So, You Want to Be in the Cigar Industry?

Let me stop you right there. If your image of the cigar world is all mahogany shelves, leather chairs, and easy money—you're about to get a wake-up call stronger than a double ligero on an empty stomach. This isn’t a fantasy. It’s a grind. But it’s also beautiful… if you’re cut out for it.

Here’s my story—and a few lessons you’ll want to learn before you start burning bridges & bankrolls chasing the dream.

 How It Started…

The year was 2000. I was 18, it was the holidays, and someone handed me a 25-count humidor and a box of Hoyo de Monterrey Excalibur No. 1s. Sounds like a classy start, right?

Nah—I butchered those cigars like a rookie surgeon. I didn’t know what I was doing, at all!

I thought seasoning a humidor meant wiping it down with distilled water and locking it shut for a few weeks. Boom, done. That’s what I read online. Turns out, that’s also how you create a cozy mold hotel inside your humidor. Spanish cedar veneer doesn’t play like that, and it raises the grain, destroying uncellophaned cigars. That lesson stuck—mostly because I had to throw away the damn humidor and half the box of cigars that came with it. But I didn’t quit.

I started visiting cigar shops to figure things out—listening, watching, asking dumb questions, and learning the hard way. Trial and error became my teacher. I tossed out more humidors than I care to admit. I wasted good cigars because I didn’t know how to store or cut them. But eventually, I figured out what the hell I was doing. That’s when the obsession kicked in.

But “obsession” doesn’t even cover it. I didn’t just want to smoke cigars, I wanted to understand them. Every nuance. Every ritual. Every damn leaf.

Back then, the internet wasn’t what it is now. No endless YouTube rabbit holes or online courses. If you wanted to learn, you had to grind for it. Most of the published material out there barely scratched the surface. The good stuff? Either in Spanish (luckily, I can read in Spanish), out of print, or locked behind industry doors.

Years passed. My palate changed, my knowledge evolved, and my curiosity turned into purpose. I started diving into blends—really studying what they were made of, why they tasted the way they did, and what story each one was trying to tell. Because that’s the thing no one talks about—"cigars tell stories”, if you know how to listen.

Eventually, I took a part-time job at a cigar shop—not because I needed the cash, but because I needed to “be there” to soak it all in. To breathe the culture, talk to the regulars, pick up the rhythm of the lounge, the rituals, the language. I was feeding a hunger, and that job became my classroom.

But like any good burn… eventually, it went out.

In 2015, life sucker-punched me. A few medical setbacks forced me to stop smoking altogether. And not just stop, I had to walk away from everything. My collection, my gear, my passion. I sold it all. Every last humidor, every cherished stick. Gone.

That was hard…

For a few years, the flame was out. I focused on recovery, family, and getting my life back in order. But the cigar world, the rhythm of it, the peace of it never really left me.

Then, about three years later, I was cleaning out a closet and found something I hadn’t seen in years: an old travel humidor. I opened it up expecting dry husks and disappointment.

But what I found? Magic.

The cigars inside were still good, damn good. Like they'd just been waiting for me to come back.

And that moment? That was the spark. The slow relight. I didn’t just return to the culture—I came back with purpose. Now the fire wasn’t just reignited—hell, it was an inferno.

I dove headfirst back into the world. I was devouring cigar blogs, flipping through every magazine I could find, buying boxes like I had something to prove. Humidors were multiplying like gremlins—big ones, little ones, desktop, tower, travel—I had one in every damn room. My house looked like a cigar warehouse run by a lunatic.

Then came 2020. COVID.

I’ve been through disasters around the world as a first responder—mass casualty scenes, catastrophic storms, chaos. But this one? It broke us. We were living in hell, day after day. Watching people fall apart. Watching our own fall apart. We needed a space to breathe, to decompress from the unrelenting weight. Just before the pandemic hit, I started teaching a few co-workers about cigars. How to cut them, light them, store them, appreciate them. The culture, the respect, the ritual. One of them told me I should start a blog… maybe even a club.

