Pre-heat a large skillet or a Dutch oven over medium heat.
Lightly season the meat with salt and pepper.
Pour three teaspoons of olive oil into the heated pan and begin browning the meat. Do not sear.
Lightly brown, about 1-2 minutes per side. If using a Dutch oven, brown the meat in batches to prevent crowding.
Transfer the browned meat into a bowl and reserve.
Add two more teaspoons of olive oil to the pan, then add the onion and garlic. Stir and sauté, trying to deglaze the pan as much as possible. Cook just until lightly softened and aromatic.
Add the ketchup and the tomato paste and stir to distribute.
Then add the browned meat, the Worcestershire sauce, cognac, and mushrooms. Stir to coat evenly.
Add the heavy cream. Season with salt and pepper to taste. Then cook for an additional 10-15 minutes to heat the cream through, slightly reduce and thicken, and to allow the sauce to take on a rich, rust color.