., built a real estate empire, and traded in spectrum—after entering college at age 12 and nearly completing a PhD as a teenager.

Schaeffer shares the wild backstory behind his entrepreneurial path, including the strategic bets that helped him turn $1 million investments into multimillion-dollar exits long before he ever touched fiber.

Their conversation dives deep into the origins of Cogent and the six core principles that have guided its long-term success—from targeting a single product (internet access) to outmaneuvering larger players with laser focus and ruthless cost efficiency. Dan and Dave also talk about the dot-com crash, how Cogent scaled through downturns by acquiring distressed assets, and what it took to build one of the largest and most profitable IP networks in the world.

This episode is packed with sharp insight, telecom history, and lessons on what it really takes to think differently—and win.

Order Dan’s Book – Bandwidth: The Untold Story of Ambition, Deception, and Innovation that Shaped the Internet Age and Dot-Com Boom: ⁠dan-caruso.com/book⁠

To nominate a founder or yourself as a future guest speaker, email: contact@loudbearproductions.com

In this episode of The Bear Roars, Dan sits down with Andy Lipman—a telecom industry trailblazer whose legal and regulatory work helped open the door to competition and laid the groundwork for the modern internet. From his early days in transportation deregulation to leading the charge against the Bell monopoly, Andy has been at the center of telecom’s most pivotal moments.

Their conversation spans the antitrust battles of the 1980s, the rise of MFS and Teleport, and Andy’s role in coining the term “CLEC” and shaping the 1996 Telecommunications Act. He shares stories about industry giants like Bill McGowan, Jim Crowe, and Bernie Ebbers, and explains how regulatory fights over interconnection fueled the explosion of internet infrastructure. Dan and Andy also talk about the dot-com bust, the legacy of WorldCom, and how today’s fiber and broadband boom traces directly back to that earlier era. They wrap by looking ahead—discussing fiber overbuilds, Starlink, and the future of telecom as critical infrastructure.

Whether you’re a policy nerd or a broadband junkie, this one’s packed with insider stories and lessons that still matter today.

Order Dan’s Book – Bandwidth: The Untold Story of Ambition, Deception, and Innovation that Shaped the Internet Age and Dot-Com Boom: dan-caruso.com/book

To nominate a founder or yourself as a future guest speaker, email: contact@loudbearproductions.com

In this episode of The Bear Roars, Dan sits down with Frank Louthan, Managing Director at Raymond James and longtime telecom analyst, to unpack the wild rise and fall of the telecom and fiber industry during the dot-com boom and bust. Frank covered many of the era’s biggest players—WorldCom, Level 3, Global Crossing—and brings a rare, unfiltered perspective on what really happened behind the scenes.