How This Real Estate Investor Built a $2.3M Business in One Year | Ramond Harris II

Some of the best real estate and business conversations happen in the hallways of the Midwest Real Estate Investor Conference, and every year since 2019 we sit down with our good friend Ramond Harris II to see what he's built since we last talked. This year Ramond walks through the full pivot from running a $3.6 million FedEx Ground operation to buying and rebuilding a commercial painting business serving apartment developers across Metro Detroit. It's an honest, unscripted look at what it actually takes to turn a struggling acquisition around, why margin beats revenue, and where a hustling operator still bleeds money when the bookkeeping can't keep up with the growth. Justin Workman joins to press Ramond on the numbers and hand him a few fixes he can use Monday morning. About Ramond Harris II Ramond Harris II is a Detroit-based operator and real estate investor. He grew a FedEx Ground route business from roughly $450,000 in revenue and four trucks into a $3.6 million operation with 36 delivery vans and 54 employees before exiting at the end of 2024. He now owns a 24-year-old commercial painting company focused on apartment new construction and repaints, and he continues to run rental property and fix-and-flip projects. What We Cover in This Episode Why Ramond exited a $3.6 million FedEx Ground business and what he kept from it Buying an established 24-year-old commercial painting company instead of starting from scratch The 12 to 18 month bid-to-start cycle that left the paint company dry for a full year How 48 bids in 2025 turned into $1.4 million in Q1 2026 contracts and a $4 million goal Networking into big general contractors like Sachse, O'Brien, Ronish, and Paragon Using Section 3 and Minority Business Enterprise (MBE) status to win work and protect margin Why the painting business has better margins and fewer headaches than logistics Niching down to apartment buildings only: new construction and repaints The Higginbotham Project, a 100-unit Detroit school-to-apartments conversion Using fix and flips as bread-and-butter cash flow to survive the dry year (resiliency in practice) Leadership on the job site: staffing cutters, rollers, sprayers, and preppers The bookkeeping and job-costing gaps that come with fast growth, and how to close them Why the leftover trucks keep costing money and the case for cutting the loss How Detroit property taxes uncapped on his rentals and doubled his assessment How Ramond uses ChatGPT for blueprints, invoices, loan packages, and decision-making Key Insight A year ago at this same conference, Ramond had just bought a painting company and had no work, because the prior owner had stopped bidding and paint jobs run on a 12 to 18 month clock. Instead of panicking, he went back to his bread and butter, ran four flips to keep cash moving, and put in 48 bids. By the first quarter of 2026 he had signed $1.4 million in contracts, with another $900,000 in the second quarter and a real shot at a $4 million year. The comeback wasn't luck. It was pricing discipline, relentless bidding, and using his Section 3 and MBE status to get in the door. Why This Episode Matters If you run a small business or a real estate portfolio, Ramond's story is a live example of two things that decide whether operators survive: staying resilient when a bet isn't paying off yet, and being honest about where you're still losing money. The episode is worth it for the on-air diagnosis alone, watching a growing operator get called out on his bookkeeping, his job costing, and the trucks he still hasn't sold, and walk away with fixes he can put to work immediately. Find Out More VR Quality Painting Instagram: @harrisfamilycontracting Instagram: @mrplayoffensedaily Facebook Sponsors Today's episode is brought to you by Green Property Management, managing everything from single family homes to apartment complexes in the West Michigan area. https://www.livegreenlocal.com And RCB & Associates, helping Michigan-based real estate investors and small business owners navigate the complex world of health insurance and Medicare benefits. https://www.rcbassociatesllc.com