Deal Diary: 9 Years, 39 Doors, and $20K a Month in Cash Flow—Here’s How Jefferson Simmons Built His Portfolio

Name Jefferson Simmons Location Manhattan, Kansas Occupation Full-time real estate investor (former underwriter, Realtor, and university fundraiser) Assets 17 properties, 39 doors, $20,000/month in cash flow Investment strategy Single-family and small multifamily buy-and-hold, BRRRR-style renovation, creative seller, and private financing Financing Parental co-sign, family JV equity, private money line of credit, seller financing Jefferson Simmons was 20 years old and about to be homeless. His entire fraternity house was getting renovated, and every rental in town wanted nothing to do with a group of college guys. On a whim, he flipped a Zillow toggle from rent to buy and found a mismarketed three-bedroom house that was actually a 2,700-square-foot property with three extra rooms in the basement. He pitched his parents to co-sign, negotiated the seller down seven rounds to $178,000, and moved his fraternity brothers into the basement. Nine years later, he’s walked away from law school, built partnerships with an uncle and a private investor, and grown that first accidental deal into 17 properties and 39 doors. Here’s how he built it. You were a sophomore in college, with no income ...