February 29, 2024

2023 has presented tremendous challenges for investors looking to get started. Financing is expensive compared to the historically low interest rates during the COVID boom. And, although they’re stabilizing, home prices have seen massive appreciation. Throw low inventory into the mix, and you’ve got an investor’s worst nightmare.

In short, it’s tough to cash flow right now, but luckily, it’s still possible. 

Take, for example, Jessica Later, a real estate broker and investor who’s crushing it in one of the most expensive markets in the country: Boston. In many ways, her story is contrarian. The lessons she shares in this article show you how to think outside the box to win big in any market condition. 

No Job? No Problem

Armed with a marketing degree and aspirations to work in the advertising industry, Jessica faced an unexpected setback. The company she had hoped to join lost a major account. Suddenly left without an income and unsure of her next move, she found herself at a crossroads. Little did she know that this challenging situation would ultimately lead her down an unconventional path toward financial success through real estate.

It was during this uncertain period that Jessica crossed paths with a real estate agent. Recognizing her potential, the agent suggested that she explore the world of real estate, starting with sales. Intrigued by the idea, Jessica decided to give it a shot. To her surprise, she quickly discovered that “I was able to make more money in a single summer through [real estate] than I would have earned in an entire year at the marketing company.”

As she delved deeper into the world of real estate, Jessica started to notice the remarkable success that investors were achieving. Eager to learn from their expertise, she sought out mentors who could guide her along the way. Fortunately, she found several experienced individuals who were willing to share their knowledge and provide valuable advice during the early stages of her career.

The House Hack Stack

A few years into her real estate agent career, Jessica decided to stop paying rent and pave a path forward as an investor. House hacking was the perfect place to start. It offered a low-money, low-risk way to start investing in Boston’s expensive market. After consuming hours of content about investing, she felt confident that house hacking was the right decision.

In her mid-20s, Jessica took her first significant step towards building her real estate empire when she bought a small condo in the Jamaica Plain neighborhood of Boston with the intention of living there for a year or so, then repeat the process.

A year later, Jessica had successfully found her first long-term tenant at $1,600/month. Suddenly, her one-bedroom, one-bathroom condo was cash flowing $400/month. Today, the same property rents for $4,200/month. 

“Starting is the most important part. Even if it means buying the smallest condo in your area. To wait for something bigger and better means you’re missing out on opportunities down the line because you didn’t invest sooner,” says Jessica.

On to the Next One…And the Next

Buoyed by the success of her first investment, Jessica decided to expand her portfolio further. She purchased a small condo in Boston’s trendy South End neighborhood. Instead of moving in, she furnished the place and began renting it out.

Meanwhile, Jessica moved into her van and traveled around the country for six months. She noted, “I was willing to make the short-term sacrifice of living in a van for the long-term benefit of living the way I want to.” 

On the BiggerPockets podcast, she’d heard stories of investors like Craig Curelop, who famously lived behind a curtain in his living room while house hacking. Living in a van allowed Jessica to explore the country on a budget, save money on her housing expenses, and grow her portfolio. Though it wasn’t as trendy as living in the city, it drastically expedited her wealth accumulation process.

Driven by her entrepreneurial spirit and growing success, Jessica didn’t stop there. She continued buying properties in a similar fashion while opening her own brokerage, JL+CoRE. Through her dedication, determination, and willingness to take calculated risks, Jessica demonstrated that house hacking and real estate investments could lead to financial freedom and success.

Exploiting an Overlooked Property Type

Jessica invests in condos. This unique approach allows her to tap into a market segment that is often overlooked by investors, presenting her with untapped opportunities for growth.

When asked why, she highlighted several key advantages that condos have in expensive markets:

  • Condos often come at a discounted price compared to single-family homes and multifamily properties, making them more affordable for investors with limited capital.
  • The cost-effectiveness of condos is enhanced by homeowners’ associations (HOAs) that cover external maintenance and repairs, saving investors money and providing convenience. Plus, HOAs act as training wheels for new investors, as the association also takes care of common area upkeep and other responsibilities.

As such, investors should not overlook condos as a viable option. Depending on your circumstances, it could be a great way to get started.

Cash Flow With Furnished Units

Jessica also focuses on furnished units and renting them out as medium-term rentals (MTR). If you haven’t heard of MTRs yet, it combines the benefits of short-term rentals with those of long-term tenants. After experimenting with everything under the sun, here’s what Jessica learned and why she landed on medium-term rentals:

  • Time efficiency: Jessica discovered that the high turnover associated with short-term rentals was time-consuming. To optimize her efforts, she pivoted towards medium-term rentals. By targeting tenants who stay for a few months to a year, she reduced the frequency of turnovers and minimized the time and effort required for property management.
  • Increased earning potential: While long-term rentals can provide stable income, Jessica recognized the greater earning potential of short/medium-term furnished rentals. The lack of hotels in Boston, combined with the demand from hospitals and schools, created a niche market for temporary accommodations. By catering to this demand, Jessica tapped into a lucrative segment and was able to command higher rental rates for her furnished units.

By shifting her focus to medium-term furnished rentals, Jessica optimized her time, tapped into a demand-driven market, and provided a tailored solution for tenants. This, of course, resulted in tremendous success.

Financially Flexible

After investing for over a decade, Jessica is in a great financial position. She loves the ever-changing landscape of real estate in Boston and plans to keep building her brokerage and investment business there. By following her footsteps, you, too, can create life-changing options. Start living your life on your terms with these lessons.

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Note By BiggerPockets: These are opinions written by the author and do not necessarily represent the opinions of BiggerPockets.

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