Cigar Conversations

I saw him earlier, but now Matt says he’s taking pictures of us. Six Foot five pushing 300 lbs. Maybe he likes to take ‘before’ pictures of his victims.

He’s dressed only in black leather. Matching black bandana on his head. Thanks to his huge dark sunglasses (obviously essential in a dimly-lit room thick with smoke), you can’t tell what he’s looking at.

What on earth am I doing in a cigar bar with a guy like this behind me?

Two Years Ago

It was one of those gorgeous Michigan summers when 88 degrees feels like 107 and the air is more suffocating than a sauna. The day started at the crack of dawn with the incessant crooning of the rooster who has no real purpose. This came after a sleepless night, thanks to the unrelenting humidity. The rooster was quickly followed by the craziness of my 10 nieces and nephews who, combined with my own kids, continued going crazy throughout the day at my in-laws house. While not without joy, a day like this is not what any sane person would consider a vacation. Just before the sun receded enough to let the mosquitoes  drain the last bit of sanity I had, I witnessed it. A moment of pure brilliance. My father-in-law grabbed a lawn chair and a cigar.

My first box of cigars was a wedding present: 25 Cuban Cohibas. I knew nothing about cigars; if I had, I would have guessed they were fakes, but I was cool because I had Cubans. The rare times I would smoke a cigar I would only smoke a Cuban. I liked the idea of a cigar but knew nothing about what makes a cigar great.

There sits my father-in-law smoking, not a cuban, but a cardboard box Grenadier. I want one. Of course it isn’t the cigar itself I want, but the serenity, the moment of quiet rest I am witnessing.

Rest means recuperation: to gain strength, form ideals and make plans. In other words it means a change of occupation, so that you can come back later with a new impetus to your daily job. -St Josemaria Escriva, Furrow 514

Each day of the vacation, about the same time, we enjoyed this ritual together and for probably the first time I bonded with my father-in-law. As the week progressed, my wife would finish getting the last of the kids to bed and she would come and join us and these moments were some of the best of the whole vacation. These moments were the vacation.

When I returned to San Diego the daily cigar ritual faded away but I was hooked on the experience. I wanted to experience rest and (more importantly) the conversations that rest enables.

I slowly started acquiring cigars,

knowing nothing about them but determined this time to actually try and store them properly. I began to learn the difference between cigars. I came to admire the craftsmanship that goes into creating great cigars.

Lucky for me, my wife, having grown up with brilliance of her father, likes cigars as well and she began joining me for the occasional smoke. If you want to have a real conversation with your wife leave the iPhone inside and have a cigar (no, she doesn’t always smoke one). On a recent evening our conversation ranged from how lucky we are to live in San Diego, to explaining my thoughts on the Flor de las Antillas I was smoking, to my annoyance with people wishing their Moms “Happy Birthday” on Facebook, to the hydrangeas my wife recently planted, to people we admire and wanted to be more like. It’s a more substantive hour long conversation than happens in any other setting. I’d argue there is no better way to have a conversation with your wife.

One of my partners at work, Matt, the guy warning me about the leather guy taking pictures of us, had also started developing an interest in cigars after receiving a fully stocked humidor as a wedding gift from his father-in-law. After a few casual smokes together and one of us getting an exciting shipment of cigars (quite possibly our first shipment of Padron 1964’s), we decided we should give smoking at work a shot. So we created Cigar Thursdays.

It was a bold idea.

We were embracing the end of the week with the best way we knew to unwind and relax. Some companies have foosball or pool tables-we had Cigar Thursday.


Putting Cigar Thursdays together was often a hassle. Other men would have given up. Whether it was complaints about the smell in the building, verbal or the (far worse) non-verbal judgement about our lack of productivity, or just the challenges of the once a year rainstorm, it was never easy. It always struck me as odd that in a culture that had come to embrace cigarette breaks, smoking a cigar for 45 minutes once a week was somehow seen as irresponsible. No one understood. One of my friends would frequently harass us, going so far as asking, “What if your daughter was smoking one?” Despite the hassle we also started to realize two things: not only was this a lot of fun, but some of our best brainstorming happened around those cigars. Some of our greatest challenges were resolved over a cigar conversation.

During these conversations we also realized a fundamental disconnect in the way most companies are managed. The notion that employees sitting at their computer all day is somehow productive is absurd. People need to get away from their machines. Even if they are coders, employees should probably walk away and interact with coworkers from time to time. We became galvanized in our determination to build our company in a much more human centered way.

Which brings us back to this business meeting.

At a cigar lounge. With Mr. Leather. Joining Matt and I is our newest employee and friend Justin. The goal of the meeting is to refine our idea about launching a new online brand targeting men. The conversation varies from story pitches, to the Padres, to equitable employee ownership structures and the plight of underpaid Catholic youth ministers. In the course of two hours we flesh out the details of our first twelve feature articles while simultaneously solving several key societal challenges.

Which brings us back to Mr. Leather himself. If you understand cigars you realize he isn’t scary at all. He’s just stopped by to relax amongst the most eclectic mix of guys you’ll ever find in one place. These guys from all walks of life share only one thing: their love of cigars and more importantly the experience smoking them creates.

The next night I’m watching the sunset from a sweeping veranda perched 300’ above the Pacific Ocean, thanks to the gracious invite of one of the nicest people I’ve ever met. The only problem is that she is the only person I know at this party, and the guest list featured some of the most well-heeled and generous people in Southern California. I hate networking. After some polite conversation, individually made 8oz mojitos, a taco bar to die for, and a great speech from the guest of honor I’m ready to look for the exit until the host’s husband announces there will be cigars. Let the conversation begin! As the host later notes: “Those cigar after parties seem to be even more productive than golf course chatter!  John doesn’t play golf so it works out quite well.”

Forget Golf!

In an era where electronic devices have made us so connected that we are uncomfortable in any conversation that might last more than 3 minutes, I invite you to a real conversation, an authentic rest to form ideas and make plans. The greatness of cigars lies not in any particular cigar, though they are important, but in the rest and conversation it creates among the smokers. Come enjoy one of the ‘09 Illusione Le Grandes that arrived yesterday with me! But hurry. They’re going fast.

Click here to learn how to properly enjoy a cigar.