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Joshua Stephens | Jul 27, 2025

The Slow Burn: One Moment at a Time (Pt. II)

“$21,000 and a Cigar Brand Dream”


Events can make or break a cigar brand.

Especially when the person holding the mic fails to connect.


I've pitched thousands of people over the years.

Hosted hundreds of events….some unforgettable, others... well, I probably left a few brain cells behind.


But one night still stands out.

Not because of who was there.

Not even because of what I said.

It stands out because of the tab:

$21,000.


Yup.

Twenty-one large.


Thank God it wasn’t my card, it was the company’s.

Corporate AMEX, God rest your credit limit.


The setting?

The Billionaire Boys Club, Midtown Manhattan.


No, not the Pharrell brand.


This was an ultra-lounge sitting quietly above a Ferrari dealership, because, of course, it was. One of those velvet-rope, "invite-only," high-gloss rooms that smells like generational wealth and overpriced cologne.


The mission?

Get in with the gatekeepers.

High-net-worth individuals. Board members. C-suites and their admins.

Not just shake hands, gain influence. Make them trust you. Make them use our solution.

The truth is, our company wasn’t exactly built for this kind of entertainment.

But I was.


Young, fired up, and chasing a challenge, I got handed the keys to a new vertical:

Celebrities.


No roadmap. No playbook. Just a target and a Rolodex that didn’t exist yet.

So I built one.

Within a year, I had cracked the circle. I was working with the ACPA (Association of Celebrity Personal Assistants) and the NYCA (New York Celebrity Assistants).

I connected with Steve Harvey’s assistant. Nate Berkus’s team.

Before I knew it, we had two headline events:


One at the newly opened SLS Hotel in Los Angeles, and another in New York, the night of the infamous $21K tab.


It wasn’t just about flash. It was about making people feel seen.

Even in a room full of status, people crave sincerity.


Some folks say L.A. is fake. I get it. With 243 plastic surgeons in Orange County alone, the stats kinda back it up.


But underneath the filler and flash, there are real people in that city, grinding, dreaming, and trying to make something of themselves in a place where social currency is fame, and the price of admission is exclusivity.


One of those people was Kim, a client of mine who ran operations for the ACPA, the Association of Celebrity Personal Assistants. She was also the handler for a nationally syndicated talk show host, which meant her life was a tightrope walk of managing egos, keeping up appearances, and maintaining absolute discretion.


Over time, we became friends.


I learned she loved to travel and craved new experiences.

But I also learned how lonely it could get.

How people only invited her places to get closer to her boss.

How dating was damn near impossible because she could never be sure if someone wanted her… or access.

By her own admission, she’d grown a little calloused.

Then there was Kelly

.

Kelly was—and still is—a total badass.

You know in the movies when someone says,

“Have your people call my people?”

Kelly is those people.

She’s the high-functioning bosslady behind a nationally recognized interior designer and TV personality.

Her days were packed with international travel itineraries, renovation projects, personal appearances, brand deals… and zero room for screwups.


She didn’t just keep things on track.

She made it look effortless.


I spent months flying between L.A. and New York, meeting with Kim and Kelly, building trust, and eventually co-hosting bi-coastal events that brought the A-listers and their teams together.

And somewhere along the way, I met Patrick.


Patrick worked for a star, the kind with a résumé longer than most people’s lives.

She was a legend of the stage and screen.

A Steel Magnolia.

A Moonstruck matriarch.

The voice in Look Who’s Talking.

And a force in Mr. Holland’s Opus.

She passed in 2021, but left behind a legacy of over 130 stage productions, 60 films, and 50 television series.

Working with her team was like stepping into cinematic history.

Now, a lot of folks get starstruck.

Me? Not really.


Well...

Except for that one time I choked at the urinal next to Steven Tyler.

(We’ve covered that.)


The celebrity assistants thought their bosses were high-touch.

But I was living in a different reality.

A billionaire reality.


They didn’t know that while we were setting up gift bags and lighting votive candles, I was fielding calls from the likes of Sadie Ferguson, Laurene Powell Jobs’s right hand.


