Boom, Bust, Repeat: What the Industry Still Hasn’t Learned

By Jonathan Lipson | Founder & President | The Cigar Profit Consulting

Two Booms. One Industry That Still Doesn’t Get It.

Here’s the thing about cigars - they’re steady. The people around them? Not so much.

The mid-‘90s boom was a frenzy. Everyone with a Rolex and a handshake wanted in. Louder the better. Cigar bars popped up on every corner. Brands with no business plan got shelf space - or didn’t need it. Back then, if it was a rolled-up concoction of tobacco leaves, it flew out the door before it ever hit the humidor. And by the time it collapsed, nobody really learned the lesson...

Two Booms. One Industry That Still Doesn’t Get It.

Fast forward to COVID - same product, entirely different energy. People weren’t chasing status -they were chasing stillness. Locked down, stressed out, looking for something real. Cigars exploded again. But not because the industry did anything special. It just happened to have the right ritual at the right time.

Two booms. Two decades. And somehow, we’re still pretending like momentum is the same thing as method.

That’s why this blog exists.

This isn’t a history lesson - it’s a reality check. It’s to call out the patterns - and the problems - so the next wave of cigar professionals stops repeating them. Because the cigar isn’t the problem. It never was. It’s the operators who forget that culture, communication, and customer behavior don’t stay stuck in time.

The cigar is the constant. What surrounds it - that’s what changes. And if you’re not building for that change, you’re not building anything that’s going to last.

Let’s get into it.

Everything Moves but the Leaf

From the outside looking in, a boom is a boom. Sales spike. Inventory flies. New names enter the game. But for those of us who lived* through both the mid-’90s rush and the COVID-era surge, the differences aren’t just surface-level - they’re systemic.

*And for those who know me, and may question my age in comparison to the mid-'90s boom - I may not have been old enough to participate, but I watched on the sidelines. I watched my parents' friends 'invest' in the boom... Long story short, it didnt' work out too well.

In the ’90s, most of the noise came from the top - but that didn’t stop the flood. People weren’t buying cigars because of sharp marketing or high Cigar Aficionado ratings. They bought because the culture told them it meant something. If it was rolled and in a box, it flew.

Some brands earned their keep – savvy cigar makers who understood the business, played the long game, and aligned with Cigar Aficionado’s then-novel vision of where the culture could go.Same with tobacconists who combined passion with real operational chops.

But most? They slapped a label on a box - or bought into a fly-by-night franchise scheme - and rode the wave. No plan. No identity. No shot.

When the dust settled, the ones still standing weren’t lucky. They were built.

Today? The consumer is the gatekeeper.

To let you in, they care what you stand for right now. To let you stay, your brand story needs to be as consistent as your product. And this isn’t just about cigar makers - retail competition is just as fierce.

A cigar brand can launch overnight and gain a following from one story, one video, or one unforgettable experience. A hobbyist with some capital can open a brick-and-mortar - or jump into e-comm.But those same brands (and yes, a retail operation is a brand) can disappear just as fast if they don’t follow through.

In the COVID-era boom, attention was the new currency. And the brands that didn’t know how to earn it - or worse, didn’t understand how to keep it - burned out faster than a poorly rolled short-filler corona.

Technology widened the audience but exposed more flaws. For makers - if your packaging didn’t line up, your backstory felt fake, or your cigars weren’t consistent - word got around. Fast.

Fast enough to kill momentum you never had time to convert into loyalty.

For tobacconists - if you didn’t pivot your model to keep customers engaged, your competitors ate you for lunch.

And yet, with all that change, the cigar itself hasn’t gone anywhere. It hasn’t needed to.

The core product - the experience of cutting, lighting, tasting, and reflecting - remains untouched by trends.

It doesn’t need reinvention. But everything around it does.

Here’s the catch: if your storytelling, your operations, your retail experience, or your digital presence still looks like it did ten years ago, you’re not competing.  You’re aging in place.

The smart operators - the ones who evolved through one or both booms - understood this:The cigar doesn’t change. But the culture does. And they moved accordingly.

If you’re not doing the same, you’re not building.  You’re just waiting for the next boom to carry you.

And hope?

Hope isn’t a strategy.

Where Most Brands Missed the Moment

In both booms - ’90s and COVID - you could spot the same pattern play out: attention surged, demand followed, and suddenly, everyone thought it was their time to launch something.

A cigar. A brand. A shop. A lifestyle.

But most of them missed the moment. Not because their cigars or shops were bad. Not because they didn’t care. But because they treated the boom like a guarantee instead of what it actually was: a window.

And windows close.

In the ’90s, the mistake was excess -

Cigar shops multiplied – inventory trumped service, quick sales beat out sustainability, and the loudest Yuppie usually got the attention over the loyal regular.

