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A Real Talk With the Rubins

The cigar brand created by Alan Rubin just before the turn of the 21st century now includes his namesake sons, Alec and Bradley
By Gregory Mottola | From Dan Aykroyd, May/June 2021
A Real Talk With the Rubins
Photos/Jeffery Salter via Redux Pictures
Alec, Alan and Bradley Rubin have taken their brand to the next level.

Twenty-five years ago, with no history in the tobacco business, Alan Rubin started an obscure cigar company and named it after his two sons, Alec and Bradley. His entry into the business was precarious, and he almost went bust before the start of the millennium, but once Rubin was able to partner with the right people and secure the right tobaccos, Alec Bradley Cigar Co. went from an unknown maker of mediocre smokes to an established name in the premium cigar industry with a wide and evolving portfolio of brands, including the Prensado, which was named Cigar of the Year in 2011, the industry’s highest accolade.

Today, the company is moving into a new era, one where Rubin’s two sons, Alec, 28, and Bradley, 25, are becoming a factor in the future of the family business. As Rubin brings them more into the fold, the two young cigarmakers have formed their own creative brand, Alec & Bradley, where they can express themselves with new products while still maintaining the legacy of their father’s work. Managing editor Greg Mottola interviewed the three Rubins in a father-and-sons video interview to discuss their changing roles in the industry as well as the early critical success of their brand, The Gatekeeper, which was named the No. 7 cigar of 2020.

New World Churchill
“Alec and Bradley have very different personalities. They had to learn how to get along and respect one another in business.”—Alan Rubin

Greg Mottola: Alan, were you hesitant about bringing your sons into the business or was it always a foregone conclusion?

Alan Rubin: I don’t think it was either. When I started the business, they were little kids, but you don’t know what direction they want to take to fulfill their lives. The hesitation was really because the industry always has a target on its back. Do I want my kids getting into an industry that’s volatile instead of selling insurance that everyone needs? So, I had a little hesitation there. And I spoke to them about that and I said, “You should go sell insurance because everyone needs insurance. Not everyone needs a cigar. People want cigars. You have to decide if you want to sell a want or a need.” I said, “It’s a lot more fun selling a want.” That was my pitch to them.

Q: Some parents, before they bring their kids into the family business, make them work in the industry, but somewhere else, just to make sure that they want to do this. Did you ever consider doing something like that? Go work for someone else, and then if you still like it, come work for me.

Alan: My wife and I did have this conversation. But somewhere during that time, our company, Alec Bradley, started to hit a stride, a momentum. And I remember my wife saying, “They need to come in now.” It went from maybe they should work somewhere else to let them come into the business while things are moving. When Bradley was playing baseball as a little kid, I coached him. And then he got to the travel team and was coached by a guy who was evil. And then he never played again. So why would I want to put him with another coach that could potentially turn him away from something he would love? All I did was try to set a platform for them to be successful and grow on their own. That was my goal.

Q: You had said something before about bringing them into an industry that has a perpetual target on its back. Given the state of the industry now, do you think they have it easier than you did?

Alan: In some respects, they have it a little bit easier because the company has a foundation, so they have a built-in market. But I think it’s more difficult in some respects because now people are very much into supporting personalities, so you have to be very much in the social spotlight through social media platforms and I think that is a lot more difficult. But I think their challenges are different than mine in most respects. 

Q: What about in the future?

Alan: Moving forward, they’ll have a more difficult time. When I got in, even though the business was very traditional, there were areas for me to explore. Now that we’ve set the foundation, they’re going to have to find new areas, new customers, new alternatives, new sources to find revenue. They’re going to have to be more creative than I was.

Q: Alec and Bradley, have you worked outside the family business or is this all you know in terms of the professional field?

Alec: I had other jobs growing up, whether it be Dunkin’ Donuts or a sandwich shop, but professionally, this is all I know.

Bradley: This is my first job ever, and hopefully, my last job ever.

Q: How long have you both been working for the company?

Bradley: I’m coming up on four years.

Alec: Full-time for me about seven years and I worked part-time before that for two years.

