

Reinventing Professionals
Ari Kaplan
The business of providing professional advice is changing. Today, anyone can go online and access a wealth of information about any topic, from legal and medical advice to financial planning and accounting suggestions. This blog is designed to offer ideas, guidance, and perspectives on how to effectively navigate a perpetually shifting professional landscape, with a unique focus on the legal industry and the technology that is driving its evolution.
Episodes
Mentioned books

Oct 27, 2025 • 17min
Midsize Law Firms are Balancing Potential and Pitfalls in Charting an Unpredictable Path Forward
I spoke with Olivia Mockel, the Chief Brand and Market Strategy Officer at SurePoint Technologies, Debbie Foster, the CEO of Affinity Consulting Group, and Laura Wenzel, the Global Marketing & Insights Director at iManage. The three companies are part of a consortium that supported a new market research report featuring the perspectives of midsize law firm leaders called "Midsize Law Firms Are Balancing Potential and Pitfalls in Charting an Unpredictable Path Forward." We discussed how chief financial officers, chief operating officers, chief information officers, and executive directors are approaching generative AI, data and financial intelligence, technology adoption, and training to help drive their firms into a new era of legal services.

Oct 24, 2025 • 9min
The Most Common Financial Challenges Law Firms Face and How Leaders are Using Technology to Address Them
I spoke with Rick Hellers, the CEO of Scan Logic, the provider of BillSync and APSync, designed to simplify law firm finances. We discussed the most common financial challenges law firms face, how leaders are using technology to address them, best practices for ensuring prompt and full payment of legal invoices, and how the economy is affecting the financial health of law firms.

Oct 22, 2025 • 22min
*Special Episode* Featuring Caroline Hill, Editor-in-Chief of Legal IT Insider, on Charting Change in Legal Ep 48
In this 48th episode of Charting Change in Legal, Caroline Hill, Editor and Publisher of Legal IT Insider, and I discussed the value of practical conversations about AI pricing, promoting wellness at conferences, and empowering change.

Oct 17, 2025 • 4min
The 2025 ACC Annual Meeting and How Corporate Legal Departments are Evolving
I spoke with Capri Miller and Matt Mahon, the Customer Partner and Vice President of Customer Experience, respectively, at Level Legal, a provider of managed services, about the Association of Corporate Counsel's 2025 Annual Meeting in Philadelphia and how corporate legal departments are evolving.

Oct 15, 2025 • 14min
The Convergence of Knowledge Management, Innovation, and Legal Tech Investing
I spoke with Kevin Klein, Co-Founder of LegalTech Connect and Head of Content & Programming at the KM&I for Legal Conference, and Patrick DiDomenico, who founded InspireKM Consulting and KM&I, and is now Co-Founder at LegalTech Connect. We discussed the convergence of KM&I and LegalTech Connect, the evolution of law firm knowledge management and innovation, and how conversations about KM and AI will drive the legal profession forward.

Oct 13, 2025 • 10min
The Most Exciting Opportunities AI is Creating for Lawyers
I spoke with Tom Martin, the founder and CEO of LawDroid, an Adjunct Professor teaching Generative AI and the Delivery of Legal Services at Suffolk Law School, and a co-founder of the American Legal Technology Awards. We discussed the most exciting opportunities AI is creating for lawyers, best practices for persuading AI skeptics, the ethical and practical guardrails lawyers should consider, and the objective of the American Legal Technology Awards.

Oct 10, 2025 • 10min
Mixtape: Relativity Fest 2025
It was a privilege to speak with these leaders for this Relativity Fest 2025 mixtape:
Brett Chalmers, Website and Product Marketing Director, Opus 2.
Mathew Corfield, Surveillance Product Owner, Theta Lake.
Blake Ferger, Senior Consultant, Complete Discovery Source.
Shawn Gaines, Chief Marketing Officer, OnDean.
Frank Perrone, Founder and CEO, ReVia
Matt Rosenthal, Senior Vice President of Sales, Cimplifi.
Alex Sappington, Co-CEO, Page Vault.
Ben Sexton, Senior Vice President, Innovation and Strategy, JND Legal Administration.
Marcin Święty, Chief Security Officer, Relativity.
Alston Walker, Senior Discovery Consultant and Executive Client Services Liaison, HaystackID.
Freya Zhou, Co-Founder & COO, Fileread.

Oct 8, 2025 • 14min
Avoiding the Pitfalls of Using AI in a Legal Practice
I spoke with Binit Agrawal, the Chief of Staff at Lucio, an India-based AI-native workspace for lawyers. We discussed the pitfalls of using AI in a legal practice, the mindset and skill set that junior lawyers should adopt, and how AI in the legal profession is evolving.

Oct 6, 2025 • 9min
Where Lawyers Should Leverage Technology to Enhance Their Business Development
I spoke with Timothy Keith, the Founder and CEO of Propense.ai, which develops technology to empower cross-selling in professional services, including at law firms. We discussed how AI can help law firms improve cross-selling, the most common business development challenges they face, and where lawyers should leverage technology to enhance their business development.

Oct 3, 2025 • 11min
How the Value of CLM Has Changed Since the Emergence of Generative AI
I spoke with Matt Patel, Founder and Chief Operating Officer at Malbek, an enterprise CLM company providing comprehensive contract management solutions for procurement, legal, sales, and other functions. We discussed who gains the most value from CLM, how its value has changed since the emergence of generative AI, and how it is evolving.


