Zen and the Art of Real Estate Investing with Jonathan Greene

052: Perfecting the House Hacking Strategy with Craig Curelop


Ready to unlock the secrets of real estate investing and house hacking?

In this episode of Zen and the Art of Real Estate Investing, Jonathan sits down with trailblazer Craig Curelop, the founder of The FI Team and author of the acclaimed House Hacking Strategy book for Bigger Pockets. Craig shares his journey from his very first investment property, a duplex near the Bigger Pockets office, to becoming a respected figure in the industry. His advice? Break some comfort zones!

Together, Jonathan and Craig navigate the ever-evolving world of house hacking, from its humble origins to the booming trend that it is today. Hear firsthand how pioneers like Brandon and Scott shaped the industry and how platforms like Airbnb have revolutionized house hacking. Craig emphasizes the need to stay abreast of industry trends and the value of having a diverse investment portfolio. 

In the heart of their conversation, Jonathan and Craig get practical. Craig shares his expertise on building a competent real estate team and the fluctuating dynamics of house flipping. They also outline the pros and cons of different investment strategies and assess their relevance in current market conditions.

Whether you’re an experienced investor or just starting, get ready to venture into the exciting world of real estate investing and house hacking!

In this episode, you will hear:

  • How Craig discovered real estate investing and the significance of stepping out of your comfort zone, using his first investment property as an example

  • The evolution of house hacking and Craig’s  balanced perspective on the potential benefits and pitfalls of adopting such trends

  • Why it’s important to understand market trends and the potential risks and benefits of being an early adopter of a new investment strategy

  • The pros and cons of residential versus commercial investing and renting-by-the-room as an alternative strategy in areas where housing is becoming more expensive

  • Different kinds of house hacking strategies and why you must understand the market you’re investing in as well as the potential value of auxiliary dwelling units (mother-in-law suites)

  • Craig’s experience with house hacking and how it highlights the importance of having the right team for real estate investing and the difference between residential versus investor appraisals

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If you enjoyed this episode, we’ve created a PDF that has all of the key information for you from the episode. Just go to the episode page at to download it.

Supporting Resources:

Craig Curelop’s website –

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Get The House Hacking Strategy book –

Visit Bigger Pockets –

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