The Moves You Don’t See Coming: Why the Cigar Industry Needs a Better Way to Transition

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

The Loudest Moves Happen Quietly

This wasn’t a service I set out to offer.

It started with a few quiet conversations at PCA… then a few more after the Post-PCA Cigar Industry article I wrote dropped… then a handful of calls that all started the same way:

"I’m not ready to go public with this... but I think I’m ready to move on."

Or just as often:"I’m ready to step in — but I don’t know who to call, and I don’t want to waste time."

Buying or selling a business in the premium cigar industry seems overly complicated. But, does it have to be?

I didn’t post anything. I didn’t advertise.

But what I realized is that The Cigar Profit was already doing the work.

Not as a broker. Not as a deal-hunter.

As a translator. A sounding board. A filter.

I’ve been in this business for over 20 years — from retail to brand management to boardroom.

And somewhere along the way, those relationships turned into trust. That trust turned into opportunity.

And that opportunity revealed a gap this industry doesn’t like to talk about:

We have no real system for what happens when a cigar business changes hands.

We rely on whispers.

We wait too long.

And sometimes, we let good businesses die instead of setting them up for the next chapter.

This blog isn’t a pitch.

It’s a breakdown of what I’ve seen, what’s being asked for, and why I’m formalizing something I was already doing — for people who need clarity but don’t want noise.

Because in an industry this small, legacy isn’t something you sell.

It’s something you pass on — if you do it right.

Why Deals Fall Apart Before They Start

On the outside, most cigar industry exits look like they just… happened.

A shop closes.

A brand goes quiet.

Maybe you hear whispers. Maybe you don’t. Either way, one day it’s there, and the next it’s gone.

But when you’ve worked in this business long enough — really worked it — you start to see the pattern.

It’s not that people don’t want to sell.

And it’s not that no one’s looking to buy.

It’s that the people who want to step out are usually waiting for some perfect moment… and the people looking to step in don’t know how to ask the right questions — or even who to ask.

No one wants to look desperate.

No one wants to broadcast that they’re sniffing around.

So what happens? Nothing.

Or worse — a rushed deal, a mismatched buyer, a brand that gets absorbed, hollowed out, or quietly shelved.

Not because it wasn’t valuable.

Because there wasn’t a structure in place to make the handoff work.

And let’s be honest — this isn’t tech or finance.

This is premium cigars.

There are no bankers at the table.

No roadmap for transition.

No system for matchmaking that respects the unspoken codes this industry is built on.

A lot of founders don’t think about exit until they’re tired.

A lot of aspiring buyers think capital is enough.

But if you’ve ever seen a deal blow up over ego, legacy, or lack of readiness, you know it’s never just about the numbers.

What you’ve built isn’t just a brand. It’s an identity. A community. A story.

Handing that off without burning it down? That takes more than a handshake and a checkbook.

And that’s where the problem usually begins — and ends.

Before anyone says a word.

Before anyone makes a move.

In a business that thrives on discretion, it's not surprising most deals die in silence.

But that doesn’t mean they have to.

The Gap No One Talks About

For an industry built on history, there’s not much guidance on what happens when one chapter ends and another’s supposed to begin.

There’s no central marketplace for cigar businesses.

No formal pathway for transition.

No real system designed for people who want to exit quietly — or for those looking to enter without broadcasting it.

And maybe that’s not surprising.

This is a relationship business. Reputation matters more than paperwork.

But when you step back and look at it, it feels like there’s a missing layer. Something between the quiet conversations and the few public deals we actually hear about.

I’ve been paying attention to that space for a while now.

It seems like a lot of folks are interested in passing the torch.

It also seems like a lot of folks are trying to find one to carry.

But because there’s no structure, they rarely find each other.

Or if they do, it’s clumsy. It’s rushed. Or it gets abandoned because there’s no one in the middle to help translate the intent.

I don’t pretend to have all the answers.

But over the last year, I started noticing a trend:

People began reaching out to me quietly — just to feel out their options.

