Salt the meat well.
Heat the olive oil over medium heat in a heavy bottom pan and start to brown the beef in small batches, being careful not to overcrowd the pan. Remove and set aside until all the meat is browned. If the bottom of the pan looks like it’s getting a bit burnt, that is ok - those dark bits are flavor! Add more olive oil if need be.
Smash the garlic with the back of your kitchen knife to release its aroma.
Return the meat with its juices to the pot and add the garlic and pepper, scraping the bottom of the pan to incorporate the crusted bits into the stew.
Add the red wine and bring to a simmer.
Gently simmer over very low heat, covered, for at least 2.5 hours and up to 3 hours, checking occasionally that the wine has not evaporated and that the meat is not drying out. If so, add a bit of water and continue to cook until the meat is extremely tender but just shy of falling apart. Taste for salt and add if need be.
Remove the meat with a slotted spoon and set aside.
Simmer the sauce for another 25-40 minutes or so over medium-low heat without the lid, allowing the liquid to reduce into a thick and silky sauce (it should be reduced by at least half but even more if you want less sauce).
Remove the garlic pieces if it hasn’t dissolved.
Serve piping hot with crusty bread, preferably Tuscan bread if you want to be truly authentic.