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Invest Like the Best
Deep conversations with investors, founders, and operators about business quality, capital allocation, strategy, and enduring competitive advantage.
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Gabe Stengel - Building Investing Superintelligence - [Invest Like the Best, EP.492]
Patrick O'ShaughnessyGabe 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.
The Anatomy of Ramp's Hyper-Growth | Karim Atiyeh Interview
Patrick O'ShaughnessyKarim 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.