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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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Latest episode
Alex Sacerdote - How to Invest Through Technology Cycles - [Invest Like the Best, EP.477]
→ WHAT IT COVERS WhaleRock Capital founder Alex Sacerdote explains his three-part investment framework — S-curves, competitive advantage, and...
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This Week's Recap

1 episode · Jun 1 – Jun 7

Latest Insights

Key takeaways from recent episodes

Alex Sacerdote - How to Invest Through Technology Cycles - [Invest Like the Best, EP.477]

  • **S-Curve Timing Framework:** Technology adoption follows a predictable flat-then-vertical pattern. Barriers must be eliminated before the "tornado of demand" triggers. iPhone needed touch screen, 3G, and sub-$200 pricing simultaneously. Investors can miss the first 100% gain and still profit enormously if the S-curve top is large enough — AWS reached $600B TAM from near-zero penetration over a decade.
  • **AI Penetration Baseline:** Sundar Pichai estimated only 10 basis points of global knowledge workers currently use AI in a meaningful, agentic way. Anthropic has roughly 14–15 million DAUs, but few use it deeply. Sacerdote projects penetration rising from 10bps to 2–5% within four years, calling the trajectory an "L-curve" — essentially vertical — rather than a traditional S-curve.

Dara Khosrowshahi - Uber's Bet on AVs, AI, and Building a Super-App - [Invest Like the Best, EP.476]

  • **AV Supply Aggregation:** Uber's competitive moat in autonomous vehicles is supply aggregation, not technology ownership. With 30+ AV partnerships including Waymo, Nuro, WeRide, and Pony.ai, Uber provides go-to-market infrastructure — depot securing, EV/AV financing via a $1B Santander facility, insurance, and instant demand. AVs on Uber's network run 30%+ more trips per vehicle per day than single-operator deployments, directly improving partner ROI.
  • **AI Budget Reality:** Uber burned through its entire annual AI budget in a single quarter, forcing a recalibration. The framework that emerged: use expensive frontier models (OpenAI, Anthropic) for exploration and new interaction design, then migrate scaled experiences to cheaper or open-source models. Engineers in India are producing 10x previous code commit volumes using autonomous agents, making headcount growth slower than output growth.

Dan Loeb - Lessons from 30 Years of Investing - [Invest Like the Best, EP.475]

  • **Event-Driven Foundation:** Joel Greenblatt's *You Can Be a Stock Market Genius* remains the foundational text for identifying mispriced securities created through spin-offs, demutualizations, and post-reorganization equities. The core edge: newly created securities face forced selling from mismatched institutional holders, management teams sandbag earnings to set favorable incentive packages, and underlying operations are sub-optimized within larger conglomerates — creating a repeatable, structural mispricing pattern that still exists in sub-$2B market cap companies today.
  • **AI Stack Mental Model:** Structure AI investment analysis using Jensen Huang's layered framework: power and energy at the base, then chips and infrastructure, then large language models, then software and applications. Loeb narrows focus further to three pivotal entities — NVIDIA, Anthropic, and Elon Musk's collective companies — as prisms through which to evaluate capital flows and competitive positioning across the entire ecosystem rather than analyzing individual companies in isolation.

Darren Farber on Iran, China, and the Rise of Neoprimes - [Invest Like the Best, EP.474]

  • **Winning Definition in Iran:** Define political victory narrowly and precisely before engaging: a reopened Strait of Hormuz plus degraded Iranian military capacity that cannot reconstitute quickly through oil revenues constitutes a win. Without that pre-defined target, democratic societies lose political will, congressional support, and executive authority mid-conflict, making any outcome strategically ambiguous.
  • **Magazine Depth vs. Nuclear Deterrence:** The Taylor flexible-power model and Eisenhower massive-retaliation model both remain necessary. Tomahawks, HIMARS, and 155mm artillery rounds require multiyear procurement contracts — which Congress has never previously authorized for ordnance — to build stockpiles sufficient to deter small incursions without triggering nuclear escalation thresholds in bilateral defense agreements with nations like the Philippines.

Recent Episode Summaries

20 AI-powered summaries available

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.

66 min episode3 min read

→ WHAT IT COVERS Paul Tudor Jones reflects on 50 years of macro trading with Patrick O'Shaughnessy, covering the structural differences between trading and investing, current equity market overvaluation at 252% of GDP, AI safety risks, the mechanics of identifying major market moves, and how kindness and philanthropy shape a meaningful life beyond markets. → KEY INSIGHTS - **Trading vs. Investing Identity:** Jones envies long-term investors like Buffett but acknowledges his fund maintains a -0.

