We Study Billionaires (TIP)

We Study Billionaires (TIP)

OTC Markets Group operates as a quasi-monopoly infrastructure provider for over 12,000 over-the-counter securities, serving as the essential 'picks and shovels' play for small-cap capital markets. The company has generated exceptional shareholder returns through a capital-light model that has compounded free cash flow at 14% annually for a decade while maintaining zero debt and operating margins exceeding Alphabet.

We Study Billionaires (TIP)

CoStar Group, the dominant commercial real estate data company with an unassailable 37-year data moat and 59 consecutive quarters of double-digit growth, has invested $5 billion to enter the residential market with Homes.com, sparking a 50% stock selloff and activist investor revolt over concerns of capital misallocation.

We Study Billionaires (TIP)

Ryan Sablan shares his asymmetric value investing framework, revealing how Charlie Munger's simple mathematical insight—that you only need one winner among three bets to achieve 33% returns—combined with rigorous balance sheet analysis and position sizing, can lead to market-beating performance without requiring a high win rate.

We Study Billionaires (TIP)

The hosts conduct a quarterly review of their concentrated 17-stock portfolio, announcing plans to sell two positions and add to one, while deep-diving into Exor's 60% discount to NAV as a Ferrari proxy and debating the future of their small TransDigm stake.

We Study Billionaires (TIP)

This episode analyzes Constellation Software's smaller spinoffs and copycats—including Topicus, Lumine Group, Signity, and Aiko Poland—as potential 'next 10-baggers' that replicate the vertical market software (VMS) acquisition playbook without facing the law of large numbers constraining their parent company.

We Study Billionaires (TIP)

Spotify is transitioning from a low-margin music utility to a diversified global audio platform, finally achieving operating leverage by layering podcasts, audiobooks, and targeted advertising atop its massive habitual user base despite intense competition from tech giants.

We Study Billionaires (TIP)

Kelly Partners Group (KPG) is an Australian serial acquirer consolidating fragmented accounting and tax firms through a unique "partner-owner-driver" model that incentivizes original owners to remain. After a 50% stock decline from early 2025 highs, the company—valued at roughly A$300 million with minimal share dilution and founder ownership near 50%—presents an early-stage opportunity analogous to Constellation Software but within essential, relationship-driven professional services.

We Study Billionaires (TIP)

Drew Cohen of Speedwell Research argues that Constellation Software's 50% drawdown due to AI fears is overblown, explaining that mission-critical vertical market software customers prioritize reliability and switching costs over marginal cost savings, making disruption by AI-generated alternatives unlikely despite the technology lowering barriers to entry.

We Study Billionaires (TIP)

Following an 80% post-IPO decline, Figma now trades at a $12 billion valuation—40% below Adobe’s blocked $20 billion acquisition offer—despite maintaining 45% annual revenue growth and establishing itself as the dominant collaborative design platform that defeated Adobe XD.

We Study Billionaires (TIP)

Duolingo trades at a surprisingly reasonable valuation of 20x free cash flow despite 30% growth, but investors are divided on whether its gamified learning model can overcome high user churn and limited fluency outcomes to capture a trillion-dollar education market.

We Study Billionaires (TIP)

Lyft trades at a $7 billion market cap but could be worth 3x or more to tech giants like Amazon or Alphabet, who would pay a premium for its 30% North American market share and Flex Drive fleet management capabilities to accelerate autonomous vehicle deployment.

We Study Billionaires (TIP)

Constellation Software (CSU) has experienced its largest drawdown ever, falling 50% amid AI disruption fears, creating a potential buying opportunity in a high-quality compounder often called the "Berkshire Hathaway of software." The company operates a decentralized model acquiring over 1,000 niche vertical market software businesses with a permanent capital mindset under founder Mark Leonard, who recently stepped down due to health concerns.