Monthly Commentary

September 2026

I wish I could remember where I first came across the idea, but it stuck with me: Stop asking people you meet socially what they do for a living. That assumes their work defines them. Instead, ask them what they’re passionate about.

On vacation last week, I fell into my old habits while sitting at an outdoor bar listening to live music and asked the gentleman next to me what he did for work. He told me that he had recently retired but was happy to share with me that he made his money on Pac-Man and cigarettes.

This was a first for me.

Knowing there was some lesson here, and there was, I started asking what became too many follow-up questions. It turned out that back in the early 1980s, at the age of 18, his father had decided to walk away from the business of owning the local bar in town since it wasn’t making any money. As a young man with little direction at the time, he offered to “buy” it from him. I would imagine, like many family transactions, he got a pretty good deal.

The father was happy to step away and pursue something more profitable, and the son was thrilled to have some direction in life.

The gentleman told me that everything was going great until six months after his acquisition, when he was called into the bank for a mandatory meeting with the local branch manager. Confused, since he wasn’t behind on any payments and hadn’t bounced any checks, he still knew the meeting wasn’t optional.

It turned out that the bank president was upset because, unlike his father, most of the cash deposits he was making were in quarters. So many, in fact, that the branch needed to hire a part-time teller just to roll the quarters for a few hours each week.

Surprised by what the agenda became, our young entrepreneur told the manager that he was eager to find a solution to protect the relationship. He confided in the executive that he would be needing more of the bank’s services since he was already in talks with a commercial realtor to secure leases to open two more locations in town.

Now the bank manager was the confused one.

How, as an 18-year-old with no business experience, could you take a failing dive bar, turn it around in six months or less, and already be talking about expansion?

The teenager told him that he simply needed to find a way to increase his margins. With the addition of two Pac-Man video games and a cigarette machine for the patrons, it was almost all profit. The video games required little attention other than the occasional reboot, and the cigarettes were placed in the machine on a consignment basis. He simply had to gather all the quarters and bring them to the bank.

Fast-forward five years. His chain of bars now numbered eight locations, and a much larger equity group offered to pay him a handsome sum, allowing him to walk away with a big check.

He told me that after a short break, he spent the rest of his career as a consultant for restaurants and bars, helping them design their locations to maximize revenue and profits.

The real lesson may be that his father thought he owned a bar, while the son realized he owned a place where people gathered and spent money. He wasn’t particularly attached to where the profits were supposed to come from. He simply paid attention to what his customers wanted and where the margins were.

Too often, we become emotionally attached to the product, service, career, investment, or plan we originally thought would get us where we wanted to go. There’s nothing wrong with having a plan, but there is something to be said for remaining flexible enough to recognize when a better opportunity presents itself.

Sometimes the smartest move isn’t working harder at the original plan. It’s being willing to change the plan.

And occasionally, the better opportunity comes disguised as a pile of quarters.

August 2026

When we are younger, our calendars are filled with weddings and graduations, and as we age there’s a gradual shift toward retirement parties and, unfortunately, funerals. The former celebrate the anticipation of joy and success, while the latter recognize successful careers, as well as lives well lived.

Over the past two weeks, two friends called it a career, sailing off into the sunset to start a life of leisure, each having spent 43 and 40 years, respectively, with their first and only employer. One spent his entire career as a financial advisor, helping others build wealth through saving and investing in order to provide for their families and, hopefully, leave a legacy in the process. There’s no doubt his clients are in a better place because of the impact he had on those decisions.

The second recent retiree never sat in an office or conference room, spending four decades as the first and only Head Tennis Professional for a country club that opened in 1986. Barry did more than teach tennis lessons, though, and although he never bought a stock or mutual fund for a client, he likely had just as much of an impact on the same community as the aforementioned broker.

For those who can remember when late-night television was filled with more jokes and less politics, you may recall a segment David Letterman did frequently called “Stupid Human Tricks.” Barry had one of his own, although there was nothing particularly stupid about it. When someone met Barry for the first time, he shook their hand while repeating their name back to them. By the second encounter, that same new member would be given a nickname—some flattering, others, like mine, not so much—but always funny and in good taste.

Our tennis club has hundreds of members, and when you extend that to their spouses and children, I would imagine that number gets into the thousands. Anthropologist Robin Dunbar famously suggested that the human mind can maintain meaningful social relationships with only about 150 people at a time—a figure that became known as Dunbar’s Number.

Barry apparently never got the memo.

Having met you just once, he would never need to ask your name again.

If you thought of this simply as a “trick” of memorization, then you missed the very lesson Barry was teaching us. It requires a genuine interest in others to learn members’ names, nicknames, and interests while making everyone feel welcome and special.

This skill was on full display multiple times a year when the club sponsored member tournaments. Prior to the first match, Barry would gather all the participants into a very large circle—sometimes as many as 40 or 50 players. In rapid succession, he would start with the player on his left and introduce the entire field to one another, first and last name, without a single mistake—including people he may have met for the first time earlier that morning.

