Use 4 (16-ounce) or larger wine glasses or snifters (note that the idea of a trifle is to see the layers). Dissolve gelatin and sugar in boiling water. Add cold water. Cover and set aside at room temperature.
For creme anglaise:
Pour the milk and heavy cream into a heavy bottomed sauce pot and scrape the seeds from the vanilla bean into the pot (or add vanilla extract). (If using a vanilla bean, put the vanilla pod in the pot as well.)
Add half the sugar to the pot and bring to a simmer (just below a boil). In a small bowl whisk together the egg yolks and the rest of the sugar and temper it by adding a small amount of the heated milk mixture to the bowl while whisking constantly (known as a liaison).
Now pour the liaison (egg mixture) into the milk pot, stirring constantly. You are only heating it. Do not boil. Do not cook. The idea of a liaison is to incorporate the eggs and avoid making them into scrambled eggs!
You want the mixture to begin to thicken so it will coat the back of a spoon. Remove from heat and allow to cool, then remove vanilla pod and discard and refrigerate until chilled.
Spoon fruit into each glass as a base layer. Follow with a layer of cubed pound cake, then a layer of strawberries. Spoon about 1/3 cup gelatin on top of the fruit and refrigerate for 2 to 4 hours until the gelatin is set.
Spoon crème anglaise over the chilled trifle, spoon whipped cream on top to finish, and top with shaved chocolate.