76. How House Hacking And Partnerships Built A Chicago Portfolio With Hart Turner

Send us Fan MailHart Turner joins us to tell the full story: 15 years as an actor in LA, a hard reset on money and career, and then an 18-month sprint that turns into three Chicago multifamily properties. Along the way, we connect the dots between endurance mindset (yes, he finished the Hawaii Ironman) and the day-to-day reality of underwriting, leasing, and staying calm when the deal goes sideways. We get specific about Chicago house hacking with 5% down, why BiggerPockets can be the gateway but local meetups create real acceleration, and what it looks like to buy in Humboldt Park when inventory is tight and interest rates are unforgiving. Hart walks through his first REO purchase and a five-month closing delay, the DSCR-funded second deal with a partner, and the midterm rental experiment that turned into an expensive lesson about seasonality and unit mix. Then comes the curveball every investor fears: a lender decides a key partner can’t qualify after you’re already under contract. We unpack how Hart pivots to a new partner, improves the financing, and still closes on a four-unit graystone after negotiating a rare $50,000 credit in a multiple-offer situation. If you’re trying to start late, scale with partnerships, or simply avoid rookie mistakes in multifamily investing, this one is packed with real numbers and real decisions. Hart Turner Bio: After beginning his real estate investing journey in 2024, Hart quickly focused on small multifamily acquisitions and house hacking. In just 18 months, he has built a portfolio of three multifamily properties (all Greystones!) totaling nine units, and all located in the Humboldt Park neighborhood. He currently lives in and manages a four-unit property that serves as his second house hack.In addition to his direct ownership portfolio, Hart invests passively in larger Chicago-based apartment syndications through his self-directed IRA, giving him experience with both active and passive real estate investing.Outside of investing, Hart works as an apartment locator specializing in downtown Chicago high-rises and luxury apartment communities, helping renters navigate the city’s most competitive rental markets. When he’s not working on deals or helping clients find their next home, you can usually find him on a pickleball court working on his game.Find Hart on Instagram: @hartturner and TikTok: @hartturner