About

Tough Lessons, True Insights

John Crook has dedicated over 40 years to mastering and implementing the unconventional yet highly effective principles that drive exceptional, long-term business performance – the very principles at the heart of InverseMBA. His career, particularly his extensive tenure within the Constellation Software Inc. (CSI) ecosystem, provides a rare, practical insight into how contrarian strategies can build enduring, high-value enterprises.

John isn't just a theorist; he's an experienced leader who has lived and breathed the "Inverse MBA" approach. From 2013 onwards, he was deeply embedded in the Constellation Software model, a period during which he:

  • Led as CEO for three Constellation Software portfolio businesses, experiencing firsthand the power of autonomous leadership, deep vertical focus, and the pursuit of sustainable, profitable growth within niche markets.
  • Key role in strategic acquisitions and the integration of acquired businesses from 2018 to 2024, mastering the art of identifying and nurturing small, specialized software companies for permanent ownership.
  • Coached and mentored numerous business leaders and CEOs across CSI's diverse portfolio, instilling the disciplined capital allocation, operational excellence, and long-term thinking that are hallmarks of the Constellation way.

This hands-on experience in a uniquely decentralized, high-performing environment has equipped John with a profound understanding of how to build resilient businesses. His journey from software engineering roots to executive leadership within one of the world's most successful (and unconventional) software conglomerates makes him a compelling guide to the "Inverse MBA."

Today, through InverseMBA, John shares these hard-won lessons, helping other leaders and organisations understand and potentially apply these powerful, contrarian principles to their own contexts. 

Key Milestones Reflecting an "Inverse MBA" Journey:

  • Late 1970s: B.Sc. Physics – University of Sussex, England (Foundation in analytical thinking)
  • 1980s - 2000s: Progressive leadership roles, including Software Engineer at British Telecom, Engineering Manager at Intel, and ascending to CEO at Softlink (Brisbane) – demonstrating a climb through operational and leadership ranks.
  • 2013 - 2024: Decade of Immersion at Constellation Software Inc. (CSI)
    • CEO, Softlink Information Centres
    • CEO, Edumate
    • CEO, Pegasus Systems
    • Integrations / Group Leader / Strategic Role (2018-2024): Focused on M&A, portfolio company integration, and CEO mentorship, directly applying and refining "Inverse MBA" principles across numerous vertical market software businesses.
    • AI strategy business coach. (2019 -2024).  Coached dozens of Constellation businesses for the upcoming AI disruption.
  • 2016‑22: Stanford & Coursera ML specialisations (Continuous learning, bridging technical depth with strategic insight)
Testimonials

·       John’s session and engaging delivery has really helped our business turn abstract concepts into tangible actions.” Sebastian Vaitus, CEO Function Software, Toronto, Canada.

·       John has the rare ability to take complex information and present it in a way that is comprehensible and engaging for audiences of any kind, I can’t wait to hear him speak again! Craig Ford, CEO Function Fox, Vancouver, Canada.

·       John can keep an audience enthused and leaves them wanting more of the education he provided. He takes the complicated subject and simplifies it for all to understand. Syam Menon, Director - Integrations at Volaris Group, London.

·       The session was terrific, a real tour of Intelligence on Artificial Intelligence. Michael Schrage, Massachusetts Institute of Technology | MIT Research Fellow.

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