How a single mom went from making $20k a year as waitress to building a real estate empire

At a very young age, Ashley Hamilton started showing interest in the real estate business. Her interest was pricked by a real estate show that she usually watched on TV. But she hailed from a poor family, which meant that her chances in life were somehow limited.

Her parents were unemployed and so they were on government assistance while living in Detroit. Nonetheless, Hamilton said she had a “perfect childhood” as it never occurred to her at any point during her formative years that she didn’t get the luxuries that others had.

“I just kind of grew up that way. I knew that early on that I wanted to be independent and that I wanted to be an entrepreneur, but I kind of did not have anybody to look up to or anybody to ask for help,” she told the BiggerPockets podcast.

According to her, her goal was to become a millionaire by the age of 30, retire and enjoy the fruit of her labor. For instance, she intended to acquire 10 properties and then sell them off for $100,000 when she turns 30, and that would have fetched her $1 million.

But it didn’t materialize as she planned. To set her ambition in motion, she needed to eliminate her biggest expense, which is rent. “I was paying $700 a month in rent at 22. I had two kids, single parent,” she said.

At the time, she was working as a waitress, which was bringing in $20,000 a year. Therefore, many people said she couldn’t get started because she didn’t have money. “That is everybody’s biggest thing. Well, I did not have a mother who I can borrow $10,000 from. I did not have a 401K, I did not have a line of credit I can get. I had to find some way,” she said.

However, not having money worked to Hamilton’s advantage. She got a tax refund every year. Making $20,000 a year and having two children was able to earn her five to $6,000 tax return. Her first tax return was in 2009.

“When I got the tax return for $6,000 I was able to slowly save up the rest of the money for the clothes and I did not need much but probably like another thousand dollars to add with it,” she explained. Hamilton would go on to purchase her first property.

“I went ahead and bought the property. It was $6,300 to close and made it an extra $1,000. Once I got the property, I needed about $3,000 to $4,000 worth of work. I saved up for that and it took me about five months to get that to do the work.

“But basically, I just wanted the house to be livable. It was for me and my kids, but I did not have to have granite countertops or anything that. Basically, I went on craigslist, hired a contractor to paint the house. Of course, he ripped me off and only painted it halfway, painted over wallpaper, whatever.”

The young investor now has a portfolio of 24 rentals and five vacant lots. Also, she has decided to quit her part-time banker teller job and pursue full-time entrepreneurship. Despite promising real estate business and other ventures, Ashley decided to work 20 hours a week to have a steady source of W-2 income.

“I finally did it. This has been well overdue. I know a lot of people ask me why do I even still work there. But the truth is I really enjoyed what I did. I was also recycling wealth and using a ton of leverage last year,” Hamilton shared on Instagram.

“When you use any of these real estate strategies like Brrrr, house hack, or buy and hold, most of the time you’re going to need some kind of W-2 income to be approved for loans. That’s why a lot of people get stuck after just one or two deals. I know everybody says they want to hurry up and quit their job. But unfortunately, it’s just not smart especially in the beginning,” she added.