Real Estate Investor Who Is Financially Free Shares Strategy Process

  • Dana Bull built a 22-unit real estate portfolio in five years and is now financially independent.
  • She breaks down real estate investing into three phases: acquisition, stabilization, and optimization.
  • Bull spends most of her time in the acquisition phase looking for great deals, focusing on revenue.

When Dana Bull decided to get serious about real estate investing, she started by setting a specific, annual revenue goal.

Then, she worked backwards and calculated how many units she’d need based off of current rental rates in her market (Salem, Massachusetts), which was $1,500 at the time, she said. Her math indicated that she would need to own 21 units in order to hit her six-figure goal. 

Over the next five years, between 2014 and 2019, Bull acquired 22 units across seven multi-family properties and exceeded her revenue goal.

Scaling up her portfolio in such a short time frame required “a lot of hustle and making sacrifices,” said Bull. But now, at 33 years old, Bull is financially independent thanks to her real estate investments. “I was heads down, either working, hanging out with friends, sleeping, or eating. I didn’t waste any time.” 

She still works full-time in real estate in a variety of capacities: She’s a licensed agent, does real estate consulting and coaching, and is still very hands-on when it comes to managing her rental properties.

When teaching clients how to become a successful investor, Bull breaks down the business into three phases: acquisition, stabilization, and optimization.

“You can do this on any timeline,” she said of her three-phase process, noting: “Mine was pretty compressed because I did it in about five years.” 

Whether you’re just starting out and wanting to buy your first investment property or you’re looking to expand your portfolio, here are three phases required to build a successful real estate business, according to Bull.

1. Acquisition 

Bull spent most of her time in the acquisition phase. After all, finding the right investment property in the right area is critical.

You want to start by identifying where you want to invest. Bull prefers to invest locally, though other investors Insider has profiled have had success investing outside of the city or state that they reside in.

“I’ve always invested in areas that I have an intimate knowledge of,” said Bull, who owns properties in Salem, Marblehead, and Boston. “That actually saves a lot of time because I’m never second-guessing the location — and location is one of the most important aspects of what you buy.”

dana bull

Bull and her husband live and invest in Massachusetts.

Courtesy of Dana Bull

When figuring out where to invest, the most important factor to consider is: Do people rent in the area? 

“Look at communities where people are actually renting, because you need renters,” emphasized Bull. “You need tenants. They are the lifeblood of your business. They’re the ones that are paying for everything.”

Keep in mind that the nicest part of town might not necessarily be where renters are looking, she added:  “For a lot of first-time investors, their knee-jerk reaction is, ‘I’m going to buy in the nicest town that I can afford.’ Well, that town may not be primed as a rental community. There might be more single-family homes and people who own.”

Besides finding a market with a strong rental community, you want to look at job opportunities in the area.

“You want people to stay in the community,” said Bull. “I would be very hesitant to invest in an area that just has one big employer. If that company goes under, that’s a problem.” 

Other factors to consider are public transit, access to a downtown area with shops and restaurants, and school systems. 

“People really tend to focus on the property itself, but the first thing you want to do is take a step back and look at the surroundings,” she said. ” Is there anything around the property that you perceive is going to impact its value in a positive or a negative way? Is it next to some unsightly utility plant, and will people view that as a positive or a negative? Because that is something that you can’t change.”

People really tend to focus on the property itself, but the first thing you want to do is take a step back and look at the surroundings. Dana Bull, real estate expert and investor

Once you figure out where you want to buy, you can start exploring actual properties in that area. Bull prefers investing in multi-family homes. These are single buildings that are divided into multiple units to house more than one family living separately, and range from duplexes to triplexes to fourplexes. 

Bull 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 in multi-family properties, including the “acquisition discount,” said Bull. If you buy a multi-family, you’ll likely pay less than if you were to go out and buy two to four separate condos or apartments, she explained: “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. If you buy them all together, you get that discount.”

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. “You have one driveway to shovel. You have the shared hallways to take care of.”

2. Stabilization 

After you acquire an investment property, you move into the stabilization phase, which involves things like renovating and re-leasing the property — anything that will get your property into a position where it’s actually performing and cash-flowing. 

“When it’s ready to be rented and I have money coming in, I consider it stabilized,” said Bull, who could technically live off of her rental income at this point in her life and career. 

However, when exploring or purchasing older properties, there can be a lot of work to do between closing on the property and renting it out. 

“The typical situation is, somebody will have owned the property for 20 or 30 years and they’re just done with it — they’re tired of it and they want to sell,” she explained. “So many of these buildings have deferred maintenance. Maybe it needs a new roof or the units haven’t been fixed up. In some cases, the tenants have been there for a long time paying under-market rent. There’s all this stuff that usually needs to be done at the change in ownership.”

Bull finds herself doing quite a few renovations, as she likes finding properties that “are cosmetically out of date,” she said. “I always went after diamonds in the rough at low price points and was very strategic about upgrades.” Updated flooring and paint jobs, for example, are relatively simple ways to transform a space. 

3. Optimization 

Once your investment is stabilized and cash-flowing, you can move into the final phase: optimization, in which you develop systems and processes to make your business more efficient.

Bull self-managed her properties up until 2018, when she and her husband decided to start a family. At that point, she hired a property manager, but was still involved in the leasing and marketing of her properties. After years of experience being a landlord, she has a specific process when it comes to renting out her units and signing leases. 

dana bull

Bull with two of her kids.

Courtesy of Dana Bull

Before listing anything, she organizes her promotional assets (photos, videos, and floor plans of the unit) into a Dropbox folder that she can send to prospective tenants. She then promotes the listings on Zillow and When leads start coming in, she’ll share the Dropbox link and then set up showings for people who are interested and have been pre-screened. Anyone who’s interested fills out an online application through

She always runs a background check and credit check before signing a lease. She uses the site, which costs about $50 per applicant. When it comes time to sign the lease, she’ll schedule a


call to walk the tenant through the paperwork. Finally, all of the paperwork is signed electronically with Dotloop or DocuSign and saved to Dropbox.

The optimization phase also involves building up your contact list of “key players,” like 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,” said Bull. “Hiring the right people for the job was something that I learned not to skimp on.”

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