TIVP060: Constellation Software (CSU): Historic Drawdown, Historic Buying Opportunity w/ Daniel Mahncke & Shawn O’Malley

Daniel Mahncke and Shawn O’Malley take a deep dive into Constellation Software — the popular Canadian compounder that has turned buying “boring” vertical market software into one of the most effective capital-allocation machines in public markets.

IN THIS EPISODE, YOU’LL LEARN:

00:00:00 - Intro 00:03:33 - How Mark Leonard founded Constellation 00:08:43 - What principles drive Mark Leonard 00:15:23 - What Constellation looks for in acquisition targets 00:19:20 - About the metrics that matter to Constellation 00:21:15 - How Constellation is structured and incentivized 00:46:26 - Whether AI is a threat or chance 01:04:50 - Why Constellation considers investing outside of VMS 01:08:50 - Whether Shawn and Daniel add Constellation to the portfolio

*Disclaimer: Slight timestamp discrepancies may occur due to podcast platform differences.

BOOKS AND RESOURCES

• The Investors Podcast Network is excited to debut a new community known as The Intrinsic Value Community for investors to learn, share ideas, network, and join calls with experts: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Sign up for the waitlist(!)⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠
• Sign up for ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠The Intrinsic Value Newsletter.⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠
• Learn how to ⁠⁠⁠⁠⁠⁠⁠⁠join us⁠⁠⁠⁠⁠⁠⁠⁠ in Omaha for the 2026 Berkshire Hathaway shareholder meeting.
• Track ⁠The Intrinsic Value Portfolio⁠.
• Shawn & Daniel use ⁠Fiscal.ai⁠ for every company they research — use their ⁠referral link⁠ to get started with a 15% discount!
• WSB episode on Constellation Software.
• Synopsis Podcast on Constellation Software.
• Business Breakdown Podcast on Constellation Software.
• Mark Leonard Shareholder Letters.
• Saber Capital: How to Think about ROIC.
• Check out our previous Intrinsic Value breakdowns: