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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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Christina Cacioppo - Building an Enduring Software Company in the Age of AI - [Invest Like the Best, EP.496]
→ WHAT IT COVERS Christina Cacioppo, founder of Vanta, a security and compliance platform serving 16,000 customers, discusses how the company evolved...
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This Week's Recap

1 episode · Oct 12 – Oct 18

Latest Insights

Key takeaways from recent episodes

Christina Cacioppo - Building an Enduring Software Company in the Age of AI - [Invest Like the Best, EP.496]

  • ✓**Data moat as competitive foundation:** Vanta built integrations with 400+ tools, creating a proprietary "trust graph" security data lake that powers automation and AI agents. This data foundation proved more durable than any feature advantage, enabling faster product development and making it structurally difficult for competitors to replicate the same breadth of security context.
  • ✓**Token pricing is a strategic trap:** Charging customers based on token consumption positions software companies in direct comparison against foundation models like Claude. Users quickly calculate the markup and question the value differential. Vanta's approach is to absorb token costs entirely, prioritize usage and deployment at scale across 25% of customers now, and revisit commercialization after achieving deep product adoption.

David Vélez - Building Nubank and the Future of Global Banking - [Invest Like the Best, EP.495]

  • ✓**Cost Structure Advantage:** Nubank serves 140 million customers with 10,000 employees while competitors need 100,000 employees and 6,000 branches for similar scale. This produces a cost-to-serve roughly 3% of traditional banks, enabling zero fees and higher yields. Companies entering financial services should quantify this structural gap before competing, as it determines how much value can realistically be returned to customers.
  • ✓**Three-Bucket Framework for Banking Disruption:** Vélez categorizes global banking problems as access, cost, and intelligence. Access: 3 billion people lack credit. Cost: US banks pay depositors 40 basis points on $15 trillion while rates sit at 4.5-5%, representing roughly $600 billion annually flowing to fund branches. Intelligence: AI can deliver private-banker-quality financial optimization to the bottom 99% of earners who currently receive no personalized guidance.

Andrew Huberman - The Frontier of Neurotechnology - [Invest Like the Best, EP.494]

  • ✓**Sleep shutdown protocol:** Falling asleep requires three simultaneous physiological shifts — quieting thoughts by moving attention to pure sensation rather than planning, slowing heart rate through extended exhales that activate the vagus nerve via respiratory sinus arrhythmia, and disrupting proprioception by slowly moving eyes side-to-side under closed lids. Combining all three creates the fastest path from high-arousal waking states to sleep onset without pharmacology.
  • ✓**Rocking frequency and REM amplification:** Beds oscillating at a specific measured frequency put adults to sleep faster by generating compensatory eye movements that disrupt the retina-brainstem-cerebellum proprioception circuit. An MIT-developed eye mask replicates this effect using mild stimulation behind the ears, directly measures REM sleep (unlike Whoop, Oura, or Eight Sleep), and amplifies REM duration once sleep begins — expected commercial release within seven to twelve months.

Noah Shinn - Building Instinct: The Personal Agent - [Invest Like the Best, EP.493]

  • ✓**Trust-building timeline:** Users require approximately three weeks to meaningfully trust an AI agent with sensitive data. At the three-week mark, 40% of Instinct's user base voluntarily shares a personal credit card. Once any single piece of sensitive information is connected, retention jumps to 80%. Founders building agent products should design onboarding around gradual trust accumulation rather than immediate data capture.
  • ✓**Business model alignment:** Agents monetized through advertising create a structural conflict — a smarter-than-user system can manipulate behavior against user interests. Instinct avoids this by charging merchants a transaction take rate (similar to Apple Pay or Shopify's 2.5–3%) rather than running ads. Founders should evaluate whether their revenue model incentivizes acting for users or against them before scaling.

Recent Episode Summaries

20 AI-powered summaries available

57 min episode3 min read

→ WHAT IT COVERS Christina Cacioppo, founder of Vanta, a security and compliance platform serving 16,000 customers, discusses how the company evolved from SOC 2 automation into a multi-product security platform, how AI agents are reshaping their product architecture, and the talent and pricing pressures facing software companies in the current AI era.

71 min episode3 min read

→ WHAT IT COVERS Nubank founder David Vélez explains why digital banking's disruption of incumbents is still in early innings, with fintech holding under 10% of a $10 trillion global market. He covers AI's role in democratizing financial intelligence, Nubank's expansion into the US and 35 countries via stablecoin accounts, and how the company rebuilt its organizational structure using AI workflows.

72 min episode3 min read

→ WHAT IT COVERS Andrew Huberman joins Patrick O'Shaughnessy to map the frontier of neurotechnology — from practical sleep protocols and waking brain state optimization to invasive neural interfaces, optogenetics, and genetic engineering. Huberman argues that Meta, OpenAI, Anthropic, and Neuralink are converging toward a single goal: non-invasive read-write access to the human brain.

86 min episode3 min read

→ WHAT IT COVERS Noah Shinn, founder of Instinct, describes building a personal AI agent that operates through existing communication channels — text, call, email — with no dedicated app. Growing at 10% daily with zero marketing spend, the platform processes over $1 billion annually in transaction volume on an invite-only user base, with 50% from travel alone.

64 min episode3 min read

→ WHAT IT COVERS Gabe Stengel, founder of Rogo, describes building an AI platform for capital markets that automates deal-making workflows across private equity, investment banking, and M&A. He covers the product's evolution through model generations, why private markets outpace public equities as an AI target, and how financial firms must restructure around AI over the next two to five years.

72 min episode3 min read

→ WHAT IT COVERS Michael Moritz, Sequoia Capital partner for 40 years, traces how his family's refugee history shaped his investing instincts, explains why the venture business of the 1980s and 90s is structurally unrepeatable today, and reflects on what endures across great leaders, institutions, and human character under pressure. → KEY INSIGHTS - **Early childhood imprinting:** The behavioral patterns absorbed before age 12-14 — not stories told, but daily reactions, emotional atmospheres,...

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.

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