You know that idiom about the mountain coming to Muhammad? That is how I felt when Clio founder and CEO Jack Newton came to my small seaside town of Rockport, Mass., to interview me, complete with film crew and entourage.

It was Jack turning the tables on me. I’ve interviewed him for my own LawNext podcast at least a half-dozen times, and many times more for news stories. But this time, it was Jack asking the questions, all for an all-new season three of Clio’s Matters podcast.

The topic of our conversation: The Evolution of Legal Tech: A 30-Year Perspective. Here’s Clio’s description of the episode:

“In this conversation, Jack Newton sits down with longtime friend and legaltech journalist Bob Ambrogi to explore the evolution of legal technology, the role of journalism in educating the market, and the biggest trends shaping the industry today. Together, Jack and Bob reflect on how far legaltech has come, where it’s headed, and what law firms need to do to stay ahead. From the rise of AI to the ongoing debate between niche and all-in-one solutions, this conversation is packed with insights from one of the most respected voices in legal tech.”

Honestly, I hate being on the wrong side of an interview. But I was enormously honored that Jack took the time and made the effort to visit me and hang out in my hometown.

By the way, this was recorded a year ago, on April 1, 2025, so if anything we said sounds out of date, that is why.

Watch here:

Listen here:

Photo of Bob Ambrogi Bob Ambrogi

Bob is a lawyer, veteran legal journalist, and award-winning blogger and podcaster. In 2011, he was named to the inaugural Fastcase 50, honoring “the law’s smartest, most courageous innovators, techies, visionaries and leaders.” Earlier in his career, he was editor-in-chief of several legal publications, including The National Law Journal, and editorial director of ALM’s Litigation Services Division.