David Calzaretta

I graduated from Indiana University in 1996 with my degree in accounting. I started out with my first deal in 1997 when I bought a 2 bedroom condo in Chicago in the Lake View neighborhood. I had a roommate that helped pay my mortgage. I lived there until 2003 when I sold my unit for almost double the purchase price. I used the proceeds to buy a 3-flat in the Little Italy neighborhood. I lived on the second floor and rented the other two, allowing me to cover my mortgage. I got married in 2005 and moved out to the suburbs, but held onto the building. I have never had a vacancy in 13 years. This property is a home run. I also own a 4-unit building in Grayslake, IL that I bought in 2007 at the peak of the market. This deal has not been as good. It is a long term hold if I want to get my money out of it, or it is a sell for a loss if I want to reduce my Advil bill. I am on the lookout for more property at this point. I am a successful musician and talent agent and want to prepare for my second act in life at age 42.