Backing independent sponsors on a deal-by-deal basis is more than an investment strategy; it is an extended due diligence process. This approach provides deep, real-time insights into a manager's problem-solving skills under pressure, offering transparency that is impossible to achieve before a Fund I commitment.

Top growth investors deliberately allocate more of their diligence effort to understanding and underwriting massive upside scenarios (10x+ returns) rather than concentrating on mitigating potential downside. The power-law nature of venture returns makes this a rational focus for generating exceptional performance.

Private credit allows investors to act like chefs—deeply involved from ingredient sourcing (diligence) to final creation (structuring). Liquid market investors are like food critics, limited to analyzing the finished product with restricted access to information, which increases risk.

Oaktree's co-CEO highlights a critical flaw in applying venture logic to debt. In a diversified equity portfolio, one huge winner can offset many failures. In a diversified debt portfolio, the winner only pays its coupon, which is grossly insufficient to cover the principal losses from the losers.

An expert reveals two shocking statistics: 80% of new founders fail their first diligence attempt, and 85% of early-stage investors don't perform confirmatory diligence. This highlights a massive, systemic weakness and inefficiency in the startup ecosystem, creating significant risk on both sides of the table.

A core discipline from risk arbitrage is to precisely understand and quantify the potential downside before investing. By knowing exactly 'why we're going to lose money' and what that loss looks like, investors can better set probabilities and make more disciplined, unemotional decisions.

PE deals, especially without a large fund, cannot tolerate zeros. This necessitates a rigorous focus on risk reduction and what could go wrong. This is the opposite of angel investing, where the strategy is to accept many failures in a portfolio to capture the massive upside of the 1-in-10 winner.

Meritech co-founder Paul Madera warns against relying on others for due diligence, even if the referral comes from a top-tier firm. Investors must personally understand the company's internal dynamics and its sector to make sound decisions. Outsourcing this fundamental work inevitably leads to bad investments.

A credit investor's true edge lies not in understanding a company's operations, but in mastering the right-hand side of the balance sheet. This includes legal structures, credit agreements, and bankruptcy processes. Private equity investors, who are owners, will always have superior knowledge of the business itself (the left-hand side).