How a 24-Year LP Actually Diversifies a Private Portfolio | Jeremy Roll

Jeremy Roll has been a full-time limited partner (LP) for over 24 years and has lived entirely off his private-market cash flow since 2007. In this Vyzer Weekly conversation, he breaks down what diversification really means once you're investing in syndications, funds, and private deals, and why most investors get it wrong. Litan Yahav (co-founder of Vyzer) and co-host Mike go deep with Jeremy on: Why five deals with one operator isn't diversification Diversifying across asset class, geography, AND operator Cash flow vs. capital events: why a refi or sale gets reinvested, never spent Living off cash flow and the 2:1 (vs. 3:1) coverage ratio Fully-amortized deals (ATMs, equipment leasing) and the hidden trap of blended principal Funds vs. single-asset deals, and what that mix tells you about the cycle Reading blind-pool fund documents before you commit Position sizing: 2.5-5% per deal, ~10% per operator How Jeremy selects operators (background checks, meeting in person, 7+ deals per asset class) This is an educational conversation for LP investors. Nothing here is financial advice, and nothing is being sold. Jeremy is not a financial advisor and shares his perspective as a long-term investor. Learn more about tracking and underwriting your private investments at https://vyzer.co/start