New World Churchill
“When you’re coming out with your first cigar, you need to come out swinging.”—Alec Rubin

Q: When you started, Alec, where did your dad start you out?

Alec: Growing up, I worked in the summers in the warehouse. A couple of summers I worked the phones. As I went full time, I started traveling with the reps, started learning logistics, started learning a little bit of everything to see where I fit, and to this day I’ll tell you my job is always evolving, so I still don’t necessarily know where I fit.

Q: So you don’t have one job description?

Alec: In a family business, things come up every single day that you just need to handle. I do a lot with sales, with working on new projects, blending, being down at the factories, a lot of the private label stuff that we do I work on, it’s kind of always changing.

Q: Bradley, did you come in the same route as your brother or did you start differently?

Bradley: It was pretty similar. My father did the same thing where it’s kind of like figure out where you fit. Where you gravitate toward and what you’re good at. When I first came in, it was “You’re a young person, so you must know social media.” So he just kind of threw me in there and I’ve been learning ever since. I started two weeks before an IPCPR. That was nerve-racking. 

Q: What year?

Bradley: 2017. The first day, I had interviews to do at the tradeshow. Didn’t know anything about tobacco really, and they’re asking me about blends and new releases—we had just come out with Black Market Esteli and Prensado Lost Art. Someone gave me a cheat sheet before I had to talk to all these people, but I knew the quickest way I could be effective was to travel because people want to know who we are. So, I went to InterTabac that year [in Dortmund] and I was basically going out for events every month and then as things developed, my role kind of turned into continuing to do social media. Now, it’s a lot of focusing on packaging, art work and the marketing of our product.

Q: When you have brothers in the same family business, sometimes you have one that focuses more on sales and marketing, and the other on craft and raw materials. Is that the case with you two? 

Bradley: I think we both gravitate towards separate things. Alec gravitates more towards the tobacco side. I still want to be involved in the process but I’m more excited about how we’re going to package something and how we’re going to market it. 

Alec: I would agree with Bradley completely. Even though I like to have my hand in the packaging and marketing side, my focus is definitely on the tobacco, and then we’re both pretty involved with sales, we both travel with the reps, we both work with everyone on the road and try to help out in that way.

Q: Tell me about the first time you tried your hand at blending. 

Alec: I was involved with some of the releases like Coyol and Sanctum and some of these things that we did in the past, but we really didn’t start blending until Blind Faith. And that was a really tough process. When you add a lot of flavor you tend to lose strength when you add strength you tend to lose flavor and Bradley wanted this perfect balance in the cigar that was as much strength and as much flavor that we could give to a
cigar without compromising.

Q: Did you go through a lot of prototypes?

Alec: I think we went through a total, with test blends and tweaks, around 38 blends and it took almost nine months for us to complete that blend and it was a rough, tough experience.

Q: Why?

Alec: Because this was our first time and we were not asking for any help from our dad in the process. We were trying to accomplish this on our own. And when you’re coming out with your first cigar, you need to come out swinging. We wanted to make it everything that it could be as our first release. We definitely had a great time doing it and we fought a lot, but we were both super proud of the result.

Q: You and your brother fought, or the three of you?

Alec: Me and Bradley fought a lot. My dad kept his hands out of it. He was like “This is Alec & Bradley. You guys have to figure it out.”

Q: How old were you at the time?

Alec: I was 25. Bradley was 22.

Q: How do you remember the experience, Bradley?

Bradley: Exactly like him. When we sat down and discussed what we want the cigar to be like before we started blending it, we both agreed that we don’t want to put out a cigar that’s necessarily for everyone. We wanted to make sure that we absolutely love it, no matter what people said. 

Alec: We actually broke a lot of blending rules. We were trying to push boundaries in terms of the blending and do something different than what had been in the market previously, whether it was Alec Bradley or any other company.

New World Churchill
“We both agreed that we didn’t want to put out a cigar that’s necessarily for everyone. We wanted to make sure that we absolutely love it.”—Bradley Rubin

Q: How did you break rules with Blind Faith?

