“I’ve Been in Their Shoes - That’s Why I See the Game So Clearly”

Last week didn’t just stir the pot - it cracked it wide open.

June 27, 2025 | Jonathan Lipson | The Cigar Profit Consulting

I Said the Quiet Part Out Loud

Last week I lit a fuse on two platforms - and not everyone liked what they heard. Good.

On Light’em Up Lounge with Reinhard Pohorec, we exposed the illusion of “premiumization” as performance art. Then Take It To The Nub (with Boston Jimmie and the Panel) pushed it further - peeling back the pricing models, branding gimmicks, and the quiet panic hiding in every “$20 cigar” pitch. (Didn’t catch them live? Links at the bottom of the article).

MUDA thrives where no one’s willing to say no.

After that? My inbox lit up.

Some said, “Finally - someone said it.” Others… not so polite. But what they all made clear

is this:

Most people don’t actually understand why I see it the way I do.

They see the titles - Director of Marketing, Senior Brand Manager, rep for legacy brands - and assume I was raised in a conference room. Decks. Margins. Spreadsheets. But that’s not where I learned to win.

What they miss? I started at the register. I built my instincts where tangible goods actually get sold. I learned the game from the floor up, not the suite down. Part-time cashier during my high school years. Tobacconist at 19. Planograms, promotions, and POS before I ever picked up a catalog or flew coach to a sales meeting.

I’ve walked the humidor. Lived on the road. Taken the heat from angry customers and misinformed managers. And later? I led the campaigns that sold to both.

This isn’t just an opinion. It’s a reflection.

On experience. On grit. On burnout. And on what this industry still hasn’t learned:

This business bleeds MUDA - waste of time, energy, resources - because people keep chasing approval instead of results.

Retail, Reps, and the Register: Where I Learned the Real Lessons

Let me say this up front – this part might sound like a resume.                                    It’s not.

It’s the kind of insight you only get from walking the floor -                                   

which is exactly why most execs miss it.

Before cigars ever paid my bills, I was 16, working a part-time job at a publicly traded discount goods retailer. Not glamorous, but it taught me everything the boardrooms forget.

There, I wasn’t just a cashier - I was a student of human behavior. I learned merchandising, display theory, and how the slightest inefficiency in layout could cost thousands in lost sales. At 17, I was promoted to frontline supervisor. I managed associates, executed planograms, and drove add-on purchases through what we called “speed tables” - a subtle hustle at the point of sale that turned impulse into revenue.

But what really stuck with me wasn’t just the planograms or the promo strategy. It was the first moment I realized that insight has value - even when no one wants to hear it.

I kept the part-time gig through college - my home store between semesters and the one near my dorm in Boston.

Over spring break freshman year, the home store was prepping for a district manager visit. Tension was high. We were told: stay sharp, stay quiet, don’t make waves.

But I had just picked up something in class - a single checkout line feeds multiple registers faster than separate queues. Less confusion. More throughput. More upsell opportunities.

So I brought it up in the all-hands.

My manager didn’t even let me finish. Scoffed. “Not your place.”

So I brought it up to the district manager directly. My manager - she was pissed!

A few years later, that same company rolled out the very concept nationwide: one queue, more impulse lanes, more product per linear foot.

Coincidence? Maybe.                                                                                           

But I stopped waiting for permission after that day.

That experience made one thing clear: vision doesn’t always come from the top. And neither does leadership.

How Listening Made Me a Killer

If this is starting to sound like an autobiography,                                                                              hang in there. These aren’t war stories - they’re how I learned to actually listen.

After class, I was still working the discount store. First summer back home, I picked up hours at a local tobacco shop. That’s when it all clicked.

The big-box rules still applied: Merchandising mattered. Traffic flow mattered. Product positioning mattered.

But this time, the stakes were real.

It wasn’t socks or hand towels - it was cigars. Not just a product. A lifestyle.

And the customers? They cared.

If you paid attention - really listened - you became indispensable.

I did.

I got obsessed with consumer psychology.

I staged the humidor using planogram logic. Built displays that told stories. Paired brands that made money.

Every shelf was a silent pitch.

Every pitch became a close.

But what really shifted things?

I stopped focusing on what they bought - and started listening to why.

