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Invest Like the Best with Patrick O'Shaughnessy
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Invest Like the Best with Patrick O'Shaughnessy

Hosted by Colossus | Investing & Business Podcasts

Invest Like the Best with Patrick O'Shaughnessy features conversations with the world's top investors and business leaders. Each episode explores investment frameworks, mental models, and business strategies from hedge fund managers, venture capitalists, and CEOs. Read AI summaries with the key investment insights from every episode.

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Walter Russell Mead - How America Keeps Winning - [Invest Like the Best, EP.490]
→ WHAT IT COVERS Historian Walter Russell Mead joins Patrick O'Shaughnessy to analyze American global power across 300 years, tracing the...
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This Week's Recap

1 episode · Aug 31 – Sep 6

Latest Insights

Key takeaways from recent episodes

Walter Russell Mead - How America Keeps Winning - [Invest Like the Best, EP.490]

  • **Maritime Power Formula (UP

Sarah Guo - What the 250 People Building AI Believe - [Invest Like the Best, EP.489]

  • **Technology-forward investing:** Rather than starting from customer problems alone, Conviction evaluates which workflows and professions structurally match current model capabilities. This led to early investment in Harvey, reasoning that law is fundamentally structured language requiring document retrieval and text generation—a direct fit for 2022-era models—before the thesis became consensus.
  • **Researcher disempowerment at scale:** A notable shift within the past 12 months shows frontier lab researchers increasingly believing either that their individual contributions are irrelevant or that compute scale alone determines outcomes. Both conclusions reduce personal ownership of results, creating a psychological dynamic that affects retention and motivation at the largest AI labs.

Neil Movva - Making AI 10x Cheaper - [Invest Like the Best, EP.488]

  • **Latency vs. Throughput Trade-off:** GPU hardware forces a fundamental choice between low latency and high throughput. Batching more users' work together maximizes GPU utilization but increases per-request wait time. Sail deliberately optimizes for throughput, accepting slower individual responses in exchange for dramatically lower cost per token — a viable strategy only when users aren't actively waiting on results.
  • **Scavenger Chip Strategy:** Rather than competing with Anthropic or OpenAI for Blackwell allocations, Sail buys underpriced chips from AMD, TPUs, Trainium, and emerging vendors like Etch or D-Matrix. Because other providers lack kernel expertise for non-NVIDIA architectures, Sail exploits the perception gap — treating "no bad chips, only bad pricing" as a core acquisition principle to build aggregate compute capacity.

Ben Thompson on Big Tech, China, and the AI Boom Running Out of Money - [Invest Like the Best, EP.487]

  • **AI Capital Stack Risk:** AI investment has burned through free cash flow, then debt markets, and now equity issuance — Google issuing equity being the signal. The next funding source is pension funds and insurance floats via vehicles like NVIDIA's $500B structure. If revenue doesn't scale fast enough to return to free cash flow funding, a railroad-era capital gap could trigger a significant blowup before AI's economic impact fully materializes.
  • **Inference Cost Stratification:** Treat AI inference costs as a spectrum, not a single number. A user asking basic recipe questions costs near zero to serve — comparable to loading a webpage. A researcher running extended reasoning tasks costs orders of magnitude more, as every additional second of compute is direct marginal cost. Microsoft's shift to usage-based enterprise pricing above $100/user/month reflects this reality and risks breaking the "thoughtless revenue" headcount-linked billing model.

Recent Episode Summaries

20 AI-powered summaries available

78 min episode3 min read

→ WHAT IT COVERS Historian Walter Russell Mead joins Patrick O'Shaughnessy to analyze American global power across 300 years, tracing the maritime-commercial strategy from Dutch United Provinces through Britain to the US, while examining how Trump, AI dominance, China rivalry, Taiwan, India's rise, and the information revolution are reshaping the international order in 2025.

