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 × 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 $11B of ARR in March while tech reached its cheapest relative valuation in 10 years, making the drawdown a differentiated demand signal rather than a capitulation event.At a rumored $900B on $50B ARR, Baker estimates unconstrained run-rate revenue of $100–200B, while TSMC’s capacity choices remain the key bubble test and orbital compute threatens terrestrial power-and-cooling ramps.

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 × 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 × Tal Zaks

Biotech returns still depend on capital required, time to proof, and two unknowns: whether biology is disease-relevant and whether a drug can alter it safely in the right tissue.Moderna shows the platform mechanism: mRNA generated neutralizing antibodies against eight viruses before COVID-19, while its personalized skin-cancer vaccine cut recurrence about 50% in randomized phase 2.AI can accelerate discovery, but clinical testing, reimbursement, deployment economics, and ethical questions around lasting DNA changes remain the constraints investors must monitor.