So, I did, & that’s when Big Chief Cigar Review (BCCR) was born. But even with that going… something was missing. There was knowledge out there—but I didn’t want what was on the surface. I wanted to dig deeper. I wanted to understand everything. Not just the cigars, but what made them what they were—why they mattered, how they came to be, who poured their soul into each stick.

And here’s the part that kicks you in the teeth: Even now, with years behind me, I know I’ll never learn it all. But back then, I didn’t care & I still don’t. Because I still want to try.

I want to learn. I want to earn it. I want to be the best. I want to honor the old heads who built this industry with their bare hands and maybe, just maybe, earn the right to pass something real onto the next guy.

I told my friends that one day, when I finally retire from EMS, I’d open a cigar shop. Maybe even launch my own cigar line. But the truth? I had no idea where to start. The business side?

Revenue, taxes, staffing, loss margins, inventory management? Or the product side?

Tobacco strains, primings, fermentation, rolling techniques?

So, we kept pushing the blog. Built a little following. Then I got my hands in the dirt. Learned about tobacco. Learned how to roll. Got certified as a tobacconist. And it was great, but it still wasn’t enough.

I want it all. Yeah, I’m greedy. But it’s not about money or recognition. It’s about purpose. It’s about mastering every angle of this world so I can carry this torch and maybe light a few others along the way. This industry is in my blood now. It keeps me up at night. And every waking moment, I’m thinking: What’s my next move What’s the next thing I need to learn? How do I keep this dream alive and build it into something that lasts?

So, You Want to Be in the Cigar Industry?

My answer? Don’t. Stay a consumer. Keep it fun. Keep it light. Keep your money, because this industry, it’s not the fantasy you’ve been sold. I listen to a lot of cigar podcasts—probably more than is healthy. And you know what they all say? The same thing: It’s not glamorous.  And they’re right.

“The Cigar Authority” said it best. They’ve been blunt about the grind, the margins, the pressure, the reality behind the curtain. They’ve opened the doors to how the sausage gets made. But truth is—I didn’t want to hear it. I was already in too deep.

This wasn’t a hobby anymore. It was my obsession. And no matter how hard it got… I wasn’t going to quit.

In 2023, I signed the paperwork. I made it real. Tabacalera del Monte, LLC was born. Just weeks before my son came into this world, I gave life to a company I hoped he could one day be proud of. A name I wanted him to carry with pride. The only

problem? I still had no clue what the hell I was doing. No roadmap. No mentors. Just grit, caffeine, and a dream.

Part I: So You Want to Open a Cigar Shop?

Alright, hotshot. Here’s where you make a choice: Do you want to be a “cigar shop owner” brick-and-mortar or online? Or are you aiming higher? Brand owner, maybe even a manufacturer? We’ll get to that in a bit. But first… let’s talk shop. Literally.

Whether you're dreaming of that cozy lounge with leather chairs and jazz in the background or just launching a slick online boutique, let me break something to you: This ain't easy. This ain't passive. This ain’t a "set it and forget it" kind of game. You’re going to need a business plan.

Actually, scratch that.

You’re going to need several:

·       A 3-year plan

·       A 5-year plan

·       A 10-year vision

·       And most importantly… a “what if this all goes to shit” plan

Now ask yourself:

·       Do you have the capital?

·       If not, where’s it coming from?

·       And how the hell are you going to pay it back?

You got a location in mind? Cool. Are you renting? Leasing? Buying outright? Each of those comes with its own set of migraines.

If you're going brick-and-mortar, you’ve got to manage 

·       Air filtration systems (because yes, people will complain)

·       Humidors—walk-in or cabinet, and properly calibrated

·       POS system setup (and if you think Square’s gonna help you, think again)

·       Lounge setup (furniture, spacing, ventilation)

·       Product sourcing—and can you even qualify to carry some of the premium brands you’re dreaming about?

Oh—and don't forget:

·       Insurance (and it won’t be cheap)

·       Rent

·       Utilities

·       Website

·       Advertising (which is damn near impossible in this industry thanks to federal red tape)

And here’s the real kicker: Did you check your state’s tobacco licensing requirements?

