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Webinar: Tax-Efficient Portfolio Architecture, Concentrated Position Strategies, and Liquidity Event Strategies
A client webinar covering tax-advantaged investment solutions for complex portfolios, including concentrated position risk, multi-asset allocations, and anticipated liquidity events.
The Madman Who Speaks the Truth
AI is beginning to disrupt the software industry it once powered. This letter examines how AI may be disrupting not just industries, but software itself, raising questions around valuation, competitive advantage, and the durability of long-term cash flows.
Policy as a Catalyst for Market Divergence
Tariffs, crypto regulation, energy policy, and AI are reshaping which companies win and lose. This letter looks at the growing role of policy and AI in driving market winners and losers, from tariffs and regulation to the rise of agentic AI and shifting currency dynamics.
The Policy-Driven Market Regime
Government policy is emerging as a primary driver of market outcomes, with deregulation, reshoring, and fiscal shifts shaping sector performance. This letter explores how alignment with policy priorities may matter more than traditional fundamentals, creating clear winners and losers across industries.
Alternative Investments In a Portfolio Context
Alternative investments are increasingly mainstream, but most investors lack a clear framework for using them. This piece outlines Chesapeake's approach: alternatives should serve as either return enhancers or true diversifiers.
Fool in the Shower
Consensus has shifted toward a soft landing, but the full impact of the Fed's rate hikes has yet to be felt. Using Milton Friedman's "fool in the shower" metaphor, this letter examines why the lag in monetary policy could still catch markets off guard.
Apothenia
Investors often rely on patterns that worked in the past - even when the environment has fundamentally changed. This letter examines the risks of applying a disinflation-era playbook to today’s economy, and why a new market regime may require a different investment framework.