Aditya Shivkumar on Why Legal AI Needs Empathy

Salvador Carranza sits down with Aditya Shivkumar, founder of RDO (Resolve Disputes Online), to unpack how an AI-native online dispute resolution platform gets built from inside a court system instead of around it. They go deep on the access-to-justice problem, why legal AI still has to sit next to the empathy of a human judge rather than replace it, and the Tyler Technologies partnership that puts RDO in reach of more than 45% of US state courts. Aditya breaks down the AI negotiator RDO trained for sub-$100K monetary disputes, why founder resilience is the real moat in legal tech, and how a two-month ICU stay reset his view of time and purpose. Watch the full conversation for a grounded look at what legal AI looks like when it is designed to enable the judiciary, not replace it.

CHAPTERS

00:00 Introduction
00:57 Life beyond the hustle: wildlife, sports, and law
04:47 Safari lessons on perseverance
09:09 Becoming a sports administrator
13:52 Premier Futsal and sports law in action
18:42 Law, politics, business, and the rise of AI
22:15 AI as a bull in a china shop or a focused Malinois
23:27 Cardiff, mediation, and a first startup failure
28:46 What failure teaches entrepreneurs
34:56 India, resilience, and original thinking
39:59 Access to justice and the role of AI
44:40 RDO and the Tyler Technologies partnership
51:15 How online dispute resolution actually works
54:29 An AI negotiator for small-claim disputes
58:23 COVID, the ICU, and finding purpose
01:01:22 Where to find Aditya

Takeaways

Access to justice is a global problem UN Sustainable Development Goal 16.3 names but most systems still do not operationalize.
Legal AI should enable dispute resolution, not replace the empathy a human judge brings to a contested case.
Courts, not lawyers, are the real customer for B2B legal AI in dispute resolution because the judiciary controls the workflow.
Roughly two-thirds of US court disputes are under $100,000 and are strong candidates for asynchronous AI-assisted settlement.
An AI negotiator trained on dispute history can bring two parties into a settlement zone without a human in the loop.
First attempts fail. The B2C version of RDO failed before the B2B court-integrated version that now ships.
Resilience compounds. Safari after safari with zero sightings teaches the same lesson a failed startup does.
The Tyler Technologies partnership expands RDO's reach to more than 45% of US state courts through existing case-management integrations.
Purpose is easier to find after a forced reset. Aditya's two-month ICU stay clarified how he invests his next few decades.
Indian entrepreneurship is shaped by policy (tax breaks, self-reliance framing) plus a cultural default of adaptability.

👤 Guest Bio
Aditya Shivkumar is the founder of RDO (Resolve Disputes Online), a B2B online dispute resolution platform that integrates with court case-management systems to let litigants, lawyers, judges, and mediators resolve disputes asynchronously. RDO operates across four to five US states and recently announced a partnership with Tyler Technologies that makes it the preferred ODR supplier across North America and Canada, reaching more than 45% of US state courts. Aditya earned his law degree at Cardiff University and began his career as a sports lawyer, including work on the launch of India's Premier Futsal League with players like Luis Figo, Paul Scholes, and Deco. He sits on the committee of the Madras Motorsports Club, the oldest motorsports club in India, and frames his work through the lens of resilience and original thinking after recovering from a severe case of COVID in 2021 that left him in the ICU for two months.

🔗 Connect With Aditya
• LinkedIn: https://www.linkedin.com/in/aditya-shivkumar-5b40837/
• RDO: https://resolvedisputes.online

🔗 More From Salvador
PossibLaw: https://www.possiblaw.com
Full podcast library, essays, and tools for legal professionals who are done watching from the sidelines.
LinkedIn: https://www.linkedin.com/in/salvadorcarranza

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