Alec: I believe all the filler in Blind Faith is all ligero and maduro, which is not the wisest thing when you’re trying to come up with good combustion, but we fixed that in other ways because we were trying to get the flavor to be everything it could be. Naming it Blind Faith, consumers and retailers had to have blind faith in what we were putting out as our first project.

Q: Alan, when they brought this blend to you, were you smoking with them through the process at all, or did they just give you the finished product to try?

Alan: At the end they presented two blends to me that they were kind of stuck between. And I smoked them, and knew which one that I felt I not only enjoyed, but that the market would accept. They asked for my opinion and I said I’m not giving you my opinion. You need to tell me which one you guys believe is the one to bring to market. You have to know within your heart which one you feel represents your best. And then they did and we were all in agreement.

Q: Did you like it?

Alan: Loved it.

Q: You still smoke it?

Alan: I do. It’s interesting because both Alec and Bradley have very different personalities in how they view things and how they go about things. One of the things they had to learn was how to get along. They do as brothers, but how to get along and respect one another in business. When they said they were fighting, it’s because they both wanted to somewhat be heard and they both had their own opinions, so I said, “While I’m still here, I can mediate this for a while, but you guys have to learn how to get it together because eventually this is going to be yours, so you have to learn how to do that together on your own.” And they did. I had almost nothing to do with any part of that release.

Q: What was the next Alec & Bradley cigar after Blind Faith?

Alec: The Gatekeeper.

Q: When you guys blended that, were you conforming to the Alec Bradley house style? Or was it something completely different?

Alec: The thought was, “Here’s the Alec Bradley style, now let’s do the exact opposite in every way possible.” Let’s put out a completely different type of product. Bradley came to me and said, “I want to do something Dominican because Alec Bradley doesn’t do anything Dominican. Let’s go in that direction.” 

Bradley: The first thing was how do we do something different. And the first answer was do something out of the Dominican Republic with Dominican tobacco. Then it was a question of who will make a cigar with us. I became a fan of Ernesto [Perez-Carrillo’s] cigars when I began exploring other lines. I didn’t know much about him except that I thought he looked really scary and unapproachable and I saw my father talking with him at an event. I said, “You know Ernesto Perez-Carrillo?” and I asked, “Do you think he’d make a cigar for us?”

Q: What did he think about that idea?

Bradley: I think my dad was kind of confused that we wouldn’t make it at Raices Cubanas or one of the Plasencia factories. I wanted to do something different and how cool would it be to do something with one of the legends in our industry? It wasn’t too much later that my father talked to Ernesto about doing it. He said he was in.

Q: We’ll get back to Gatekeeper later. Let me change directions here. Remember the interview that we did with your dad? It was called “Life After Number One,” and it had to do with some of the quality control issues that had arisen after demand skyrocketed for the Prensado when it was our Cigar of the Year. Your dad gave a very candid interview where he admitted there was a problem. What did you learn from all that?

Alec: Our dad had always taught us to deal with integrity and be honest. Those were the two themes growing up. Make sure that whatever you do, you’re honest about it, and always deal with integrity. So, it just confirmed the lessons that he always taught us growing up and we got to see it in action. That was huge. Getting to see him doing the things he always taught us just confirmed what I needed to do in my professional career.

Bradley: I’d make it as simple as possible and say honesty is the best policy. I guess it’s cliché, but when it comes to running a business in our industry where the faces of a company are important, people respond to that. I don’t know how many times while I’ve been traveling, people tell me about “Life After Number One” and how they thought it was so great that our father got in front of an issue with our cigars and was straightforward about the problems. It’s reasons like that that people stick with a brand.

Q: The three of you are going through something right now that’s a first for all of you, being a cigar company in the middle of a pandemic. After a year of Coronavirus, how did you do as a company?

Alan: The cigar industry benefitted. People are now working from home. They don’t necessarily want to be indoors 24 hours a day. If they’re a cigar smoker, they want to sit down and maybe have a cigar outside, try and figure out how to do work and relax. All of a sudden you start to see this momentum pick up. People couldn’t go away on vacations, they didn’t have much form of enjoyment, yet they could get their cigars and have that little vacation. And people who were smoking one a day were then smoking two or three a day because they were home. So the demand on our company was boom-time type of demand.

