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September 10th, 2025

THE $92B SILENT EMPIRE

  1. THE $92B SILENT EMPIRE Jon Stoddard 44:48

This conversation explores the remarkable journey of Mark Leonard and his creation, Constellation Software, which has grown from a modest $25 million investment in 1995 to a $92 billion empire through a unique acquisition strategy focused on vertical market software companies. Leonard's approach emphasizes patience, discipline, and a decentralized management structure that empowers individual business units while maintaining rigorous financial standards. The discussion highlights the importance of long-term thinking, frugality, and the cultivation of a strong company culture that values autonomy and stewardship over short-term gains.

Acquiring businesses, teaching entrepreneurs how to acquire businesses and helping entrepreneurs scale businesses through acquisitions and marketing. Jon is adept at negotiation, marketing strategy, structuring and funding of mergers and acquisitions IPOs and exit strategies.