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.