59 min episode3 min read

→ WHAT IT COVERS Sarah Guo, founder of Conviction, discusses the beliefs and concerns of approximately 250 frontier AI researchers and entrepreneurs, covering compute independence, open source model policy, investment decision-making frameworks, and why regulatory barriers—not technical capability—represent the primary obstacle to US AI competitiveness.

78 min episode3 min read

→ WHAT IT COVERS Neil Movva, founder of Sail Research, explains how his "token factory" targets background AI agents running hours or days rather than real-time chatbots. By scavenging underpriced chips, tolerating 95% uptime data centers, and optimizing software kernels for throughput over latency, Sail aims to reduce inference costs by 10x or more. → KEY INSIGHTS - **Latency vs. Throughput Trade-off:** GPU hardware forces a fundamental choice between low latency and high throughput.

76 min episode3 min read

→ WHAT IT COVERS Ben Thompson joins Patrick O'Shaughnessy to analyze AI's geopolitical stakes, capital structure risks, and competitive dynamics across Big Tech. Thompson applies aggregation theory to the AI era, examines TSMC's capacity constraints, evaluates OpenAI, Anthropic, Meta, Google, and Amazon's strategic positions, and warns that AI investment may face a railroad-era capital gap before revenue catches up.

65 min episode3 min read

→ WHAT IT COVERS Benchmark partner Eric Vishria draws on a decade of software and hardware investing—including Fireworks AI, Sierra, and Cerebras—to map how AI infrastructure, enterprise adoption, robotics, and venture capital strategy are evolving, using cloud computing's trajectory as a historical lens for sizing today's AI opportunity. → KEY INSIGHTS - **AI Infrastructure Complexity:** Running large-scale AI models (2–4 trillion parameters) on identical open-source code and identical NVIDIA...

65 min episode3 min read

→ WHAT IT COVERS Gavin Baker and Patrick O'Shaughnessy analyze July 2025's AI market selloff, arguing that every quantitative demand metric — GPU spot pricing, token growth, hyperscaler operating cash flows — is accelerating, while the narratives driving the 40-60% drawdowns in AI stocks are largely factually incorrect, with credit risk being the sole legitimate concern.

53 min episode3 min read

→ WHAT IT COVERS Sam Altman, CEO of OpenAI, covers the company's strategic refocus on core AI infrastructure, the early compute acquisition bets that defined OpenAI's trajectory, the Hugging Face security incident, robotics timelines, the Jalapeno chip, and what abundant intelligence means for future generations and labor markets. → KEY INSIGHTS - **Strategic focus over diversification:** OpenAI spread across too many initiatives in 2024 because early revenue uncertainty pushed them toward...

55 min episode3 min read

→ WHAT IT COVERS Matthew Smith, founder of Cronometer Partners, presents well-level modeling of every US natural gas asset to argue that AI data center demand plus committed LNG exports totaling 35 BCF/day will exhaust US working gas storage by 2030, creating an unprecedented structural energy crisis with unbounded upside price risk. → KEY INSIGHTS - **Supply-Demand Gap:** US natural gas production can realistically grow to 128–132 BCF/day maximum, but committed LNG exports alone will reach 35...

50 min episode3 min read

→ WHAT IT COVERS John Kim, former General Catalyst fundraiser who helped build the firm into a multi-billion dollar operation and now leads capital formation at Lila Sciences, breaks down the mechanics of raising capital — covering trust-building frameworks, the three laws of fundraising, and how consensus moves large institutional pools of money. → KEY INSIGHTS - **Persuasion Formula:** Persuasion equals desire minus fear, where desire encompasses far more than financial greed — it includes...

75 min episode3 min read

→ WHAT IT COVERS Jeremy Giffon, investor and frequent collaborator with Patrick O'Shaughnessy, covers eighteen months of observations from hundreds of conversations with founders and capital allocators in private markets. Topics span cap table strategy, the rise of "poster class" influence over billionaires, SaaS structural decline, the shift from debt-driven to equity-driven finance culture, and how to evaluate emerging fund managers.

