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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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Born in 1983, I grew up during a strange and wonderful time to be alive.


I remember summer mornings when parents encouraged you to leave the house and didn't expect to see you again until the streetlights came on. Nobody had Ring cameras. Nobody was posting

neighborhood warnings on Facebook. We weren't worried about the "big bad wolf" down the street. We had one family phone hanging on the kitchen wall...unless your parents were absolute ballers and paid for a second phone line.


Weekends were spent at sleepovers. We'd roam the aisles of Family Video or Blockbuster looking for the perfect movie. If we got lucky, we'd stop by Little Caesars next door and grab a Bigfoot Pizza before heading back to somebody's house.


Late nights meant MTV, TRL, Beavis and Butt-Head, and Twisted Metal tournaments that felt like they carried the weight of the world. Mellon Collie and the Infinite Sadness played through cheap speakers while we argued over who cheated and who got robbed.


Then, seemingly overnight, everything changed.


Dial-up.

24k modems.

The internet exploded.


Half my childhood happened before the online world. The other half happened after it arrived. The soundtrack of my life changed from guitars and arcade machines to the sound of AOL connecting.

You know the one.


Suddenly there were chatrooms. Screen names. Endless possibilities. Every conversation started with the same question: A/S/L?


As a tweenager, I found myself staring into a world I wasn't quite ready for.

I came from humble beginnings.


My Grandpa T-Mack…better known as "Smokey" Stephens…passed away around the time I was born. My birth father was never in the picture. My birth mother was just a kid herself, carrying a responsibility no fifteen-year-old should have to carry alone.


I spent time in foster care and bounced between homes before eventually landing with my grandmother, Joyce.

Joyce was a firecracker.


She worked at the county courthouse, where she met my grandfather. But by the time I came along, life had taken its toll. COPD. Asthma. Brain aneurysms. Most of my memories of her involve oxygen tubing and a wheelchair.


But none of that stopped her.

When she gained custody of me, she and her husband Bobby owned a little honky-tonk in East Dallas called The Junkyard Club.


To a kid, it was magic.


The place wasn't fancy. About 2,500 square feet. A full-service bar and kitchen. Cheeseburgers and fries served in hubcaps. Pool tables. Shuffleboard. An Elvira pinball machine. A Galaga cabinet tucked in the corner. Live music every Friday and Saturday night.


Grandma would bring me to the club after school while she worked the books.

I'd spend hours wearing out my wrists on Galaga while the cook fed me an endless supply of grilled cheese sandwiches. Every plate came with maraschino cherries.


The regulars all knew me.


One afternoon, an older gentleman dared me to eat a handful of jalapeños. Since Grandma didn't raise a quitter, I accepted the challenge. A few seconds later, I was sprinting through the bar screaming while tears rolled down my face. The regulars laughed. Grandma never looked up from her paperwork.


But the coolest thing in the entire place wasn't the arcade games. It was the school bus. After getting past security, you'd walk inside and immediately see it sitting on the right side of the club. A full-sized yellow school bus.


Somehow it had been disassembled, moved inside, and put back together as the centerpiece of the bar. Inside were booths and tables. But at the very front, beside the driver's seat, was The Table.


You could look out over the entire room from there.


It wasn't elevated much, but it felt like it was. To a kid, it looked important. It felt important. Like some kind of white-trash luxury suite. A little reserved sign sat on the table.


But here's what I eventually learned:

It wasn't reserved for the people with the biggest wallets.

It wasn't reserved for the loudest people.

It wasn't reserved for the owners.

It belonged to the regulars.

The people who knew everyone by name.

The ones who threw twenty dollars into the jukebox and played Creedence Clearwater Revival until everyone else was sick of hearing it.

The ones who showed up.


Again.

And again.

And again.


They had earned a seat at the table simply because they were part of the story.

Early in the evenin', just about supper time...

Down on the corner, out in the street...

Willy and the Poor Boys are playin'...


That was our place.


A place to know people and be known by them. As a kid, I didn't have the words for it. I just knew it felt different.


The smell of cigarette smoke hanging in the air.

The beer-soaked bar mats.

The sound of live music echoing through the room.

The laughter.

The conversations.

The feeling of belonging.

I felt connected.


When my grandfather died from cancer, Grandma sold the club. Eventually the building became something else. These days it's called The Lone Star Cafe. It's still there.


Back before I got sober, I'd stop by every December 21st…Joyce's birthday. I'd order her favorite drink. A margarita. No mix. Just tequila, fresh lime juice, a salted rim, and a lime wedge. Then I'd feed a few dollars into the jukebox and play CCR.


The school bus is long gone now. But when I close my eyes, I can still see it.


The band is playing. People are laughing. Someone just beat my high score on Galaga. Another guy is staring at Elvira. Pool sharks are running the tables. Sherry the bartender slides me another cup of maraschino cherries.


For a moment, life is exactly as it should be.


That's what Back Booth is about.


Back Booth is our boldest core cigar. A 5x50 Robusto wrapped in Mexican San Andrés. Medium-plus in strength. Full of character. Rich, dark, and unapologetic. My friend Austin described it as tasting like the best barbecue bark he'd ever had. Granted, he's from New York, so we'll take that review with a grain of salt.


But he wasn't wrong.


Because barbecue and cigars have a lot in common. Neither can be rushed. The best briskets aren't built in minutes. The best friendships aren't either. Both require time, patience, smoke, and a willingness to stay put longer than everyone else.


That's what the Back Booth represents.

Not exclusivity.

Not VIP status.

Not some velvet-rope version of cigar culture.

It's a seat that's available to everyone.

But it takes time to appreciate why it's special.

It's for the people who understand that the best conversations happen after everyone else has gone home.

The ones who know that community isn't built overnight.

The ones who keep showing up.

Again.

And again.

And again.

So pull up a chair.

Look out over the driver's seat.

Watch the crowd.

Catch the glow of the neon signs.

Listen as some up-and-coming band works their tail off trying to move the room.

Then take a look at the person sitting across from you.

Because moments like those don't last forever.

And that's exactly what makes them worth savoring.

So Light Up & Lean In.

Enjoy the moment because the "good 'ole days," well…you don't know you are in them until they are gone.

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