Ari Kaplan Advisors
Ari Kaplan, a leading legal industry analyst, is an inaugural Fastcase 50 honoree, a finalist for ILTA’s Thought Leader of the Year award, and a fellow of the College of Law Practice Management. His most recent book, Reinventing Professional Services: Building Your Business in the Digital Marketplace, was released in Japanese, and West Academic published the second edition of The Opportunity Maker: Strategies for Inspiring Your Legal Career Through Creative Networking and Business Development in 2016.
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*Special Episode* Featuring Caroline Hill, Editor-in-Chief of Legal IT Insider, on Charting Change in Legal Ep 55
In this 55th episode of Charting Change in Legal, Caroline Hill, Editor and Publisher of Legal IT Insider, and I discussed our impressions of Legalweek 2026, the ROI of legal AI, and the maturation of AI deployment in…
The Importance of Guardrails to Rely on the Output of AI-Assisted Technology
Leveraging Technology to Draft Trademark Applications and Process Renewals
I spoke with Alex Sappington, the Co-CEO of PageVault, a tool for capturing online content in a legally defensible manner. We discussed PageVault’s launch of Stencil, the problem Stencil solves for trademark teams, how PageVault’s work in litigation…
Building a Software Company While Practicing Law Full-Time
I spoke with Matt Basile, the CEO of Naya Software, a software company that automates the legal aspects of originating commercial real estate loans for law firms and institutional lenders. We discussed building a software company while working…
Transforming the Application of AI in E-Discovery
I spoke with Cristin Traylor, the Senior Director of AI Transformation and Law Firm Strategy at Relativity, a legal data intelligence company that builds technology to help users organize data, discover the truth, and act on it. We…
Legalweek 2026 Day 1 Mixtape
Thanks to the following leaders for speaking with me for this mixtape at Legalweek on Day 1:
Kevin Clark, Right Discovery
Richard Gorelick, ChronoTracer
Steve Salkin, ALM
Danny Thankachan, CaseGuild
Jessie Torres, McDermott, Will &
How Legal Teams Can Leverage AI to Improve and Accelerate Their Investigations
I spoke with Raj Chandrasekar, the Chief Technology and Innovation Officer of Consilio, a provider of e-discovery, document review, flexible legal talent, and legal advisory and transformation services. We discussed the biggest disruptions in the legal industry, how…
Legalweek 2026 and the Value of Tailoring the Client Experience in E-Discovery
I spoke with Matt Mahon, the Vice President for Client Solutions at Level Legal, a concierge digital forensics, e-discovery, and managed review partner for law firms and corporate legal departments. We discussed how AI is changing e-discovery, the…
*Special Episode* Featuring Caroline Hill, Editor-in-Chief of Legal IT Insider, on Charting Change in Legal Ep 54
In this 54th episode of Charting Change in Legal, Caroline Hill, Editor and Publisher of Legal IT Insider, and I discussed preparing for Legalweek 2026, reallocating legal work, and formalizing vibe coding.