We caught up with the brilliant and insightful Richard Rowland Jr. a few weeks ago and have shared our conversation below.

Alright, Richard thanks for taking the time to share your stories and insights with us today. Coming up with the idea is so exciting, but then comes the hard part – executing. Too often the media ignores the execution part and goes from idea to success, skipping over the nitty, gritty details of executing in the early days. We think that’s a disservice both to the entrepreneurs who built something amazing as well as the public who isn’t getting a realistic picture of what it takes to succeed. So, we’d really appreciate if you could open up about your execution story – how did you go from idea to execution?

It began outside Bourbon One Bar on what seemed like an ordinary evening. The old ball coach was enjoying a Perdomo Champagne cigar when the aroma caught the attention of my barber. The two struck up a conversation right there on the sidewalk, and by the time they walked away, they were dreaming about opening a cigar lounge — a brick-and-mortar space where community could gather around good cigars and Kentucky bourbon.

From there, the idea spread. The barber shared it with different gentlemen in the community — many of us who didn’t know each other at the time. Eventually, those conversations brought us together, and that’s when the real brainstorming began. At first, the focus was on a private lounge, but it didn’t feel right. We didn’t want exclusivity; we wanted inclusivity. We wanted to create an atmosphere where the everyday man and woman could sit down, light a cigar, sip bourbon, and enjoy the kind of ambiance and conversation that makes both feel timeless.

That shift in vision opened the door to something new. We looked at examples outside the cigar world, like Mike’s BBQ — a restaurant that started on wheels and built a loyal following before becoming a successful brick-and-mortar. That model clicked with us. Why not build our reputation the same way? Why not start mobile? A mobile cigar lounge would allow us to build a name without the heavy overhead, bring the experience directly to people, and give them something they would want more and more of.

Once we landed on that idea, the process of turning it into reality began. We had to research trailers and layouts, figure out how to install proper ventilation, and navigate smoking ordinances and compliance rules. We looked into licensing, permits, and insurance — all the less glamorous but necessary parts of the business. We sketched out designs, debated seating and atmosphere, and worked on sourcing a humidor that matched the luxury feel we wanted. And of course, we had to decide what our cigar selection would look like — not just “cigars,” but a curated experience that matched the level of quality we envisioned.

The first year was full of trial and error. We poured sweat equity into building the lounge, outfitting it with leather seating, TVs, and all the little details that make it feel special. Marketing was another learning curve — how do you sell an experience people haven’t seen before? But once we booked our first events and rolled out the black carpet for guests, we knew we had something. Watching people’s faces light up when they stepped inside the lounge told us everything: the dream had become real.

Looking back, Ember & Ash wasn’t born overnight. It started with the smell of a cigar outside a bourbon bar, grew through countless conversations, and took shape step by step — idea, research, build, and launch. Today, when someone walks into our lounge, they’re walking into that original vision: a space built for community, conversation, and the timeless pairing of bourbon and cigars.

Awesome – so before we get into the rest of our questions, can you briefly introduce yourself to our readers.

I’m Richard Rowland, Jr., co-founder of Ember & Ash Mobile Cigar Lounge. I spent several years in the engineering field and later in environmental compliance, where I learned the value of structure, systems, and problem-solving. At the same time, I’ve always been drawn to cigars, bourbon, and the kind of community they create. Ember & Ash became the bridge between my professional discipline and my personal passion.

Ember & Ash is Kentucky’s premier luxury mobile cigar lounge. We bring a fully furnished, upscale lounge experience anywhere — weddings, corporate events, distillery pairings, alumni gatherings, or festivals. Guests step inside to find leather seating, curated premium cigars, and the atmosphere of a private club. What makes us unique is mobility and inclusivity: in a world where ordinances often restrict cigar culture, we take the experience to the people and open it to everyone.

