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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