Add the olive oil, onion, bell pepper, and garlic to a large skillet over medium heat. Sauté until the onion is translucent, which should take about 5 minutes.
Add the beef, salt, pepper, cumin, and chili powder to the mixture. Break up the beef with a wooden spoon. Cook and stir the combination until the beef is no longer pink, which should take about 15 minutes.
Add potatoes and tomatoes. Stir thoroughly to combine them into the mixture. Make sure the potatoes are completely submerged in liquid. Continue to cook the combination for 10 minutes, until the potatoes are cooked through.
Add olives, capers, and raisins. Stir them into the mixture until it's an even consistency.
Cook the picadillo for 5 more minutes.
Serve your picadillo over white rice and your choice of toppings