TRCO
Tribune Media Co
stockNYSE

As someone who worked at a L/S hedge fund in NY, I can share a few, but I'll start with one. Buying anything purely on valuation or trailing financial metrics is a recipe for disaster. Tribune Media (legacy TRCO) was one where the sum of the parts included unrealized value from spectrum monetization and other media assets. Lots of moving pieces and assumptions about what those assets would eventually be worth. Lesson: Cheap stocks can always get cheaper. A 5x EBITDA business with declining fundamentals can be much more expensive than a 20x business that's growing. Other mistakes I think investors COULD be making right now: * **ADBE:** Thinking a historically great software business trading at a lower multiple is automatically cheap. What if AI permanently changes pricing power? * **ORCL:** Underestimating how much capital needs to be invested upfront before AI infrastructure contracts actually turn into free cash flow. * **WBD / PARA:** Betting on asset value and M&A while the underlying linear TV business continues to deteriorate. * **CVNA:** Assuming exceptional recent margins and growth represent normalized earnings rather than potentially favorable conditions that may not last. The biggest lesson is that the market doesn't care what a business was worth yesterday. It cares what the earnings power looks like tomorrow.