BiggerPockets Real Estate Podcast Retiring 15 Years Early by Buying Rentals on Repeat (HELOCs!)
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Jul 28, 2025 Tony DiGiacomo, a real estate investor who retired 15 years early, shares his journey of building a rental property portfolio. He reveals how he strategically bought 15 properties while living with his parents, directing every dollar toward investments. Unlocking the power of HELOCs, he explains how he turned one rental into multiple. Tony discusses making money in real estate regardless of market conditions and his recent shift from buying to building for better returns. His insights offer a roadmap for anyone looking to retire earlier and achieve financial freedom.
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Early Start in Real Estate
- Tony DiGiacomo started investing young, buying his first rental property in his early 20s.
- He gained early experience managing properties with his father, which shaped his financial freedom vision.
Multiple Jobs, Living at Home
- Tony worked multiple jobs and lived at home to save aggressively for down payments on rental properties.
- This frugality helped him amass three rental properties while still living with his parents.
Buying Troubled Properties During Crash
- During the 2008 crash, Tony bought cheap, troubled multifamily properties needing major rehab.
- He acquired properties others avoided, embracing their challenges to build equity.