Invest Like the Best

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 × Sarah Guo

Sarah Guo says competitive open-source AI is already widespread, so US restrictions could handicap law-abiding American businesses while adversaries ignore them.Her roughly 250-person network sees recursive self-improvement and “some sort of exponential intelligence” as a one-to-two-year possibility, while Sunday Robotics targets home-robot beta by year-end.Compute independence, regulation, and physical supply chains remain constraints, while Chai Discovery’s $10 million contract and customer adoption test AI’s ability to capture value in biology.

Patrick O'Shaughnessy × Alex Sacerdote

Anthropic’s agentic coding release helped reverse Whale Rock’s view, supporting its August 2025 investment at the $180 valuation after it passed on the $60B round.Enterprise AI is less than 1% penetrated, yet Anthropic has only half the compute it needs, while a three-horse model oligopoly and infrastructure bottlenecks support monitoring adoption, supply, and the risk that open source catches up.

Patrick O'Shaughnessy × Gavin Baker

Anthropic added $11 billion of ARR in one month, while Asian AWS prices doubled, GPU availability fell, and DRAM went vertical as reasoning increased inference demand.Baker sees compute-constrained revenue upside, but TSMC capacity remains the key test for whether AI becomes an infrastructure bubble.

Patrick O'Shaughnessy × Scott Nolan

America’s zero commercial uranium-enrichment capacity makes fuel the bottleneck for advanced nuclear power, with HALEU scarcity and the January 1, 2028 Russian-import ban creating defined market openings.General Matter targets dollars per kilogram-SWU as its cost metric, while data-center demand and behind-the-meter SMRs could accelerate deployment; execution, permitting, and the economics of nuclear construction remain key risks.

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 × Jesse Zhang

Decagon’s enterprise AI wedge is customer service, where existing resolution rates of 15–20% create a quantifiable path toward 50–80% while escalation to humans de-risks deployment.The moat is continuous improvement: models can review every one of a million monthly conversations, identify the 2% failing, and draft fixes that compound into a brand-level digital concierge.Voice remains the largest unresolved frontier, with voice-to-voice hallucinations probably “like 8x higher” than text, while falling model costs intensify the race for market share and mindshare.

Patrick O'Shaughnessy × Joe Liemandt

Alpha School claims AI tutors and a motivation-first model let students learn twice as much in two hours as standard schools deliver in six hours plus homework, with third-party MAPS tests and AP World History scores cited as evidence.The Timeback platform, targeted for next year after August-to-December betas, could expand through Texas’s $1B school-choice program, but homeschool tests with 50+ students are not yet achieving 2x results without the in-building motivational model.

Patrick O'Shaughnessy × Dinakar Singh

Singh’s daughter’s SMA turned investing into a race for research capital, leading to three parallel programs that all became approved drugs.Shared testing, natural-history evidence, and coalition-building accelerated approval, while regeneration and affordable access remain the next unresolved challenges.

Patrick O'Shaughnessy × Matt Huang

Matt Huang argues that illegibility can preserve upside because easily explained frontiers are more likely to be priced, favoring unusual founders and technical paths over memes and consensus.His ByteDance investment backed Yiming’s judgment despite disliking personalized news, while Paradigm paired builder-led crypto investing with Bitcoin near $6,000-$3,000 and Ethereum near $100.Stablecoins now exceed $200 billion on-chain and could modernize global payments, while FTX and organizational overconfidence show why trusted counterparties and technical conviction remain major risks.