Full-Time Investor at 19

I was so hungry for success,” Jordan Dooley started off as he began describing his first foray into real estate investing. “I remember when I realized that real estate investing was actually a possibility, that I could really do it. It lit a fire under me.”

Dooley sounds like a seasoned investor looking back fondly at his first deal, and he is. However, unlike most seasoned real estate investors, Dooley is just barely 20 years old, has been investing for more than a year, and credits real estate for “changing my life in almost every way.”

It may be hard not to smile upon hearing that sort of grandiose statement from a 20-year-old, but Dooley’s story backs up his statement. He originally entered investing almost on a whim after a conversation with his mother, Kimberly Dooley.

“We were riding together in her car and she jokingly said she wished we could be some sort of mother-son power duo,” he recalled. “I said, ‘Why can’t we?’” That could have been where it ended, but Dooley was inspired and began reading the real estate investing course books scattered around his house. Kimberly, herself an experienced real estate investor and agent in addition to being the Ten-X (formerly auction supervisor for the southeastern region of the U.S., had plenty of relevant reading material on hand.

One thing Kimberly did not provide was funding for her son’s first deal, however. Nor did she take on his instruction personally. “He has always believed he could pave his own way,” she said proudly.

Although Dooley certainly could have relied on his family connections to smooth his path, neither he nor his mother were comfortable with that route. Kimberly did make an initial investment with a local real estate coach, but then stepped back. It all worked.

“I did my first deal about 60 days after I started investing,” Dooley recalled. “45 days,” his mother corrected.

Learning Big Lessons Fast

So far, Dooley has favored real estate investing strategies with fast turnarounds, wholesaling or a strategy he refers to as “co-wholesaling” wherein he simply acts as a middle man between the buyer and the seller. “With co-wholesaling, you never even see a property if all goes well, and both strategies require no money down,” he explained.

Since that first deal, Dooley has done three more for a total of four in the roughly 12 months since he got started. “I backed off quite a bit to pursue my real estate license,” he explained. He now is a licensed agent. He is also a full-time college student.

Dooley plans to do “a couple residential deals” now that he has a license under his belt to “solidify my niche as an investor’s agent.” He added, “I want to save up capital to buy my first rental when I’m 24.” In the interim, he said he is using the proceeds from the last year’s deals to pay for his car and “a few suits.” He laughed, “Other than that, I usually just take vacations or save it.”

The other thing Dooley has taken away from his remarkably quick and early start in real estate is the importance of planning and being organized. “These days, I run my life similarly to how I run my business: planning with the end in mind, organization, the importance of a networking, and positive thinking all play a part,” he said. “They’re all important tools that real estate investing has forced on me.”

Real estate investing has given Dooley many tools for success, but he believes that investing is, at its heart, just another effective life tool to be used and shared. “I want to use my knowledge and ability to create wealth as an example to encourage other young adults to believe in themselves and live a passionate life,” he explained.

Pride Doesn’t Always Go with the Sunglasses

As is typical of most successful real estate investors, Dooley recalls one of his worst early moments in real estate as one of his fondest. “My proudest moment was actually a ‘failure.’ I was a day away from closing my second deal and I received a text saying my buyer fell through,” he said.

“I was hurt, but I told myself that I could either let the moment destroy me and all my momentum or define me. I was utterly shocked by my own mental strength in that situation,” he said proudly. Spoiler alert: He went on to do not just one, but three more deals by the end of his first year in the business.

While his proudest moment may be tied to a deal that didn’t happen, Dooley says his favorite deal so far is absolutely his first. “I wanted that deal so badly. I was willing to do anything, and I learned right away that real estate can get messy,” he said. It started when his sellers gave him permission to show their property but forgot to leave a key.

Dooley set the stage: “The buyers are going to show up in five minutes, and uh-oh, no key! I had to find a way inside.” He went on to describe how he tried every door and finally went in through the kitchen window, “breaking my favorite sunglasses” in the process. He unlocked the front door just as the buyers arrived and got the deal done.

“Classic,” he said. Much like the young investor himself.

Categories | Article | Profiles
  • Carole VanSickle Ellis

    Carole VanSickle Ellis serves as the news editor and COO of Self-Directed Investor (SDI) Society, a membership organization dedicated to the needs of self-directed investors interested in alternative investment vehicles, including real estate. Learn more at or reach Carole directly by emailing

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