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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


Light Up & Lean In,

Joshua Stephens

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The Slow Burn: Kansas City Cigar FestivalThe Slow Burn: Kansas City Cigar Festival
The Slow Burn: Kansas City Cigar Festival

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...

The Slow Burn: CallusesThe Slow Burn: Calluses
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: CurrentsThe Slow Burn: Currents
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 The Slow Burn: The Things We Love
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 MirrorsThe Slow Burn: Rearview Mirrors
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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 BeachThe Slow Burn: Maroma Beach
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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.