Some states will demand:

·       Tobacco retailer permits

·       Use tax licenses

·       Local smoking ordinances

And let’s not pretend landlords are always cigar-friendly. If your neighbor upstairs doesn’t like the smell? You might be getting eviction papers faster than you can say “box press.”

 Okay, maybe you’re thinking, “Screw that—I’ll just go online.” Cool. You still have to do all of that plus a bunch of extra crap.

Because now, you’re high risk.

Tobacco = regulated.

Which means you can’t just hop on Square, Venmo, PayPal, Stripe, or any other cookie-cutter processor.

You’ll have to:

·       Apply to a specialty payment processor

·       Submit your site and policies for legal review

·       Implement their terms and restrictions

·       Pay transaction fees, plus a $1,500 annual fee just to be allowed to accept Visa/Mastercard

You also need:

·       A professionally built site (unless you can code in your sleep)

·       Full ADA compliance

·       Transparent privacy and return policies

·       Functional cookies and trackers

·       FDA warnings on every page

·       21+ verification systems

·       Age-gates and disclaimers everywhere

And here’s the most brutal truth: You’ve already spent tens of thousands of dollars…

And you haven’t made a single dime yet. Let that sink in.

Part II: So, You Want to Be a Brand Owner?

Alright, so you don’t want to run a shop. Fair enough. You’ve got bigger dreams—you want your own brand. Respect. But now we’ve got to ask the real questions: What kind of brand owner do you actually want to be? The “I Own a Brand” Brand Owner? Are you just putting your name on a cigar made by someone else? There’s nothing wrong with that.

A lot of people start that way:

·       You choose a factory.

·       You give input on the blend.

·       They handle production, and you handle sales and branding.

This is called “contract manufacturing” or “private labeling”, and it’s a legit route— “if” you’ve got a vision and know what you’re doing.

But ask yourself:

·       Who’s really controlling the blend?

·       Will they make it the same every time?

·       What if they ghost you or decide you’re too small to matter?

Because spoiler alert: You’re not their biggest client. You’re probably not even in their top ten. And if push comes to shove, guess who gets bumped to the bottom of the list? You!

The “I Want It All” Brand Owner. Now if you’re thinking bigger. I’m talking own the brand, the blends, the factory, the fields then buckle the hell up.

Because now you’ve got to answer a mountain of questions:

·       Where will your cigars be made?

·       Who’s rolling them?

·       Who’s blending them?

·       What country is supplying your tobacco?

·       Can that tobacco be consistently sourced?

·       Are the farmers selling to ten other companies before they get to you?

Again... are you at the bottom of the chain?

You better believe the big players get priority. That means:

·       Your orders may be delayed

·       Your materials may run short

·       And your cigars may never even hit your timeline

Now, let’s talk about capital. You’re going to need a lot of it. Again. Blending takes time. Rolling takes labor. Packaging takes coordination—and every one of those vendors has their own schedule, their own priorities, and you're likely dead last if you're not placing 6-figure orders.

Let's Talk Logistics, Baby:

·       Can your cigar be made consistently?

·       Who’s doing quality control?

·       Will this end up a one-time drop because the blend can’t be repeated?

·       Will your packaging be on time?

·       Is it even being made correctly—or are your bands being slapped on upside down because someone was rushing to meet someone else’s order first?

Oh, and don’t forget about these little love notes:

·       Excise taxes (federal and state)

·       Import tariffs

·       Shipping delays

·       Damaged boxes

·       FDA compliance

·       Customs seizures

·       Labeling regulations

All that before you even get your first box into a customer’s hand.

So, you still want to be a brand owner?

Then start thinking like a logistics manager, not a dreamer. Start planning for backups on top of backups. Start realizing that tobacco is a living product with seasons, variables, and hundreds of human hands in the mix before it ever reaches you. Because if you don’t… Your “brand” is just a logo on a fantasy. And that doesn’t cut it.

Part III: So You Want to Be a Manufacturer?

