Invest Like the Best

Patrick O'Shaughnessy × Vlad Barbalat

Liberty Mutual’s $120B balance sheet combines roughly $70–75B of reserves with growth credit and equity, while permanent mutual capital avoids shareholder pressure and supports 7–10% portfolio targets.Barbalat now questions whether AI makes future cash flows—and therefore multiples—structurally less visible, with four-year software credit appearing safer than 30-year Salesforce or Oracle debt and potentially steeper credit curves ahead.

Patrick O'Shaughnessy × Mark Bertolini

Oscar Health is pursuing a defined-benefit-to-defined-contribution shift in healthcare, targeting 125 million people through individual ACA plans, while its cloud-native platform and “almost two dozen” LLMs support lower operating costs and disease-management economics.The CHOICE provision’s Senate removal over a $30B tax score underscores regulatory resistance, while Bertolini’s Aetna record—75% lower end-of-life costs and 652% eight-year TSR—illustrates the potential payoff from operational and benefit redesign.

Patrick O'Shaughnessy × Bill Gurley

Venture’s private-company backlog reflects roughly 1,000 firms raising more than $1 billion each, while mega-funds and paper marks weaken incentives to reset valuations.With IPOs closed, holding periods stretching toward 10-to-15 years, and annual dilution of 3%-6%, LP liquidity pressure and a potential reset remain the key catalysts.

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.