Charlie Munger may be the coolest 90-year-old on the planet.

He’s certainly among the savviest investors of his or possibly any other age.

His partner is a gentleman named Warren Buffett and together Warren and Charlie have built Berkshire Hathaway into a colossus.

Last I checked, a single share of Berkshire was trading at nearly $210,000—that is not a typo.

The market share is over $330 billion, more than GE, way, way more.

So when Charlie talks—which is rare—people listen.

So last week, when he spoke at a meeting at a tiny legal publishing firm owned by Berkshire, people flocked from all over to hear him speak.

What they heard was pure wisdom, delivered with a huge dose of humor.

I didn’t go to the event and sadly I am still saving up to buy a single share.

But I did catch the coverage of the talk in the Wall Street Journal and one Charlie statement jumped off the page and struck me.

Next year, Warren and Charlie will be celebrating their 50^th anniversary together at Berkshire. To honor their golden anniversary, Warren asked Charlie to ponder two questions: “Why did it work? And will it continue?”

Simple questions– on the surface at least –until you start to think about them and realize how deeply you have to delve to figure out why something was successful.

Since this blog is about Delray and Boca, I thought about Warren’s questions and how we might answer them.

So why did Delray and Boca work?
I think we can agree that while both cities are not perfect and must grapple with serious issues, for the most part fair minded people would characterize them as successful cities.

Boca has a famous brand name and is known for its great schools, superior parks, booming economy and manicured neighborhoods. I could go on.

Delray is known for its rocking downtown and its beautiful beach. It also has some interesting cultural assets as does Boca.

But those are symptoms, indicators, outcomes that don’t really answer why these cities have worked? They also aren’t guaranteed to continue, which is interesting to think about because it points out the fact that nothing is permanent. Success is not permanent, and happily neither is failure.

Downtowns can dry up. Big employers can move in and move out. Natural disasters can do damage and great schools can suffer if you take your eye off the blackboard.

So again, why did it work?
Let’s take a look at Delray first.

I think Delray worked because the city was entrepreneurial when it needed to be.

I recently had lunch with a former veteran department head, one in a series of thought provoking lunches that I have come to look forward too. We spoke about how Delray was focused on outcomes more so than process.

The leadership tasked city staff with getting things done (legally and morally of course) which allowed for some creativity and innovation on the staff level.

The results were dramatic: the city came a long way and went from Dull Ray to Delray over a two decade period of time. Problems were solved, solutions were shared and the city earned a reputation for innovation and a style that some called the “Delray way.”

There’s a lot of upside to focusing on outcomes. But there are some downsides as well.

When process is sacrificed, it can sometimes stray a little too far (for instance, you need to bid contracts, you should always engage the public and even flexible zoning should have limits).  So yes, cities and businesses need process, but not at the expense of creativity, fairness and predictability. City planning is more art than science; which is why it was genius in Delray to have something called “conditional use.”

Conditional use has been demonized and misunderstood over the years. It’s been lumped in with waivers and variances and all those other loaded terms, but in reality conditional use is a tool that allows developers (another loaded term) to get something if they give something. As a policymaker, I loved it. Why? Because it allowed us to make good projects happen and it allowed us to kill bad projects.

I liked having that flexibility.

Conditional use was one of the reasons why it happened, Mr. Munger.

I can’t be as opinionated about Boca, I don’t know that city as well. So I would invite readers to opine. But my guess is that Boca placed a high value on business and quality of life, as evidenced by a magnificent parks system, funded in part by a tax district.

As for whether it will continue, that’s up to us and who we elect to lead us.

Stray too far from the winning formula and it probably won’t continue. There are all sorts of examples of places that boomed and then went bust. But if you refuse to innovate and acknowledge change, you’re also dooming yourself.

Regardless, Warren’s questions of his partner Charlie are queries we all should ponder.