Take your roast and pat dry with paper towel. Preheat an enamel pot over medium-high heat. Drizzle olive oil into your pot. Place your roast into the hot pan, pressing down. Sear all sides. Remove from the pot and set aside.
Add your onion, garlic, celery, carrot, and half of your rosemary to the pot. Saute. Pour in red wine, scraping at the bottom of the pan. Once your pan is deglazed, add in crushed tomato, heirloom tomatoes, and a generous serving of salt and pepper. Place your beef back into the pan, coating completely in sauce.
Cover, and reduce heat to the lowest setting. Let simmer, checking on occasion.
Pour your flour into a bowl. Make a well in the center, and add your eggs and kosher salt. Stir from the center, adding more flour with each swirl. Once you have a loose dough, drop on to the counter and knead. Add the remainder of your rosemary to your dough, and continue kneading until smooth. Cover with plastic wrap, and set aside.
After approximately five hours, carefully remove the lid and shred your beef. Taste, and add additional salt and pepper if required.
Remove your pasta from the plastic wrap. Roll with a rolling pin, then move it to the pasta maker. Feed your dough through the pasta maker until thin. Slice with a knife into 1-inch pieces. Bring a large pot of salted water to a boil, and drop in. Fresh pasta only takes a couple of minutes to cook, so keep a close eye on it.
Strain your pasta and plate. Add a generous ladle of homemade ragu sauce. Garnish with fresh parmesan cheese and coarsely grated peppercorn.
Serve, alongside leftover Chianti!