Patrick O'Shaughnessy

Patrick O'Shaughnessy × Gabe Stengel

Rogo’s model-era progression—from o1 Pro’s reliable search to Opus 4.5 handling junior finance work—supports a two-year race to redesign investment firms, not wait for better models.Its wedge is private-market dealmaking, where data rooms, DDQs, CRM and LP reporting still lack infrastructure, while high-value ideas can justify extreme token spend.The watchpoints are compaction, standardization, and whether incumbents move aggressively enough.

Patrick O'Shaughnessy × John Kim

John Kim frames fundraising as a trust problem: desire minus fear drives action, while returns alone miss the motivations of most LPs and committees rarely make contrarian bets.His operating rules are to anchor scale to the first close, simplify the story, choose two of size, speed and terms, and build pipeline through conversion and bite size without sacrificing the differentiation that created the franchise.

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 × William Hockey

Column combines a bank’s regulatory permissions with software economics, earning 90%+ of revenue from per-API-call infrastructure for payments, deposits, and credit across fintech and emerging markets.Hockey’s debt-funded acquisition and near-bankruptcy experience shaped an earnings-funded, employee-owned model, while AI may reward banks and distribution-heavy brands; the open question is which specialized financial rails can compound without venture capital.

Patrick O'Shaughnessy × Ben Horowitz

Ben Horowitz expects AI’s economic impact within 12–24 months because adoption needs no new infrastructure, while lower energy prices, less regulation, and a friendlier tax code strengthen the backdrop.AI-native companies such as Cursor can reach over $1B in revenue rapidly even as Salesforce and SAP remain difficult targets, but policy remains the tail risk and private markets must support companies toward a roughly $1B IPO threshold.

Patrick O'Shaughnessy × Karim Atiyeh

Ramp is moving beyond LLM-assisted work toward agents embedded in finance workflows, with a policy agent enforcing expense rules 24/7 and inferring undocumented policies from customer behavior.The shift from TPV to paid software accelerated growth because customers demanded more, but agent pricing remains unresolved as Ramp expands from cards into self-driving finances and evaluates which payment rails ultimately matter.

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 × Peter Lacaillade

Private markets delivered 3-5% alpha over public equities for 25 years, while persistent top-manager performance can add 5%+.SCS underwrites 16-18% net IRR and 2.5x through pooled vehicles, targeting lower-middle-market businesses bought at 5-8x EBITDA and sold at 12-18x after operational growth.The retail wave bears watching: interval funds bid mid-90s versus sophisticated buyers at mid-80s, while quarterly liquidity may still mean being locked up for five, six years.

Patrick O'Shaughnessy × Ramtin Naimi

Abstract’s thesis is that multi-stage firms historically led most power-law seed rounds, while Naimi’s concentrated 5% from a $100M fund can exceed 15% from a $1.5B co-lead in look-through exposure.His sole-node Series A process claims highest-decile valuations and lowest dilution, but 4–5x markups and 30–40% IRR within months echo 2021, while AI application valuations remain undetermined.

Patrick O'Shaughnessy × Alan Waxman

Alan Waxman’s edge is unitizing risk by business quality, capital-structure attachment point, and documents, letting Sixth Street compare disparate deals across asset classes.With 450-500 monthly deals, 15-25 live themes, and a $30B TAL vehicle, the firm can migrate as themes decay over 12 to 36 months, but leverage-driven returns, AI labor disruption, and wealth-channel structure remain watchpoints.