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

The Intrinsic Value Podcast - The Investor’s Podcast Network

The Investor's Podcast Network

Education, Investing, Business

4.6 • 592 Ratings

🗓️ 22 February 2026

⏱️ 87 minutes

🔗️ Recording | iTunes | RSS

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Summary

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: ⁠Transdigm⁠, ⁠Salesforce⁠, ⁠Berkshire Hathaway⁠, ⁠FICO⁠, ⁠PayPal,⁠ ⁠Uber⁠, ⁠Nike⁠, ⁠Amazon⁠, ⁠Airbnb⁠, ⁠Alphabet⁠. Related ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠books⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ mentioned in the podcast. Ad-free episodes on our ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Premium Feed⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠. NEW TO THE SHOW? Follow our official social media accounts: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠X (Twitter)⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ | ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠LinkedIn⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ | ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Facebook⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠. Browse through all our episodes (complete with transcripts) ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠here⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠. Try Shawn's favorite tool for picking stock winners and managing our portfolios: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠TIP Finance⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠. Enjoy exclusive perks from our ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠favorite Apps and Services⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠. Learn how to better start, manage, and grow your business with the ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠best business podcasts⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠.⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ References to any third-party products, services, or advertisers do not constitute endorsements, and The Investor's Podcast Network is not responsible for any claims made by them. Learn more about your ad choices. Visit megaphone.fm/adchoices Support our show by becoming a premium member! https://theinvestorspodcastnetwork.supportingcast.fm

Transcript

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0:00.0	In early 2025, Mark Leonard, founder and CEO of Constellation Software, basically said the stock has over value.
0:07.5	You should expect returns of 8% investing at those levels.
0:11.0	He said it would need a massive drop to get back to 25% annualized returns.
0:15.5	Well, patience has paid off for us in this one.
0:18.0	The stock is amid its largest drawdown ever, down 50%.
0:22.8	And we all know why. AI strikes again, but CSI's management team keeps buying more shares,
0:28.2	so we might get the best deal on CSI stock in many, many years today.
0:42.3	You're listening to the Intrinsic Value podcast by the Investors Podcast Network. Since 2014, with over 180 million downloads, we've learned directly from the world's best investors.
0:49.3	Now, we're applying those lessons to analyze businesses and investment opportunities every week,
0:55.9	helping you uncover intrinsic value.
0:58.9	And now, here are your hosts, Sean O'Malley, and Daniel Monker.
1:10.5	A couple of weeks ago, I pitched eggser here on the show, and I more or less jokingly said
1:15.5	it's kind of like an Italian Berkshire Hathaway.
1:18.0	And that might have been a somewhat superficial comparison just to kind of explain that
1:22.2	Exeter is a holding company that owns many companies across various industries.
1:27.3	But today, we will discuss a
1:29.7	company that is a lot closer to the actual Berkshire Hathaway, although the industry it
1:35.6	invests in really could not be more different. And so the company I'm talking about is Constellation
1:40.3	software. And the industry I'm talking about is vertical market software. And we will,
1:45.2	of course, get into exactly what that means and why it is such an attractive business to be in.
1:50.3	But really, if I had to take a guess as to why you brought this stock before us today, Daniel,
1:54.9	I would say that it's because Constellation is currently going through its largest drawdown in
	...

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