One guy lit up because it reminded him of his father.Another wanted to impress clients. One swore by Connecticut wrappers so he wouldn’t get overwhelmed on the golf course.

Each story rewired how I sold the next.

That attention to behavior? That’s what made me a top rep.

Not charisma. Not hype. Pattern recognition.

Because listening beats selling - every time.

It worked. Too well.

Listening made me dangerous. Sales followed. Recognition came next.

But success has a price - especially when you don’t know where to draw the line.

The Downside of Winning: When You Let the Territory Work You

Still with me? Good.

Because this part’s not about glory - it’s about the cost. If the last section made it sound like everything just clicked, it didn’t. Winning had a dark side. And I walked right into it.

Let me be blunt.

Being the # 1 sales rep looks great on paper. But no one tells you this:

If you’re not careful, the territory will run you.

That happened to me.

I wasn’t just selling cigars - I was living in my accounts. Merchandising their shelves. Reworking floor sets. Hosting events. Training teams.

It wasn’t “sell and bounce.” It was “sell, service, stay.”

And I loved it - until it drained me.

The very thing that made me successful - giving a damn – turned into a fire extinguisher. I got too invested. Took on too much. The wins were addictive, but the pace broke me.

What started as partnership became people-pleasing. What started as strategy became survival.

That’s the dark side of overperformance: when you cross the line from value-added rep to unpaid brand therapist.

And that’s not unique to sales. It’s everywhere in this business.

Retailers overextend to please vendors. Brand owners chase the wrong accounts. Factories pump out too many SKUs.

Everyone’s doing too much for too many - with too little return.

You can call it hustle. Loyalty. Commitment.

But ask yourself: is it scalable - or are you just spinning wheels?

Back then, I didn’t have a ‘No Man’ - someone to challenge bad orders, dumb strategy, or leadership drift. I just kept marching.

Until I couldn’t anymore.

That was my wake-up call.

That’s when I made the pivot.

Burned Out, Not Burned Down

So yeah, the plot thickens - I got promoted.

Burnout didn’t break me. It sharpened me.

I didn’t quit - I recalibrated.

I stepped off the road and into the strategy room. And the second I did, the whole game looked different.

As a rep, I was the bridge between product and people. In strategy, I was suddenly designing the bridge - and deciding if it even needed to be built.

That’s when I saw what no one upstream wanted to admit:

There’s a massive disconnect between the folks making the product and the people buying it.

Manufacturers talk to brand owners. Brand owners talk to reps. Reps talk to retailers. Retailers talk to consumers.

And once in a while –

·         A rep plays brand ambassador.

·         A brand owner parachutes in for a handshake and a photo op.

But rarely - rarely - does anyone upstream stop to listen downstream.

That’s why things break.

Strategies look sharp on a PowerPoint - but fall flat in the humidor.

• Brand decks written by people who’ve never stood behind a register.

• Launches driven by ego, not insight.

• Campaigns built to reinforce groupthink, not engage customers.

That burnout? It became my advantage.

Because I knew what failure smelled like in a walk-in humidor. I knew what silence on a shelf sounded like. I knew what questions real retailers ask when no one’s watching.

So I flipped the script.

I started asking:

• Who’s this really for?

• What problem does it solve for the retailer?

• Why would a customer buy it a second time - not just once?

• Where does the data show that the market needs this?

And every time the room went quiet, I knew I had struck a nerve.

That’s when I stopped trying to impress anyone. I started building things that actually worked.

Because once you’ve carried the bags, missed the numbers, fought for a reorder, and still showed up the next day -

you stop guessing.

you start seeing clearly.

And that’s when you get dangerous.

You might be thinking - so what? What does my burnout have to do with you - running a lounge, moving product, building a brand?

Here’s the answer:

The same waste, ego, and chaos that burned me out? It never left.

And it’s bleeding everyone now.

The Blind Spot That’s Bleeding the Industry

Still think this was just story time? Now you know better.

Every industry has its blind spots. But in premium cigars, the gap between the brand, the retailer, and the consumer isn’t just a blind spot - it’s a canyon.

And no one seems eager to bridge it.

Manufacturers think they know their consumers because they shake hands at multi-vendor events and visit their favorite shops on a market visit. Retailers think they know the brands because they hear pitches from reps and get free swag. Consumers think they know everything because they hang on every word of a certain periodical’s review section, read a blog, watched a review, or got into a “Nicaraguan Habano is the best wrapper” argument on Reddit.