No pressure. No commitment. Just the need to talk it through with someone who’s lived all sides of the business.

And the more I listened, the more it felt like the industry was already asking for something — even if it didn’t have a name for it yet.

That’s what this is about.

Not launching a new service.

Not “disrupting” anything.

Just stepping into the gap that’s already there, with respect for the silence that’s surrounded it for so long.

Because sometimes what’s missing isn’t the buyer or the seller — it’s the bridge between them.

How It Actually Works

This isn’t a listing service.

You won’t find an inventory of cigar shops or brands on a public page.

And that’s intentional.

Most of the people reaching out aren’t asking to sell tomorrow.

They’re asking what it might look like if they did.

Same for buyers — they’re not hunting deals like it’s real estate. They’re trying to figure out what’s possible, and what’s actually worth pursuing.

So instead of offering a traditional marketplace, The Cigar Profit acts more like a translator.

We spend the first part of the process just listening.

• What are you trying to do?

• Why now?

• What are you trying to avoid?

• What do you want this to feel like when it’s done?

From there, we begin the slow, quiet work of identifying possible alignment.

If you’re a seller, that means understanding your business well enough to speak on your behalf without giving away who you are.

If you’re a buyer, that means getting clear about what kind of story you want to carry forward—and what kind of situation you’re really prepared for.

Only when both sides feel like the context is right do we move toward an introduction.

And even then, it’s a conversation. Not a pitch.

No one’s pushed.

No one’s blasted with paperwork.

And no one’s exposed before they’re ready.

Some conversations stop there.

Others turn into long-term relationships.

A few evolve into full-service consulting — working together through the due diligence, the brand positioning, or the operational transition after the handshake.

But at its core, this process is built on one idea:

Moves that matter can’t be rushed.

And in an industry this small, discretion isn’t a luxury — it’s a requirement.

If you’ve been thinking about what’s next — but haven’t found the right person to talk to — now you do.

Who It’s For (and Who It’s Not)

This isn’t for everyone. And it’s not supposed to be.

If you’re just looking to unload a business as quickly as possible, there are brokers for that.

If you’re looking to buy a cigar brand like it’s a sandwich shop or a gas station — this probably isn’t the right door either.

This is for people who care about what happens after the deal is done.

People who want to preserve something they’ve built, or build something that lasts.

People who know there’s more at stake than just product, equipment, or space on a shelf.

So who is this really for?

It’s for the brand owner who’s done the work. Who has a reputation. A following. A story that means something.

But now finds themselves wondering if they’ve taken it as far as they want to go — or as far as they can.

Maybe they’ve started thinking about succession. Maybe they’re just tired.

But what they’re not interested in is blasting out a “for sale” sign and seeing who bites.

It’s for the shop owner who’s thinking about retirement — or relocation — but doesn’t want their customer base turned over to someone who doesn’t understand the culture they created.

It’s for the buyer who’s ready to step in but doesn’t want to get stuck in a dead-end deal because they didn’t ask the right questions — or because they didn’t know who to trust.

It’s for the industry veteran who’s spent a career building up others, and wants to quietly take the next step — without having to start from scratch.

And it’s for the silent partners, the second-generation operators, the folks holding onto something they didn’t build — but care deeply about carrying forward.

This process isn’t about flipping inventory.

It’s not about maximizing EBITDA on a spreadsheet.

It’s about fit. Alignment. Legacy.

Because when that’s right, everything else tends to follow.

Who is this not for?

It’s not for people looking to cut corners.

It’s not for brands built on borrowed equity or smoke and mirrors.

And it’s definitely not for buyers who think a cigar brand is just another asset class.

There’s plenty of transactional noise in the world already.

This is for people who want to move differently — and make it count.

Why Now Matters

If you’ve been paying attention, you already feel it.

The industry is shifting — not just slowly, but meaningfully.

Ownership is aging. Consolidation is accelerating. And the next wave? It isn’t on the horizon. It’s already at the door.

Some of the biggest names in cigars are in succession mode.

