How to Win Any B2B Contract Using Jose Mourinho's Playbook
B2B Growth

Confessions of a B2B Entrepreneur

How to Win Any B2B Contract Using Jose Mourinho's Playbook

Confessions of a B2B Entrepreneur•Nov 13, 2025

AI Summary

In this episode, Tom Hunt interviews Aditya Shivkumar, co‑founder of Resolve Disputes Online, about his shift from litigation lawyer to legal‑tech entrepreneur and how his courtroom analytical skills powered RDO’s successful pivot to online dispute resolution. He explains how the COVID‑19 crisis became a growth catalyst, securing funding and accelerating the B2B rollout. The conversation culminates with Aditya mapping Jose Mourinho’s defensive ‘Catenaccio’ strategy to a systematic approach for winning high‑value B2B contracts, emphasizing preparation, adaptability, and tactical positioning. Listeners walk away with a playbook for leveraging legal expertise and strategic thinking to close deals in the B2B space.

Why It Matters

RDO’s approach demonstrates how legal expertise and strategic defensiveness can unlock scalable B2B revenue, signaling a blueprint for other legal‑tech startups seeking growth in competitive markets.

Episode Description

In this episode of Confessions of a B2B Entrepreneur, Tom Hunt speaks with Aditya Shivkumar, Co-founder of Resolve Disputes Online (RDO), about his transition from lawyer to global legal-tech founder. Aditya reveals how the analytical skills honed in litigation became the most valuable asset for their successful B2B pivot into Online Dispute Resolution (ODR). He shares the entrepreneurial mindset that allowed RDO to treat the COVID-19 crisis as a "watershed moment" for growth and securing funding. The conversation culminates with Aditya detailing how he applies Jose Mourinho's strategic 'Catenaccio' philosophy directly to winning high-value B2B contracts.

Show Notes

Confessions of a B2B Entrepreneur

How to Win Any B2B Contract Using Jose Mourinho's Playbook

November 13, 2025

In this episode of Confessions of a B2B Entrepreneur, Tom Hunt speaks with Aditya Shivkumar, Co-founder of Resolve Disputes Online (RDO), about his transition from lawyer to global legal-tech founder. Aditya reveals how the analytical skills honed in litigation became the most valuable asset for their successful B2B pivot into Online Dispute Resolution (ODR). He shares the entrepreneurial mindset that allowed RDO to treat the COVID-19 crisis as a "watershed moment" for growth and securing funding. The conversation culminates with Aditya detailing how he applies Jose Mourinho's strategic 'Catenaccio' philosophy directly to winning high-value B2B contracts.

Confessions of a B2B Entrepreneur is handcrafted by our friends over at: fame.so Check out our five most downloaded episodes:

  1. How To Start A Movement with David Heinemeier Hansson of 37signals

  2. Chris Walker Rants On Dark Social, Creating Demand & Company Building

  3. CEO Spends 70% Of Time On His Personal Brand? Guillaume Moubeche Shares All

  4. OLD WAY/NEW WAY with Adam Robinson of Retention.com

  5. Nathan Latka Shares His “King-Maker Strategy"

Hit me up on Twitter or LinkedIn with any questions or feedback, I reply to them all. Guest submissions here: fame.so/cbe-guest

Powered by Fame

Comments

Want to join the conversation?

Loading comments...