The Road to Hell is Paved with Good Intentions
- The Cigar Profit
- Sep 16
- 11 min read
Why most cigar companies lose by following the crowd
9/16/25 | Jonathan Lipson | The Cigar Profit | Schedule An Exploratory Call
Failure is the Default
This industry isn’t built on easy wins. It’s hard. Unforgiving. And more often than not, brutal to the very people who give it everything they’ve got.
In business, the odds are stacked against you. In premium cigars, the graveyard of failed brands makes it plain.
Once upon a time, the industry had a bible - Perelman’s Pocket Cyclopedia of Cigars. Every brand was a chapter, every sub-brand a verse.
From its first issue in 1995 to its last in 2009, the faithful flipped through those pages.
The Old Testament was the classics - domestic brands with Cuban names, Habanos themselves, family lines that seemed eternal.
The New Testament was every upstart claiming they’d be the next Fuente or Padrón.
But flip enough pages and the story read less like scripture and more like a Greek tragedy…
Too many Icaruses. Too many Oedipuses. Too many Ajaxs. Reduced to footnotes: forgotten logos, forgotten stories, forgotten ambitions.
The last edition logged 1,360 brands.
Sixteen years later, who knows how many still exist?
And here’s the twist: the guide itself went extinct. Failed brands don’t even get remembered in print anymore. They just vanish into the abyss, as if they never existed.
That’s not legacy. That’s oblivion.
Failure is the rule. Survival is the exception. And most of those failures didn’t come from laziness. They came from passion.
Owners mortgaged homes, emptied savings, poured themselves into building a brand.
They had good intentions… And the road to hell in this business is paved with them.
Because good intentions don’t pay invoices, they don’t drive re-orders, and they don’t keep the lights on.
The business world is a classroom. The cost of tuition – not cheap. If you don’t learn fast and own the misses, every mistake is tuition out the window.
And if you don’t want your name, and your money, fading into oblivion, pay attention-
You need more than romance in this industry. Because every one of us is selling the same thing: rolled-up dead leaves.
Rolled Leaves and False Differentiators
Strip away the romance and cigars are an agricultural product. Tobacco harvested, cured, fermented and rolled. That’s the baseline.
Every year at PCA or InterTabac you hear the same tired chorus: “This is our newest blend,” “We updated the packaging to stand out,” “This cigar tells a story customers will love.”
It reads like a template, not a plan. Those lines aren’t innovation. They’re camouflage. And camouflage doesn’t sell when every booth is saying the same thing.
Blending matters. Packaging matters. Storytelling matters. But when those are your only plays, you’re not innovating, you’re recycling.
Retailers know it. Consumers know it. Walk into any humidor and you’ll see the proof: 600 SKUs fighting for inches of space, most gathering dust.
True innovation is when the consumer knows why to pick your rolled leaves again and again when they could grab one of a thousand others. The cigar is the ticket to the game.
The system you build around it is what keeps you in.
I’ve watched it play out in real time. Saturday afternoon in a mid-sized humidor: a buyer scans rows of bands, trips over tongue-twister names, then asks the staff for something familiar.
If your rep left nothing behind but a story and a sample, you lose that moment. If you left a reason the staff can repeat in one breath: body, core notes, price, why it exists - you win.
I’ve seen shops carry fifteen facings from one brand and only three move. Those three had names buyers remember, profiles staff could explain and prices that made sense. The rest, tuition.
Operators who accept that truth stop launching for ego and start launching for velocity. That’s how you earn reorders instead of buying a clearance table.
And if you think this is just a product problem, think again, because love of the craft is often the very thing that blinds operators next.
The Love Affair Trap
Most cigar brands start as love stories: first trips to factories, father son rituals, lounge moments that felt like royalty.
That pull is powerful, but it blinds you.
The market doesn’t share your sentiment. It doesn’t care about your pilgrimage to Estelí or the soul you poured into your blend. It cares about reliability, consistency and value.
That’s why corporations rule. General Cigar, Altadis, Swisher, Davidoff started from passion too - then they structured it, scaled it and ran the playbook.
Predictability wasn’t the opposite of passion, it was passion disciplined and delivered every time at a price that makes sense. Consumers reward that.
Same story in whiskey, watches, cars. For every boutique darling clawing for relevance, there’s a giant dominating by giving the majority what they want: stability and scale.
Pet projects might win cult fans, but conglomerates own the market.
That’s why the love affair trap is lethal.
You believe your own appetite is enough to move the consumer. But the numbers don’t lie.
Most smokers want ‘vanilla’, affordable, consistent, reliable.
Emotion without discipline burns hot and fast, then leaves you empty.
I track a lot of brands and founders in this space. The pattern is consistent. The outfits that last build to demand: clear profile, a name buyers repeat, a price that makes sense and a marketing drumbeat that never goes quiet.
The ones that fade build shrines to themselves and then wonder why no one shows up.