What I’m most proud of is how far we’ve come in just two years — from an idea sparked outside a bourbon bar to a respected brand. More than anything, I’m proud of the reactions we see when people step inside for the first time. Their surprise, excitement, and the way conversations naturally spark affirm our goal: to build community, create memories, and celebrate culture through the timeless pairing of bourbon and cigars.

Can you open up about a time when you had a really close call with the business?

I’ll never forget the close call we had before a wedding on a rainy Saturday in the fall of 2024. The day had started like any other event day — I was walking the beautiful grounds of Bourbon Luxe Estate & Venue, focused on details and timelines — when a phone call changed everything.

On the other end, my stomach dropped as I heard the words no business owner ever wants to hear: there had almost been a wreck. Our lounge — the centerpiece of what we do — and more importantly, the people I trust to help me run this company, had barely escaped disaster.

Later I learned the full story. One of my partners — the old ball coach who also drives for us — was behind the wheel of our Ram 2500, hauling the 24-foot v-nose trailer. With him were our vice-president and a contractor. Instead of taking the interstate, they’d gone the scenic route — a winding two-lane highway between Louisville and Bardstown. As they climbed one of those rolling Kentucky hills, pedal down, they had no idea what waited on the other side.

At the top of the hill was a nightmare: a line of cars stopped in the road, waiting for someone to turn off onto a narrow country lane. There was no way to hit the brakes in time. In that split second, my partner envisioned the worst — our truck and lounge plowing through unsuspecting motorists, lives lost in an instant, and his own family never seeing him again.

With nothing but faith and instinct, he yanked the wheel, stomped the brakes, and prayed. Miraculously, the opposite lane was clear. The truck and lounge shot past the stopped cars while oncoming traffic skidded to a halt, narrowly avoiding a head-on collision. When everything finally stopped, everyone inside was shaken but alive. The Ember & Ash lounge was still hitched, still standing, and by God’s grace, no one was hurt.

When I hung up that call, my entire perspective shifted. In that moment, it wasn’t about cigars, bourbon, or bookings. It was about people — my partners, my team, my friends. That near-tragedy reminded me that Ember & Ash isn’t just a business; it’s a dream held together by the lives of those who make it real. Since then, we’ve made safety and preparation just as much a part of our story as luxury and hospitality. Because no event, no client, no amount of money will ever matter more than the people who bring Ember & Ash to life.

Any fun sales or marketing stories?

Every business has that one milestone client or venue that feels just out of reach. For us, it was Churchill Downs — until now.

When we received an email from Ring Power about their upcoming Customer Appreciation event, my heart skipped a beat. They were planning to host it at the historic Churchill Downs, in the brand-new FanDuel Starting Gates Rooftop Garden. This was the shot we’d been waiting on since Ember & Ash began — the chance to prove we belonged on one of Kentucky’s most iconic stages.

The request, however, wasn’t straightforward. Ring Power wanted services we had never provided before. Instead of turning them away, we leaned in. We began reaching out to new vendors, subcontracting, and piecing together a plan to create the Bourbon & Cigar Lounge ambiance they envisioned. It pushed us out of our comfort zone, but it also showed us just how flexible Ember & Ash could be when opportunity knocks.

Then came the pivot. After reviewing budgets, Ring Power asked if we could instead provide our tabletop experience — an offering that has quickly become a crowd favorite. It was a reminder that sometimes the simpler solution creates the biggest win. By thinking creatively and keeping the conversation open, we sealed the deal.

As I’m speaking to you now, the ink is still wet on the contract. On October 7, Ember & Ash will celebrate alongside Ring Power and their customers at Churchill Downs. For us, it’s more than an event — it’s a milestone. Churchill Downs isn’t just a venue; it’s validation that Ember & Ash belongs on the biggest stages in bourbon country.

Contact Info:

• Website: www.emberandashcigars.com
• Instagram: https://www.instagram.com/emberashmobilecigarlounge/
• Facebook: https://www.facebook.com/p/Ember-Ash-Mobile-Cigar-Lounge-61550091106650/

Image Credits
Taken by the Team @ Ember & Ash