New World Churchill
The Gatekeeper, the first major release from brothers Alec and Bradley Rubin.

Q: So your 2020 sales were up from 2019?

Alan: Yes.

Q: How much? What percentage?

Alan: Thirty-plus.

Q: Wow! That’s huge. Would you say that 2020 was your biggest year ever?

Alan: In terms of total revenue, yes. In terms of growth, no, because coming off of No. 1 [in 2011] was over 60 percent growth that year. I think that what has come out of this is that our industry has picked up a lot of new consumers. Whenever this may change, we’re still going to retain some of that. The biggest issue we had was getting enough production. The toughest scenario was not being able to fulfill the orders that we had.

Q: You have these new Alec & Bradley brands—Gatekeeper, Kintsugi—how are they selling? Are they starting to outsell some of the core Alec Bradley lines?

Alec: I’d say they’re in the mix. They’re not outselling the best Alec Bradley sellers, not even close.

Q: Which are?

Alec: I’d say Black Market and Magic Toast are our two best-sellers. But Blind Faith, Kintsugi and Gatekeeper are starting to grow, especially when Gatekeeper got No. 7. Huge spike. So, we’re definitely becoming more relevant.

Q: When you saw that Gatekeeper was named the No. 7 cigar for 2020, were you surprised?

Bradley: Immensely. Just like everyone else in the industry, we’re all waiting by the computer, hitting refresh hoping to see our band and logo on that Top 25 list.

Q: When you created Gatekeeper, how did that collaboration come about? 

Alec: I would say it’s a collaboration because it’s not like we went down to Ernesto’s factory and said, “Show us your tobaccos, we’re going to blend this and you’re not going to be a part of it.” We came up with the profile that we were looking for and the tobaccos we were going to use as a collaboration between the three of us, or even the four of us because dad got involved at one point. 

Q: Alan, how did you feel when you saw your kids’ cigar made the Top 25

Alan: To get that kind of recognition and credibility early in their career, the level of pride is hard to even explain. It was really, truly a collaborative effort. It wasn’t as if Ernesto just said, “Here’s four blends, pick one.” And what was interesting was when I smoked the cigar, I said, “This is not an Alec Bradley” in terms of its style. Yet I spoke with someone at Ernesto’s company and he didn’t think this was an EPC. So I found it interesting that they all had a hand, and I was a little bit along for the ride. It took me 10 years for anyone to know that I was even in this business, and in three years, they got Top 10.

Q: I imagine there’s a lot of pressure to not only carve your own path but to also maintain the quality and legacy of your father’s work and his reputation. How do you deal with that?

Bradley: That was the whole reason that I decided to work at Alec Bradley. What my father has done for us as a family, putting Alec’s and my name on the brand in honor of us, that was the most important thing. He’s given so much of his time and energy and life to this business, and if I could do the same for my future children and if I could pass down Alec Bradley if they wanted to join, that’s my ultimate goal. To deal with the pressure I think of it like gambling. Given the chance to run this company I may screw it up, I may lose everything, but I might hit the jackpot. I think I can continue to grow this business. My father has risked it all and has given Alec Bradley a great foundation, now 25 years, so my goal is the next 25 years.

Alec: Growing up, my father was always my hero, so I always wanted to be Alan. Coming into this business I wanted to act like him, I wanted to do things like him, I wanted to essentially be him and be able to step into those shoes. More recently, I realized I will never be him. I will never be able to fill those shoes. The only thing I can do is be me, do things my way with his influence and for Bradley and I to find our own paths in this industry. It was weird coming to the realization I’ll never be my dad, but it also was a very exciting thought when it hit me.

Note: After this article was published in Cigar Aficionado magazine, production of the Gatekeeper brand was moved from Ernesto Perez-Carrillo’s factory in the Dominican Republic to Plasencia in Honduras. Click here for more details.

Alec Bradley Alec Bradley Cigar Distributors Inc.

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