Heather Phillips - the future CEO of one of the country’s most popular lines of premium, hand rolled flavored cigars - had just worked her way from cocktail waitress to assistant manager at a Naples, Florida cigar bar called Heaven Cigar Bar. The hotspot was riding the wave of the ‘90s cigar explosion and became a sort of stogie Mecca for southwestern Florida. “It was a really popular place, very busy all the time,” recalls Phillips. “The money was great, the cigar boom was just getting started, and I had the chance to learn all about cigars.” Heather made numerous contacts and, during her tenure there, served drinks and smokes to Floridian cigar royalty with last names like Toraño and Perdomo. Besides featuring over 300 brands of beer, wines up to $85/glass, and the finest cigars from the world over, the bar also showcased a small run of vanilla-flavored cigars that the Ontario-born Phillips also had a hand in selling and distributing to other retailers. But Heaven Cigar Bar’s moniker proved ironic when the decidedly unsaintly dealings of the bar’s owner, financier David Mobley, came to the attention of the press, Federal authorities, and the cigar world at large.
Besides enjoying the occasional fine cigar, Mobley - it turns out - enjoyed lots of other popular hobbies including wire fraud, money laundering, and tax evasion, all of which he would eventually plead guilty to in 2001. “I remember getting a call from a friend that the Feds were raiding Mobley’s offices a few miles away from the bar - like you see on TV, with guys in FBI jackets piling out of trucks,” recalls Phillips, and then with a smile adding: “I remember I had a girlfriend pick me up to go check it out - I had to go and see if it was real. I was so scared. I was afraid they were going to arrest me for something. So, as we drove by his offices, I was crouched in the backseat of her car so no one could see me, and just peered out the back seat window as we drove by. The whole top floor was lit up like a Christmas tree with FBI guys running all over the place.”
No authorities would come to arrest Heather, but Mobley’s assets were seized and Heather’s last paycheck bounced like a jumping bean in the sun. Shortly after the raids on Mobley’s office, but before Heaven had its gates unceremoniously closed via court order, co-workers began to think it might be time to just close shop and walk away from the whole mess. With an owner dancing a precarious legal rumba, walking away wasn’t exactly an unappealing option. But Heather’s mindset at the time was decidedly different. “I felt compelled not to give up something I had put so much time into. And the fact of the matter is that I really enjoyed it. The cigar business is fun. So, when I finally got the call that the bar was shut down and I was officially out of a job - that was that day I decided I wanted to produce a line of cigars and I wanted to do it under the Heaven name.”
With her own savings, a few active remaining accounts for the bar’s line of vanilla cigars, and without even a day’s worth of formal business training, Phillips started to build what would become one of the most prevalent names in flavored smokes.
In order to legally continue using “Heaven” (as well as the “Heavenly” name for the parent company) as a cigar brand, Phillips was forced to pay some of Mobley’s outstanding debts and ended up taking a loan from her mother to secure the Heaven trademark in her name. So, let it never be said that Heather Phillips built Heaven up from nothing: she actually started her business from much less than nothing. While it might have been cheaper to set up shop under a whole new name, Phillips - who often mentions a belief in a vague cosmic destiny when recounting her personal story - knew that she had come to be associated with Heaven Cigars for a reason: “When I was a kid I used to have a friend and we used to sit and talk about what we would do when we got older and - I’m not going to lie and say it was cigars - but I said that one day I’m going to own a store and call it ‘Heather’s Heaven.’ Maybe I thought it would be lingerie or something.”
Starting out with the original Heavenly Vanilla variety - soon to followed by the roster’s first of many Heavenly expansions including Cupid’s Cherry Cream, Angel’s Spice Cinnamon, and Chocolate Thunder - the Heavenly cigar company was born in a tiny office with a $20 phone from Wal-Mart and an inventory room that moonlighted as a utility closet. Eventually, Phillips worked out an attractive deal on office and shipping space in a facility that was owned by “religious” people who, apparently, liked the idea of a business named “Heaven.”
