The following is part two of a three-part story. If you missed part one, well, you should probably start there.


Let me start with some history. Jim’s paternal grandfather came from a middle-class family. He went to a prominent public university and started his own garment manufacturing company in Nashville, Tennessee. He was a good businessman and eventually landed a contract with the United States government to produce garments for the military.  It was quite the windfall. Jim tells me the company’s annual revenues in the 1970s were in the neighborhood of $50 million per year. That’s equivalent to over $270 million in revenue in 2018. Not bad for a sole proprietor. Jim’s dad eventually started a marketing company that partnered with another garment company where he amassed his own small fortune.

On the other side of the family, Jim’s mother’s family had owned a newspaper since the 1860s. In fact, Jim still owns a significant share of the newspaper company, but with the way the print industry has (d)evolved in the last few decades, it certainly isn’t the cash cow it once was. The point is that Jim’s dad had money, and Jim’s mom had money. And they had lots and lots of it.

Thinking back on his childhood, Jim remembers living a lavish lifestyle. For example, he recalls flying on his grandfather’s private airplane to his beach house down in Florida. His dad used to boast that he was the first person in Kentucky to own a corvette. These sorts of things were just normal to Jim. Money was never an object to him. It didn’t need to be, really. In a town of around 30,000 people, if Jim wanted to buy something from the local sporting goods store – or any store, for that matter – all he needed to do was charge it to the company account. Spending money was as easy as signing a receipt.

Despite the lavish lifestyle replete with resources, whether he realized it or not, something was missing. This lack of understanding of how money worked sort of bled into other parts of Jim’s childhood. He was raised with a sense of entitlement. When he wanted something, he’d ask for it until his parents relented and gave him what he wanted. He was never taught the concept of serving others or giving back. Or even being thankful for what he had.

When Jim was in high school, he started receiving $10,000 each year from his grandmother’s estate. She had a large amount of assets and wealth, and as she grew older her financial advisor convinced her to start distributing some of her assets. Now, I’m going to stop here a second and ask you to let your mind wander a little. What would you do with $10,000 as a high school student? Now imagine you got that every year. Some people would save it for college. Some would invest it.

Jim blew it all. Why should I save it? There’s plenty more where that came from. That was Jim’s mentality. Personally, I had a very different upbringing, so when he told me this part, I nearly got up and strangled him. Why was he so flippant with that kind of money? Why wouldn’t he tuck some of that away for the future? Didn’t he understand the importance of saving?

He didn’t. “Nobody ever taught me anything about personal finances. I didn’t think about money like it was a limited resource. I just knew we had money, and others didn’t.” He laughs a little when he tells me the first person to teach him about personal finances was Dave Ramsey. But that was when Jim was in his 40s. Ironically, a few years ago when I was unemployed for four months, Jim was the first person to tell me I needed to start pinching pennies. He eventually learned that lesson.

“Growing up, I guess I just sort of felt like there was something special about me. Like, we had all this money, so that must mean I’m better than other people, in some way. Those aren’t really the right words…I believed I was more than I was. It felt like that was part of my DNA. That’s who I was.”

But here’s an unusual twist. Despite being able to get whatever he wanted, Jim is no stranger to hard work. He’s a super competitive guy, so that drove him to work hard even if didn’t need to. It’s tricky, though, because Jim also tells me that he felt entitled to things. So he felt that if he put in the work, he deserved to get whatever he wanted.

At this point in the story, you may find yourself forming a fairly negative view of Jim. Rich. Spoiled. Bratty. Selfish. Ego-centric. Those are all words that crossed my mind when he told me about his childhood. And he’s the first to admit that it’s true. At the same time, though, I had a hard time believing he was telling me about himself. It seemed like he was talking about a completely different person. And that’s because he was, in a way.

Things started the change slightly after Jim graduated from Vanderbilt University. Rather than working for either of his parents, he decided to get a job at a bank as a way to prove to himself that he didn’t need their help. The problem was that he hated it. He stayed for about four years, and once his point was made, he went to work for his dad, ostensibly to train and take over the company. It was his legacy, after all. About a year later, Jim’s parents divorced. And shortly after that, his dad remarried.

Jim certainly wasn’t crazy about his parents getting divorced, and it was likely fairly hard for him to see his dad remarry so quickly, but things really heated up when Jim’s new boss was his step-mom. He worked for his stepmom for a short time, but eventually, like the short story above suggests, things turned ugly and she fired him.

“She called me out on my entitlement attitude,” Jim explains. “She saw right through it and hated it.” In hindsight, he knows she was right. But at the time, Jim was livid and deeply hurt.

For the first time since he was a teenager, Jim was unemployed. He felt betrayed. Betrayed by his dad and his dad’s new wife. This wasn’t the sort of thing that was supposed to happen to him. It was a shot to his pride, to his ego. He was supposed to take over his dad’s marketing business, but she was going to come in and fire him? And his dad was going to sit back and let that happen?

It was a tough time for Jim. As easy as it is to say you’d use that sort of adversity as motivation to become a better person, it’s just as easy to use it as an excuse to spiral out of control. Jim did neither to its fullest extent, but he dabbled in both. He eventually landed a job with another textile company that produced socks, and it turned out to be his favorite job he’s had in his career, but he harbored a lot of resentment toward his dad and step-mom.

At this point in his life, there was a strong dichotomy. Some things were going well, while others were not. His career started to progress – he bounced around a little, but each position he took led to better pay and greater status. Conversely, he ended up getting divorced from his wife and struggled more and more with alcoholism. He realized he needed some balance in his life. A firmer foundation and maybe a little structure. He decided to volunteer.

Shortly after the divorce, Jim started volunteering with “Big Brothers, Big Sisters”, an organization that provides mentoring for at-risk youth. The staffers there quickly noticed Jim’s energy and drive, so they asked him to sit on the board to help develop their marketing efforts. It was the perfect venue in which to put his competitive juices to work, and he helped grow their volunteer base over 300%. It was one of the first times, if not the first time in his life when Jim decided to use his skills to help someone other than himself.

The message Jim was taught over and over growing up was that wealth and status were the most important things in life. But as his life was starting to fall apart, Jim found something in volunteering that he’d never known before.



Part I: Started From The Top 
Part III: A New Legacy