All Things Real Estate with Ari Wintraub

From Agent to Investor: Ari’s Journey to Owning Real Estate


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How do you transition from selling real estate to building a personal investment portfolio? In this episode, I sit down with Thomas Lord, my right-hand man, to share my journey from getting licensed in 2014 to growing a 36-unit portfolio while managing a full-time real estate brokerage.


Learn how I:

- Went from a new agent in 2014 to real estate investor by 2016- Used Airbnb & house hacking to start generating income

- Scaled from a single-family home to multifamily investing

- Navigated California’s rent control & property management challenges

- Balanced selling homes, managing tenants, and expanding my portfolio


This episode dives into my real estate journey, key lessons, and investment strategies that helped me build a long-term business in one of the most competitive markets in the U.S.

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All Things Real Estate with Ari WintraubBy Ari Wintraub