All the time. Michael Kratsios, former Federal CTO, and prior close associate of Peter Thiel gives a contract to a Thiel portfolio company (Scale) for $92M while he's Federal CTO and also undersecretary of the DoD with a fairly opaque budget and procurement (something called a "broad agency announcement"). He retires as Federal CTO and surprise, he's now an executive at Scale. This is all in the open not even subject to innuendo or implication.