Unlike equity investors hunting for uncapped upside, debt lenders have a fixed return and are intolerant to losing principal. This forces them to be paranoid about downside risk and worst-case scenarios. Their diligence process is often more thorough and thoughtful, providing a different and rigorous lens on the business.

Contrary to the idea that all capital is good capital, elite founders strongly dislike SPVs. They want to know exactly who is on their cap table and view SPVs as a risky, obfuscated way to assemble capital that compromises control.

Anduril's COO highlights a dangerous trend of "wildcat" secondary market brokers selling access to company shares they don't possess. These deals often involve multiple layers of SPVs with hidden fees. He warns that many retail investors will discover their shares don't exist during a major IPO, leading to significant financial losses.

Complex, multi-layered SPVs used to sell private stock to smaller investors are creating massive hidden risks. With stacked fees and lack of transparency, a wave of litigation from aggrieved investors is inevitable when these companies IPO and the true, diluted returns are finally revealed.

In hot secondary markets, investors often buy shares in a Special Purpose Vehicle (SPV) that holds the stock (L1). These SPVs can be nested (L2, L3), moving the investor further from the actual asset and introducing hidden layers of fees and significant counterparty risk.

When considering debt, the most critical due diligence is not on deal terms but on the lender's character. Investigate how they have treated portfolio companies during challenging times. Partnering with a lender who will "blow you up" at the first sign of trouble is a catastrophic risk.

Many secondary market SPVs don't grant investors direct ownership of shares. Instead, an employee holds the stock in a separate entity and sells shares of that entity. This structure can allow the employee to sell the underlying stock without the SPV investors' consent, introducing a major risk.

Matt Grimm of Anduril highlights that many secondary share offerings are structured as "forward contracts," which he calls notoriously hard to settle and explicitly disallowed by his company's bylaws. This means investors in such SPVs face extreme counterparty risk and may never actually take possession of the shares.

Prompted by a viral post about brokering profits, AI companies are publicly reasserting stock transfer restrictions. They warn that unapproved sales are void, creating massive legal and financial risk for buyers and sellers who used Special Purpose Vehicles (SPVs) or other workarounds to trade shares on secondary markets.