Millennial Finds Out His Boomer Parents Are Millionaires After Being Forced To 'Bootstrap' His Way Through Life

He was shocked at discovering that his parents had the ability to financially help him and his siblings through rough times.

dad and son having discussion on couch at home PLotulitStocker / Shutterstock

A millennial admitted that he was shocked after discovering the actual amount of money his parents had during his life despite thinking differently. 

Posting to the subreddit "r/BoomersBeingFools," he claimed that he'd always known his parents had done fine financially but was flabbergasted after going through some of their tax documents and realizing that they'd withheld a lot of information about how much money they'd made.


He found out his boomer parents were actually millionaires after having to 'bootstrap' his way through life.

In his Reddit post, he explained that during the '90s, his parents did pretty well for themselves. They owned quite a large farm, and his dad had a couple of businesses, but he and his siblings were raised not to expect a lot of material possessions. 

As a child, he was forced to work and earn his own money so that he could buy the brands of clothes he actually wanted.

seniors happy with their finances Robert Kneschke / Canva Pro


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"I joined the Army for the GI Bill in the early '00s and was deployed. I joined for the GI Bill because I was told there would be no educational help from them unless I lived at home, paid rent, and went to the local community college," he recalled. Despite his and his siblings' struggles through school, the 2008 recession, familial struggles, and the pandemic, their parents never offered them financial support.

Instead of trying to help, his parents would send $100 Walmart gift cards as compensation and even cut his sister off when she got pregnant outside of marriage. At the time, she was 27 and living with her boyfriend of 2 years. They all managed to survive, and now, as adults, they make a good amount of money themselves.

Now, in his 40s, he found some of his parents' tax documents while helping them clean out their garage. He noticed their income had been $2 million yearly from 1995 to 2001. They eventually sold their farm and all of the accompanying equipment for millions when they retired in 2002. 


man looking through documents holding a cup of coffee DAPA Images / Canva Pro

"They own two rental homes and their own house outright. And that’s just what I know about; they have talked about their annuities and investments in passing. I knew they were doing ok, but they have always talked like they were on the brink of losing everything."

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To make matters worse, in 2023, his parents bought and bragged about their six-figure RV.

He claimed that after his parents bought their RV, they endlessly bragged about it as if they hadn't just spent their inheritance on it. Not only were they leaving nothing for them, but also for their grandkids.

While it's important to raise your children to be self-sufficient and learn that they need to earn their own living, it's equally crucial to find a balance between teaching independence without allowing them to struggle if they don't have to. This whole "American Dream" of working until you drop and having to pull yourself up by your bootstraps is nothing but an outdated and harmful belief.

seniors smiling in front of their RV DAPA Images / Canva Pro


In reality, there are endless obstacles and roadblocks that change and often get difficult from generation to generation. There are recessions, the pandemic, inflation, the housing crisis, and the rising cost of basic living necessities, like groceries and rent. What was once affordable and easy for boomers has become a challenge for the generations preceding them. 

It seems to be a Westernized idea that once a child turns 18, they're on their own: no support, no help, and no safe haven from their parents. 

This expectation not only overlooks the varied experiences that happen but disregards the fundamental aspect of parenthood — providing emotional, financial, and practical support for their children, especially when they desperately need it. Sure, this man's parents didn't have to give their kids all of their millions, but during their moments of need, they were made to believe that their parents couldn't help when that wasn't the case.


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Nia Tipton is a Chicago-based entertainment, news, and lifestyle writer whose work delves into modern-day issues and experiences.