The mindset for underwriting a loan to hold for years is fundamentally different from one intended for quick syndication. It requires a higher level of seriousness and diligence, akin to vetting a long-term roommate versus offering someone a couch for one night.
In a non-control deal, an investor cannot fire management. Therefore, the primary diligence focus must shift from the business itself to the founder's character and the potential for a strong partnership, as this relationship is the ultimate determinant of success.
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.
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.
To write a billion-dollar check, a firm needs "dogmatic conviction." Thrive Capital achieves this through extremely long diligence and relationship-building periods, often spanning years. This deep familiarity, like their 10-year relationship with Stripe before a major investment, is the foundation for making huge, concentrated bets.
A compressed diligence process relies heavily on projections. A superior approach is building a relationship over 1-2 years, which allows an investor to witness the company's actual execution against its stated goals, providing far greater conviction than any financial model.
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.
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.
The rise of Liability Management Exercises (LMEs) has fundamentally changed credit analysis. Performing credit teams must now embed legal and workout specialists in the *front-end* underwriting process. This proactive approach is essential for assessing documentation and potential bad actors before an investment is made, rather than reacting during a restructuring.
By eliminating late fees and compounding interest, Affirm removes any financial upside from borrower mistakes. This forces the company's business model to depend solely on successful repayment, demanding superior, transaction-by-transaction underwriting to survive.
Unlike syndicated loans where repricing can be threatened easily by banks, direct loans have structural protections. Borrowers must find an entirely new lender and pay new fees to refinance, making it much harder to reprice debt downwards and thus preserving higher returns for investors.