Everyone’s talking around each other.

No one’s really listening.

This was the gap that kept bothering me - not just because it existed, but because it was costing everyone money.

It was costing:

• Manufacturers money because they were building products with no resonance or shelf strategy.

• Retailers money because they were stocking SKUs that wouldn’t turn, built on hype instead of insight.

• Consumers money because they were buying into branding that wasn’t built for them - or ignoring products that were, but got buried in noise.

And the kicker?

The market was rewarding the wrong things.

Brands with no plan got hype. Reps with no training made promises no product could fulfill. Retailers were handed goods, not partnerships. And consumers were expected to just… keep paying more.

So I built The Cigar Profit not as a soapbox, but as a sounding board - a place to tell the truth, ask the hard questions, and help the people in this business stop bleeding time, money, and relevance.

This business can be better. It just needs someone unafraid to call the bluff.

That’s the mission.

Not to be right. But to be real.

And if you’re building something - or trying to figure out what the hell happened to what you already built - you’re already living it.

And at the end of all this - beneath the bad buys, the bloated inventories, and the executive pivots - the consumer gets hit. They pay more. They get less. And they have no idea who made the call that shifted the industry off-course.

But maybe – just maybe - it’s not a who. Maybe it’s a what…

MUDA.

I mentioned it earlier-  the Lean Six Sigma concept that means waste – waste of time, waste of materials, waste of effort, etc.

The hardest part isn’t seeing the MUDA. It’s admitting you’ve become part of it.

But once you do? That’s when the game changes.

When you stop playing along and start asking harder questions - about your SKUs, your sales model, your customer, your voice.

That’s when you stop tolerating your own inefficiencies.And start building something that earns its keep.

It doesn’t mean burning it all down. It means cutting what no longer serves your mission - and rebuilding from there.

The Lessons I’d Take Into Any Industry

Let’s land it - before the next bad idea takes off.

Let’s be honest -  

I’ve fallen for the same groupthink I now critique.

Not all at once - and not without good intentions - but it happened.

When I was a rep, I hated being told to push product that didn’t belong. You’d feel it in your gut. You’d walk into an account you cared about, knowing the thing in your bag wasn’t going to work for them. But the pressure was on.

“We need to move this.”

“The warehouse’s full.”

“It’s just a short-term push.”

What got lost was the long-term relationship.

Then I moved up. And I found myself doing the same thing.

Not because I didn’t care. Not because I forgot. But because I was caught in the gears of something bigger - campaign launches, internal deadlines, forecasting, pressure from the top. Suddenly, I was the one creating the conditions I used to complain about.

That’s the most dangerous kind of MUDA.

The kind that comes from smart, well-meaning people doing things they swore they’d never do - because the system says it’s “just how things work.” I was in it. Fully. No excuses. That’s why I know where the traps are - because I stepped in every one of them.

So if you ask me what I’ve learned, it’s this:

You need someone who’s not afraid to say no.

Not just a voice of reason, but a mirror. Someone who’s seen all sides of this business and isn’t looking to climb your ladder or stroke your ego. Someone who’s been a rep, a brand builder, a marketer - and who’s been burned out by all three. Someone who now knows exactly where the traps are buried because he’s stepped in every one of them.

And that’s how I became a No Man.                                                                         Get one… I’m here when you’re ready.

Not negative. Not cynical. Just honest. Strategic. Unafraid to challenge you when your decisions don’t match your mission.

MUDA thrives where no one’s willing to say no.

Feeling Stuck in the MUDA ?

That’s what The Cigar Profit is for.

If you’re ready to do things differently - intentionally, efficiently, profitably - get yourself a No Man. Someone who’s lived this business from every angle and isn’t afraid to call the play that actually wins.

That’s what I do. That’s who I am. I’m The Cigar Profit.

Let’s stop wasting time, money, and opportunities. You’ve got two choices: keep wasting time - or fix what’s broken. I’m here for the second one.

Schedule your Exploratory Call Today

Watch: The Cigar Profit on Light'em Up Lounge

Watch: The Cigar Profit on Take It To The Nub (with Boston Jimmie and the Panel)