Shlomo Chopp: Complexity is the opportunity. Binary thinking is the trap.

On this episode, Kevin chats with Shlomo Chopp, the Managing Partner of CASE, a distressed commercial real estate advisory and investment firm that runs about 90% advisory work and a small, highly selective book of opportunistic investments. Shlomo and his team are currently working on roughly 20 loans totaling more than $2 billion of debt, and he comes out of a family office with over 35 years of experience owning and operating about 70 properties across the country. He's a college dropout with no formal finance training who taught himself structured finance by cracking open CMBS loan documents during the 2010 downturn, and has since invested in, structured, or advised on nearly $5 billion of commercial real estate. His role is fundamentally one of translation, bridging the gap between the language of the operator and the language of the lender. The conversation covers why complexity is where the opportunity lives, why binary thinking is the trap most owners fall into, how to argue the inputs rather than the outputs in a workout, and the rolling consequences of not reading your loan documents.