MEET THE COACH
About Jonathan Fleming
Principal, Openworld Properties
Founder, CoachingLandlords.com
California Licensed Real Estate Broker
I'm Jonathan Fleming — a hands-on real estate professional, Principal of Openworld Properties, and licensed California Real Estate Broker. I lead a high-performing team that delivers cash flow–oriented results for property owners in both residential and commercial markets.
I founded CoachingLandlords.com to bring professional guidance to independent landlords who want to operate smarter, avoid costly mistakes, and maximize their returns with confidence.
Real-World Experience You Can Trust
My expertise comes from years of on-the-ground experience in East Oakland. I’ve handled illegal squatters, court-driven evictions, lease enforcement, tenant negotiations, and housing compliance — personally and directly.
I’ve coached landlords through tough situations and helped them regain control of their properties while staying legally sound and financially protected. If you’re facing complex rental challenges, I’ve probably seen it — and solved it.
Expert Guidance Across the Board
I specialize in Section 8 and affordable housing programs, offering support with inspections, rent determinations, and compliance while protecting owner profitability.
I also advise investors by analyzing rental property deals — helping assess tenant profiles, rent control risks, zoning, and long-term income potential.
Whether you're self-managing or working with a property manager, I’ll help you make informed, strategic decisions every step of the way.
Why Work With Us?
Straightforward Support
No fluff. Just clear, actionable advice.
Landlord-Focused
Every service is designed for independent rental owners.
Flexible Options
From one-time calls to annual plans, we meet you where you are.
Our Mission
To empower landlords to self-manage smarter—by providing tools, templates, and expert guidance without the overwhelm.
Not sure which service is right?
We’re here to help you choose confidently.
Email us at info@coachinglandlords.com to figure out which plan is the best fit for your rental situation.