Tech Startup to Real Estate Wholesaling: Stephen Keighery's Path in Louisiana

Written by:

Steve Marcinuk

Date:

24 Jun 2025

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Stephen Keighery began his career far from the bayous of Louisiana. Originally from Australia, he was a founding partner at hipages Group, a two-sided marketplace that connected contractors with homeowners. That early experience in tech laid the groundwork for a striking pivot. Today, as the founder of Home Buyer Louisiana, Keighery is applying his marketplace expertise to real estate, leading one of the state’s most active wholesale operations.

From Tech Success to New Orleans Discovery

Keighery’s entrepreneurial roots run deep. At hipages group, essentially “Angie’s List in Australia,” he helped scale the company to 300 employees before it went public on the Australian Stock Exchange in 2020. After News Corp acquired 30% of the company, Keighery cashed out some shares and took a well-deserved break.

“I left in 2018… startup life is hard. I sacrificed many things. The goal was to take a year off and figure out my next move,” Keighery recalls. That sabbatical brought him to New Orleans for what was initially planned as a six-month vacation. The city’s unique charm quickly won him over.

With six rental properties already in his Australian portfolio, Keighery had always valued real estate as an asset class. In New Orleans, his investor’s eye immediately spotted opportunity in the distressed property market.

“I saw significant distress. There are numerous code violations,” he notes. After purchasing his first rehab property from a wholesaler, Keighery became curious about the wholesaling business model itself. “I wondered what wholesalers actually do. These guys have the deals,” he explains.

The Lightbulb Moment: Recognizing Transferable Skills

The pivotal realization came when Keighery understood that real estate wholesaling was fundamentally similar to his previous business: “That’s just a two-sided marketplace, and I ran Sales and Marketing [at hipages]. That’s my skill set. I can do that. It gave me an unfair advantage.”

This insight led him to establish Home Buyer Louisiana, securing an E2 visa (business investment visa) to remain in the country based on his economic impact. The transition wasn’t just about changing industries—it was about applying proven expertise to a new context.

Tech-Powered Real Estate in an Analog Industry

What distinguishes Keighery in the Louisiana real estate market is his application of technology and marketing sophistication to an industry that often operates on outdated systems.

“My website’s sophisticated. I don’t think most people in this space even understand how it’s optimized and built, and how we track leads,” he explains. His operation leverages advanced technology at every step: “We use AI now to speed assess. We have AI that listens to the phone calls with my sales reps and gives us a valuation of how they went.”

This tech-forward approach has yielded impressive results. “We completed our 200th deal about a month ago,” Keighery shares. Beyond wholesaling to other investors, he’s strategically built his own portfolio by keeping select properties.

“I kept the easy deals, not the good deals. I mean, all my deals are good, but I kept the easy ones I could just BRRRR (Buy, Rehab, Rent, Refinance, Repeat).” This approach has allowed him to accumulate 36 units across approximately 25 properties.

Thriving Through Market Challenges

The Louisiana real estate market has faced significant headwinds in recent years, particularly around insurance issues following Hurricane Ida. While many competitors retreated from these challenges, Keighery saw opportunity.

“Many wholesalers stopped, many investors pulled back. We doubled down. I hired a disposition person and just leaned harder into it. Even though it was difficult, we started to move the deals. During that time, we captured market share.”

This contrarian approach stems from Keighery’s perspective that market conditions are relative to strategy. “In 2021, flippers thrived when selling properties but struggled when buying. So is this a worse or better market? In Louisiana, the market’s much tougher to sell, but it’s much easier to buy. What’s worse? It’s relative to strategy.”

Building Community from Scratch

Perhaps most impressive is how Keighery, arriving in Louisiana without connections, built a substantial network from the ground up. He serves as a director of the New Orleans Real Estate Investors Association (NOREIA) and hosts regular meetups that are professionally produced.

“We host a real estate meetup and video it with high production quality. I’ll take the video, use ChatGPT to transcribe it, turn it into an article on a blog, and repurpose it,” he explains, demonstrating his approach to content marketing and community building.

“Because I arrived without a network, I built one from scratch. I know many people here from running the meetups, and I manage a Facebook group with about 5,700 members.”

The Opportunity in “Bad” Markets

Despite the challenges, Keighery remains optimistic about the Louisiana market. “The serious buyers are still purchasing real estate because the deals are attractive,” he observes. “Everyone’s complaining about the market being bad, but it’s relative.”

For investors willing to adapt their strategies to current conditions, opportunities abound. The reduced competition from investors who have pulled back means those who remain active can capitalize on deals that might have been inaccessible in a hotter market.

Keighery’s journey illustrates how transferable skills from technology and marketing can create competitive advantages in traditional industries like real estate. By applying systems thinking, leveraging technology, and maintaining flexibility in strategy, he’s been able to thrive even as market conditions shift.

For real estate professionals and investors watching the Gulf Coast markets, Keighery’s experience suggests that success comes not from waiting for ideal conditions, but from adapting approaches to extract value from whatever conditions exist. As he puts it: “We’re seeing lots of people still being very active here. We’re being very active here, but it’s a tough market.”