It’s Tuesday morning. I’m already inside my favorite cigar bar: a cavernous 80-seat lounge in Milwaukee that opens at 9am.
I grab a spot on a couch, like I usually do, and wait for Father Kevin to walk in. He always jokes around, asking if I want to make a confession. I have to remind him that there’s a time and a place for that. This is neither. And today, more than usual, our typical banter was about to give way to a deeper conversation.
It's just the two of us this morning. Then, this big guy walks in. He's huge, and he's dressed to the nines in a well-coordinated outfit. The place is basically empty, but he walks up and asks, “Do you mind if I sit with you?”
“Absolutely. Come sit,” I say to him. We're sitting, talking, and the guy starts telling us about himself.
It turns out he’s a pastor. He used to be in prison, but finished his time, found religion, and is ministering.
Who walks in next? A hippie from Colorado. He’s like, “Hey, man, do you mind if I join, too?” I'm thinking to myself, what is going on here? A Catholic priest, a born-again Baptist minister, a hippie from Colorado, and a businessman? It sounds like the start of a bad joke, but I move over, and he sits down next to me.
Soon enough, we're talking about all sorts of things, with four very divergent viewpoints.
There are always those points in time where you're kind of scared to admit who you are or if you have a political or a social belief. That morning, we were all saying what we believed, knowing that no one's going to look at any of us differently, because everyone’s actually authentically listening. I'm confident that I said things to the guy from Colorado that he didn't agree with, but he listened.
It’s so different from listening for the sake of humoring someone. No one was tallying up talking points or getting ready to belittle someone with a zingy one liner. Oftentimes we do this as humans. When we're listening, we're kind of already formulating a response, which means we’re not really listening. We’re not really absorbing the information and understanding it.
But in the cigar room, everyone's listening.
Every conversation that we had during these two hours together culminated with the same points of agreement: we’re all in this together and we need to be leaving things better than we found them.
I originally started going to cigar bars because I enjoy cigars. I like fine tobacco. But then it morphed into a desire to find that secret spot. I like finding those cigar lounges where I can sit down and know that there'll be a conversation that will be truly enjoyable.
When I go to industry events, there are certain expectations: maximizing your time with attendees; interacting with your employees – all the typical stuff, which I try to do as much as possible. You're running fast and you're working hard.
But my staff always knows that there's going to be a moment where I’m going to go off to the cigar bar.
In the cigar room, the world around you continues to go, but you stop. There's this break. You sit down. Maybe you get a cocktail, maybe an iced tea, and you have a cigar.
And then, I guarantee you, within 10 minutes, a conversation begins.
It's really kind of fascinating. The filters go away. The conversations are truly organic. All that media that you choose to consume, all the mediums of communication, they’re all gone.
Let's be honest, the circles where we interact, they’re mostly the same. You’re reluctant to break the circuit of your favorite restaurants. The industry conferences feel repetitive. The social events, well, they start to look alike.
In the cigar room, it's anybody. That's what makes them so enjoyable. You have these edifying conversations with people, from all walks of life. You need to truly think about what you want to say, you need to listen, and you need to formulate an opinion, whether you’re in agreement or not. It’s old school.
To find unique perspectives, you’ve got to seek out unique places. It’s a lesson I learned while attending a series of industry events.
I was at an event in Baltimore and a long-time industry salesperson introduced me to a well-known industry journalist who covered the industry for a major cable news network. After two or three minutes of interaction, we walked away.
I thanked the salesperson for the introduction and that’s when he said, “I forgot to mention to you, the reason why I wanted to introduce you to the journalist is that he also enjoys cigars.”
I was like, “Well, that would have been helpful information during our first interaction.” But that was it.
Six months later, I was at a conference in San Diego. I saw the journalist walking the floor. I mentioned that we shared a bond in both enjoying cigars and invited him to grab one with me over lunch in the Gaslamp District.
I pulled up my phone and showed him a couple of locations I was looking at. The places I had highlighted looked good. They were highly reviewed. They looked like they had a great selection of cigars.
But the journalist told me to skip all the spots I was looking at and suggested I try another place instead.
I pulled it up on my phone. It was off the beaten path. It didn’t even have a website.
“Trust me,” he said. “It’s the best spot in San Diego to have a cigar.” And that was it.
I took him – a man I’d met one time, for two minutes – at his word. I gave it a shot and walked there.
As I got closer to the place, I had my doubts. It’s very nondescript. There's a small sign hanging off the wall. Then, there are these old, used, tattered camping chairs out front, and there’s a gentleman completely passed out in one of them with his chin on his chest.
There's a woman at the counter. On the racks are four-year-old magazines for sale. There are a few lighters. I walk into the humidor and it’s about half full. It’s got a good selection of cigars, but it’s definitely not what I'm used to.
I grabbed a cigar that I liked and purchased it. I asked the woman, “Do you have bottles of water or anything for sale?” It was sunny out and I was craving iced tea.
