Anthony M. DeSimone is a leading advocate for integrating generative AI into the legal profession, specializing in helping law firms harness AI to enhance efficiency, profitability, and client service. With more than 25 years of experience as a CPA and CMA, Anthony began his career at Deloitte before transitioning to focus on business optimization. Today, he operates "You're the Expert Now, LLC" and serves as a faculty member at the University at Buffalo Center for Entrepreneurial Leadership.
In addition to delivering keynote presentations at national conferences, Tony leads AI accelerator courses and shares insights through his YouTube channel and podcast, "AI Mastermind." His groundbreaking work, including publishing a book in under 24 hours and producing AI-generated illustrations, underscores his expertise at the intersection of AI, data, and legal practice.
WHAT’S COVERED IN THIS EPISODE ON AI STRATEGY FOR LAW FIRMS
Many law firms are intrigued by AI, but unsure how to move forward. Questions about confidentiality, security risks, and the reliability of AI tools leave many lawyers hesitant, and expose firms to risks they don’t fully understand.
But AI isn’t about replacing lawyers. It’s about amplifying their capabilities while safeguarding client trust. Firms that learn how to integrate AI strategically will not only protect sensitive data but also position themselves for greater efficiency, profitability, and resilience in a changing legal landscape.
In this episode of The Lawyer’s Edge Podcast, Elise Holtzman talks with Anthony DeSimone, a CPA, CMA, and AI strategist who advises law firms on safe and effective AI adoption. Tony shares practical insights on the risks lawyers can’t afford to ignore, how to train teams to use AI responsibly, and how the right AI strategy can streamline firm operations without sacrificing security or professionalism.
2:10 – How law firms are approaching AI today — early adopters versus laggards
4:20 – The hidden risks when lawyers use AI tools without firm oversight
6:00 – What AI hallucinations are and why they matter for law firms
8:42 – Practical ways lawyers are using AI now — drafting, research, and more
13:14 – How to safeguard client confidentiality when using AI
17:23 – The leadership role in encouraging smart AI experimentation
21:35 – Why large language models struggle with numbers and how that impacts legal work
24:50 – What’s next — how AI will reshape law firm operations in the next five years
MENTIONED IN ANTHONY DESIMONE | MAKING AI WORK FOR YOUR LAW FIRM WITHOUT COMPROMISING SECURITY OR EXCELLENCE
You're the Expert Now, LLC | LinkedIn
Get connected with the coaching team: hello@thelawyersedge.com
SPONSOR FOR THIS EPISODE…
Today’s episode is brought to you by the coaching team at The Lawyer’s Edge, a training and coaching firm that has been focused exclusively on lawyers and law firms since 2008. Each member of The Lawyer’s Edge coaching team is a trained, certified, and experienced professional coach—and either a former practicing attorney or a former law firm marketing and business development professional.
Whatever your professional objectives, our coaches can help you achieve your goals more qu
Popular Podcasts
On Purpose with Jay Shetty
I’m Jay Shetty host of On Purpose the worlds #1 Mental Health podcast and I’m so grateful you found us. I started this podcast 5 years ago to invite you into conversations and workshops that are designed to help make you happier, healthier and more healed. I believe that when you (yes you) feel seen, heard and understood you’re able to deal with relationship struggles, work challenges and life’s ups and downs with more ease and grace. I interview experts, celebrities, thought leaders and athletes so that we can grow our mindset, build better habits and uncover a side of them we’ve never seen before. New episodes every Monday and Friday. Your support means the world to me and I don’t take it for granted — click the follow button and leave a review to help us spread the love with On Purpose. I can’t wait for you to listen to your first or 500th episode!
Crime Junkie
Does hearing about a true crime case always leave you scouring the internet for the truth behind the story? Dive into your next mystery with Crime Junkie. Every Monday, join your host Ashley Flowers as she unravels all the details of infamous and underreported true crime cases with her best friend Brit Prawat. From cold cases to missing persons and heroes in our community who seek justice, Crime Junkie is your destination for theories and stories you won’t hear anywhere else. Whether you're a seasoned true crime enthusiast or new to the genre, you'll find yourself on the edge of your seat awaiting a new episode every Monday. If you can never get enough true crime... Congratulations, you’ve found your people. Follow to join a community of Crime Junkies! Crime Junkie is presented by audiochuck Media Company.
Ridiculous History
History is beautiful, brutal and, often, ridiculous. Join Ben Bowlin and Noel Brown as they dive into some of the weirdest stories from across the span of human civilization in Ridiculous History, a podcast by iHeartRadio.