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How a Couple Paid Off $100,000 and bought $1.3 Million In Real Estate

Imagine going from six figures in debt to well over $1 million in assets in a few short years – and you’re only in your early 30s!

That sounds like the stuff of financial fantasies, but it’s the real, everyday life of a surprisingly ordinary couple from Upstate New York.

Dissatisfaction is often the fuel that powers individuals and couples to step out of their comfort zones and accomplish great things. So it is with Josh and Ali Lupo. If you’re struggling with your own finances or wonder what could be if – this is a story you’ll want to read.

Meet Josh and Ali Lupo – And Their $100,000 Debt

It can be surprising to learn how a couple who achieve financial independence are just like you and me. But that’s the case with Josh and Ali Lupo. Their climb to success was motivated, perhaps more than anything else, by the realization of their own financial limitations.

When Ali graduated with her master’s degree in social work in 2017, they began planning their 2018 wedding. But weddings are expensive, and the Lupos didn’t have any money. In fact, it was even worse than that.

“For the first time in our three-year relationship, we sat down to discuss finances,” Ali recalled. “Not only did we realize we had no money, but we actually had negative money – we were six figures in debt.”

Making the financial shortfall even more difficult to comprehend was that the Lupos did all the “right things”. They went to state colleges, took advantage of scholarships, and worked during their college years. And when it was all over, they even landed their “dream jobs”.

Nonetheless, they found themselves living paycheck-to-paycheck. Working multiple jobs didn’t help and left them feeling completely burned out.

One of the underlying problems the couple faced was one that’s all too common to so many who have found themselves mired in financial chaos: both grew up in families that never talked extensively about money.

In addition to low wages, the Lupos were struggling with financial illiteracy.

The Lupos were also struggling with another dilemma that’s all too common to millions of Americans: excessive student loan debt. Their combined student debt was in the neighborhood of $100,000.

A six-figure student loan debt, no money, and living paycheck-to-paycheck hardly seem like the beginning of a successful run for financial independence.

But that’s exactly what makes this story so compelling.

The Road to Financial Recovery

The Lupos did have one advantage: they knew they didn’t want to live this way for much longer.

It wasn’t much to go on, but it was a start. The couple gradually began to self-educate themselves about personal finance. That included learning about money management, budgeting, paying off debt, and investing.

The overriding objective was to concentrate on two goals, 1) paying off their student loan debt, and 2) eventually investing in real estate. But as is so often the case, life didn’t cooperate with their plans – at least not initially.

In the first two weeks of 2018, Josh was fired from his job. At about the same time, he also totaled his car.

But if the couple was discouraged, it was only temporary.

“It felt like our world was crashing down around us,” Josh confessed. “But the reality was that experience further reinforced our goals and desires to improve our financial situation. We realized how risky it really was to rely on a single source of income, especially one that wasn’t within our control.”

The bad experience only cemented Josh and Ali’s decision to pursue financial independence.

Getting Their Finances Under Control by Tiptoeing into Real Estate

Inspired by the financial independence movement, the Lupos started by implementing strategies to radically reduce their expenses. It made even more sense given that the two were engaged in moderate-income professions, Josh as a career counselor for workers with disabilities, and Ali as a licensed clinical social worker in the local public school system.

Expense reduction started by developing a budget. But unlike so much of the personal finance advice given on the Internet and elsewhere, they knew the answer wasn’t going to be simply to eliminate lattes, subscription services, or date nights. No, they knew they needed to target the bigger costs.

Early on, Josh and Ali realized that 70% of their money was going towards just three expenses: housing, food, and transportation. If they were going to make any progress in controlling their finances, they knew they needed to seriously cut the expenses that were the biggest drain on the budget.

To eliminate their $250 per month car payment, they paid cash for a used, high-mileage vehicle instead. To reduce their food budget, the Lupos prepared most of their meals at home.

But at the heart of their cost-cutting strategy was an ambitious plan to deeply reduce their housing expense.

“House Hacking” Their Way to Cutting Living Expenses

The Lupos established a plan to cut their housing costs by 60% initially, and eventually, by 100%. Though it sounds radical, it can be accomplished through a strategy referred to as house hacking.

