Kevin Grossman: Lending to the Next Inflection Point

In this episode of the Credit Bubble, I sit down with Kevin Grossman, Partner at Decathlon Capital Partners. Kevin's banking career began at Silicon Valley Bank in 1999, on the asset-based lending and factoring desk, and it wasn't long before he was leading a tech deal team out of Boulder. From there he moved to Hercules during its go-go days, spent a stretch in leveraged lending at White Oak, and eventually found his way to Decathlon. We dig into Decathlon's core idea, which is non-dilutive term capital built to help a company reach its next value inflection point. Instead of raising equity too early, a founder can use the loan to bridge to a milestone they can already see, and hold onto more ownership along the way. Kevin explains why that works across software, healthcare services, and branded food and beverage. From there we get into what borrowers tend to get wrong, why leverage cuts both ways, and where AI actually helps the underwriting process.