Home Featured This millennial couple went from being $100K in student loan debt to real estate investors with nearly a dozen apartment rentals valued at $1.35M

This millennial couple went from being $100K in student loan debt to real estate investors with nearly a dozen apartment rentals valued at $1.35M

This millennial couple went from being $100K in student loan debt to real estate investors with nearly a dozen apartment rentals valued at $1.35M


Ali and Josh Lupo met in college as human service majors. Professors always told them they weren’t going to make a lot of money—and just to accept it. Even though they both graduated from a state school, worked part-time jobs while studying, and “lived a frugal lifestyle,” the couple left with a combined $102,000 in student loan debt. 

The weight of their debt and financial challenges became even more evident when they started planning their wedding in 2017. They were living paycheck-to-paycheck working very low-wage jobs, Ali says. The couple, who made a combined $85,000 at the time, had no idea how they were going to pay for a wedding, so Josh went to the drawing board and brainstormed how they could pay off their debt and save money, she recalls.

“That process really thrust me into the world of personal finance,” Josh says. “Money wasn’t anything that we ever talked about in the time that we were dating. Neither one of us grew up from wealthy families where money was talked about.”

By investing more time into studying organizing personal finances, the couple started understanding more the importance of budgeting and paying off debt. But it was difficult to budget when most of the couple’s expenses were necessities, including rent and car payments. The couple did end up selling their car, but wanted to “reduce our rent without moving back in with our parents,” Josh says.

That’s when they discovered a method called “house hacking,” which ultimately became a major boon for the couple’s finances. This method requires a low down payment on a multi-family home and using some of the rent to cover the remaining house payment where the couple would live. They skipped their honeymoon and took all of the money they had saved from an old 401(k) to buy their first rental property in 2018.

The couple’s first real estate purchase was a $158,000 two-family home with a 30-year-fixed mortgage rate of 4.8%. The down payment was $14,200, or about 5% of the price of the home including closing costs. The couple rented the upstairs of the five-bedroom, two-bath home for $925 per month and paid the remaining balance of $459 per month. Today the building is rented for $2,425, Josh says.

Getting there wasn’t necessarily easy, though. They made somewhere between 15 and 20 offers and lost out on every single one because people were paying all cash and over asking, Josh recalls. 

“There was a lot of out of state investors because back then rates weren’t 7%-8%. Rates were between 4% and 5%, so everyone wanted to lock in those low interest rates,” he says. “We were losing out time and time and time again.”

Their first deal was actually an off-market deal. They purchased from a local couple who had outgrown a duplex and wanted to sell the property off-market and weren’t “looking for a bunch of investors,” Josh says. After closing on that deal, the couple went from paying about $1,400 in monthly rent to under $500.

“As two low-income people, that was a big saving for us,” Josh says. 

Even though they had radically reduced their housing costs, the couple continued hustling in 2019. Between the two of them, they worked six jobs including side gigs and full-time jobs all while networking and educating themselves on real estate. 

“When Josh and I first started, we had no money to buy real estate, so we had to get very, very creative,” Ali says. “Money was our pain point.”

But in 2019 alone, the couple managed to pay off more than $30,000 of their student debt. They went into 2020 committed to buying more real estate, only to have the world shut down. 

“That was scary for us not only because we wanted to buy real estate, but also as people who owned real estate and there were moratoriums on people collecting rent,” Josh says. “Luckily, none of our tenants missed any rent. They continue to pay.”

Then in the late spring of 2020, the couple decided to pursue purchasing their next rental property. They bought another house down the street, moved there, and rented out their old duplex. That ended up covering the entire housing cost. Plus, Ali had earned a new job, so “cost of living was actually very, very low relative to our income,” Josh says. 

Having significantly reduced housing costs allowed the couple to make their final student loan payment in February 2022. In just about three years, Ali and Josh managed to go from being six-figures in debt to owning multiple properties.

“Our initial goal wasn’t necessarily to build a big real estate portfolio,” Josh says. “We just didn’t want to have $100,000 of student loans.” 

And in April 2023, the couple purchased their own personal home in Albany, New York, for $260,000 at a 6% mortgage rate. The couple pays about $1,900 in monthly mortgage payments and put 10.5% down on the home.

The couple plans to continue growing their real estate portfolio by buying a couple of properties each year. Unlike some investors, however, they’re focused on making off-market deals where the competition might not be as steep. 

“We built a lot of systems for finding deals at a discount, networking with people to find the deals before they hit the market,” Ali says. “Because it is crazy [in our market]. Right now, you have houses that are listed on MLS for a day, have dozens of offers, many of them cash, many of them well over asking. That can really feel daunting for a new investor.”

The couple also doesn’t buy “aggressively,” she explains, meaning that they’re only doing a couple deals a year and only deals that make financial sense for them. The couple now owns five properties consisting of 11 apartments—plus their own personal home. They declined to disclose their current income.

“For us, there is no emotionality,” she says. “With this, it is all a numbers game.”

Now the couple advises other prospective homeowners or other folks yearning to get their finances back under control. Branded as The FI Couple, Ali and Josh offer finance and real estate coaching services. 


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