Why buying and selling companies is a barbaric sport: how buyers price risk, what changes after the LOI, and how deal structure shares risk with the seller. Originally recorded with Ryan Tansom on his podcast (Ep. 231). ►EXECUTIVE SUMMARY 1) EVERYONE HAS SHARP ELBOWS: Buying and selling private companies is a barbaric sport, whether the other side shows it or not. Know who you're dealing with and what they want from the deal. 2) BUYERS PRICE RISK THROUGH PRICE AND TERMS: Concentration in customers, vendors or employees cuts value. Structure is how you share that risk with the seller instead of making them your enemy. 3) THE LOI IS THE START, NOT THE FINISH: What happens after the letter of intent decides the deal. Slow data from a seller is a signal. If something mathematical can't be explained, someone is lying. ► CHAPTERS 0:00 The reality of buying and selling companies 1:22 From engineering to private equity 5:42 Private equity vs family offices vs independent sponsors 8:49 Business valuation beyond the multiple 12:55 Why different buyers want different deals 26:40 The letter of intent and why prices shift in due diligence 38:52 Deal structure: balancing price and terms 57:27 How to spot deal-breaker red flags