Some things can only be learned the hard way.
As a writer, I wage a lot of wars against a blinking cursor.
I get caught somewhere between what I want to say and what I think people want to hear. And I’m beginning to believe that’s a dangerous intersection.
Some things can only be learned the hard way.
As a writer, I wage a lot of wars against a blinking cursor.
I get caught somewhere between what I want to say and what I think people want to hear. And I’m beginning to believe that’s a dangerous intersection.
Being true to thine own self is becoming a lost art.
We live in a strange time. Anthropic, OpenAI, Google and a growing army of large language models have put an almost incomprehensible amount of knowledge at our fingertips. Ask the right question and, within seconds, you can sound remarkably informed about almost anything.
I know. I use them.
As an aspiring communicator, writer, artist and entrepreneur, though, there’s something about all of this that bothers me.
I wonder if we’re beginning to confuse access to knowledge with understanding.
Because knowing about something and knowing how to do it are two very different things.
Elon Musk once criticized the MBA mentality by saying people can become very good at presentations without actually knowing how things work.
That idea has stuck with me.
With a few keystrokes, all of us can increasingly have the presentation.
But do we know how the dang thing works?
When I first got serious about tobacco, I thought I had a pretty good head start.
For years, I had kept cigar journals. Pages and pages of tasting notes, blends, comparisons, wrappers, regions, ideas, and observations. I read. I studied. I smoked.
Eventually, when the technology got good enough, I digitized much of that library.
Then I started playing.
What happens if you put this wrapper over that binder?
What does Estelí do here?
Could more seco balance this?
What happens if we pull back the ligero?
I refined. Drilled down. Compared. Researched.
Eventually, I had some blends on paper that made a hell of a lot of sense.
Then I went to Nicaragua.
I’ll never forget sitting across from our blender and smoking one of the first cigars built from my ideas.
A few minutes into it, tears started running from my eyes.
Not because I had just experienced some beautiful, poetic moment where years of dreaming had finally become reality.
No.
The dang thing was so spicy I felt like somebody had poured swimming-pool chlorine directly into my sinuses.
My eyes watered.
My nose burned.
And I loved it.
Personally, I’d smoke that cigar all day long.
Commercially?
Not a chance in h-e-double-hockey-sticks.
Maybe one day we’ll release it as some ridiculous Joshua’s Private Reserve and twelve other psychopaths can smoke it with me.
Until then, that cigar taught me something.
There is a chasm between theoretical knowledge and functional knowledge.
You can read about tobacco.
You can catalog tobacco.
You can ask AI about tobacco.
You can memorize growing regions, primings, fermentation techniques, wrappers, binders and fillers.
But eventually somebody has to light the cigar.
And the tobacco gets the final word.
Before my cigar-aficionado aspirations, I spent years touring the country as a musician.
The older I get, the more similarities I see between music and tobacco.
You can put five incredible musicians in a room and still make terrible music.
Everybody can play the right notes.
Everybody can understand theory.
Everybody can own expensive gear.
But sometimes it just doesn't move.
Then you put the right group of people together and something happens that you can't quite explain.
There’s chemistry.
One person leaves space where another fills it. Someone plays behind the beat. Somebody else knows when not to play. Years of mistakes, shitty gigs, broken strings, bad soundchecks and thousands of hours playing an instrument begin communicating without anyone saying a word.
Those are calluses.
And you can't download them.
Tobacco feels remarkably similar.
Every leaf brings something to the room.
Strength. Sweetness. Pepper. Earth. Cream. Combustion. Aroma.
On paper, they might look like the perfect band.
Then you light them up and realize the drummer and bass player hate each other.
Back to the blending table.
There’s another similarity between music and cigars that has kept me awake more nights than I care to admit.
Do you make something people will buy?
Or do you make something you believe in?
Some musicians make music to sell.
Others make music for the art.
I don't think those things have to be mutually exclusive.
I believe there can be a duality in marketable art.
But there’s danger in trying too hard to make something for everybody.
You can sand away every rough edge until there's nothing left to grab onto.
You can follow the formula.
Study what's selling.
Watch what everyone else is doing.
And make the cigar equivalent of a radio single.
Maybe it works.
Maybe it sells like crazy.
Maybe six months later nobody remembers it existed.
That question has followed me into Brolo.
There have been nights when I’ve stared at the ceiling while Kaitlyn sleeps next to me, running through all of it in my head.
Because we know what sells.
We know what retailers are accustomed to.
We know what sizes move.
We know what the safe decisions look like.
And we could make them.
But somewhere along the way, we had to decide whether the goal was simply to make cigars that sell...
or to make Brolo.
The hottest vitola in the cigar business is the toro.
There's a reason for that.
People like them. Retailers sell them. Consumers recognize them. They give you plenty of smoking time without becoming an all-night commitment.
So naturally, our original plan was to launch Brolo in both robusto and toro.
It made sense.
On paper.
Then I kept smoking the cigars.
Robusto.
Toro.
Robusto.
Toro.
Again.
Again.
Again.
And eventually I had to admit something that wasn't particularly convenient for the business plan:
The robustos were better.
Not dramatically.
Not in some way I could put into a spreadsheet.
They just were.
The blends felt tighter. More intentional. More complete.
They sounded like the band playing together instead of five talented musicians playing the same song.
So we changed the plan.
Brolo will launch in robusto.
Not because our research told us robustos were the hottest thing in the market.
They aren't.
Not because it gives us the widest possible audience.
It probably doesn't.
We're doing it because if someone walks into a humidor, spends their hard-earned money on Brolo, cuts the cap and gives us an hour of their life, I want them smoking the best version of what we created.
We only get one first impression.
Why wouldn't we put our best foot forward?
Maybe that's what I love most about cigars.
Tobacco doesn't particularly care how smart you are.
It doesn't care about your research.
It doesn't care about your spreadsheet.
It doesn't care what an algorithm predicted.
And it sure as hell doesn't care about your PowerPoint presentation.
Eventually, you have to put fire to leaf.
Then you find out what you actually know.
There are tools today that can give us more information in ten seconds than generations before us could have gathered in months.
That's incredible.
Use them.
Learn.
Study.
Ask questions.
Fill notebooks.
But don't confuse the map for the road.
At some point, you've got to walk the miles.
You've got to play the shitty gig.
You've got to make the cigar that burns your sinuses out.
You've got to build something that doesn't work.
You've got to change your mind.
You've got to develop some calluses.
Because knowledge might tell you what should work.
Experience teaches you what does.
And somewhere between the two...
maybe you make something worth remembering.
Light UP & Lean In
