 He became a real estate broker at the age of 21 and was a home builder for 18 years.In 2015 Caballero became the first real estate professional to exceed $1 billion in home sales in a single year.Caballero was ranked as the top individual U.S. real estate agent in 2018 for total transaction dollar volume and total number of real estate sales transactions by REAL Trends as published in "The Wall Street Journal".