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Joshua Stephens | Jul 17

The Slow Burn: Pushing The Chips In...Again

I knew a lot of people, but I wasn't truly known by anyone. That realization changed everything. What followed was addiction, recovery, reinvention, and another chance to choose the life we wanted to build.

Spending my days at Lifeway Christian Bookstore and our local community college, I remember thinking:

What's the worst that could happen?

When I entered high school, I didn't have much direction. Growing up the way I did, there wasn't a lot of time to think about what I wanted my life to become. There was no 10-, 20-, or 30-year plan.

I was a social butterfly. Jocks, freaks, geeks, thespians, band kids…it didn't matter. I floated between all of them.

Living for the moment, I sacrificed a lot of "what could be" for "what could be right now."

Looking back, I can see the early signs of addiction. But it would be many years before I eventually lost myself in little white lines.

I joined JROTC as a freshman and quickly discovered I had a problem with authority.

Truthfully, it was probably exactly what I needed at the time, but I couldn't see the forest for the trees.

A few months in, the Sergeant pulled me aside.

"Stephens, you're not going to cut it here. You might know all the right answers, but you don't look or act the part."

He wasn't wrong.

I never wore my dress uniform on designated days because I thought it made me look like a pickle, and I was far more concerned with being cool than being disciplined.

Standing outside a portable classroom under a blistering Texas sun, I thought:

You're right. I don't have what it takes.

So I pivoted.

I joined DECA, a work-study program. Our school operated on A and B day schedules, and my afternoons were spent working at a NASCAR memorabilia shop.

The store was perpetually dead.

Three customers in an afternoon was considered busy.

So I brought my drumsticks and practice pad to work and practiced relentlessly.

If I wasn't going to make it in the military, surely I could become a rockstar.

So I practiced.

A lot.

After graduation, I attended community college.

Not because I knew what I wanted to do, but because it was what you were "supposed" to do.

I knocked out the basics while buying time.

Meanwhile, I gigged constantly.

Churches. Pubs. Dive bars.

Anywhere that would let me perform, I was there.

Then it happened.

A band I was in got signed.

I thought we'd made it.

I transplanted to West Hollywood…though "living in a van" would be a more accurate description.

For a while, it felt like my dreams were coming true.

I pushed all the chips in on myself.

A few years later, van life became less romantic.

Every time I came home, someone was getting married, buying a house, or having children.

Meanwhile, I was playing sold-out venues while living the life of a blacktop gypsy.

I had stories.

I had experiences.

But eventually I realized my ambitions outweighed our talent.

So I took a calculated reprieve.

I got a corporate job.

A few years in call centers eventually led to sales.

Then life changed.

For the first time, I accumulated a little money.

Ironically, that's when things began to unravel.

Addiction crept in.

Before long, I found myself trapped in the insanity cycle.

A lot of people stop me here and ask:

"Why then?"

Everything looked successful from the outside.

Why not when you were a struggling musician?

The truth is, I don't know.

Maybe it's genetics.

Maybe it was the environment.

Maybe the soil was fertile ground for sin.

What I do know is this:

I surpassed my wildest financial expectations and still felt empty.

Sales is a lot like being a musician.

There's always another crowd to win over.

You perform to get paid.

You live off the highs.

And the high-paying sales jobs?

They require a lot of travel.

I knew a lot of people.

But I wasn't truly known by anyone.

So nearly ten years ago, I recognized I had a significant drug problem.

And once again, I pushed all the chips in on myself.

At 33 years old, I checked into rehab.

Recovery is no joke.

Especially in those early years.

We moved.

I got a new job.

New friends.

Everything changed.

Becoming a barista after holding a senior leadership role at a global sales organization taught me a great deal about humility.

The first time a nine-year-old carrying a Gucci bag pulled out a debit card and barked an order for a Vanilla Bean Frappuccino, I had a moment.

How did I get here?

The answer was simple.

I had spent most of my life drifting.

Living without intention.

And it showed.

So I got focused.

A little over a year into slinging bean juice, Kaitlyn and I decided I should take some time off.

It was my version of an Eat, Pray, Love moment.

I wanted to find myself.

And oddly enough, I found myself in words.

I started a recovery blog.

I shared my story.

I wrote a book.

At the time, there weren't many gospel-centered recovery resources available, and I wanted to contribute something meaningful.

Eventually, though, I realized something.

I didn't write the book for other people.

I wrote it for me.

Maybe one day I'll publish it.

For now, it sits on a proverbial shelf, collecting dust while I wait to see whether it can withstand the sands of time.

Eventually, another opportunity came along.

A Brazilian startup looking to expand in the United States hired me to help lead the organization.

And like many performances before, I showed up ready.