Alright, so you don’t want to open a shop. You don’t want to own a brand. You want to go all in becoming a manufacturer. The real deal. From raw leaf to rolled perfection. Your hands, your team, your name on the box. Cool. Now here’s the hard truth: You’re stepping into the most demanding, resource-draining, patience-shredding part of the cigar industry And like with everything else—**capital is king**.

First Hurdle: Money (Again) There’s no way around it. You need cash. Not a couple thousand—six figures just to get going. And then more to stay afloat when things go sideways (and they will).

Next Up: People

 Your staff is everything.

But here’s the catch:

·       If you don’t own the farm, you don’t control the quality of the leaf.

·       And if you don’t train your people properly, you don’t control the consistency of the cigar.

Let’s break it down:

·       Graders (to classify the leaf)

·       Separators (to sort it by size, texture, and priming)

·       Blenders (to build the flavor profile)

·       Rollers (to craft the final product)

·       Draw testers (to ensure the thing even smokes)

So, are you hiring people who already know what they’re doing? Or are you training them yourself? Either way, here’s what’s happening behind the scenes: The old guard is leaving. Veteran rollers, tobacco masters, and experts in fermentation—they’re either retiring, dying, or getting scooped up by larger factories in other countries, and they’re not training their replacements. Finding experienced hands is getting harder every year. And the new generation? They don’t want to work in tobacco fields or factories. They’re moving on. That’s your reality check.

Let’s Talk Tobacco, now we get into the dirt—literally. You want to grow or source your own tobacco? Great.

Hope you like playing God with variables you can't control: 

·       What varietals are you buying or growing? Corojo? Criollo? Habano? Connecticut?

·       What’s the soil like? Clay? Sandy? Rich in minerals or completely drained from over farming?

·       What about altitude and temperature swings?

TDM Family farm, burley tobacco

TDM Family farm, burley tobacco

TDM Family farm, burley tobacco

TDM Family farm, burley tobacco and tractor

TDM Family farm, burley tobacco

TDM Family farm, burley tobacco

·       What’s your pest management system?

·       Blue mold

·       Black shank

·       Leaf spot

·       Tobacco beetles

·       Too much rain, too little rain

·       Vermin tearing up your curing barns

You better have a fermentation plan, a storage solution, and a master blender who can adapt to all these variables, or your entire harvest is going to waste. This is agronomy, not fantasy.

Tobacco is a living, breathing thing. You can’t just plant seeds and expect magic.

You need to understand:

·       pH levels

·       Humidity windows

·       Leaf respiration

·       Fermentation heat cycles

·       Water drainage

·       UV exposure

·       Timing your harvest down to the damn week

Not every tobacco flower can grow anywhere. Try growing broadleaf in Puerto Rico and let me know how that goes. (You’ll cry. I promise.) So yeah—you want to manufacture? Better get ready to be a farmer, a scientist, a builder, a boss, and a magician at the same time.

 Part IV: The Hard Truths

Let’s get something straight:

Cigars are not required.  No one “needs” a cigar. They’re a luxury product, and they’re treated like one by the government—taxed to hell, regulated like uranium, and constantly under fire from public health crusaders who don’t know the first thing about what we do. From the top to the bottom of this industry shop, brand, manufacturer—there are roadblocks. Legal, financial, logistical, moral Hell, sometimes it feels like the world “wants” you to fail before you even begin.

Trying to enjoy cigars is hard enough these days. Trying to sell them? Manufacturing them? Build a legacy with them? That’s a damn war. You will be tested. You will doubt yourself. You will burn money, time, and sanity trying to carve out your place in this world. And if you’re not built for that kind of fight? Then don’t even try. This ain’t for the lighthearted or the timid.

It takes “nerves of steel”—regardless of whether you’re a man or woman.

It takes resolve, discipline, passion, and a “never-say-die” attitude.

Steve Saka—one of the real ones in this game—told me once:

“If you’re really that passionate about this, don’t let anything stop you.”

And that stuck with me.

So, I’ll ask you one more time: Do you still want to get into the cigar industry? If the answer is Still yes…

Welcome to the jungle, because this is just step 1...