Successful leaders can be found in the boardroom and, in this case, on the tennis courts. But there’s a second lesson in leadership hidden within this success story.

I’m certain both the broker and the tennis pro gave ample notice to their employers prior to their decisions to retire. Even so, how do you replace someone who held the same position for four decades? In most cases, there are just two options: promote from within or hire from outside.

Whereas the members appreciated the longevity of Barry’s tenure, there’s no doubt that many associate tennis professionals came and went over the years, perhaps not seeing a path for progression within the club. Now that the senior-level position is available, the younger teaching professionals understandably see a great opportunity for advancement, should one of them be tapped on the shoulder to succeed a legend.

So, with a deep talent pool of future leaders—no doubt, in part, a result of Barry’s mentorship—why might an organization choose to hire from outside the club to fill the position?

I have seen this dilemma before. The rationale is often that bringing in someone from the outside will infuse new ideas and additional talent into an already successful organization. There can certainly be merit to that thinking. However, what appears logical from an organizational perspective can be perceived very differently by those most directly impacted, whether they are members of a club or clients, employees, and vendors of a business.

And that’s when unexpected turnover can occur, because the loyalty required to “wait your turn” can feel like a gut punch when the eventual message is, “We’re going in another direction.”

Barry’s position has not yet been filled, and there’s no reason to criticize a decision that hasn’t even been made. I’m hopeful that one of the associate pros we’ve learned to appreciate gets promoted, but I’ll embrace whatever decision is made.

After all, I know Barry would want us to make the new Director feel as welcome as he made every one of us feel on the very first day we met him.

Maybe that is the simplest measure of a leader’s legacy: not how long you held the position, but how many people felt like they mattered while you were there.

July 2026

We have two modern taquerias in our small town—or perhaps they’re better described as craft taco restaurants. They are nearly identical in concept, located less than half a mile apart, both on Main Street. When the second one opened just over a year ago, the locals were understandably confused. How could there possibly be enough business to support two such similar establishments?

In fact, the running joke in our town whenever we see an “Opening Soon” sign is whether we’ll be getting another brewpub, wine bar, pizza place, or coffee shop. But two taco joints seemed like one too many.

At first, my wife and I supported both restaurants. We really enjoy Mexican food, and there’s something to be said for chips and salsa arriving at your table in sixty seconds or less. The food is good at both places. I couldn’t grade one above the other when it comes to the bar, the number of televisions showing sports, the background music, or the weekend entertainment. I haven’t closely compared the menus, but the prices seem comparable as well.

From what I understand, both operate under licensing agreements with small chains, with each proprietor also serving as the general manager.

So why do we walk past the first restaurant to reach the newer one every Thursday night for happy hour and dinner?

Energy. Energy alone.

I suppose you could call it atmosphere, but those are different things to me. As I mentioned earlier, I’m not sure there is much difference between the two restaurants when it comes to the physical environment or the amenities they offer.

Although we can probably be categorized as regulars now, our visits weren’t always predictable enough to earn that designation.

The owner’s name is Chris, and he comes over to talk with us every single time we show up. It’s not the obligatory “How’s everything today?” fly-by you see at other restaurants. It’s a genuine conversation, and I always take the opportunity to learn more about him, his business, and his team.

Last week, I told Chris how much we appreciate that his employees know both of us by name. Even though they wear name tags, I think they knew our names before we memorized theirs. I also told him I was impressed that, in such a high-turnover industry, he had almost exactly the same staff on the restaurant’s one-year anniversary that he had on opening day.

Chris politely corrected me.

Most of his staff had been with him for years, he explained. They had simply followed him from the other restaurants he managed before he was fortunate enough to own a location of his own.

They seem to wear permanent smiles throughout their shifts. They enjoy playful banter with one another, with their customers, and with the owner himself.

Recently, we sat at the bar next to a couple who handed Chris a pink box with a scripted logo on top. Curious, I asked what it was.

With a thick New York accent, the gentleman to my left gladly informed me that it was a cheesecake from a famous bakery in Brooklyn. He had flown back that afternoon and couldn’t wait to bring this small piece of his past to Chris and his team to enjoy.

Since I’m also from the New York metropolitan area, we spent the next fifteen minutes discussing pizza, bagels, hot dogs, and why a bacon, egg, and cheese sandwich somehow always tastes better when it’s made in the Bronx.

Oh, and I had a couple of drinks and a burrito bowl for dinner. Or at least that’s what I think I had. I wasn’t really there for the food.

That’s the thing about the intangibles that often determine whether a business succeeds. The food may bring someone through the door once, but the energy makes people walk past one restaurant to reach another.

Perhaps that’s why we keep walking the extra half mile. We aren’t simply choosing between two places that serve tacos. We’re choosing the place where the employees seem happy to see one another, the owner seems happy to see us, and a customer returning from New York thinks to bring back a cheesecake for the entire team.

Some businesses serve food. Others create a place where people feel they belong.