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In this episode of Zen and the Art of Real Estate Investing, Jonathan sits down with Niyi Adewole—real estate investor, short-term rental operator, and investor-friendly agent—to discuss the journey from first house hack to a thriving real estate business. Niyi shares how he transitioned from medical device sales to building a 30-unit portfolio in Louisville, Kentucky, before shifting into short-term rental management, new development, and becoming a trusted guide for other investors through his real estate team and podcast.
Jonathan and Niyi explore the realities of house hacking, the importance of building systems, and why consistency and a long-term outlook matter more than chasing quick wins. Niyi offers advice for new investors, from how to get started in a high-interest-rate environment to what to look for in a truly investor-friendly agent.
In this episode, you will hear:
What led Niyi to house hacking, and how it helped him build early momentum
Lessons learned from managing rentals, handling evictions, and scaling with systems
How a move to Atlanta sparked a shift into full-time real estate entrepreneurship
Tips for investors navigating short-term and mid-term rental strategies
How to vet property managers and protect your cash flow
The difference between a real estate agent who says they work with investors and one who actually does
Follow and Review:
We'd love for you to follow us if you haven't yet. Click that purple '+' in the top right corner of your Apple Podcasts app. We'd love it even more if you could drop a review or 5-star rating over on Apple Podcasts. Simply select "Ratings and Reviews" and "Write a Review" then a quick line with your favorite part of the episode. It only takes a second and it helps spread the word about the podcast.
Supporting Resources:
Ekabo Home website - linktr.ee/ekabohome
Ekabo Home on YouTube - www.youtube.com/channel/UCo-iogGt9tlPsMDFKB7B-1Q
Ekabo Home's Facebook page - www.facebook.com/groups/530839468550185
Ekabo Home on Instagram - www.instagram.com/ekabohome
Connect with Niyi Adewole on LinkedIn - www.linkedin.com/in/niyiadewole
Ekabo Home on TikTok - www.tiktok.com/@ekabohome
Website - www.streamlined.properties
YouTube - www.youtube.com/c/JonathanGreeneRE/videos
Instagram - www.instagram.com/trustgreene
Instagram - www.instagram.com/streamlinedproperties
TikTok - www.tiktok.com/@trustgreene
Zillow - www.zillow.com/profile/StreamlinedReal
Bigger Pockets - www.biggerpockets.com/users/TrustGreene
Facebook - www.facebook.com/streamlinedproperties
Email - [email protected]
Episode Credits
If you like this podcast and are thinking of creating your own, consider talking to my producer, Emerald City Productions. They helped me grow and produce the podcast you are listening to right now. Find out more at https://emeraldcitypro.com Let them know we sent you.
By Jonathan Greene4.9
102102 ratings
In this episode of Zen and the Art of Real Estate Investing, Jonathan sits down with Niyi Adewole—real estate investor, short-term rental operator, and investor-friendly agent—to discuss the journey from first house hack to a thriving real estate business. Niyi shares how he transitioned from medical device sales to building a 30-unit portfolio in Louisville, Kentucky, before shifting into short-term rental management, new development, and becoming a trusted guide for other investors through his real estate team and podcast.
Jonathan and Niyi explore the realities of house hacking, the importance of building systems, and why consistency and a long-term outlook matter more than chasing quick wins. Niyi offers advice for new investors, from how to get started in a high-interest-rate environment to what to look for in a truly investor-friendly agent.
In this episode, you will hear:
What led Niyi to house hacking, and how it helped him build early momentum
Lessons learned from managing rentals, handling evictions, and scaling with systems
How a move to Atlanta sparked a shift into full-time real estate entrepreneurship
Tips for investors navigating short-term and mid-term rental strategies
How to vet property managers and protect your cash flow
The difference between a real estate agent who says they work with investors and one who actually does
Follow and Review:
We'd love for you to follow us if you haven't yet. Click that purple '+' in the top right corner of your Apple Podcasts app. We'd love it even more if you could drop a review or 5-star rating over on Apple Podcasts. Simply select "Ratings and Reviews" and "Write a Review" then a quick line with your favorite part of the episode. It only takes a second and it helps spread the word about the podcast.
Supporting Resources:
Ekabo Home website - linktr.ee/ekabohome
Ekabo Home on YouTube - www.youtube.com/channel/UCo-iogGt9tlPsMDFKB7B-1Q
Ekabo Home's Facebook page - www.facebook.com/groups/530839468550185
Ekabo Home on Instagram - www.instagram.com/ekabohome
Connect with Niyi Adewole on LinkedIn - www.linkedin.com/in/niyiadewole
Ekabo Home on TikTok - www.tiktok.com/@ekabohome
Website - www.streamlined.properties
YouTube - www.youtube.com/c/JonathanGreeneRE/videos
Instagram - www.instagram.com/trustgreene
Instagram - www.instagram.com/streamlinedproperties
TikTok - www.tiktok.com/@trustgreene
Zillow - www.zillow.com/profile/StreamlinedReal
Bigger Pockets - www.biggerpockets.com/users/TrustGreene
Facebook - www.facebook.com/streamlinedproperties
Email - [email protected]
Episode Credits
If you like this podcast and are thinking of creating your own, consider talking to my producer, Emerald City Productions. They helped me grow and produce the podcast you are listening to right now. Find out more at https://emeraldcitypro.com Let them know we sent you.

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