It was also around this time that Phillips took her first trip to the Dominican Republic to meet with Heaven’s cigar maker, a poor little run-down factory that was owed thousands of dollars worth of unpaid invoices, previously undiscovered when Phillips bought out her partner. (The deal proved to be a great move, as the factory continues to produce all of Heaven’s cigars to this day).
Once the trademarks were secured and the financial dust had started to settle, Heather went to her first cigar show to introduce the new company. The reception wasn’t open arms for the future industry icon. “We were new. I even went to the show with unbanded cigars, because the bands weren’t even done yet. A lot of people didn’t want to do business with us because they heard what happened to Heaven, the bar. I remember different companies coming around with shock and awe that I was even there.” Then in the same breath, and without a hint of smugness she adds “but some of those people are some of my best clients today.”
With salesmanship and an ever-growing roster of products, Heaven assured an initial foothold in the market. Heather then introduced one of the modern cigar game’s most cherished marketing tools - and one the company will forever be associated with - Heaven’s Angels. The Angels (with Heather counted among them) are a group of young women who can be found roaming events where Heaven is being promoted and where men have eyes. Often adorned prosthetic wings and - especially in the case of their recent promotional calendar featuring completely nude angels with the exception of body paint - little else, the angels have become an institution. There had always been “angels” associated with Heaven - even during the Naples cigar bar days. But they were little more than young pretty faces selling cigars, which while always appreciated, are a fairly ubiquitous sight in this male-dominated industry. But it wasn’t until some years later Phillips decided to give her angels wings found at a lingerie store - a small accessory, but a successful branding that could turn any million-dollar ad agency green. The newly feathered beauties made a splash with a handful of angels at the industry’s big annual trade show in Tampa Bay in 2001. Seeing the initial result, she decided to bring in a roster of 10 winged beauties to the 2002 conference in Vegas where Phillips remembers being “mobbed with people wanting to take pictures and getting a lot of attention. It was great from a marketing perspective. We wrote a lot of orders.”
The angels are mostly culled from Phillips’ group of personal friends, but as Heaven forges into foreign markets, she’s had to seek out pairs of hired wings with command of foreign tongues to mix in with her regulars. But these angels are no mere winged eye candy, “yes, these girls are attractive. But it’s also about demeanor,” Phillips adds proudly. “These girls are sharp, incredibly social, and they’re also very educated in the product.” In addition to promotional events, the angels are also hard at work in the virtual realm as featured “Angels of the Month,” on the company’s web page: www.heavencigar.com.
Throughout our conversation, Phillips mentions that with all the pangs of launching Heaven against all odds, she kept at it for a feeling of external destiny. We can leave it up to theologians and philosophers to debate if those little voices that guide us all come from inside or from out, but as Phillips would discover - in a Shakespearesque twist of events, and completely unknown to her - the cigar biz was in her genes. A few years ago, Phillips had returned to Canada for a grandmother’s funeral. At a family gathering everyone was catching up on their lives, Phillips admits that, at the time, she felt “a little silly” mentioning how this farmer’s daughter had made her way into the cigar business. After she returned home she received an e-mail from a distant cousin who also attended the family gathering, had noticed Phillips’ awkwardness in talking about her line of work, and felt that there was something that she should know. Phillips’ great great grandfather Louis Sievert was a tobacconist. “It’s in your blood,” her cousin said. Louis Sievert came over from Germany without anything. And like his great-great granddaughter would do a century later, built his business by himself from the ground up. At the time of his death in 1918, Louis Sievert had eight tobacco shops and was the oldest and most respected tobacconist in Toronto.
Currently, Phillips is hard at work pushing Heaven into the European market, which has yielded some early successes, including breaking into the Deutschland of her great great grandfather’s birth. While some may call that circle of events destiny, others might see it merely the twists and turns of a path lit by determination and flavored smoke. Whatever it was, the thing we can be sure of is that, with a vision and a confidence that may or may not have origins in the mystical, Heather Phillips has built her own little kingdom of Heaven.