Over 90% of law firms are using AI, and I sit down with Jayanth “Jay” Madheswaran, the visionary founder and CEO of Eve, to uncover how his billion-dollar legal tech company is changing the game for plaintiff firms everywhere.

Jay explains how Eve’s AI reads medical records, builds chronologies, drafts demand letters, and even handles discovery—all in minutes instead of hours. We talk about his journey from Facebook and Rubrik to launching Eve, the lessons behind their $103M raise, and how they’ve built a team of engineers and lawyers obsessed with one goal: helping firms deliver stronger outcomes with less stress.

From practical examples to future predictions, this episode dives deep into what AI can really do for contingency-based firms—and how leaders can adopt it today without disrupting their teams or client relationships.

Key Topics

00:44 – Learn how Jay’s vision for Eve Legal began after seeing how inefficient law firm workflows really were.

02:10 – Hear how Eve secured $103M in Series B funding and what drove investor confidence.

04:32 – Discover why plaintiff firms are adopting AI faster than defense firms—and how that’s flipping the script.

08:18 – See how Eve’s AI creates detailed medical chronologies from complex record sets in minutes.

09:23 – Learn how firms are drafting demand letters that sound like their best writers—without starting from scratch.

09:56 – Explore how discovery responses and interrogatories can now be turned around same-day.

11:40 – Find out what 500+ law firms have learned about AI adoption and the importance of guided support.

12:54 – Understand how “Blueprints” let firms train Eve to write exactly the way their attorneys do.

18:27 – Learn how Eve’s pricing model aligns perfectly with contingency-based firms.

19:48 – See how AI lets firms reduce costs, boost margins, and redeploy team members into higher-value roles.

20:46 – Explore how specialization or scaling volume both become easier with AI-driven workflows.

23:23 – Hear what’s next: voice-enabled AI agents and faster product cycles for legal operations.

27:02 – Discover how Eve’s tech team built proprietary models trained only on legal language and data.

30:52 – Understand the pros and cons of “best-of-breed” vs. “all-in-one” AI tools for law firms.

38:02 – Reflect on how AI is reshaping the roles of young lawyers, paralegals, and the next generation of “AI-native” legal professionals.

Resources Mentioned

Tech & Apps

• Eve Legal – https://eve.legal
• OpenAI / ChatGPT – https://openai.com/chatgpt 
• Google Gemini (Deep Research) – https://gemini.google.com 
• Zoom – https://zoom.us 
• RingCentral – https://www.ringcentral.com 
• Case Status – https://www.casestatus.com 
• Hona – https://www.joinhona.com

Books

• Antifragile by Nassim Nicholas Taleb – https://a.co/d/i6C3FC5 
• The Ride of a Lifetime by Robert Iger – https://a.co/d/clxWn8y

Podcasts

• Founders – https://podcasts.apple.com/us/podcast/founders/id1141877104
• AI Daily Brief – https://podcasts.apple.com/us/podcast/the-ai-daily-brief-artificial-intelligence-news/id1680633614 

About our Guest:

Jayanth “Jay” Madheswaran is a seasoned technologist, founder, and investor, with more than 15 years of experience in AI, machine learning, and product development. Before founding his current venture, Eve Legal, Jay held leadership roles at Facebook, Rubrik, and Lightspeed Venture Partners.

At Eve Legal (based in Palo Alto), Jay serves as CEO and is driving innovation at the intersection of legal technology and automation.

Known for blending deep technical insight with entrepreneurial acumen, Jay also invests via Lightspeed and acts as a mentor and advisor to many early-stage startups.

He holds a degree in Computer Science from the University of Illinois at Urbana-Champaign and continues to champion growth and impact in tech and legal innovation.

https://www.eve.legal/ 

About Jay Berkowitz:

Jay Berkowitz is a best-selling author and popular keynote speaker. Mr. Berkowitz managed marketing departments at: Coca-Cola, Sprint and McDonald's Restaurants, and he is the Founder and CEO of Ten Golden Rules,  a digital marketing agency specialized in working with attorneys.

Mr. Berkowitz is the author of Advanced Internet Marketing for Law Firms, The Ten Golden Rules of Online Marketing and 10 Free Internet Marketing Strategies that went to #1 on Amazon.  He is the host of the Ten Golden Rules of Internet Marketing Webinar and Podcast. He has been profiled by the Wall Street Journal, The Business Journals and FOX Business TV.

Mr. Berkowitz was selected for membership as a TITAN for Elite Digital Marketing Agencies, he is the recipient of a SOFIE Award for Most Effective use of Emerging Media, and a Special BERNAY’s Award.

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