Real Estate Investor Financial Independence Building a Portfolio
Real Estate

Real Estate Investor Financial Independence Building a Portfolio

After graduating from UMass Amherst in 2011, Dana Bull landed a job at an architecture firm in Salem, Massachusetts and started apartment hunting. 

“I was looking on Zillow for rentals, but then I clicked on the ‘buy’ tab,” she told Insider. “I ended up getting sucked into the Zillow tunnel.”

Bull and her boyfriend at the time, now husband, rented a one-bedroom in Salem, but Bull continued perusing home listings. She realized that when combining incomes with her boyfriend, Andrew, the two could buy a place and their monthly mortgage payment would be similar to, or potentially less than, what they were paying in rent.

“It was the


— there weren’t a lot of jobs available and the housing market was a bit of a mess at that time,” recalled Bull. “Even though everybody was talking about how scary buying real estate was, it didn’t really seem to impact me. I was 22 years old, didn’t have any dependents, and had worked full-time in college, so I had money saved up.”

Using savings from the slew of jobs she’d had since 13 — from working in a bakery and retail shops to writing and marketing gigs — Bull bought her first home, a $200,000 condo in Salem, in June 2012. 

A decade later, she has 22 rental units around Salem and Marblehead, two coastal towns north of Boston. She also owns a property in Boston. Insider verified Bull’s property ownership and 2021 revenue, which she prefers not to disclose.

“I call the portfolio our second wife: It’s like another partner in our marriage that’s working and bringing home the bacon,” said Bull, now 33 and a mother of three. She considers herself financially independent, thanks to her investment properties. “I want to work because I love to work, but I don’t necessarily need to work. It’s really powerful to be in that position in my early 30s without feeling like I need to compromise on my lifestyle.”

She works in real estate full-time in a variety of capacities: She’s a licensed agent, does real estate consulting and coaching, and launched a course in 2022 specifically geared towards investing in small, multi-family properties. She also does some tech consulting part-time.

Bull admits to “kind of blindly falling into real estate.” When she first started investing, “there was no strategy.​ I just had to learn as I went and work through the problems — and there were a lot of problems.”

Here’s how she fine-tuned her investing strategy and went from rookie investor to real estate expert in less than a decade.

Buying her first home during the housing crisis at age 22

Bull graduated debt-free with a degree in marketing. She went to a state school, which lowered tuition, plus she earned scholarships and worked several jobs as a student.

“Knowing that it wasn’t going to be permanent, I basically took the highest-paying job that I could,” said Bull, who worked as a marketing director at an architecture firm for nine months before transitioning to tech marketing. “It wasn’t my dream job or anything. They were just offering me more money than other companies, and that was important to me at the time.”

dana bull

Bull with two of her kids.

Courtesy of Dana Bull

Thanks to savings she had from her high school and college jobs, plus a year of savings from her first full-time gig, Bull had enough to buy a $200,000 condo in Salem in 2012. 

Andrew went in on it with her. They put down 17%, which was “just a random amount,” she admitted, and Bull covered a little more than half of the

down payment

. “We didn’t know what we were doing.”

They moved into the condo and lived there for about 16 months — until 2013. That’s when Bull made her first major mistake: she succumbed to the lifestyle creep mentality of, “I can afford it, so let’s live bigger and better,” she said. “At that time, I felt like I was missing out because all my friends were living in Boston and I decided, ‘I don’t want to live in this condo anymore on the outskirts of the city. I want to be in the city.'”

The couple rented out their condo and moved into a “gorgeous, luxury apartment,” she described. “It was amazing.” 

It was also extremely expensive, she added, and made it difficult, if not impossible, to save a portion of her income. She wasn’t side-tracked for long: “It was a brief nine-month period where I was living larger than I ever have. Then I came back down to earth and got back to smart saving and investing.”

During that time frame, she did gain valuable experience managing tenants for the first time. 

“It was my first time being a landlord,” she noted. “That first year, we had a mouse problem and the water heater blew out, and I was like a deer in the headlights. You don’t know what to do.” 

She navigated the intricacies of managing a property, while also earning passive income for the first time. Rental income from her tenants in the condo covered her mortgage payment completely, plus it left her with about $200 in profit each month, she said. 

Since that first year renting out a property, Bull has learned the importance of building up your contact list of plumbers, electricians, and handymen. 

“There is a person or a specialist out there for every single problem that you’re going to face in this line of work and you just need to figure out who they are,” she said. “Hiring the right people for the job was something that I learned not to skimp on.” 

Shifting from homeowner to investor and building a 22-unit portfolio in 5 years

Up until 2014, Bull hadn’t been thinking about real estate as a path to financial independence, she said: “We were just going through the motions without an underlying game plan.”

She and Andrew did buy an investment property — a two-family house located two streets over from their condo — in 2013. “We weren’t serious investors,” said Bull. “We just sort of bought it because our mentor said it was a good buy. And we had money to spend because both of our careers were taking off.”

The real estate agent who helped Bull find her first condo, Matt, ended up becoming a mentor and instrumental to her success. 

“I think he recognized that I had the work ethic and the earning potential to really make it in the investment side of the business,” she said. “On the tactical level, he didn’t have all the answers but he really gave me the motivation to get started.”

dana bull

Bull and her husband Andrew.

Courtesy of Dana Bull

It was in 2014 when Bull decided to get serious about real estate investing. She and Andrew were out of town one weekend and at a restaurant when she put her plan into motion, she recalled: “We had a napkin and pen, and we thought, ‘What revenue numbers do we feel like we want to hit for this to be worthwhile?'” 