Brands overextended - production outpaced quality, greed outran operations, and reputation became a race to the bottom. When the moment dried up, so did the distribution deals. Retailers were left with boxes they couldn’t sell; and consumers, burned by inconsistency, retreated to the brands they already trusted, the cigar shops that stuck around, or just quit the lifestyle all together.

During COVID, the mistake was ego. Some believed the boom was proof they’d nailed it. That attention equaled loyalty. That a few good months on social media meant they’d earned a seat at the table. But they didn’t ask the harder questions:

• Can we fulfill consistently?

• Can we survive once the rush wears off?

• Can we create an experience that outlasts the trend?

Most couldn’t. Because most never built for longevity-they built for applause.

And that’s where they lost.

The operators who got it right didn’t just react to the moment. They prepared for what came after. They reinvested. They refined their positioning. They streamlined their back-end systems. They treated the boom as a test, not a trophy.

Because in premium cigars, a spike in demand isn’t a payoff - it’s a proving ground.

If you didn’t use the momentum to clean up your margins, lock in your messaging, and build customer loyalty that would carry you forward, you missed the point.

And if another wave comes - and it might - you’ll miss it again.

What Always Brings Us Back

Cigars aren’t like anything else. They’re not consumed out of necessity. They don’t fix a problem or check a box on a daily routine. No one needs a cigar.

That’s why they matter.

Cigars exist in a category of their own - an indulgence that rewards patience, a ritual that resists speed. And no matter what changes - tech, culture, distribution, regulation - the soul of this thing doesn’t budge. It just waits for us to return.

What’s wild is that we always do.

Some people come back because of nostalgia. The aroma. The memory. A moment they want to relive. Others return because they finally have the time - or the money - to understand what the fuss is about. And for a growing number, especially during and after COVID, it’s about control. About taking one moment in the day that isn’t rushed, digitized, or dictated by someone else.

And when they walk from the humidor to the counter, they’re not buying cigars. They’re buying space.  

That’s what most outside the industry will never understand. And it’s why, for all our debates about branding, packaging, market shifts, and regulatory battles, the cigar keeps showing up as something that ties generations together.

You don’t need to be born into this. You don’t need to speak the language perfectly. If you get it - you get it. And if you don’t, no marketing campaign will ever make it stick.

The smart brand builders know this. They don’t try to reinvent the leaf. They just respect it enough to build around it with intention - so that when the moment comes, their cigar is the one a consumer reaches for without hesitation. Or their store is the one that customers visit.

Because at the end of the day, it’s not about hype. It’s about the ritual we keep coming back to.

What the Industry Needs Now

If there’s one lesson to take from the two booms, it’s this: timing gives you a shot. Execution decides if you stay.

Right now, premium cigars are sitting at a strange intersection. Monty Hall could host Let’s Make a Deal: Tariff Edition, regulations - though currently relaxed in the US - still loom, international laws and regulations consistently seem schizophrenic, the economy's shaky, and consumer attention is more fragmented than ever. But the interest? It’s still there. The category still carries weight. People are still discovering cigars - not just as products, but as portals to something deeper.

So what does the industry need?

It needs focus. Real business focus.

Not just more blends or new packaging. Not just another event with a raffle table and a four-hour happy hour. It needs people- at every level- who are willing to stop chasing waves and start building boats.

That means:

Retailers who run shops like businesses, not hobby clubs.

Brand owners who care more about long-term shelf presence than short-term buzz.

Sales reps who aren’t just chasing orders, but actually training the market.

And media voices that know the difference between advocacy and echo chambers.

Because whether you’re legacy or upstart, independent or scaled, there’s one universal truth: the cigar won’t carry your business. You will. Or you won’t. But the leaf isn’t the variable. You are.

The operators who will survive whatever comes next - recession, consolidation, legislation, AI, or some new twist none of us can see yet - are the ones who understand this moment isn’t just a reset.

It’s a responsibility.

And if you’re not building with that kind of clarity, you’re not preparing - you're gambling...

And this industry doesn't reward the same bet twice, let alone three times.

The Draw That Still Matters

Every industry needs a mirror. This is ours.

Two booms. Decades apart. Entirely different in shape, but nearly identical in outcome: a flood of attention, a flurry of activity, and too many players who thought momentum was enough.

It never is.

The cigar is the constant. What surrounds it? That’s always changing. Culture. Communication. Consumers. Capital. And if you’re not evolving alongside those variables – intentionally - you’re asking for irrelevance to come quietly through your front door.

But here’s the upside: it’s not too late. It never is when you’re willing to confront the truth and start working smarter.

That’s what The Cigar Profit helps people do.

We aren’t just about branding or buzzwords. We’re about building infrastructure that holds when the wind picks up. We’re about helping you see what’s coming - before the floor shifts underneath you.

And if you're trying to build a brand, open a shop, scale a business, or step into ownership through acquisition - there’s probably a better way than doing it alone.

Let’s figure out what that looks like - together.

Ready to take your next step in cigars - without wasting time or capital?

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