EP 005 | Jerry Garrison: Madisonville, Margins, and 20 Years of Cincinnati Investing

What does it take to survive a real estate crash, rebuild from scratch, and come out the other side with a thriving portfolio? Jerry Garrison has done exactly that, and he's here to share every lesson.With two decades of experience as both an agent and investor in Greater Cincinnati, Jerry has seen these neighborhoods transform firsthand, from distressed and overlooked to some of the most sought-after zip codes in the city. In this episode, Jerry breaks down the arc of his investing journey, from a high-flying pre-2008 multifamily run that nearly broke him, to a disciplined single-family strategy centered on margins, geography, and repeat execution.We dig deep into the neighborhoods shaping Cincinnati real estate in 2026, including Madisonville, Fairfax, Evanston, Newport, and Northern Kentucky, and what strategies are actually working right now.In this episode:Whether you're new to Cincinnati real estate or looking to sharpen your strategy, Jerry's journey is a masterclass in resilience, market knowledge, and the power of showing up in the same neighborhood long enough for the deals to find you.🎙 Guest: Jerry Garrison, veteran Cincinnati realtor, investor, and house flipper with 20+ years in the market🏙 Topics: Surviving the 2008 crash · Single family buy and hold · Fix and flip margins · Fairfax neighborhood · Madisonville 2026 · Newport & Northern Kentucky · New construction on tight lots · Hyperlocal investing strategy00:00 - Introduction: Jerry Garrison's Cincinnati Real Estate Journey01:45 - From Corporate Life to Property Management & Real Estate Sales03:30 - 2008 Crash Survival: Lessons from Losing 100 Units06:15 - Transitioning from Multifamily to Single Family Investing08:00 - Why Geographic Focus Maximizes Real Estate Profits09:30 - Fairfax, Ohio: Hidden Gem Near Mariemont School District12:00 - Roof Pop Strategy: Turning 2/1s into 4/2.5s for Profit14:15 - Madisonville Buy & Hold: From $1,000 to $2,000+ Monthly Rent17:00 - Madisonville 2026: Value-Add Plays & Rising Property Taxes19:30 - Fairfax 2026: New Construction & Townhouse Style Builds22:45 - Crossing the River: Flipping Houses in Newport, Kentucky25:30 - Northern Kentucky vs. Cincinnati: Costs, Contractors & Taxes28:00 - Old Milford & Greater Cincinnati Real Estate Opportunities31:00 - Advice for New Investors in Cincinnati in 202634:30 - Cincinnati Hidden Gems: Little Miami River & City LifeThe Cincinnati Real Estate Investing Show is hosted by Slocomb Reed and Ian Cruz. New episodes every week. Subscribe, leave a five-star review, and share with a fellow investor.