Podcast

Zen and the Art of Real Estate Investing with Jonathan Greene

247: Going From Investor To Investor-Friendly Agent with Niyi Adewole

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

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