Jeremy Roll: What Diversification Actually Means for LPs

Jeremy Roll has been a full-time LP for 24+ years and has lived off his private-market cash flow since 2007. He joins Litan Yahav and Mike to unpack what diversification really means once you leave stocks and bonds behind. The big idea: spreading money across five deals with the same operator isn't diversification. Real risk-spreading happens across three axes at once, asset class, geography, and operator. In this episode: Why capital events (refis, sales) get reinvested, never treated as spendable cash flow The trap in fully-amortized deals like ATMs and equipment leasing Funds vs. single-asset deals, and what the mix reveals about where we are in the cycle Reading blind-pool fund docs before you wire Position limits and why proper private diversification takes 5-10 years How Jeremy vets operators, and where gold and Bitcoin fit An educational conversation between LPs. Not financial advice, and nothing is being sold.