Or that at any moment, the RNC (Reince Priebus) or DNC (Debbie Wasserman Schultz) might call with a last-minute ask.

Or that Philip Falcone might demand a car at the East 34th Street Heliport right now to get to the Hamptons by sunset.

Hell, one time Air Force One entered NYC airspace unannounced and rerouted every flight.

Suddenly we had heads of state and hedge fund execs scrambling for ground transportation.

Another time, a volcano erupted, and I spent two days rerouting a Bronfman (yes, that Bronfman) back to U.S. soil.


And yes...

Trump was impossible.

But I still landed the 2014 GOP Convention transportation contract.


Looking back, it’s easy to laugh.

It was wild.

It was chaotic.

And somehow…

It worked.

Not because I was “selling” something flashy.

Not because I knew all the right names to drop.


But because I understood what people really wanted.


Genuine connection.

And a baller service or product to back it up.


That’s it.

That’s the whole play.


And it’s the same thing I’m building with Brolo.

Because no matter who you’re dealing with…celebrity, billionaire, boardroom boss…

People remember how you made them feel.

They remember the experience.

They remember the connection.

They remember the moment.


And the people who remember those moments?

They come back.


It’s not about being the loudest.


It’s about being real.

Present.

Human.


The best brands aren’t built in boardrooms.

They’re built at the bar.

In lounges.

Over stories and smokes.

One moment at a time.

Light Up & Lean In,

Joshua Stephens

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Last week, several of the Brolos and I attended the Kansas City Cigar Festival. The festival was Saturday, but we decided to make a weekend out of it. Because apparently a bunch of grown men with an unhealthy amount of cigars can't simply arrive at an event, attend it, and go home like normal people.


We left Dallas around 6-ish Friday morning and pulled into Kansas City around 4:45 that afternoon. In between were gas stations, snacks, questionable decisions, lunch at Bite Me BBQ in Wichita, and a quick stop at Old Town Cigars. Shoutout to Old Town, by the way. They had an awesome selection of boutique cigars, including some of the old-school Metapas from before Foundation rebranded them as Aksum. Those aren't exactly sitting on every shelf anymore.


But I'm getting ahead of myself.


Shawn arrived at my place a few minutes late and blamed traffic. In his defense, he wasn't lying. 380 in the morning is a complete nightmare. North Texas has grown at a ridiculous pace, and it seems like no amount of construction can keep up. Every road is simultaneously being expanded and somehow getting worse.


We loaded Shawn up and headed to a bougie neighborhood in Prosper to grab Justin. We made it through the gate, pulled up to the house, and there he was...sitting in a camp chair, bags packed, already smoking a cigar.


It was a sight for sore eyes.


Naturally, we immediately started roasting him for not even making it to 6:00 a.m. before lighting one up. His defense was that he was "afraid he would be left out." Justin is the newest cigar smoker in the group, but the man put the first number on the board that weekend. Kudos.


Next up was Mr. Babyface himself, Mark. Picture this: it's roughly 5:30 in the morning and Mark is standing outside next to his truck, bags packed, looking like his parents just told him they were taking him to Disney World. Everybody was ready. And for the next eight hours, we absolutely destroyed my car.


Four men. A few boxes of cigars. Windows cracked. Ash everywhere. I don't think it will ever smell the same again. But that's the price you pay for making memories around something you love.


We put Justin in charge of picking lunch.


This was our first mistake.

The Slow Burn: MaineThe Slow Burn: Maine
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A reflection on Maine and the fear, pressure, and freedom that come with finally letting go of something you created.

Heritage: Recently, I’ve been thinking quite a bit about heritage and what that word actually means to me.Heritage: Recently, I’ve been thinking quite a bit about heritage and what that word actually means to me.
Heritage: Recently, I’ve been thinking quite a bit about heritage and what that word actually means to me.

It’s an all-encompassing term.


There are the tangible things and the intangible ones. The personal and the cultural. Traditions, values, stories, recipes, land, names, beliefs, habits, and physical objects passed from one generation to the next.


Some things are handed to us intentionally.

Others just arrive.


