My dad once said that my mother could pinch a penny until Lincoln screamed. It was a metaphor but there was more than a seed of truth in what he said. My grandparents lived in the country when I was a child. On long winter nights, they occasionally ran into their neighbors—deer, possums, skunks—and I mean that quite literally. One morning while visiting, I awoke and watched my grandfather weave a length of spindly chicken wire into the grill of his car. The hood was connected to the grill. The grill was connected to the bumper. The whole front end was held together by chicken wire and it was a sight to behold. When he finished, my grandfather stood in front of the gash and gushed. His pock-marked teen-aged Grand Marino was good as new. After all, as he was fond of saying, the purpose of any car was to get you from point-A to point-B in one piece. Speed and performance weren’t even secondary issues. He couldn’t care how it looked or even how it felt. He was a fifth-grade dropout and a welder in multi-patched pants. But he was also a self-made millionaire and man with personality. He influenced everyone that knew him—or so I thought. My family has a pervasive history of thriftiness. But, lately, my brother has made me consider Poor Richard’s old saw: penny wise, pound foolish.

I was the eldest grandchild and education was the one thing my grandfather urged us to splurge on. He regretted his early departure and always suggested that he could have done more, been more, if he’d only studied more. So, I found scholarships and spent family savings to attend a private school. After graduating from Transylvania University in Lexington, Kentucky with degrees in Finance and Psychology, I worked crappy jobs for a year and returned to school. I paid for myself and I went to a state school. After graduating from the University of Kentucky-College of Law, I worked for a corporation and a couple of law firms in Georgia. Then I started my own firm. I saved some money and returned to school once more. After graduating from the Owen Graduate School of Management at Vanderbilt University, a top-ranked and high-priced business school, I could have chased a “cush” corporate job and restocked my coffers—like my family might wish I had—but I didn’t. I stayed with my own firm and re-oriented my practice. Stick with what you know. And what feels comfortable.

Anyone who’s started a business has worried about cash on hand and, more generally, cash flow. Will there ever be enough? Rent grabs an ungodly share. The lights have to stay on. We can turn off the printers at night. But what about the fax? Alright, already. When is enough—enough? Living in Nashville, is it any wonder that I like music? My wife grew up in the radio business and together we have amassed quite a CD collection. But no one listens to CDs any more. Everything’s digital and MP3s are easier to manage and easier to play on computers and iPods (or so I hear—I still don’t have one). Rather than lug CDs to and fro the home and office, last fall, I spent odd hours over several days (weeks) slowly but surely ripping all of our CDs (turning them) into MP3 files on my desktop computer. I could only listen to the music on my PC but, hey, I could listen to any song in my collection at any time with just one flick of the wrist and one click of the mouse. It was nice. But I wanted to hear the music on my stereo, too. So, I surfed the ‘net and found a device made by Griffin Technologies that was USC-compatible and capable of broadcasting the MP3 audio from my PC to my stereo. Score! Life was perfect until I hit that “Del” key one day.

For months or maybe even years—I’m sure my wife would know, if I asked her—I’ve talked about backing up my computer data. The problem was though that there was just so much. Computer memory gets cheaper every day—and therein lays the dilemma. Why spend $100 for 100 gigabytes of storage now when I can wait 6 months, 8 months, or just a year and get 200 gigabytes for the same $100? That’s the way I thought about it. Besides, I was sure that so much of my data was redundant. Too many times, I copied files from this directory to that one and then on again somewhere else. How many backups did I need? Hell, how many could I find? Given enough time, I thought I could pull of the important information from one hard drive or another and piece it all together. I finally broke down and bought an external hard drive like those typically used for backing up files and used it. I backed up photos and videos and suddenly I was out of space. Digital photos and videos are space hogs. But I had a few old, smaller but certainly useful hard drives around. I plugged them into my desktop, played around, and shuffled data here and there. Okay, good enough. The MP3s only took up 40 gigabytes and I could have put them on any hard drive but I opted for the network drive. I wanted access. I wanted to be able to stream the audio on my laptops, too. And I did for awhile. Each time I moved large quantities of data, I consolidated and cleaned up. I thought I was doing myself a favor.

One day, in the midst of consolidating, I discovered that the network drive was behaving badly. For some reason, there were two distinct folders with copies of all of my MP3s. I didn’t need that redundancy—especially not on my network drive—I needed access and I needed capacity. So, I deleted one of the folders. It took a long time. So long, in fact, that I decided to see what was going on. When I checked I discovered that it was doing double-time. Deleting one folder, I was deleting both folders. They were linked—one and the same in two different locations—who knew? I didn’t. Oh, hell. There went my MP3s.

Six months later, I decided once again that I was tired of hauling around CDs. I wanted my music, so I started ripping CDs again. I’m still ripping CDs, in fact. But this time, I’m doing something different.

For the longest time, my parents and I secretly wondered what was wrong with my brother. We pinched pennies. He did not. Well, at least not like we did. We were amazed at his ability to break wide on the wallet and spend money. How could he? What was he thinking? Where? Why? So many questions went unanswered as we watched and waited for some great calamity to befall him. We worried that he might soon be destitute. Okay, maybe we didn’t but we worried about his sanity and our relationship. Was it possible that he had been switched at birth? No, he was the spitting image of my father. Hmm. We never understood. I never understood but I do understand—a bit more, at least—now. My brother is a successful real estate broker. He wheels and deals in large sums every day—for many of us, real estate is the most expensive investment we’ll ever make. Maybe he’s jaded then and large costs for us look like small costs for him. Maybe but that’s not all of it, I’m sure. Piece of mind counts for much and there is where my brother had—to us, unwittingly—always had the advantage.

While my parents and I worried, wondered, and wished how we could save a few more pennies, my brother spent dollars and earned hundreds of dollars for his time and trouble. But we simply didn’t see it. We couldn’t understand. Or to be polite, I should limit my words: I didn’t see it, I didn’t understand. But now I do. When I decided to rip my CDs again, I decided to spend some money and do it right. I had the same CDs, used the same ripping process, but stored differently this time. While my PC read dots and saved them as 0s and 1s, I surfed the web and found new storage. Two external hard drives with 500 gigabytes storage at a good price but more than I wanted to pay. I bit my lip then paid anyway. I lived with buyer’s regret—it’s a feeling I know well—until I held the drives in my hand. I hooked them to my PC and suddenly I was good to go. I had enough space on each of the hard drives to copy every one of my essential files, including the space-hog photos and videos! What a relief! After I backed up all of my files on one drive, I backed that drive up on the other one. My backup was one redundancy. But backing it up was a double redundancy. I wasn’t taking chances. Was I just plain crazy?

As I mentioned before, I’m still ripping the CDs. Twice is enough. I don’t plan on doing it again. And barring some ridiculously unlikely event, I won’t have to. Two hard drives have my back. Who or what has yours? Although I’d like to pretend that everyone would find the bits and pieces of my life and lessons intriguing, I understand that many won’t. The primary lesson I would offer those who have stuck with it and read this far is this: save time, spend money. A secondary lesson I would offer is this: always have a backup. Be successful and you can make more money but you cannot make more time. Don’t be afraid to spend money—just spend it wisely.  Finally, understand that you can’t mentally or physically be or hold on to all things at all times. You have to rely on other people and tools of the trade. Wise people have others who they can fall back on and tools to rely on. Good people and good tools are always a good deal.