Pushing the Chips In...Again
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.
