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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