Talks

Learn from the Operating Manual of a $100B Software Compounder

What drives a company to grow from $25 million to over $100 billion without chasing scale, diluting discipline, or bowing to bureaucracy?

This lecture series offers a rare window into the philosophies, structures, and decisions that have shaped Constellation Software Inc. - one of the most enduring and idiosyncratic compounders in the global software space. Each session reflects decades of lived experience building a decentralized, acquisition-driven organization focused on vertical market software. The aim isn’t to glorify success, but to dissect the thinking, mistakes, and frameworks that underpin sustained performance.

These talks are intended for business students, faculty, and future entrepreneurs interested in the practical realities of capital allocation, organizational design, and long-term value creation. The approach is blunt, grounded, and unapologetically focused on fundamentals—drawing directly from CSI’s history, its 1000+ acquisitions, and over two decades of shareholder letters.

If you're interested in hosting a session, please reach out via the Contact Page to discuss availability. Invitations are accepted on a limited basis.

1. From $25M to $100B: Laying the Foundations
This session chronicles the founding and early scaling of Constellation Software Inc., focusing on the initial vision, pivotal moments, and the critical decisions that set the stage for its extraordinary growth. It will explore the challenges of bootstrapping, establishing a foothold in niche markets, and the evolution of leadership thinking during the formative years—providing a narrative foundation before other sessions dive into specific operational pillars.

• The initial vision and the unique challenges of bootstrapping a VMS aggregator
• Pivotal early acquisitions and how they shaped CSI's operational DNA
• Evolution of the core philosophy: from startup hustle to disciplined growth engine

2. The Art of Capital Allocation
Constellation isn’t just a software company—it’s a capital allocation machine. This talk explores how CSI decides where and when to invest, why it avoids growth at any cost, and how it balances reinvestment, dividends, and acquisitions. This is a deep dive into how capital is used as a strategic tool.

• Understanding ROIC + Organic Growth as core metrics
• Why hurdle rates drive investment decisions
• Avoiding the trap of undisciplined reinvestment

3. Scaling Without Bureaucracy: Organizational Design at CSI
While most large firms bloat with middle management, CSI has scaled with a flat, decentralized model. This session unpacks how small business units are empowered to operate autonomously while still benefiting from shared knowledge and governance discipline.

• How decentralization builds resilience
• Why autonomy attracts and retains top managers
• Lessons from scaling without losing culture

4. The Illusion of Mastery: How Luck, Timing, and Humility Shape Real Outcomes
Success stories tend to get polished in hindsight. We highlight foresight and grit, downplay randomness, and rarely admit when we were simply in the right place at the right time. This session unpacks the role of luck in entrepreneurial journeys and capital allocation outcomes, arguing that underestimating luck is both intellectually dishonest and operationally dangerous. Through CSI’s own missteps and near-misses, we explore the value of humility in decision-making, the dangers of overconfidence, and how to build systems that work even when you're not as smart as you think you are.

• Why survivorship bias distorts your mental models
• The difference between process and outcome in capital allocation
• Learning to recognize when you’ve been lucky—and how not to bet on it repeating
• How humility builds better teams, sharper decisions, and more durable systems
  
  

5. The Enduring Survivors: Why Boring, Niche, and "Good Enough" Often Outlasts Innovative & Exciting in VMS
While the tech world chases disruption and exponential growth, Constellation's portfolio of 1000+ acquisitions reveals a different path to enduring value: the quiet strength of businesses that are often overlooked. This session dissects why "boring" vertical market software, with its deep moats built on customer inertia, regulatory complexity, and "good enough" functionality, often demonstrates far greater long-term durability and cash flow stability than their seemingly more innovative or high-growth counterparts. We explore the counterintuitive power of being essential but unexciting.

• The "Indispensable Infrastructure" Play: How deeply embedded, mission-critical software in niche industries creates unbreachable moats, even with older tech.
• Why "Good Enough" is Often Better Than "Cutting Edge": The economics of customer inertia versus the high costs and risks of constant innovation in mature VMS markets.
• Spotting "Hidden Champions": Identifying businesses whose lack of glamour belies their exceptional profitability, resilience, and low-risk profile.
• The Durability Paradox: How focusing on incremental improvement and customer retention in stable niches can lead to superior long-term outcomes compared to chasing disruptive breakthroughs.
• Lessons from businesses CSI didn't buy (or regretted buying): When "exciting" proved fragile and "boring" would have been better.

6. The “Earned Secret”: How to Spot Founder-Driven Opportunities
VMS Ventures and other internal CSI initiatives rely on identifying employee-entrepreneurs with “earned secrets”—deep domain knowledge that uncovers hidden opportunity. This talk explores how these secrets emerge, and how they’re turned into competitive advantages.

• What qualifies as an “earned secret”
• How CSI funds and supports internal founders
• The strategic edge of embedded expertise