Building Brolo has me thinking about heritage quite a bit.


The cigar industry, maybe more than most, loves heritage. Many brands benchmark their quality against generational pedigrees, old-world traditions, luxury positioning, or some combination of the three. Families who have worked with tobacco for generations. Names that stretch back a hundred years or more. Stories with roots deep enough to make whatever they're selling today feel connected to something much older.

And there's something beautiful about that.


But where does that leave a kid like me?


I didn't grow up with a mother and father.


There isn't some great family enterprise being handed down to me. I didn't serve in the Armed Forces, and the only time I was involved with law enforcement was usually in the back of a squad car.


What the heck is my heritage?


And if heritage matters so much, how am I supposed to compete with that?


So I started digging.


Not through ancestry records or old family photographs, but through the things that got me here. The memories. The scars. The people. The failures. The things I learned accidentally and the things life taught me, whether I wanted the lesson or not.


I started asking myself:


What makes Brolo, Brolo?


The first image that came to mind wasn't tobacco.


It was a hay bale.


I was probably six or seven years old.


During the summer, my Grandma would drop me off for a week at my birth mother's trailer in East Texas, back behind the Pine Curtain.


Every summer, I dreaded it.


My second stepdad was quite a doozy...a real piece of work. Abusive. Violent. Looking back now, I can see he was probably just an angry boy trapped inside a man's body.


But when you're six, you don't have that kind of perspective.


You just know you're scared.


They lived in the country....or, as East Texans pronounce it, the cunnnn-trrrryyyyyyyy.


The acreage seemed to stretch forever, with a little creek running along the back of the property. My mother worked all day as a nurse, and my stepdad worked as a carpenter, taking odd jobs here and there.

I don't remember him being particularly great at woodworking.


But the man sure knew how to rip a doobie.


Wherever they were, I wasn't.


Most days, I was on my own, traversing the countryside. Climbing hay bales. Jumping hay bales. Falling off hay bales.


And, eventually, crying next to hay bales.

I remember getting hurt out there once.

And I remember being angry with myself for getting hurt.


Scared because I didn't know if I'd be able to survive a sprained ankle, let alone another week unsupervised.


Broken because I was alone and hurting.

And nobody showed up that day to help me.


Although that was the first time I remember feeling it, it certainly wasn't the last.


Those experiences taught me independence.


Eventually, they also taught me control.

If nobody is coming, you learn to handle things yourself. You learn to anticipate problems. You learn not to need much. You learn how to survive.


Useful skills.

Until they're not.


Because somewhere along the way, independence can become isolation. Self-reliance can become control. And learning not to need anyone can leave you desperately wanting someone.


Maybe that's heritage, too.


Not everything passed down comes in a box.


A few weeks ago, I went to the doctor for a regularly scheduled checkup. Somewhere between the blood pressure cuff and the usual questions, she started asking about my family.


Heart disease?

Cancer?

Diabetes?

High blood pressure?


She was trying to understand my family history...to identify the things buried somewhere in my DNA that might eventually become part of my story.


In other words, she wanted to know:

What runs in your family?


It's a clinical question.

But I've thought about it differently ever since. Because a lot more than disease runs in families.


Work ethic runs in families.

Faith runs in families.

Temper runs in families.

Generosity runs in families.

Addiction runs in families.

The way we handle money. The way we argue. The way we love. The way we apologize....or don't. The things we celebrate and the things we refuse to talk about.


Somewhere along the way, all of it becomes inheritance.


We tend to romanticize heritage.


Grandpa's watch. Dad's old truck. Mom's recipe written in her handwriting. The family Bible with names and dates scribbled across pages yellowed by time.

And those things matter.


But heritage has a shadow side, too.


Some things are worth preserving.

Some things are worth restoring.


And some things need to end with us.


My childhood was a lonely one through no fault of my own.


As I got older, I started pursuing people.

At first, probably because I was afraid to be alone.


I was tired of being alone.

I was starving for belonging.

But somewhere in that pursuit, I discovered something much better than simply not being alone.


I found connection.