She said, “No, we don't have any of that here, but if you want, there's a beef jerky shop 200 feet away where you can buy bottles of water. That's also where the public bathrooms are, if you need them.”
Alright, great, I’m thinking to myself.
I grab the cigar. I cut it. I light it. I sit down across from the guy asleep at the doorway.
That's when I realized how special this place was.
There’s this unobstructed view of the bay. It’s a beautiful, quiet setting.
Immediately, I was reminded of how the cigar lounge pauses time. The people around me were busy. They were walking or shopping. But here I was, sitting next to a guy that's asleep, and watching the world go by.
As I'm enjoying my cigar, the journalist walks up. He had found some time to smoke a cigar with me.
He got a cigar, lit it, sat down and woke up the guy who was sleeping in the chair next to me – who was the shop’s owner.
We just sat there and listened to the shop owner tell us his view of the world. Five hundred feet away was the conference center with hundreds, if not thousands of wealth management professionals, buzzing around working. Here I was with the opportunity to take a 45-minute break to enjoy a cigar between sessions.
The three of us had a really awesome conversation. What makes it even more special is that other individuals from our conference were sneaking off to the same location. They knew about this magic gem in San Diego.
Even when the conversation shifted to the RIA industry, it was unfiltered, with divergent viewpoints. We all just kind of talked and it really broke down some of those preconceived boundaries about who you can interact with, or who's higher up in the echelon. Sometimes a change of scenery – and a change of speeds – is all it takes to inspire a new mindset.
Not long ago, a consulting job brought me down to Naples, Florida, where I was helping a large RIA with some work.
One of the RIA owners knew that I enjoyed cigars, so we brought some to the Italian restaurant where we had dinner. Not wanting to bother anyone who was eating, we asked the owner if we could get a table outside to have our cigars.
He's like, “Yeah, absolutely. We can set that up for you, but why don't you just enjoy dinner inside and after you're done, I'll put you at another table to enjoy the cigar.” He was insistent.
We eat and by the time we're wrapping up, the owner comes back up and asks us if we’re ready. He had set up a table for us out back.
It was a little surprising. He could’ve been setting us up right next to the dumpster. But the three of us followed the owner anyway.
We walked into the kitchen. We could see the service line and all the cooks. They didn't even bat an eye, as if three guys in suits didn't even register.
They knew where we were going.
We walked through a few more rooms, past the freezers, out the back door, and outside.
It all felt very clandestine, but here we were in a beautiful backdoor spot, hidden behind a nice fence hung with string lights. In front of us was a large table with a few ashtrays and a variety of chairs.
We brought our own cigars, but the owner offered some of his. We sat down. The owner sent a server to take our drink orders.
After about a half hour of talking, just the three of us, more people started trickling in. Some people were by themselves. There were a few small groups. But before long there were somewhere around seven or eight of us out back.
People didn’t just come in and sit with their groups. Everyone was moving chairs as they filled up the table. They wanted to diversify, to foster conversation.
I sat next to a guy who owns a thousand-acre buffalo ranch in Texas. He worked for presidential administrations and the Bureau of Land Management. He's an inventor. Next to him were several successful business owners.
At one point, the restaurant owner sat down and smoked a cigar. They kept bringing out wine and bourbon.
It was magical.
It was midnight and 80 degrees outside. There are string lights. Drinks. Cigars. It was surreal.
Through all of this, everyone had completely divergent viewpoints. You name the topic: political, socioeconomic, global affairs. It was all discussed and we didn't agree on many things.
But it was never contentious. The tone never changed. Attitudes didn’t emerge.
We had an edifying conversation. We enjoyed each other's company. We talked about things. We listened to different viewpoints.
That night in Naples, in the backlot of an Italian restaurant, was a special one. It was the most impromptu cigar lounge.
Then all of a sudden, we all just left. We went to our cars, went our own separate ways. I’ll probably never see those people again.
The greater lesson that cigars have taught me is that if you're going to experience something different – whether it’s a topic of conversation, new information, a business opportunity, or even a different culture – you need to seek it out. You need to find it. You need to leave your comfort zones, your typical circles, and to be welcoming, too.
These experiences were completely organic. Sometimes it’s not even about the cigar. I’ve gone to cigar lounges with people who don’t even smoke, and they walk away with a new perspective and respect for someone they just met.
Right now, we're in this contentious time in the world, where it feels like everyone's just anxious. We’re on pins and needles.
When you get those special moments, the cigar room moments, where the barriers break down and where you're subjected to other people's opinions, you have to listen.
The person who’s talking is sitting right there, across from you. They're not hiding behind a social media handle or emailing, or whatever. They're right there and they're human. They have the right to their opinion, and they have the right to their viewpoint because of their experiences.
It really changes your perspective on everything. Quite frankly, it gives you hope, too.
You begin to realize that having those conversations shows that we're not all that different. It's just different viewpoints and different walks of life that change the way you express something, or your expectations.
We need to be willing to slide down the couch and let someone squeeze in, to be open to conversation. It’s the only way we’ll be able to have these really amazing conversations, with people we’d never imagine.
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