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.

ReSeed highlights a key milestone: becoming "default alive," where management fees from existing assets cover the firm's operating costs. This financial self-sufficiency removes the pressure to deploy capital into subpar deals simply to generate fees, allowing for true long-term discipline.

Federal agencies are more reliable clients than state or local governments because they can print money to cover debts. State and local entities often have balanced budget requirements and can face shortfalls after disasters, risking non-payment on fulfilled contracts.

CoreWeave’s project debt is structured with a "box" system for maximum lender security. Customer payments flow into a controlled account where a waterfall automatically pays for operating expenses and lender debt (principal and interest) before CoreWeave itself receives any profit, minimizing lender risk.

A major hidden cost in carve-outs is vendor contract renegotiation, as change-of-control clauses can trigger price hikes. State Street mitigates this by stating in its LOI that the valuation assumes all third-party contracts remain at or near historical costs. This forces the issue early and protects the buyer's valuation model.

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.

Third-party contracts with change-of-control clauses are a major carve-out risk, as vendors may hike prices post-acquisition. To mitigate this, explicitly state in the Letter of Intent (LOI) that your valuation is based on the assumption that key contracts will renew at or near historical costs. This provides critical leverage for future negotiations or price adjustments.

To de-risk value-add projects, ReSeed funds acquisitions entirely with equity. This avoids the pressure and risk of debt service during unpredictable renovation and lease-up periods. They only introduce leverage once the asset is stabilized, which has a surprisingly minimal negative impact on the overall IRR.

A common operator pitfall is fixating on hitting pro forma rents, leading them to hold units vacant. ReSeed actively coaches its partners, reassuring them that the fund is aligned and prefers meeting the market to fill a perishable asset. The goal is maximizing cash flow, not hitting a spreadsheet number.