PodcastInvest Like the BestGabe Stengel

Why OpenAI and Anthropic Won't Win Finance

The guest sees AI reshaping finance by automating research and transactions, while emphasizing that proprietary data, institutional trust, and auditable systems may distinguish successful firms. He expects investment firms and banks to build more value in software, data, and systems, but says adoption and the pace of change remain uncertain. AI could also lower barriers to smaller deals and improve private-market liquidity, provided firms can meet the demands of compliance, distribution, and execution.

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Key Takeaways

The guest sees public equities as a strong AI application because relevant data is available, but argues that a durable edge may depend on inputs others lack—such as field research, expert insights, and relationship networks. He also says AI could erode expertise based mainly on being smarter or better read, making unique context and information more valuable differentiators.

The guest predicts that leading investment firms and banks could derive 90% of their enterprise value from software, data, and systems within 10 years, and says firms should capture employees’ expertise in systems they own and operate. A banker’s goal of making his thinking, context, and relationships available to junior colleagues illustrates how those systems could scale individual expertise.

The guest sees private markets as an opportunity for AI because coordination, due diligence, and transactions remain largely manual, while unstructured data has impeded standardization. He argues that standardization can support more transaction volume and liquidity, and describes agent-led infrastructure that could assess portfolio-company sales in minutes rather than months, though the pace of change is uncertain.

The guest argues that AI in finance must be auditable, not merely accurate: firms need to preserve how outputs were produced, inspect assumptions and sources, and manage material nonpublic information appropriately. Those controls become more important as AI moves from copilots to agents that make decisions or take actions and must be explainable to users and regulators.

TECHNOLOGY

AI Investment Research — The guest sees public equities as a strong application for AI because relevant data is available. He argues that hedge funds can justify extensive agent-driven research when investors may pay $50,000 for one strong idea.

“And the reason you're able to do that is because investors are happy to pay $50,000 for one really good idea…”—

Systems-Driven Value — The guest predicts that within 10 years, leading investment firms and banks could derive 90% of their enterprise value from software, data, and systems rather than people. He says firms should capture employees’ expertise in systems they own and operate.

“In 10 years, the world's best investment firms, best banks will be have 90% of their enterprise value, not in people, but in software and data and systems…”—

Investment Workflows — The guest identifies integrating AI into the investment life cycle as a major challenge over the next five years. He compares the work ahead to Jane Street’s 15-year effort to build a dominant market-making and quantitative-trading franchise.

“And if you look at what happened to market making and quant trading, Jane Street took 15 years to build the dominant franchise…”—

MARKETS

Series A Rejections — The guest says that after two and a half years of building the company, 40 investors—including Sequoia, Kleiner, and Benchmark—passed on its Series A. He describes the fundraising process as emotionally difficult.

“We've been building for two and a half years and David introduced us to 40 40 investors and I met with everybody…”—

Finance Market Potential — The guest argues that investors underestimated finance’s total addressable market, partly because San Francisco investors were less familiar with the sector and had fewer venture-backed precedents.

“I think people underappreciated the TAM in finance, which was silly…”—

Intro

The host asks how Rogo has evolved as models improved; the guest traces its path from failed early attempts to reliable search and tools capable of junior finance work, crediting workflow details and usability.

Building Rogo

The guest describes emerging multi-agent research, Rogo’s dealmaking focus, and how agents support transaction preparation, diligence, and execution while connecting to firms’ systems of record.

10,000 AI Agents

The guest argues judgment and unique information gathering will matter to investors, while explaining that proprietary data, domain expertise, compliance, and auditability remain central to AI-enabled finance.

Skills That Still Matter

The guest says vertical AI firms can coexist with foundation-model companies by building finance-specific workflows, integrations, data rooms, transaction systems, and auditable infrastructure.

Beating OpenAI and Anthropic

The guest compares enterprise seat pricing with token-based models, anticipates a shift toward outcome-based pricing, and imagines AI making private transactions faster, more transparent, and more liquid.

Bloomberg of the AI Era

The guest says banks see individual productivity gains but must decide how to turn them into firm-wide growth, while insisting that explainability and audit trails are essential as AI takes action.

Rogo’s Company Brain

The guest describes Rogo’s recorded, searchable internal knowledge system, which helps employees retrieve company context and prepares teams for customer meetings.

Chewing Glass

The guest recounts the difficulty of scaling Rogo, the persistence needed through hiring and fundraising setbacks, and the aggressive plans required to win enterprise finance customers.

AI-Native Finance

The guest defines an AI-native finance firm as one willing to reinvent every workflow, encode employees’ knowledge into systems, and identify which advantages come from truly proprietary data or relationships.

What Humans Still Do Better

The guest says private-market automation depends on standardization, trust, and adoption; human relationships may persist in some sales, while other transactions could become increasingly automated.

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Important Disclaimers

Not Investment Advice: For education only — not financial, tax or legal advice.

AI-Generated: Made by AI from source transcripts and may contain errors.

No Guarantees: Past performance does not predict future results; investing carries risk.

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