How I Invest with David Weisburd

E417: The Mental Model That Built Citadel

E416: Why the World’s Biggest Investors Are All Investing in Data Centers

E415: Why Every VC Is Suddenly Investing in Defense

Defense technology has become a focal point for venture capital, driven by heightened global geopolitical competition and the proven success of companies like SpaceX, Palantir, and Anduril. This $2 trillion ecosystem is transitioning from legacy, capital-intensive "exquisite" systems toward asymmetric, software-defined...

E414: How LPs Evaluate GPs in the AI Era

Building a distinctive brand in the private capital market requires General Partners to move beyond generic, risk-averse communication toward authentic, differentiated messaging. In an era where LLMs and institutional investors prioritize third-party verified, authoritative content, GPs must cultivate a clear value pro...

E413: How AI Will Reinvent Venture Capital

AI-native venture capital firms fundamentally rethink operational processes by embedding AI agents at the core rather than merely layering tools over legacy workflows. Footwork, a firm operating with this model, utilizes agentic workflows to automate CRM updates, synthesize board meeting context, and provide proactive ...

E412: UPENN Endowment: Why AI Will Create a New Generation of PE & VC Firms

E411: How AI Is Creating a New Generation of Venture Firms

Venture capital requires a shift from traditional, manual processes toward AI-driven, data-centric decision-making. Andre Retterath, an investor at Earlybird, demonstrates how machine learning can automate redundant tasks, such as sourcing and screening, to allow investors to focus on high-level judgment. The industry’...

E410: How Relationships Built a $3.6B Venture Firm

E409: The Leadership Lessons That Built a $6.5 Billion Firm

Jason Koenig, founder of ITE, manages $6.5 billion in assets by targeting overlooked industrial sectors like railcar leasing. His strategy centers on identifying stable, cash-flow-positive assets that others ignore, leveraging a contrarian mindset developed during the post-financial crisis era. Koenig advocates for a "...

E408: HarbourVest: Why Venture Capital Is Chasing Trillion-Dollar Companies

Venture capital operates as a power law business where a tiny fraction of investments generates the overwhelming majority of portfolio returns. Success requires identifying "futurists" capable of spotting market-defining companies early, while maintaining the discipline to concentrate capital in high-conviction winners...

E407: Why Venture Capital is Becoming a Winner-Take All Market

Venture capital is evolving into a winner-take-all market where a tiny fraction of firms capture the vast majority of returns. Data indicates that fewer than 20 out of 3,000 U.S. firms have consistently generated 3x net returns over the last two decades, highlighting the extreme dispersion of success. This concentratio...

E406: Why AI Won't Transform Most Enterprises for 10 Years

Fortune 500 companies face a five-to-ten-year horizon for meaningful AI integration, hindered not by technological limitations but by complex organizational inertia, legacy tech stacks, and poorly documented tribal knowledge. Successful implementation requires top-down leadership involvement, where executives actively ...

E405: Why AI Has Made Venture Capital Harder (Not Easier)

AI has fundamentally altered the venture capital landscape by lowering startup barriers, enabling companies to launch overnight while simultaneously intensifying competition for early-stage investors. This shift necessitates a move away from consensus-driven growth metrics toward rigorous diligence focused on gross pro...

E404: Why This Billionaire Family Office Doesn't Rebalance Its Portfolio | Pincus Family CIO

Maximizing after-tax returns remains a critical yet neglected challenge for family offices due to complex entity structures, varying tax jurisdictions, and significant calculation difficulties. Scott Abookire, CIO of Pincus Capital Management, advocates for moving beyond traditional, arbitrary asset allocation models t...

E403: Why the Best Investment Firms Stay Small | Sound Point Capital Founder

Excess capital frequently compromises investment returns by forcing managers to deploy funds into marginal opportunities, making it essential to prioritize having more ideas than capital. Steve Ketchum, CEO of Sound Point Capital, emphasizes that maintaining discipline—such as self-imposing fund size caps—protects perf...

E402: $92B Coatue: Where the Value in AI Will Accrue

The central challenge in the AI landscape is determining who captures value as foundational models rapidly advance. While coding applications are increasingly tied to core model outputs, verticals requiring deep integration, compliance, and proprietary data—such as legal and finance—provide durable moats for independen...

E401: Einstein Was Wrong About What Actually Compounds

Relationships, reputation, and access to information serve as more potent compounding forces than financial capital alone. While compound interest is widely celebrated, the true drivers of long-term success are the compounding of brand and institutional knowledge. Exposure to excellence—often found in rigorous environm...

E400: Anthony Pompliano on Power Laws, Conviction, and Compounding

Power laws govern wealth creation, where 5% of inputs consistently drive 95% of outcomes. Achieving outsized returns requires identifying durable, asymmetric opportunities and maintaining the conviction to hold them for decades, as selling often proves more difficult than buying. True investment success stems from conc...

E399: How General Catalyst Finds Billion-Dollar Startups

Seed-stage investing serves as the foundational core of venture capital, providing unique access to generational founders and superior long-term returns. Large funds like General Catalyst maintain this early-stage focus by operating as generalists, prioritizing deep relationships over thematic sector bets. To mitigate ...

E398: Hamilton Lane ($1T AUA) on Venture Capital, AI, and Private Markets

Venture capital now constitutes 31% of private markets, necessitating a strategic shift for institutional investors who can no longer ignore this asset class. Miguel Luina, co-head of Global Venture Capital at Hamilton Lane, explains that while venture is historically high-risk, it is essential for capturing value from...