Invest Like the Best

Patrick O'Shaughnessy × Caryn Seidman-Becker

Clear is repositioning from travel security toward a vertically integrated identity platform, with 30M+ opt-in members and expansion into enterprise and healthcare.The model reached positive cash flow in 6.5 years after burning $53M and reduced shares from 155M to 133 and change, but enterprise identity remains unproven to the Street while regulation has already disrupted throughput.

Patrick O'Shaughnessy × Jens Grede

SKIMS shows how pop-culture reach, timely celebrity partnerships, and product-led trust can overcome fragmented algorithms and capital-intensive physical retail.Grede’s evidence—from a two-million-person waitlist to an app generating over 20% of business—supports global stores and a possible IPO, but scaling without killing the brand’s speed is the unresolved risk.

Patrick O'Shaughnessy × Jay Hoag

Hoag sees contrarian opportunity in consumer internet as capital crowds into SaaS and AI despite 5 billion-plus engaged smartphone users.TCV targets companies after technology risk falls, emphasizing monetization, defensibility, adoption, high incremental margins, and limited leverage; private-market liquidity remains unresolved.

Patrick O'Shaughnessy × Cliff Sosin

Carvana’s moat is an integrated system spanning acquisition, logistics, reconditioning, software, lending, registration and trust, built over more than 10 years and roughly $10 billion rather than through online retail alone.EBITDA margins around 10.5% and rising toward management’s stated 13%-14% range compare with roughly 4.5% for the average dealership, but the 99% collapse exposed the continuing risks of immature operations, leverage, demand pull-forward and irrational auto-loan pricing.

Patrick O'Shaughnessy × Neil Mehta

Greenoaks concentrates its capital and attention on 10–15 founders annually, seeking future S&P 500 companies rather than broad deal coverage, with more than $13 billion of profits and a 33% net IRR across nearly $15 billion of AUM.Mehta’s edge is identifying jaw-dropping customer experiences that break accepted trade-offs, as Coupang’s 12-to-24-hour delivery lifted retention from market levels in the 30s to Rocket cohorts in the 60s; concentration, growth endurance and AI economics remain key tests.