Some aren’t even talking about it — but they’re quietly preparing anyway.

You can see it in the brand refreshes. The new hires. The whisper campaigns.

And if you know where to look, you’ll start to see the same thing at the retail level.

Shops that anchored their communities for 20 years are suddenly up for grabs.

Shop owners who never returned a call are now open to conversations.

And new blood — with funding, ideas, and market savvy — is circling the space, trying to figure out where they fit in.

This isn’t speculation.

This is timing. And in any business, timing changes everything.

Here’s what people tend to get wrong:

They assume opportunity shows up with a neon sign and a countdown clock.

But that’s not how this works.

Deals don’t appear when you want them to.

They appear when someone else decides they’re ready.

And by the time that happens — if you’re not already prepared, aligned, and connected — you’ve missed it.

That’s why this isn’t about marketing urgency.

It’s about recognizing market conditions before the crowd does.

We’re entering a moment where reputation and relationships are going to determine who gets to scale, who gets to exit, and who gets left trying to find a seat after the music stops.

You don’t need to move just because others are.

But you should be honest about where you are — and what it might take to get to the next step.

Whether you’re holding something you’re no longer excited to grow…

or you’re watching the door open and wondering how to walk through it…

The time to figure that out isn’t after the opportunity knocks.

It’s before it even knows where to find you.

When the landscape shifts this fast, the most valuable thing isn’t speed.

It’s readiness.

What If You Didn’t Have to Start from Scratch?

There’s another conversation that doesn’t happen often enough.

What if you have the capital… the vision… even the team…but you don’t want to spend the next two years building something from nothing?

What if someone else already did the hard part?

A working brand.

A functional shop.

An established bar with a loyal following — but no next move.

These opportunities exist.

They’re just not advertised.

And in an industry this insulated, the best openings never hit the open market.

They pass quietly from one set of hands to another.

Which means, if you’re not already in the room, you’re not even on the radar.

That’s why part of this matchmaking isn’t just about exits.

It’s about acceleration.

There are founders out there who would rather see their legacy continue — than watch it quietly fade out.

And there are aspiring builders who could skip years of setup… by stepping into something that’s already halfway there.

If that’s you — someone with the means, the mindset, and the appetite to grow something real — don’t assume you have to start at zero.

The next chapter you’re looking for might already be written.

You just haven’t been handed the keys yet.

Skip the guesswork. Build from where someone else left off — the right way.

Final Word: The Moves You Don’t See Coming

Most people think the big moves in cigars happen on the shelves.

New blend. New box. New campaign.

But the real power moves?

They happen before that. Off the radar. Behind closed doors.

It’s the deal that didn’t get announced.

The sale that happened six months before anyone noticed.

The brand that quietly changed hands — and came back stronger.

That’s the space we’re working in now.

Not with a megaphone. Not with a pop-up banner.

Just with a different level of alignment — between the people ready to step out and the ones ready to step in.

Some of you have been circling this idea for a while.

Thinking about the next move. Wondering how to bring it up.

Maybe it felt like too big a conversation. Maybe you thought it wasn’t time yet.

Or maybe you’ve been looking for something to buy — something with history, substance, a real shot at scale — but every opportunity felt either overexposed or underwhelming.

Either way, if you’ve made it this far into the blog, then you’re not just kicking tires.

You’re thinking seriously. You’re trying to get clear.

Good. That’s where everything starts.

Because legacy doesn’t get passed on by accident.

And the best opportunities don’t come from noise — they come from people who’ve been doing the work long before you found them.

That’s how The Cigar Profit has operated since 'Day 1.'

Quietly. Strategically. Inside the room, not chasing the spotlight.

This isn’t a service we dreamed up in a brainstorming session.

It’s something we were already doing — now brought to the surface, because it’s time.

So whether you’re holding something that deserves a proper handoff…

or you’re ready to build something that lasts…this might be your moment.

If it is, you know how to find me.

Click Here - Request a Confidential Matchmaking ConsultYour move. Quietly.