Episode 160: Can AI Replace Property Managers? (Bryan Jenkins)

30 snips

Sep 8, 2025

In this discussion, Bryan Jenkins, President of Gentone Property Management and a veteran with 25 years in the field, shares his fascinating journey from the military to managing properties for major corporations. He delves into the essential role of relationships amid the rise of AI in property management. Bryan highlights the importance of diversifying portfolios and navigating market cycles, while suggesting that AI should enhance rather than replace human effort. He also reflects on the challenges of remote work and the future landscape of the industry.

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ANECDOTE

Accidental Start With Corporate Housing

Bryan Jenkins fell into property management after leaving the military and partnering with Ralph Moore in Birmingham.
They built corporate housing for Honda executives and bought 52 homes, which seeded much of their early growth.

ANECDOTE

Buying Rent South And Weathering 2008

Bryan described acquiring Rent South contracts in 2003 and inheriting many accidental landlords.
Managing those doors and weathering the 2008 cycle forced the company to pivot and diversify into C-class and Section 8 housing.

INSIGHT

Institutional Cycle Drives Local Expansion

Institutional clients often keep a property manager two to four years before internalizing management or selling.
That cycle forces smaller managers to seed markets, then build retail around institutional placements.

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In this episode, Spencer and Matthew sit down with longtime friend and property management veteran Bryan Jenkins, now President of Gentone Property Management. Bryan brings more than 25 years of experience in the industry, from his early days managing corporate housing for Honda executives in Birmingham to building and selling a regional property management company, leading institutional operations at PURE, and now expanding Genstone’s multi-service real estate ecosystem.

Bryan shares his journey, lessons learned from different market cycles, and why he believes relationships will always be at the heart of property management—even as technology and AI transform the industry. The conversation covers everything from institutional investors and build-to-rent to the boutique operator’s future, remote team members, and how AI could reshape the role of property managers.

What You’ll Learn in This Episode:

How Bryan accidentally fell into property management after leaving the military.
The early corporate housing boom in Birmingham and how it fueled business growth.
Why diversification into C-class and Section 8 housing became essential.
Lessons learned managing through the 2008 housing crisis and institutional cycles.
The story behind selling his company to PURE and transitioning into institutional management.
How Genstone Property Management integrates property services, construction, insurance, and more under one roof.
The challenges and opportunities of managing across multiple states and markets.
How AI is beginning to impact property management operations and where it might go next.
Why boutique property managers and large-scale operators will both thrive, while the “middle” may struggle.
Why, even with AI and technology, property management will always be about relationships.

Memorable Quotes:

“I’m a relationship guy, so it’s always about relationships. At the and of the day, our business is still about relationships and I don’t think any amount of technology is gonna change that.”
“It’s always best to be the second property manager, not the first.”
“AI may change the way we operate, but it won’t replace the need for trust and communication.”

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Connect with Matt, Spencer, and Gray at Evernest: Evernest.co

Guest: Bryan Jenkins, President of Gentone Property Management

Link: Connect with Evernest

Link: Evernest YouTube Channel (@ThreeHundredToThreeThousand) (Watch this episode and more!)

Visit the Podcast Website: Evernest.co/podcasts

Email the Show: podcast@evernest.co

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Production House: Flint Stone Media