A CPA Couple Investing in Real Estate on the Side Share Top Strategies

Amanda Han and Matthew MacFarland stumbled into real estate early in their careers. They were both working at a Big Four accounting firm and were placed in the real estate group.

“That was sort of just by chance. They put you where they put you,” Han told Business Insider.

She’d never been interested in property investing. She grew up watching her parents and grandparents spend hours on their own real estate portfolios.

“They were super hands-on,” said Han. She didn’t think that type of active investment was for her, but as she and MacFarland spent more and more time working with real estate investors in their day jobs, the couple couldn’t ignore the tax benefits.

The “aha moment” came for MacFarland a few years into his tax manager job.

“I was reviewing somebody’s tax return, probably a gentleman in his 60s. He was retired and all he had going on was real estate,” recalled MacFarland. “From looking at his tax return, this guy was making money in real estate — cash flow — and not paying any taxes on it because of the depreciation. And I was like, ‘Hey, there’s something here.'”

It took Han a little bit longer to come around, but when her dad got sick, it highlighted the importance of having a backup revenue stream.

“You need to have another source of income because otherwise, no matter how high-paying your job is, if you have to stop working, you no longer have money,” she said. “So I then started agreeing with Matt to look into real estate.”

Buying their first rentals and expanding to syndication deals

Han and MacFarland bought their first investment property around the same time they started their own firm, Keystone CPA, in 2008.

Despite doing real estate adjacent work for years, “we were new to wearing an investor hat, so I think we had a lot of the same uncertainties and concerns that most new investors have,” said Han.

The California-based couple chose to start in a more affordable market and settled on Las Vegas, where Han grew up and still had family. From there, they started looking at properties online. Their priority was to find something that would produce positive cash flow.

They were purchasing amid the 2008 housing crash, “so we really doubted whether we were doing the right thing,” said Han. But running numbers through the cash flow calculator they built in Excel, and considering exit strategies, eased their anxieties. “We just ran the numbers and said, ‘Okay, these numbers make sense. Let’s do it,’ as scary as it seemed at the time.”

She added that it was also helpful to consider the worst-case scenario:

“Like, what happens if the property is going to be vacant for six months? And just knowing that, in the most conservative case, we had the savings to hold us out is one of the things that gave me comfort.”

As their calculator predicted, their first rental — a single-family home that they set up as a long-term rental — started to profit immediately.

“It wasn’t something that we would quit working for, but it proved we can do it, we can get a small amount of cash flow,” said Han. “As long as we weren’t losing money, we were happy with it.”

Since that first purchase, they’ve expanded their portfolio and modeled their strategy based on what’s working for their clients. They call this their “cheat code,” and it’s helped them determine what markets to invest in and what type of investments to pursue.

Adding real estate syndication deals to their portfolio was a specific strategy shift inspired by their clients.

With real estate syndications, a group of investors pools together their capital to purchase a single property managed by the syndicator. Once the investor contributes capital, their role in the deal becomes completely passive. The real-estate syndicator is responsible for finding the deal, executing the transaction, and, ultimately, delivering returns to the investors.

“We realized over the years that we’re really good at being tax strategists — that’s our specialty — and we know there are people who do real estate investing that are a lot better at it than we are,” said MacFarland. “So it makes sense to leverage their expertise.”

As of 2025, they actively manage three single-family rentals and, between their 16 passive syndication deals, own a portion of condos, apartments, and mobile home parks. They’re also the authors of “The Book on Advanced Tax Strategies” and share tax tips and information through their YouTube channel.

Having experience with both active and passive real estate investments, “I don’t think there’s one that’s necessarily better than the other,” said Han. “It just comes down to your resources: Do you have more time, or do you have more money?”

It also depends on your strengths and weaknesses.

“We have clients who do their own rentals, and they do super well. They generate much higher returns than any syndication could provide,” she said. However, if your background isn’t in real estate and you have more money than time to dedicate to your investments, syndications could make more sense.

While the couple began buying property to create an extra revenue stream in the form of rental income — and they still focus on cash flow when analyzing deals — they said that appreciation has made the biggest impact on their net worth.

Their side hustle has also led to a greater appreciation for their day jobs.

“We started the journey thinking we’re going to do real estate full time and stop working as CPAs,” said Han. “But we quickly realized that we actually love our careers as CPAs. So, it’s switched more from retire early to just having additional income.”