“Put simply, house hacking is a way to cut down on your living expenses while simultaneously building your home equity,” wrote former Forbes contributor, Tara Mastroeni. “When you house hack, rather than buying a condo or single-family home that’s just big enough for you, you shop for a multi-family unit instead. Then, once you’ve bought your home, you bring in tenants, who pay you rent and essentially cover the cost of your mortgage.”

Josh and Ali’s house hacking strategy involved purchasing a 120-year-old duplex at the end of 2018, using a low-down payment mortgage. To come up with the funds for the down payment, Ali took a second job, while Josh started a side hustle driving for Uber. The couple even passed on their honeymoon to raise additional cash.

They moved into one unit, and then collected rent from the second. The strategy resulted in a $700 decrease in their overall housing expense. The combination of buying a used car for cash and house hacking saved the Lupos nearly $1,000 per month.

Building a Real Estate Portfolio

Josh and Ali’s real estate adventure didn’t stop with house hacking their primary residence. They continued educating themselves on both personal finance and real estate investing. The money they saved from reducing expenses and from keeping multiple side hustles was eventually parlayed into other properties.

Their next real estate project was another duplex, purchased in 2020. Using the same strategy they did with the first duplex, the Lupos moved into one unit, while renting out the other. Buying the second duplex also meant they could rent out both units of their original home.

The additional income from the first property, combined with the rent from the second unit of their new primary residence, fully covered their housing expense. The couple were living rent-free.

Fast-forward to 2023, Josh and Ali now own six properties, including their primary residence. That includes 11 rentals in addition to their primary residence – which will eventually be converted into a rental as well.

“We favor small, residential multifamily properties consisting of two to four apartments,” reveals Josh. “It’s important to us that our properties are all within a 10-minute radius since we self-manage our real estate portfolio. We also make sure to invest in areas with opportunities for growth, such as developing businesses, access to public transportation, colleges, and vibrant downtowns.”

Thus far, Josh and Ali have invested a total of $95,000 in real estate, with a current market value of $1.3 million. They report a net positive monthly cash flow of $2,600.

That’s an impressive run for a couple who only purchased their first property a little over five years ago.

The Birth of The FI Couple

The FI Couple (“FI” stands for financial independence) was born while Josh and Ali were taking control of their finances and building their real estate portfolio.

Three years into their journey to financial independence – but not yet financially independent – Ali reports having a dream about starting a social media channel documenting their journey.

“We often listened to podcasts and read books of other people’s journeys as a source of inspiration,” recounts Ali. “The issue was that most of the narratives were from people who had already made it. We didn’t hear stories like ours, about people who make financial mistakes, had a ton of debt, and were still navigating in the trenches. We created The FI Couple as a way to share our perspective with people like us.”

The Lupos chose Instagram as the social media platform for one simple reason: it was the one they were most familiar with. But when they first started The FI Couple they had no specific business goal.

“We weren’t sure what the experience would be like, and figured that at least our moms would follow us,” recounted Josh, half-jokingly. “We were truly shocked and humbled when our page began to get traction and grow. We learned that you can actually make money from having a social media presence, and we learned different strategies to earn an income for providing valuable content and helping others.”

Monetizing Their Instagram Channel

Josh and Ali started with one-on-one coaching, which led to the development of an e-book. That was eventually followed by group coaching. The couple also take on a limited number of brand partnerships that are closely aligned with their mission and message.

A quick glance at The FI Couple Instagram page, where they bill themselves as Real Estate & Finance educators, shows they have 151,000 followers.

The Lupos currently have at least five income streams, including real estate, social media, group coaching, digital products, brand collaborations, and speaking engagements.

The Path to Success Isn’t Always a Straight Line

It may seem as if the Lupos journey from broke/$100,000 in debt, to a $1.3 million real estate portfolio and a successful Instagram channel has been a straight line, but it hasn’t. They’ve had their share of wrong turns, which is part of the authenticity they work to bring to their message to viewers and clients.

For example, their foray into real estate investing wasn’t a joint idea. After spending 16 months reading books and listening to podcasts on real estate investing, Josh shared his investing goal with a very reluctant Ali.