A couple of years later, some friends approached me about starting a residential valuation company.

I knew nothing about appraisals.

Eventually, I said yes.

For a season, I worked two full-time jobs until the new venture could replace my income.

That was more than six years ago.

Today, we've built one of the largest residential appraisal firms in the United States.

Last year, our peers voted us among the best in the industry.

Late nights.

Early mornings.

Planes.

Hotels.

Conference rooms.

We built something special.

Then Kaitlyn and I started Brolo Cigar Co.

And once again, we knew almost nothing.

Manufacturing.

Blending.

Inventory.

Technology.

Cash flow.

Community building.

Factory visits.

The list never ends.

People told us we'd never pull it off.

Yet here we are.

Somewhere in the middle of all of that, another opportunity appeared.

A different organization.

A different vertical.

A different future.

I didn't pursue it.

They pursued me.

Their initial offer wasn't enough, so I declined.

But I also told them exactly what it would take.

To my surprise, they delivered.

Everything I asked for.

Which brings me to one of my favorite poems by Robert Frost, The Road Not Taken.

Two roads diverged in a wood.

And here I stand.

Again.

I've started over in my twenties.

I've started over in my thirties.

Now, at 42 years old…with more wisdom, more scars, more joy, and more suffering than I could have imagined…two roads diverge once more.

One path leads toward financial security and a proven skill set.

The other leads into the great unknown.

And that, my friends, is the Brolo way.

It's easy to get philosophical about a brand.

But what I've learned is that brands only matter when they're authentic.

As a performer, there are all kinds of tricks you can use to win over a crowd.

Backing tracks.

Lighting.

Stage antics.

Call-and-response moments.

Pulling someone on stage.

All of it works.

Until the music doesn't.

Because if the songs aren't good, none of the extras matter.

You're just another solution nobody asked for.

That's how I think about Brolo.

Do people actually want what Kaitlyn and I have to offer?

Are the cigars good enough to stand on their own?

Without hype.

Without coattails.

Without smoke and mirrors.

Can we push all the chips in on ourselves yet again?

Only time will tell.

So here we are.

Standing at another crossroads.

Starting over in some ways.

Beginning again in others.

And hoping this venture doesn't end up alongside my other brilliant business ideas.

You know…the puppet show for the blind.

Or the rehabilitation center for animals with same-sex attraction.

I kid.

Mostly.

But creating a product in a crowded market is not for the faint of heart.

So my ask is simple.

Pray for Kaitlyn and me.

Pray for wisdom.

Pray for discernment.

Pray that we make the right decisions.

Two paths have diverged.

We can't walk both.

Neither path is bad.

They're simply different.

So here we are.

Hoping the one we choose makes all the difference.

Not just in our own lives.

But in the lives of those around us.

Light Up & Lean In

The Slow Burn: Calluses

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.

The Slow Burn: Currents

The ocean never asked where I wanted to go…it simply carried me. Life works the same way. Left unattended, our faith, health, relationships, and purpose all drift. Currents is a reflection on recognizing when we've wandered and finding the courage to swim back toward what matters most.

The Slow Burn: The Things We Love

Beneath a Nicaraguan moon, hidden behind a mosquito net, tree frogs wage war against my sleep. Their calls echo through the jungle like ladies of the night working a truck stop, each one louder than the last. Halloween Moon Crabs scatter across the ground beneath our cabana. I have to pee...but I'm not getting out of bed. Nature can have this one.

The Slow Burn: Rearview Mirrors

We all have a collection of "if only" moments….roads not taken, mistakes we'd undo, opportunities we missed. But the longer we stare into the rearview mirror, the more likely we are to miss the blessings sitting right in front of us.

The Slow Burn: Maroma Beach

The ocean was turquoise. The tacos were endless. Paradise was perfect. Yet all I could think about was tomorrow. Sometimes the dreams you’ve prayed for have a way of exposing what you really believe about yourself.

The Slow Burn: The Story Behind 'Back Booth'

PSA: This is going to be a sappy post. I tried to write my way out of it, but here we are.

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.

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.

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.

The Slow Burn: The Chips Are Stacked

Growing up is learning what opportunities to say "no" to. This week, that meant walking away from a lucrative offer, embracing the uncertainty of building Brolo, and realizing that regret is far scarier than failure.

The Slow Burn: Brolo Is In Production

Everyone wants to know the factory, binder, and filler. We get it. But we believe great cigars are remembered for the moments they create, not the spec sheets behind them. Here's why we're choosing experience over credentials.

The Slow Burn: Confessional

I grew up around church culture, preacher’s kids, fireworks, bad decisions, addiction, and grace. Somewhere along the way, all of it found its way into a cigar called Confessional.

The Slow Burn: Pushing The Chips In...Again

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