One of my earliest manager meetings was with Jeremy Grantham in 1992. He made a compelling case that the bull market of the 1980s had run its course. Around the same time, I learned about Warren Buffett and considered buying Berkshire Hathaway stock. At $12,000 per share, BRK.A was beyond my means.

I assumed I was too late – the easy money had already been made. But in hindsight, I was standing at the starting line of one of history’s greatest bull markets.

Over the past four years, we’ve hosted Capital Allocators University (CAU) six times (our next cohort is July 7^th in NYC). In each session, I presented a slide titled, ‘The hardest day to invest is always today.’ And every time, new market conditions made that statement ring true.

Today is no exception. We face heightened uncertainty from tariffs, economic conditions, valuations, private market liquidity, and crowding in alternatives. Even leading macro strategists have begun to question the durability of U.S. exceptionalism on the Capital Allocators podcast.

When stocks, bonds, and alternatives appear unattractive, what’s an investor to do?

I’ve been thinking about bull and bear cases across asset classes.  None of these observations are earth-shattering, but collectively, they illustrate a complex investment landscape with few compelling opportunities.

U.S. equities boast strong, resilient mega-cap companies, a lagging cohort with catch-up potential, and implicit policy backstops from the Fed and Treasury. But they face headwinds from high valuations, rising government debt, and escalating economic and geopolitical risk. The familiar comfort of buying the dip no longer feels reliable.

International developed markets appear cheaper than the U.S., but contend with structural inefficiencies, political instability, and sluggish innovation. Broad exposure remains hard to justify outside of select markets like Japan.

Emerging market equities offer compelling valuations and promising long-term growth fueled by favorable demographics. Still, they remain vulnerable to political volatility, currency risk, and shifting support in a multi-polar world.

Private equity, especially in the middle-market, purports to offer higher long-term returns. However, constrained liquidity, lengthening holding periods, and valuation uncertainty make capital commitments less straightforward.

Private credit has become the alternative of choice. It offers attractive yields, shorter durations, and adaptability to a higher-rate environment. But massive inflows have compressed spreads, raised concerns around underwriting standards, and left questions about resilience in a tougher economy.

Venture capital benefits from relentless innovation, particularly in AI. Yet intense competition, limited access to top deals and managers, and constrained exit environments temper its appeal.

Real estate remains deeply unloved, despite potential tailwinds from housing shortages and a commercial recovery. Its absolute return prospects are modest, and uncertainties around work patterns and interest rates continue to cloud the picture.

Infrastructure, especially in high-demand areas like data centers, benefits from inelastic demand and government support. But like real estate, infra faces limited upside and lingering macro risk. In a tougher return environment, relative strength is insufficient to meet objectives.

So where do we turn? The most compelling risk-adjusted opportunities may lie in the most overlooked corners of the market: real estate, emerging market equities, and middle-market buyouts. (Though it’s hard to call any part of private equity ‘overlooked’).

Beyond that, opportunities lie in idiosyncratic niches and bottom-up concentration, both of which are capacity-constrained and demand exceptional skill and judgment.

Even so, this feels like one of those moments when the risk of something going wrong is just around the corner. Or maybe, as history has shown time and again, it’s a moment full of unexpected opportunities.

The only thing I know for sure is this: the hardest day to invest is always today.