45 min episode3 min read

→ WHAT IT COVERS Dylan Patel of Semianalysis details how AI token demand is growing faster than infrastructure can supply it, using Semianalysis's own spending trajectory from tens of thousands to $7M annually as a case study, while mapping semiconductor bottlenecks in memory, logic, and fab equipment that constrain scaling through 2028. → KEY INSIGHTS - **Token spend as competitive moat:** Enterprise AI contracts with Anthropic now include rate limit increases as a strategic asset.

92 min episode3 min read

→ WHAT IT COVERS Biotech investor Alex Karnal outlines a five-layer "health stack" framework covering lipid optimization, cardiometabolic health, neurocognitive health, inflammation, and blood pressure. He argues that existing medicines — GLP-1 agonists, PCSK9 inhibitors, and anti-amyloid therapies — can already extend human lifespan by a decade if deployed proactively, and that AI-driven drug discovery will compress development timelines from years to months.

75 min episode3 min read

→ WHAT IT COVERS Scott Nolan — SpaceX early engineer, Founders Fund investor for 12+ years — explains his framework for identifying underappreciated problems, the contrarian investment philosophy behind Founders Fund's biggest wins, and why he left investing to build General Matter, a startup rebuilding US uranium enrichment capacity that vanished entirely after the 1990s.

62 min episode3 min read

→ WHAT IT COVERS Alan Waxman of Sixth Street traces the U.S. financial system through three regulatory eras—Glass-Steagall (1933), its 1999 repeal, and post-2008 Basel III reforms—to explain how private credit grew from $500B to $2T, why the "factory model" of capital raising now dominates, and what asset-liability mismatches mean for markets today. → KEY INSIGHTS - **Three-System Framework:** U.S.

66 min episode3 min read

→ WHAT IT COVERS Sergey Levine, cofounder of Physical Intelligence, explains why building general-purpose robotic foundation models — systems that control any robot for any task — is more tractable than narrow domain-specific approaches, drawing direct parallels to how large language models outcompeted specialized NLP systems by leveraging broad, weakly-labeled data at scale.

54 min episode3 min read

→ WHAT IT COVERS Mitchell Green, founder of LeadEdge Capital, details the systematic investment machine he built over 15 years with partners Brian and Nima — covering their 9,000 annual cold calls, eight-point company criteria, LP network of 800 executives, and disciplined focus on 2–2.25x net returns across 20-position funds. → KEY INSIGHTS - **LP Network as Competitive Moat:** LeadEdge's 800 LPs are 95% senior executives and entrepreneurs — not institutions — deployed across the full...

70 min episode3 min read

→ WHAT IT COVERS William Hockey, founder of Column (a software company that owns a bank), explains how he built a profitable, self-funded fintech infrastructure business serving Ramp, Brex, Mercury, and Wise. He covers bootstrapping versus venture capital, the dollar's role in global trade and national security, emerging market innovation, and why founders need more skin in the game.

81 min episode3 min read

→ WHAT IT COVERS Palantir CTO Shyam Sankar connects US military history's "heretics" — unconventional builders like Hyman Rickover and Andrew Higgins — to modern defense tech, forward deployed engineering, and the urgent need to rebuild America's industrial base before AI-era great power competition with China reaches a critical inflection point. → KEY INSIGHTS - **Talent Unlocking via Superpower/Kryptonite Framework:** Identify employees' superpowers as effortless, almost unrewarding...

75 min episode3 min read

→ WHAT IT COVERS John Arnold — legendary natural gas trader turned philanthropist — covers China's manufacturing dominance, the US energy system's structural constraints, and systemic failures across healthcare, criminal justice, education, and journalism. Arnold applies the same analytical framework he used building Centaurus Energy to diagnosing why America's core institutions underperform and where leverage points exist for reform.

75 min episode3 min read

→ WHAT IT COVERS D1 Capital founder Dan Sundheim covers his simultaneous public and private market investing approach, with major positions in SpaceX, OpenAI, and Anthropic. He analyzes LLM business models through Netflix/Spotify frameworks, explains why hyperscalers face structural deterioration, addresses the GameStop crisis of early 2021, and identifies Taiwan semiconductor concentration as the single largest tail risk facing the global economy.

63 min episode3 min read

→ WHAT IT COVERS Josh Kushner, founder of Thrive Capital managing $50 billion, explains his concentrated investment strategy behind iconic deals including Instagram, Stripe, GitHub, and OpenAI. He details how Thrive maintains a deliberately small team, writes billion-dollar checks at unconventional stages, and builds competitive advantage through deep founder partnerships and a new holdings business applying AI to transform traditional companies.

95 min episode3 min read

→ WHAT IT COVERS Alex Behring and Daniel Schwartz, co-managing partners of 3G Capital, explain their distinctive investment model: raising capital to make one investment per fund, deploying significant personal capital alongside partners, and operating as CEOs rather than traditional investors. They detail iconic deals including Burger King, Tim Hortons, Hunter Douglas, and Skechers, emphasizing business quality, operator mindset, and developing young talent with real ownership stakes.

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