Your devotion to the craft isn’t the problem. The problem is mistaking that devotion for the product.
The product is what buyers come back for. That takes humility, not poetry.
And when sentiment blinds you, the first thing you cut or dismiss is often the very thing that would save you: marketing.
Marketing as Investment, Not Expense
Marketing isn’t decoration. It’s the engine that creates demand. Positioning, story, channels, cadence, measurement. It’s what turns boxes into names buyers ask for.
Too many owners fool themselves. They think blending talent makes them brand builders. It doesn’t.
You can roll the best cigar in the room, but if your band looks like clip art and your ads look like they were made in MS Paint, nobody remembers you.
Good marketing costs money. Bad marketing costs more.
I hear it every week: “Marketing is expensive. You’re expensive. How do I know it’ll work?”
I get it.
But results don’t come free.
I led the marketing for a brand with one of the highest grossing exits in recent cigar history.
That wasn’t luck. It was campaigns, partnerships, media hits and programs that kept the brand top of mind. Marketing compounds.
If Coca-Cola, the most recognized brand on earth, still spends billions every year, what makes you think you can skip it?
And here’s the fact most won’t admit: machismo drives this industry. Owners surround themselves with yes-men. Bigger booths, bigger entourages, bigger egos. That’s not business, it’s theater.
I said this on Light'em Up Lounge with Reinhard Pohorec: consultants exist in the cigar industry, but most stay quiet because it doesn’t fit the old school narrative.
The proof: I got blindsided when Reinhard announced his consultant status during our discussion.
The truth is simple: Dollar for dollar, consultants are the better value.
We bring experience, we say no, we point out blind spots. If you can’t afford a six-figure CMO with perks, hire a fractional one.
You get what you need without tying yourself to overhead you can’t sustain.
So what does real marketing work look like week to week?
A drumbeat that never goes quiet, retailer programs that make reorders the default, a channel mix that fits how your buyer actually shops, content that explains value in plain language, training decks for staff, launch checklists that force focus and a 90-day review that ties spend to outcomes: unaided recall lift, reorder rate, CAC (customer acquisition cost) payback, turns, contribution after freight. That is investment, not voodoo.
And let’s be real:
I don’t have every answer. Nobody does.
But I’ve got receipts.
When I don’t know, I test. When I need firepower, I bring in partners who deliver.
That’s what clients buy with The Cigar Profit: systems that cut risk and raise velocity.
So the question isn’t whether marketing is expensive. The question is how much it’s costing you not to have it.
And that’s before we even talk about the most basic requirement, knowing your market.
Know Your Market (Hint – It’s America)
If you’re reading this, you’re probably not part of Habanos leadership.
Which means the biggest premium cigar market in the world is the United States.
That’s the buyer.
And facts don’t care about feelings.
What comes next - history, demographics, case studies, data - may bruise egos. If that’s too much, stop reading now.
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If you’re not speaking directly to American buyers in their language, you’re already losing.
Too many brands forget who pays the bills. Line extensions no one can pronounce. Boxes that look like art projects. Websites that crash.
That’s not heritage. It’s friction.
And friction kills sales.
Back in the 90s Boom, you could get away with it. Ride the trend train, even if you didn’t know how you got on. The shortcut was simple: Cigars = Cuba = Spanish.
So everyone was “Don Somebody.” Every other cigar started with an El or a La. Didn’t matter if it meant anything. If it sounded cigar-ish, it sold.
But hype without knowledge is dead.
Today’s buyer Googles you before they light up. They can smell the mierda before the cellophane’s off.
If you’re of Latin descent - own it if you want to. Put your roots on the line – if you’re up for it. Authenticity resonates.
But make it easy to buy. Translate it. Lead with English.
Don’t make consumers stumble at the counter.
If you’re not of Latin descent, have little-to-no frame of reference, or at the very least a ‘why- Don’t fake it.
A cigar-ish sounding name with no provenance isn’t authentic.
I said it in ‘Positioning in the Age of Exposure’ – your customers are just waiting to find a counterfeit.
And here’s the fact most won’t admit: the brand isn’t about you. It’s about the consumer.
Celebrate heritage if you have it. Honor what’s real if you don’t. And make sure the story resonates with the people actually paying for the product.
Here's an example of when branding doesn't go as plannned-
Look at Foundation’s launch of El Güegüense. Strong cigar. Strong lore.
But the market couldn’t pronounce it. Couldn’t remember it. Couldn’t search it.
Eventually, it became The Wise Man. That rebrand cost packaging, SEO, education, and trust.
Confusion is expensive.
The rule is simple: start with the consumer.
If they can’t say it, repeat it, or recall it a week later - you’re not building a brand.
You’re building an obstacle course.
And don’t think well-established superbrands and conglomerates get a pass. Brand Equity might carry you today. But consumer bases evolve.
Friction eventually kills - even giants.
I didn’t make the rules. I just keep score.
