Datadog, Inc.

“Datadog is a structurally exceptional business — widening moat, compounding multi-product flywheel, AI tailwind, and pristine FCF generation — but at 82x trailing FCF and 21x revenue near all-time highs, the current price offers market-rate expected returns (~10% CAGR) in the base case, meaning investors are paying for the upside tail rather than the central thesis. The business deserves a place on every long-term investor's watchlist; it does not deserve a buy at today's price. A 35-40% drawdown to the $130-$140 range would create a genuinely compelling entry.”