87 min episode3 min read

→ WHAT IT COVERS Etched founders Gavin Huberti and Rob Walken explain how they built a transformer-specific AI inference chip on the first tape-out attempt, raising $800M with over $1B in customer demand. They detail their low-voltage inference architecture, cluster-scale memory interconnects, and the vertical integration strategy behind their full rack-scale inference product launched in 2023.

69 min episode3 min read

→ WHAT IT COVERS Vlad Barbalat, CIO of Liberty Mutual Investments, explains how the firm deploys $120 billion in permanent insurance capital across private equity, direct lending, real estate, energy, and infrastructure. He covers the mutual insurance structure's investment advantages, portfolio construction philosophy, AI's impact on asset valuations, and how growing up in Soviet Moldova shaped his approach to risk-taking and capital allocation.

56 min episode3 min read

→ WHAT IT COVERS Kareem Amin, cofounder and CEO of Clay — a go-to-market software company valued at over $4 billion — shares the unconventional principles behind Clay's growth, including three core values (truth, justice, courage), risk-taking philosophy, and why creating from wholeness rather than lack produces better outcomes. → KEY INSIGHTS - **Three-decision framework:** Clay's entire company strategy flows from three core assumptions: give go-to-market teams the most powerful tool rather...

71 min episode3 min read

→ WHAT IT COVERS WhaleRock Capital founder Alex Sacerdote explains his three-part investment framework — S-curves, competitive advantage, and underappreciated earnings power — applied across AI infrastructure, foundational models, and enterprise software. He details his highest-conviction position in Anthropic at a $180B valuation, the decommoditization of hardware, and why enterprise software faces structural headwinds from AI disruption.

67 min episode3 min read

→ WHAT IT COVERS Uber CEO Dara Khosrowshahi outlines how Uber positions itself as the demand aggregator in an autonomous vehicle world, explains the company's path to $10B+ free cash flow, and details expansion into hotels, drones, and a super-app model built around 50 million Uber One members growing 50% annually. → KEY INSIGHTS - **AV Supply Aggregation:** Uber's competitive moat in autonomous vehicles is supply aggregation, not technology ownership.

63 min episode3 min read

→ WHAT IT COVERS Dan Loeb, founder of Third Point managing $25B across equities, credit, and insurance, reflects on 30 years of investing evolution — from event-driven deep value in 1995 to quality investing, thematic tech, and a $7B CLO business — while sharing his current conviction that AI-related semiconductors remain the most attractive sector despite the SOX index rising 40%.

46 min episode3 min read

→ WHAT IT COVERS Darren Farber, managing partner of Albion River defense investment firm, analyzes the Iranian military contingency, U.S. magazine depth deficiencies, China's structural illegitimacy, and what Congress must change in procurement law to enable neo-prime defense companies to scale and replace legacy prime contractors over the next decade.

76 min episode3 min read

→ WHAT IT COVERS Gavin Baker, CIO of Atreides Management, analyzes the two physical constraints shaping AI's next phase: power (Watts) and semiconductor manufacturing capacity (Wafers). He covers TSMC's role in preventing an AI bubble, orbital compute as a long-term power solution, GPU disaggregation extending hardware lifespans, and where economic value accrues across the AI stack.

76 min episode3 min read

→ WHAT IT COVERS Anthropic CFO Krishna Rao explains how the company manages compute as its core strategic resource, covering the allocation framework across training, internal use, and customer demand, the economics behind frontier model pricing, the $9B to $30B ARR growth in one quarter, and why enterprise returns to frontier intelligence continue accelerating rather than plateauing.

75 min episode3 min read

→ WHAT IT COVERS Airbnb cofounder Brian Chesky traces his path from industrial design training at RISD through the pandemic crisis that forced him into founder mode, explaining how those same principles now apply to AI-era company building, product market fit methodology, recruiting strategy, and shifting from adulation-driven to craft-driven motivation.

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