The hard truth – Authenticity sells. English sells.
Bullshit doesn’t.
And if you still doubt it? Analytics will show what passion and pretense try to hide.
The Case for Analytics
Most brands run on gut calls and pride. A blender likes how something smokes, so it gets boxed. A partner falls for a story, so it gets printed. A retailer orders from a buddy, so it’s stocked. Six months later, the boxes are still on the shelf.
That’s not strategy, it’s guesswork.
Analytics cut through the noise. They don’t kill creativity, they keep it from bleeding you dry. They show you what the buyer actually wants, not what you hope they want.
That’s why I’ve partnered with Cigar Sense. I’d rather know than guess. Their platform turns consumer input into direction. It shows you where to play and where to walk away.
Data isn’t just a brake. It’s an engine.
In previous lives, long before I aligned with Cigar Sense, I was the guy in the room playing devil’s advocate. I didn’t know then that I would ever partner with them, but I had a similar thought process –
Stats and sentiment reports went to every meeting. Because feelings don’t move boxes.
Nobody likes being told they’re wrong, but numbers don’t lie, customer feedback doesn’t lie, sales don’t lie.
Receipts beat feelings every time.
Here’s the real question: if the data says buyers want medium body and you keep pushing heavy spice bombs because you like them, who are you building for?
If your new cigar steals from your own best seller instead of growing share, why launch it?
If 70 percent of accounts don’t reorder inside two months, is it the retailer or is it the cigar?
Other industries already get this. Spirits test before scaling. Fashion runs micro drops. Cars hold focus groups.
Premium cigars are the holdout, still pretending instinct beats information.
Analytics don’t tell you what to love. They tell you what to stop.
They keep you from lighting money on fire and sometimes reveal gaps before anyone else sees them. That’s how you play offense.
And if you think this is only about statistics, look at what happens next when the rubber meets the register.
The next test isn’t taste, it’s payback. Let’s talk about what the money says.
ROI or Sunk Cost
Money doesn’t care about intentions. It cares about return.
Either your spend multiplies or it drains you.
Too many owners treat spending like a victory lap. New bands, more reps, a record-breaking run, none of it proves success if the dollars don’t cycle back.
That’s not investment. That’s tuition. And expensive tuition at that.
Investments show up in reorders and velocity. Sunk costs show up as dead stock and excuses.
The trap is ego.
Owners double down rather than admit they got it wrong. They say brand building takes time or retailers don’t get it yet. Meanwhile, the numbers don’t lie.
Inventory stalls. Cash chokes.
Businesses suffocate.
Smart operators treat ROI as the scoreboard.
If a campaign doesn’t earn, they cut it. If a trip doesn’t move boxes, they stop funding it. If a SKU doesn’t pull weight, they retire it.
They don’t chase ego. They chase return.
I’ve seen owners pour money into cigar‑media buys and social promotions that looked great online but never moved product.
Six months later they were discounting hits that never hit. That’s not ROI. That too is tuition.
Winners don’t pay for the same lesson twice.
Here’s simple math. If an event costs five grand, you need immediate and follow on sales to cover it and then some. If it moves one hundred boxes in the next month and triggers sticky follow ups, it worked. If it moves fifteen boxes and a pile of likes, it didn’t.
You don’t need a spreadsheet army to see that. You need honesty.
So ask yourself: are your dollars compounding, or are you paying tuition again and again?
And once you’ve faced that answer, you’re ready for the final truth.
Bottom Line
This industry loves stories. That’s the problem.
Stories don’t move boxes.
Neither does nostalgia or effort. The archives prove it, hundreds of brands built on stories, all gone.
The survivors stripped illusions away. They admitted cigars are a commodity. They knew the cigar alone wouldn’t carry them. Systems would. Marketing would. Data would.
The discipline to cut losers and double down on winners would.
And let’s be clear: survival isn’t about being the biggest. It’s about being the sharpest.
You don’t need Davidoff’s budget. You need clarity, consistency and the stomach to face facts.
Most companies that fail already know their weak spots. They just don’t want to face them.
That’s why consultants are dangerous. We tell you no. We point to blind spots. We call bullshit when the emperor has no clothes.
Most operators surround themselves with yes-men, and the yes-men march them straight into the graveyard.
So here’s the bottom line: are you willing to face the truth about your brand, the parts that earn and the parts that bleed?
Because if you’re not, the market will hand you the verdict anyway.
And it won’t care how much you loved your own story.
And if you think this sounds harsh, remember, the archives don’t lie.
Looking for a Legacy and Not an Obituary?
You don’t have to end up in the archives. You don’t have to keep guessing.
You don’t have to keep paying tuition for mistakes already made a hundred times over.
Most of your competitors won’t change. They’ll keep rolling another blend, recycling another name, burning cash on oversized booths. They’ll call it strategy. Then they’ll vanish. Let them.
The herd always goes south.
The question is simple: do you want to follow, or do you want to go north?
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