They came up with a specific, six-figure revenue goal and then worked backwards from there, using their napkin as a piece of paper to calculate how many units they’d need based off of current rental rates ($1,500 at the time, said Bull) to hit their number. It came out to 21 units.

“Now I had this goal — something to work towards,” said Bull. “Sure, it can change, but it gave me a target. And then I just went nuts for five years.” 

Between 2014 and 2019, Bull acquired 22 units and exceeded her revenue goal.

Immediately after returning home from her trip, she started searching for investment properties. She found a three-family home in Salem that she closed on in 2014, and eventually moved into with Andrew. 

In 2015, she added two more multi-family properties to her portfolio: a two-family and a three-family. That same year, she and Andrew sold their original condo to help pay for their wedding in September 2015. Some of the profit also ended up going to future investments.

The next property was a three-family home in Boston that needed a lot of work. The couple sold another property (the two-family they purchased in 2013) to help fund renovations. They eventually moved into the top floor and rented out the other units. Rental income covered their mortgage and then some, meaning they were not only living for free in their own home ​​— they were profiting. Eliminating their housing cost allowed them to save aggressively for their next investment properties.

Between 2016 and 2018, Bull added two more four-family homes and another three-family to her portfolio. At that point, she had 22 units across seven buildings. 

The process wasn’t as neat and tidy as it may sound. Scaling up her portfolio in such a short time frame required “a lot of hustle and making sacrifices,” said Bull. “I was heads down, either working, hanging out with friends, sleeping, or eating. I didn’t waste any time.” 

It helped that both she and Andrew were high-earners and didn’t have kids at the time. “We worked a lot, and in high-paying fields,” said Bull, who got her real estate license in 2015 and started working as an agent part-time, while also holding down two, full-time marketing jobs at two different tech companies. She pulled that off by working remotely. “It was easier for me to just go make more money, especially once I was working in real estate and before I had kids. I had the time, the bandwidth, and untapped earning potential.” 

dana bull

Bull and her husband live and invest in Marblehead, Massachusetts.

Courtesy of Dana Bull

Plus, she had a head start on savings, she added: “I actually graduated high school with a lot in savings because I had been working multiple jobs since I was 13 and put the majority of that into a CD, which I leveraged at some point. That gave us a good cushion.”

Still, “money was tight at some points while we were building the portfolio,” said Bull. “Outside of our nine-month stint in the city, we lived very frugally during this time.”

They occasionally problem-solved to come up with capital. “We took out a HELOC on one of our properties and tapped into it one time to help fund another property, and then quickly paid it off with holiday bonuses,” explained Bull. Selling their first two properties also helped, as they rolled a good portion of the profit into other investments.

Bull spent a lot of time in the “acquisition phase,” she said, in order to find the best possible investment properties. “I always went after diamonds in the rough at low price points and was very strategic about upgrades.” 

The seven properties she acquired during those five years were all multi-family homes. She likes this type of investment for a couple of reasons. For starters, “these properties have character,” she said. “You can get creative.” 

Plus, there are financial benefits to investing this way, including “the acquisition discount,” she said. If you buy a three-family, you’ll likely pay less than if you were to go out and buy three separate condos or apartments: “Say you’re buying a three-family that is $900,000. If you were to buy each of those as condos, maybe you’d be paying a total of over $1 million.”

When it comes to maintenance, it can be a lot simpler and cheaper to own a multi-family rather than a couple of single-family homes. 

“If you buy a three-family, when the roof goes out, you only have one roof to replace,” said Bull, who self-managed all of her properties up until she started a family in 2018 and hired a property manager. “You have one driveway to shovel. You have the shared hallways to take care of.”

Achieving financial independence at age 28

In 2018, when Bull had acquired and rented out 22 units, she not only hit her six-figure revenue goal — she achieved financial independence. She was 28 at the time.

“I was so small-minded when I was writing out the revenue goal on a napkin that I wasn’t accounting for the fact that the rents are going to increase,” she said. “And they have increased rapidly over the past decade.”

She’s now bringing in enough income from her real estate portfolio that work is technically optional. 

“I’m still working and taking on projects and clients because it’s fun and I’m excited,” said Bull. “But if I’m ever in a work-related position where I don’t feel valued, I don’t need to stay. I don’t need it.” 

She hasn’t invested in a multi-family property since 2018, but she has bought three single-family homes, including two properties that are next door to each other and one that she and her family are moving into in July 2022. 

If I’m ever in a work-related position where I don’t feel valued, I don’t need to stay. I don’t need it. Real estate investor Dana Bull

Every property that Bull has bought has been an emotional purchase in a way. 

“People always say, ‘Don’t get emotional. It’s an investment.’ I disagree wholeheartedly with that. I think what’s kept me in this business is my passion for what I buy,” she said. “I apply some of the Marie Kondo methodology to my investing: It needs to be a ‘hell yes’ for me to invest in something. For me to buy a $500,000 to $1 million asset, I want to really love it. I want to be super excited about it.” 

Bull recognizes that falling into real estate in her early 20s was a bit of “sheer luck,” but she believes anyone can use real estate investing as a tool to build wealth. 

Her advice to prospective investors is to take action today, whether that means coming up with a savings plan to be able to make a down payment or getting pre-approved and going out and looking at properties. 

“No matter what the conditions are, there’s always risks associated with real estate and you can talk yourself out of it,” said Bull. “I think the biggest mistake that people can make is focusing on what’s happening with the market and trying to time it. There are always going to be desirable things that are going on and undesirable things that are going on in the market.” 

That said, “you really need to put yourself in the center of the equation instead of putting market conditions in the center of the equation.”