3 lessons a landlord learned from his parents that helped him buy 5 properties by age 27

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• John O'Reilly learned many important lessons from watching his parents work hard. 
• He learned the importance of delayed gratification and the limits of trading time for money.
• These lessons stuck with him and helped him save enough to buy five rental properties.

John O'Reilly owned five income-generating properties by the time he was 27 years old. He purchased his very first multifamily home when he was just 23.

He wasn't able to do this because he had access to funds from his parents, or because he had a six-figure income. In fact, he's never made more than $51,000 annually from his job as a motor equipment operator in Syracuse, New York.

He was able to make these purchases thanks to a few key lessons he learned from his parents that helped him understand the value of money at a young age. Now, his real estate investments generate passive income, and he shares various tips on saving and investing on his blog, Live Off Dividends.

Below are three big lessons he learned from his parents that helped him save enough to get started as a landlord. 

1. He learned about delayed gratification 

One of the most important things O'Reilly learned from his family was the idea of delayed gratification. As a kid, he didn't always get what he wanted right away. It didn't mean he couldn't have it, he just had to put in the time and effort to earn it. 

"When I wanted a new video game or toy, I would ask my parents to buy it for me. Of course, sometimes they would oblige and buy it for me. Other times, instead of just buying the game for me, they would give me things to do around the house to earn money. These things included washing their cars, cleaning, mowing the lawn, raking leaves, shoveling snow," O'Reilly told Businss Insider. "Eventually, I stopped asking them to buy me things and rather asked for tasks to earn money."

Often, by the time he completed his chores and was able to afford the original item he wanted, it became less appealing after he realized how much hard work had to go into earning it. This mindset helped him learn to save his money instead of spending it on items that gave him instant gratification but no long-term value. By the time he was 23 years old, he had saved enough funds to make a down payment on his first property. 

2. He learned the limits of trading time for money 

From age 10, O'Reilly accompanied his father, a construction contractor, to various side jobs. It was normal for his dad to work 12-hour days during the week and put in additional hours on weekends. He remembers how long each project took and how physically challenging some of the tasks were. This made him realize that earning money by trading time and effort had its limits. 

He also witnessed his mother work hard from home. As a realtor, she would spend hours on end putting together deals and going the extra mile for her clients. At the age of 22, he got his real estate license and began working with her.

Although the job wasn't as physically demanding as construction, he was surprised by the amount of time that went into closing one deal. These experiences made him realize he didn't want to work his whole life away. 

"I can remember wishing as a child that my mother didn't have to work so much, as it seemed like she was always on the phone with clients," O'Reilly told Insider. 

3. He learned to spend on things that had value 

Since he had to earn his own money through tasks and chores, his parents allowed him to spend it how he liked. This gave him space to make his own mistakes and experience buyer's remorse at a young age.  

"Spending a whole week's paycheck to pay for a new pair of shoes was suddenly not sitting very well with me," O'Reilly said. 

As he got older, some of the financial mistakes got bigger, like purchasing an expensive car that took up a chunk of his salary. When he started investing his money, he realized the opportunity costs associated with purchasing items that had depreciating value. 

This article was originally published in March 2021.