Are you a frustrated landlord?

Maybe you own a few rental properties and expected passive income… but instead you got late-night maintenance calls, tenant issues, repairs, and endless property management headaches.

In this episode, Dave sits down with Jon Chan, who experienced exactly that — and then completely changed his real estate strategy.

Jon shares how he went from owning multiple single-family rentals across several states to stepping away from being a landlord entirely and building a more passive income stream through private lending and raising capital.

• How Jon started with house hacking in 2017

• Why owning more properties actually created more work, not freedom

• The hidden costs and stress of managing rentals across multiple markets

• Why he sold off his portfolio — even though it was cash-flowing

• How he helped his mom retire using real estate income

• A safer way to invest in real estate without tenants or toilets

• Why relationships and education beat sales skills when raising capital

• Jon’s plan to scale to $10 million in loans

Jon’s investing journey started with a simple idea: reduce his living expenses.

In 2017, he purchased a large home with a separate basement apartment and rented it out. The rental income covered a big portion of the mortgage — a classic house hacking strategy.

Encouraged by success, Jon scaled quickly using the BRRRR method and bought properties in:

• Huntsville, Alabama

• Chattanooga, Tennessee

• Baltimore, Maryland

• Akron, Ohio

The numbers looked great on paper — but reality was different.

Each market had different:

• licensing requirements

• tax rules

• permits

• management challenges

Soon, the administrative workload became overwhelming.

Even though the properties technically cash-flowed, maintenance expenses, repairs, and management responsibilities consumed his time and energy.

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Are you a business owner, executive, or professional in the DMV with a story worth sharing? We’d love to shine a spotlight on you.

DMVSpotlightShow.com/Guest

Hosted by Jon Chan, the DMV Spotlight Podcast features real conversations with business owners, executives, and professionals shaping success across Washington DC, Maryland, and Virginia.

Each episode explores the journey behind the success — from career milestones and financial growth to personal habits and local favorites.

If you care about work, wealth, and well-being in the DMV, this podcast is for you.