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Kane's One Beverly Hills asks condo buyers to lend at 5% through founder bonds that sit behind $2.8 billion senior and $1.5 billion mezzanine debt. If sales milestones slip, buyers could lose both the condo and the loan; the yield is now below Treasuries.
To manage increased risk in struggling companies, lenders are moving beyond simple repricing. They are creating novel hybrid capital instruments, like 'debt like PREF' or securities tied to EBITDA growth, which preserve debt protections while capturing equity-like upside for the lender.
Despite investor concerns about private credit, banks involved in the space feel reassured by their risk management strategy. They structure deals to be senior, are over-collateralized by hundreds or thousands of loans, and partner exclusively with established, prime sponsors, creating multiple layers of protection.
Unlike convertible notes, the SAFE (Simple Agreement for Future Equity) often lacks an expiration date or protective provisions. This loophole is reportedly being abused by some founders who take investment, fail to build, and then argue that SAFE holders aren't technically investors and are owed nothing.
High-yield returns on investment-grade private credit are not paid by the borrowing company on the entire loan. Lenders generate these returns by selling the low-risk senior debt and retaining a small, highly-levered 'first loss residual' tranche, which offers mid-teens returns for a credit-like risk profile.
To compete with top-tier firms, other VCs are using aggressive deal structures as a weapon. This includes offering huge secondary sales or other founder-friendly terms that might not be in the company's best long-term interest, simply as a tactic to win the deal at all costs.
The traditional two-tier credit market (investment grade and high-yield) has evolved. A new four-tier hierarchy of credit quality now exists: Investment Grade, High Yield, Leveraged Loans, and finally, Private Credit, which has absorbed the riskiest deals that cannot find financing in the other markets.
The saga of developer Harry Macklow defaulting on his own 432 Park Avenue condo highlights the use of "circular deals." He bought the unit with a loan from his partner, CIM Group, a non-arms-length transaction that can artificially inflate values and project market strength. The subsequent foreclosure reveals the inherent instability of such arrangements.
For underperforming companies, a gap often exists between the market-clearing leverage for senior debt (e.g., 5x EBITDA) and their current debt load. Specialized investors provide junior capital to fill this "two-turn problem" or "air bubble," facilitating a refinancing that senior lenders alone won't support.
For founders unable to get traditional loans, a viable alternative is offering high-interest (e.g., 15%) subordinated debt to angel investors. The best source for these investors can be existing, passionate B2B customers who believe in the product and want to be part of the success story.
Securitized consumer debt relies on asset quality, structure, and sponsor backing rather than purely underlying borrower health. Because senior structures are designed to absorb stress and sponsors frequently backstop troubled pools, senior tranches offer investment-grade safety without capital impairment even during consumer downturns.