They also warn that real estate is not for everyone.

“While we would still choose real estate over full-time W-2 work,” Ali confesses, “We want to recognize that it takes great responsibility and there are risks involved. Housing and people can be unpredictable, and your job is to solve (sometimes complicated) problems. And of course, unless you’re purchasing properties in cash, you’re incurring the risk of debt and economic volatility. It’s a business and should be treated as such.”

When Josh and Ali purchased their second property, it proved to be a major challenge.

“We didn’t properly assess all the repairs needed,” Josh reveals. “This led to tens of thousands of dollars of unexpected repairs and updates. We noticed a few windows that needed replacing but didn’t think much of it. But once we moved in, we realized we needed 15 new windows. That’s when we quickly realized windows are expensive, and we now routinely check the windows of any property we look at. It was a simple lesson of ‘you don’t know what you don’t know’”.

What Financial Independence Has Meant to the Lupos

As Josh and Ali ventured into the world of real estate investing, social media, and entrepreneurship, they realized that their income had the potential to be limitless. That’s in stark contrast to their original career assumptions.

“When we were in traditional 9-to-5 jobs,” Ali commented, “we were conditioned to believe that we were destined to be ‘lower/average’ income earners forever. That’s largely because we work in lower-paying occupations. But now, with at least five income streams, we realize there is no ceiling on what we can earn.”

By 2021, the couple was in a position where Ali was able to reduce her full-time job to part-time, focus on physical and mental health, and acquire “amazing” in-vitro fertilization (IVF) benefits. That break in the grind of full-time work enabled her to get pregnant by IVF. They welcomed their daughter, Zoey, into the family in July of this year.

Both continue to work in their traditional careers on a part-time basis but plan to phase these arrangements out by the end of 2023.

Josh and Ali agree that financial independence has completely changed their lives.

“We’re radically different people now, six years into our journey,” Ali discloses. “The pursuit of FI isn’t easy. It forces you to make sacrifices and hard decisions about what you really want your life to be. It forces you to be very intentional with both your words and actions. But we are more confident now than when we lived our lives on autopilot. We now live life on our terms, and we decide how we want to spend our time and our money.”

Where the Lupos Plan to Take Financial Independence

The Lupos have not confined their activities to real estate investing and Instagram. They now have The FI Couple website, have expanded into Twitter, and have launched a newsletter. Future plans include the start of a YouTube channel and a series of podcasts.

Their top priority is to focus on raising a healthy, happy baby girl, and the financial independence they’ve gained is enabling them to do just that. And since their business can be managed from anywhere, they plan to start traveling more and for longer periods of time.

Meanwhile, they plan to continue to grow their real estate portfolio and achieve complete financial independence by the time they reach their mid-30s. And just over the horizon, they plan to become millionaires by the time they reach 40.

Can Anyone Really Reach Financial Independence?

The whole purpose of The FI Couple venture is to help ordinary people accomplish financial independence. But they caution that financial independence isn’t for the faint of heart.

“It takes a very strong why to keep you committed to the path,” advises Josh. “As the saying goes, ‘It’s a marathon, not a sprint’. Instead of setting unrealistic goals that force you to be miserable for years, try to find a sustainable way to reach your goals, while still giving you breathing room to enjoy your life.”

Josh and Ali recommend the following strategies for anyone who is serious about achieving financial independence:

  1. Surround yourself with supportive people, both in-person and online. You need to find people who think like you do.
  2. Know your numbers and review them often. That includes income, expenses, assets, debts, and your ‘FI number’ (how much it will take to reach financial independence).
  3. Learn how to budget and set goals and milestones to keep you motivated.
  4. Compare yourself to you. This is a challenge of you-versus-you. What does your dream life look like, and what do you need to do to get there?

Final Thoughts

Can anyone do what Josh and Ali are doing? The Lupos are betting you can. That’s the whole purpose behind The FI Couple Instagram Channel and other resources they’ve made available.

Because of those resources, this isn’t just a nice story about how a couple went from being deep in debt to real estate entrepreneurs approaching financial independence in just a few years. Josh and Ali are making themselves available to help others who are on a similar journey to get across the finish line.

That could be you.



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