We were lucky to catch up with Whitney & Calvin Trapp recently and have shared our conversation below.
Alright, Whitney & Calvin 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?
After determining that our mobile business would be out of a trailer, the hunt began for the size that would work best for us. During covid, there seemed to be a limited number of trailers available for purchase. Calvin lucked up on a brand new one on Facebook marketplace from a guy who was unable to start a business of his own. From there we mapped out interior measurements and decided on the aesthetics for the trailer. Calvin and I wanted the trailer to bring people in and show an array of cigar selections and provided education if needed. We wanted our trailer to be intriguing and welcoming. The interior build was a project within itself since we decided to do the work ourselves to save money and make it a labor of love. Within 5 months, we accomplished the trailer build, business plan, designing a website, creating a social media presence, obtaining licensing, further cigar education for ourselves, etc. Loads of trial and error with it being our first business but it was all worth it.

As always, we appreciate you sharing your insights and we’ve got a few more questions for you, but before we get to all of that can you take a minute to introduce yourself and give our readers some of your back background and context?
A few years ago, Calvin and his friends developed a passion for cigars. Like most, it was a hobby picked up during covid. Since no one else in our area was doing the mobile cigar business it was an unique endeavor. We’re a mobile cigar bar offering premium cigars for all events. We have 2 portable humidors on our trailer and an outdoor lounge setup, whenever needed. We customize booking packages to suit any event. After only knowing a few other mobile cigar businesses in nearby states, we researched and compared business models to see what would work for us. We wanted our business to stand out. Calvin and I work the business together as a husband-and-wife team. We want the world to know that when you work with us, we will always bring you the ultimate cigar experience. Along with cigars, we sell cigar accessories and custom-made cigar box ashtrays.

What’s been the most effective strategy for growing your clientele?
The most effective strategy for us has been constant, constant promoting. We both carry around business cards to hand out or leave in businesses. We have a website, Facebook and Instagram showcasing events we’ve worked and products we sell. Recently we added QR codes to the sides of our trailer to make it easier for people to reach us even while trying to take pictures going down the road.
What’s worked well for you in terms of a source for new clients?
Word of mouth has been hands down, the best source for new clients. We’ve even gained quite a few new and repeat clients in our neighborhood. The conversations usually start out with “a friend of mine saw you guys at an event and sent us a picture of the trailer” … or “a friend of mine bought cigars from you and I wanted to buy some too”. It’s kept us busy even in between our bookings. We’re so appreciative of that. People hear great things about us and want to work with us too.
Contact Info:
- Website: www.trappdindasmoke.com
- Instagram: TrappdIndasmoke
- Facebook: Trapp’d In Da Smoke
Image Credits
Calvin & Whitney Ariel Enid Photography

