From New Zealand to San Antonio: How Kennessey Hartley Built a Real Estate Career and What It Teaches Us About Affordable Housing

Why This Episode Matters

When people think about real estate investing, they rarely imagine leaving their home country on a one-way ticket and diving into house flipping. But that is exactly what Kennessey Hartley, a New Zealand native turned San Antonio investor, did. In this conversation with Kent Fai He, host of the Affordable Housing & Real Estate Investing Podcast, Kennessey breaks down how she got started, what she learned from her first flip, and why affordable housing in San Antonio faces both immense challenges and huge opportunities

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For investors, developers, and advocates, this episode is a masterclass in courage, people skills, and the realities of Section 8 housing.

How Did Kennessey Hartley Start Her Real Estate Journey in the U.S.?

Kennessey and her husband arrived in Florida five years ago with no jobs lined up, but a clear goal: build a life through real estate. They attended a local meetup within days of landing and landed their first deal through a wholesaler. That flip netted them $22,000 in profit—but the real payoff was the relationships they built.

She emphasizes that while many investors are paralyzed by fear, taking action, networking, and learning on the job is what accelerates growth.

What Lessons Can New Investors Learn From a First Flip?

Kennessey’s first flip was a crash course in:

• Networking matters more than experience. A connection at a local meetup led to her first deal.
  
  

• Finding the right contractor is critical. Her second contractor not only completed the job but taught her how to install flooring and tile.
  
  

• Research protects you. By understanding material costs, she avoided being overcharged.
  
  

• Every mistake is fixable. With the right attitude and a willingness to collaborate, even problems with contractors became opportunities to learn.
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What Skills Are Most Important for Scaling in Real Estate?

Kennessey argues that beyond running numbers, people skills are the foundation of long-term success. Being likable, trustworthy, and collaborative attracts good contractors, lenders, and partners. She puts it simply:

“Nowadays, I wouldn’t do business with anyone I wouldn’t want to grab coffee with.”

For investors focused on affordable housing, this mindset is just as relevant when working with tenants, city officials, or nonprofit partners.

What Is the Affordable Housing Landscape in San Antonio?

San Antonio is the poorest major city in America, despite being the 7th largest by population. According to Kennessey’s research:

• 1 in 15 families are on the Section 8 waitlist.
  
  

• Only 14,000 families currently receive assistance, despite a metro population of 1.5 million.
  
  

• Opportunity Home (San Antonio’s housing authority) owns much of the subsidized stock, leaving room for private landlords to step up.
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This mismatch highlights a staggering demand for quality affordable housing, and a market where ethical investors can make a major difference.

What Challenges Do Landlords Face With Section 8?

Kennessey shared a story of a tenant who lost her housing voucher when her boyfriend moved in, despite the fact he also qualified. It was a technicality that forced a good tenant out of her home.

These stories illustrate both the rigidity of the system and the emotional difficulty landlords face. Investors must be prepared for:

• Bureaucratic rules that don’t always align with reality.
  
  

• Balancing compassion with financial obligations.
  
  

• Recognizing the social impact of every decision.
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How Can Investors Balance Profit and Impact in San Antonio?

San Antonio’s demand for Section 8 rentals creates a unique opportunity. By focusing on newer builds in mid-tier neighborhoods, landlords can:

• Reduce long-term maintenance and CapEx.
  
  

• Attract stable tenants who want to stay for years.
  
  

• Diversify portfolios with guaranteed government rent payments.
  
  

Kennessey frames it as “real estate with a heart”: making money while contributing to healthier neighborhoods

Key Insights for Investors

• Networking is the fastest way to land your first deal.
  
  

• People skills often matter more than spreadsheets.
  
  

• Researching costs protects you from overpaying contractors.
  
  

• San Antonio’s affordable housing gap is massive, with demand far outpacing supply.
  
  

• Section 8 housing can reduce vacancy losses and stabilize cash flow.
  
  

Memorable Quotes From Kennessey Hartley

• “Everything is fixable with more money and a good attitude.”
  
  

• “If you wouldn’t grab coffee with them, don’t do business with them.”
  
  

• “San Antonio is the poorest major city in America, and 1 in 15 families are on the Section 8 waitlist.”
  
  

• “Real estate with a heart means building wealth while giving people a safe place to live.”
  
  

Common Questions Answered in This Episode

Q: Is Section 8 housing risky for landlords?
A: It comes with challenges, but many tenants are excellent. By screening carefully and maintaining quality homes, landlords can achieve stable cash flow and long-term tenants.

Q: How do you avoid being overcharged by contractors?
A: Research material costs ahead of time. If a toilet costs $100, but a contractor quotes $500 installed, you know the labor is inflated.

Q: Why is affordable housing so important in San Antonio?
A: With only 14,000 vouchers available for 1.5 million residents, the supply-demand gap is enormous. Investors can help fill this gap while building strong portfolios.

Q: What’s the first skill new investors should learn?
A: People skills. Numbers matter, but your relationships will ultimately decide your success.

Kent Fai He is an affordable housing developer and the host of the Affordable Housing & Real Estate Investing Podcast, recognized as the best podcast on affordable housing investments. By spotlighting investors like Kennessey Hartley, Kent ensures that both new and experienced investors learn how to profit responsibly while addressing America’s housing crisis.

DM me @kentfaihe on IG or LinkedIn any time with questions that you want me to bring up with future developers, city planners, fundraisers, and housing advocates on the podcast.