“All I wanted to be when I grew up was a lawyer,” Casey, who graduated from SUNY Albany in 2001 with criminal justice and psychology degrees, told Business Insider. “I had no other plans.” Until she started her first job as a paralegal at one of the biggest law firms in New York City, that is.

The job was demanding and often required 18-hour work days.

“There were times when I slept in the office,” she recalled. A particularly intense case that went to trial and relocated her to Florida for two months prompted her to reevaluate her career path. “That case just killed me. I gained 20 pounds, I never saw my friends, and when you’re in your early 20s, you want to have a little bit of a life.”

At the end of the case, which her team won, Casey gave her two weeks’ notice and walked away from a comfortable salary.

Draining 6 months’ worth of savings and becoming a real-estate agent

Casey didn’t have another job lined up when she quit, but she had about six months’ worth of expenses set aside.

“Because I worked so much — and when you’re on trial, after a certain time, you get double time — I just saved my money,” she said, but her savings went fast in a city as expensive as New York. “I just needed to really destress, and that’s what I did.”

Additionally, she spent time thinking about what she wanted her days to look like. For starters, she wanted more flexibility: “I wanted something where I wasn’t sitting in an office, and I wanted something where I can control the income that I could make,” she said.

Becoming a real-estate agent satisfied both of those criteria. Plus, she hoped it would set her up to one day invest in properties.

“I grew up in New York City. I’ve seen the changes as far as property values go,” said Casey. “So yes, becoming a real-estate agent was about time freedom, but the major factor was I was going to learn how to be a landlord and do leases and figure out how to get a building.”

She executed the first part of her plan and got her real-estate license in February 2006. Over the next 15 years, she worked on the leasing side of the business while pursuing various side projects in her spare time, from Amazon FBA to launching a YouTube channel — but she didn’t buy an investment property.

From agent to investor: Buying her first property in her 40s and cash flowing $1,000 a month

Casey spent her 20s and 30s in no rush to become a real-estate investor.

“I’m single, no kids, so I definitely have a different lifestyle and a different timeline than other people,” she noted. Since she plans to adopt, “I have never been on a clock. Being single has really helped me, but also hindered me: I can do whatever I want at any point, and so that’s helped me in leading a very stress-free life, but it has hindered me because I’ve always thought, ‘I’ve got so much time, I got so much time, I’ve got so much time.'”

Her mindset changed when she turned 40.

For Casey, who has been self-employed for most of her career and doesn’t have a traditional 401(k) plan, owning real estate has always been synonymous with retirement. When her 40th birthday rolled around, she realized that taking out a 30-year mortgage would mean she’d be 70 when she paid it off.

“I don’t want to retire at 70; I want to retire at 55, maybe 59,” she said, “So I was like, ‘Wait a minute, now that I’m 40, I need to get it into gear.'”

She decided to pause the serial entrepreneurship and dedicate the next three to five years to buying real estate. Specifically, she aimed to build a $5 million portfolio.

It was a number that felt like “enough,” she said. “As long as I have my retirement set, that will allow me to feel more comfortable jumping around from thing to thing.”

Her first step was to find an affordable market. New York City, where Casey has lived her entire life, was out of the question. She had about $40,000 in savings. While that wouldn’t go far in her home city, it was enough to get started in Baltimore.

Casey settled on Maryland’s largest city after researching various markets online. One of her strategies was to follow real-estate content creators on social media and pay attention to where they were investing and their returns. After selecting her market, she contacted a Baltimore-based investor she followed on YouTube, Charles Blair, and asked for a consultation.

At the time, she’d never set foot in the city she intended to invest in.

Blair put her in touch with his agent, and Casey was off to the races. She bussed back and forth between New York and Baltimore for about six weeks before finding her first property. It was an off-market deal she found on a real-estate wholesale website.

“I put in an offer, and that was that,” recalled Casey, who used a hard money lender and personal funds to close on a $105,000 single-family home in December 2021. “When I make a decision, it’s go time. What are we waiting for? Does this look good? Do the numbers make sense? That’s it.”

The purchase nearly wiped out all of her savings, she said: “Because I was a first-time investor, I had to put down 20%, three points to the lender. Including all closing costs, it was around $37,000, almost every dime I had.”

The property also required renovations.

“When you get a hard money loan, they give you 80% of the purchase price and 100% of the renovation. But it’s in draws, so you have to front the money first, and then they refund you,” explained Casey, who used business credit cards to start the renovation project. It ended up taking three months and cost her $45,000.

“I definitely made quite a few mistakes,” she said, noting that the renovation could have been done in three weeks on a $36,000 budget. But at the end of the process, she’d converted a four-bed, one-bath into a five-bed, two-bath with a fully finished basement in an emerging Baltimore neighborhood.

A tenant placement company helped her fill the rental with a Section 8 tenant. Casey started bringing in $2,350 a month, which the government covered for her tenant. Her mortgage was $1,433 at the time, she said, meaning she started profiting nearly $1,000 a month. Insider verified her property ownership by looking at a copy of her mortgage statement and confirmed the rental price by looking at a letter from the Housing Authority of Baltimore City. She profits even more now, as rent has increased and her mortgage has decreased.

Using creative financing to expand her portfolio and focusing on appreciation over cash flow

After draining her savings to acquire her first property, Casey decided: “I don’t want to spend my money on properties anymore. It’s not really scalable using your own money.”

She started researching creative financing strategies and how investors buy properties without tapping into their own savings.

Casey bought three more properties in Baltimore over the next year and a half, including one flip, using subject to financing (when the buyer takes over the existing financing) and seller financing (when the seller acts as the lender and provides a loan).

She considers her first deal a “slam dunk,” she said. “To get $1,100 right now in gross cash flow on your first deal in a low market is really, really good, especially in Baltimore where the average is $300.”

But cash flow has never been her main objective. For her, real estate is a retirement plan. She’d rather focus on long-term appreciation.

Her latest deal, which she purchased for $250,000, was purely an “appreciation play,” she said. She had to convert it into a rooming house just to cover the mortgage, but she’s bullish on the neighborhood: “I took the chance because I’ve seen the property values just in the last two years go from $300,000 to $500,000, $600,000. The property around the corner sold for $570,000.”

The way she sees it, going for big appreciation will help her get to her $5 million goal faster.

“I don’t need the cash flow. It’s nice, but that’s what working is for,” said Casey, who documents her real estate journey on YouTube and is aiming to buy her first multi-family property in 2024. “Also, I’m the type of person that, when I have a lot of money, I’m less motivated to do things, so I try to keep myself as poor as possible.”