Bob Ambrogi Previews ClioCon 2025
On the latest Real Lawyers podcast, the longtime legal journalist shares why the conference stands apart and what to expect this year.
October 1, 2025
Bob Ambrogi has been attending ClioCon since the start and has covered legal tech longer than most of us have been online.
In this episode of the Real Lawyers podcast, he and Kevin talk about why ClioCon’s energy feels different, what Jack Newton brings to the room, and what to watch for in Boston this year. We also get into how Bob approaches conference coverage, why small product improvements matter most to working lawyers, and where LawSites and LawNext are headed.
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Episode Outline
- 03:30 — Early web and blogging roots that led to today’s legal publishing
- 04:20 — Year one of ClioCon and the vibe that set it apart
- 06:30 — Comparing that feel to other user conferences and why energy matters
- 09:35 — How Bob covers conferences and what he looks for on the ground
- 11:05 — Why hallway talks with customers beat polished product demos
- 12:15 — Jack Newton as an authentic leader and why that still shows up on stage
- 14:20 — Keynotes that land, when they run long, and why the crowd still leans in
- 16:10 — From garage days to a global company that Jack still leads
- 17:10 — Jack’s deep interest in AI and openness to founders in the community
- 18:40 — VLex + Clio: what the combo could mean for AI and research
- 20:35 — The ClioCon “why”: energy, mission, and a community that feels different
- 22:15 — Improving the system for good vs lip service at other events
- 24:20 — A lawyer’s story of leaving law, attending ClioCon, and choosing to build
- 25:20 — Two days is enough to spark action that carries home
- 26:45 — What users actually cheer for: small fixes that save real time
- 28:25 — AI reception so far and why VLex tech could change the story
- 30:15 — It comes back to people and culture you can believe in
- 32:50 — The first ClioCon podcast alley and a signal podcasting would surge
- 34:40 — Why interviewing smart people never gets old
- 36:40 — The Mark Britton conversation Bob still thinks about
- 39:10 — LawSites and LawNext as a media business: video, ad packages, PR feed
- 41:20 — Why Boston is worth the trip this year
- 42:55 — Must-attend for small and midsize firms, and growing large firm presence
- 44:10 — A note to frustrated big-law and ex-government lawyers who want to build
Key Takeaways
- ClioCon’s edge is its community and energy, not just product reveals
- Jack Newton’s authenticity still shapes the event and how the company shows up
- The most cheered updates are practical fixes that make client work and billing easier
- VLex tech plus Clio’s scale could move the needle on AI
- Lawyers leave motivated to improve how they serve clients, not just with notes from sessions
- Bob’s coverage focuses on what real users say in hallways and over coffee
- LawSites and LawNext are growing as a media business with video, ad packages, and an open PR feed