If this were one of my gospel-centered recovery pieces, this is probably where I'd spend the next thousand words talking about how human beings were created for connection.


And I believe that.


I believe true connection begins vertically...with God...and that healthy relationships with one another are a by-product of that relationship.


But that's another rabbit hole for another day.


Back to connection.


Because that's what Brolo is about.


Not heritage manufactured through some bullshit origin story.


Not luxury for luxury's sake.


Not pretending we've been making cigars since 1873.


Connection.


It's the early-morning text from a friend encouraging you to succeed while simultaneously making light of your many proclivities.


It's the random Tuesday-night HERF where, for whatever reason, the whole crew shows up, and you belly laugh until your face hurts.


It's an early-morning coffee where somebody finally stops saying they're "good" and tells you what's actually going on.


It's spending so much time smoking cigars together that you know your buddy's palate almost as well as your own. You know what he's going to love. You know what he's going to hate. And occasionally, you make a recommendation that he actually likes.


It's getting bombed by one of the Brolo's.


It's seeing the UPS truck turn onto your street....or maybe even chasing it down, and feeling that little dopamine hit because you know there's a box headed your way.


It's knowing that whatever ails you, somebody is rooting for you.


It's complete strangers finding each other in some random corner of Discord or Reddit, sharing a cigar through a screen, and eventually becoming friends in real life.


Those things probably don't sound like heritage.


At least not the way the word is usually sold to us.


There aren't any centuries-old family photographs.


No tobacco fields passed from father to son.


No crest.

No pedigree.


But maybe I've been thinking about heritage all wrong.


Maybe heritage isn't just about where you came from. Maybe it's about what you carry forward.


And maybe the things we weren't given are sometimes the very things we become most determined to give away.


I didn't inherit a great legacy of connection.


So I built my life around finding it.


And now we're building Brolo around giving it away.


Maybe that's my heritage.


Not the kind printed on the inside of a cigar box. Not a family crest, a famous last name, or some romantic story about generations of men who came before me.


It's messier than that.


There's some good in it. There's some bad. There are things I'm proud to carry forward and others I've spent most of my adult life trying to put down.


But all of it got me here.


And I suspect the same is true for you.


What's your heritage?


Not just where your family came from or the traditions you grew up with.


What did you inherit?

What runs in your family?

What did someone teach you without ever sitting you down to teach it?


What wounds shaped you?

What values stuck?

What traditions still matter?


What parts of the people who came before you can you see when you look in the mirror?


And maybe more importantly:

What are you doing with it?


Because at some point, we stop being merely the recipients of heritage.


We become responsible for it.

We decide what gets carried forward.

What gets restored.

What gets rewritten.

And what ends with us.


Heritage isn't just the story of the people who came before you.


It's happening right now.


In the way you raise your kids. The way you love your spouse. The way you treat your friends. The work you put your hands to. The things you make time for. The things you refuse to compromise. The table you build and the people you invite to sit around it.


Whether you realize it or not, you're leaving something behind.


When I think back to that little boy sitting alone in East Texas, hurt and scared and wondering if anybody was going to show up, I can't change his story.


Nobody came that day.


But I can decide what I do with what he gave me.


Maybe that's why showing up matters so much to me now.


Maybe that's why the table matters.

Maybe that's why connection matters.

Maybe that's why Brolo exists in the first place.


So maybe the better question isn't simply:

What's your heritage?


Maybe it's:

What will someone else inherit because you were here?


What impact have you made, or lack thereof?


And maybe that's convicting...if so...that was my intention.


Kaitlyn and I don't make cigars to avoid life. We make cigars to fully embrace it. The good, the bad...the hurt and the wins.


All around a shared smoke.

About This BlogAbout This Blog
About This Blog

I wrote this back in 2017 and never published it. I found it again. And reading the words of the man I was has been an uncomfortable experience. This post is a multipart post about shame and where we can find hope. Stay tuned for the next post in the series...

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Some things can only be learned the hard way.

As a writer, I wage a lot of wars against a blinking cursor.


I get caught somewhere between what I want to say and what I think people want to hear. And I’m beginning to believe that’s a dangerous intersection.


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