1. What’s the quick origin story of your brand, and what makes your product or positioning genuinely different from other options in your niche?

Brad Jackson: Other cigar manufacturers attempt to sell you a specific lifestyle. But at After Action Cigars, we sell you a moment you actually earn.
I started AAC with my time spent in the operations field, watching premium chocolates & cigars get packaged up to sell to people for their desire to appear as something that they were not. This upset me because in the military the term “after action review” is used to describe the process of taking stock at the end of a mission. Reflecting on what you have done, where you have been and knowing what to do next, is how you gain clarity through hard work and effort. I have kept this as a part of me.
So, the brand After Action Cigars is built around the concept of completion and not aspiration. When you have gone through and have succeeded at something and then you celebrate that success by lighting a cigar. The reason our customers buy cigars from us is completely different than other retailers. It’s about the journey and the reward after completing it. The separation of us from the rest of the industry is not only our method of doing business with tobacco companies. We deal directly with manufacturers and negotiate all conditions, including price and terms, rather than relying on standard terms offered by every other retailer.
One of our renegotiated long-term contracts with one manufacturer in 2025 resulted in an overall 18% reduction in packaging cost, along with a net 45-day payment term. This contract has allowed us to operate our business with a surplus and we have passed that savings on to our customers. We do not depend on a single source of traffic. I have watched too many business owners invest heavily into one source and lose it all within a matter of hours. We operate an owned email program and a fully integrated organic search marketing strategy, along with in-store foot traffic, in order to avoid having a single source of revenue.

2. Since launch, what have been the 1-2 real turning points for your brand-specific decisions, pivots, or experiments that noticeably changed your growth or profitability-and what did you learn from them?

Brad Jackson: The first significant change was not related to our product. It was related to cash flow. As with most new operators, I accepted the supply terms without questioning how they impacted my company financially. That is, until I studied my financials and realized I had a problem.
The amount of money going to packaging was weakening my margins at a rate that I could not prove to be sustainable. So, I picked up the phone and called my supplier. A single phone call resulted in a new long-term agreement. We negotiated an 18% reduction in packaging costs for the year and changed our payment terms from net-30 to net-45, freeing up cash. The cash that this freed up was directly added to our inventory. This was the first time in several months that our margins stopped eroding.
The second turning point was a more difficult lesson, as it was learned by observing my friend lose. He built his business solely through Facebook traffic, and it was working until the day his account was hacked and all revenue coming from Facebook was stopped. That same week, I went home and audited all traffic sources providing revenue and discovered we were 80% dependent upon one source. That level of concentration risk was unacceptable to me.
So, I changed my traffic strategy to include owned email, organic search, and foot traffic from stores, so that no one source could take us down overnight. The takeaway from both examples is that every supplier term, every platform and every supplier relationship is an opportunity for negotiation. Most business owners simply never ask.

3. Which 2-3 channels drive most of your revenue right now (for example SEO, paid social, email, marketplaces, influencers), and what have you learned about making those channels work in your category?

Brad Jackson: I made my first serious mistake as an operator with the launch of AAC by trying to diversify on too many platforms at once. I had paid social media, email marketing and organic search all going at once, without making a real effort into any one of them. None of the platforms were going to produce any serious results because I hadn’t put in the time and money into them to make it happen. So while I was busy on all three fronts, I actually wasn’t making a real effort on any of them.
We had to take a step back and focus on three channels: email, organic search and physical store. Email has been our most consistent revenue producer and the revenue generated from email marketing is so great that it dwarfs the money spent on acquiring new customers through advertising. Once customers join our email list, they know the brand and can purchase without needing any additional push or offering them discounts. Our average open rates are over 40% because we built the list properly by doing in store conversations and earned opt ins instead of taking shortcuts to build the list.
Organic search is a slower approach but it produces better results than paid traffic month after month, and now after 8 months of putting together content based on the real keywords our customers actually search for, we now have that content working for us every day without spending another dollar to get it published.
The third option of driving foot traffic into stores adds value that no digital platform can provide. A brick and mortar store is where the real data lives when it comes to understanding your customers. When I look at my sales reports, I see how many pieces of each product are being sold, but when I am physically standing in a store with customers in front of me, I can ask them the question of “Why are you buying that?” That question, and many more just like it, have resulted in more product decisions than any analytics tool we have ever used.
This lesson is applicable, regardless of the industry or category you are in, and if you want to utilize a channel correctly, you need to invest the necessary time and effort into that channel, before considering adding any additional ones.

4. How are you thinking about search in 2026 – Google, AI assistants like ChatGPT, and other discovery platforms? What, if anything, have you changed in your content or site to stay visible as AI search grows?

Brad Jackson: Search in 2026 looks nothing like it did three years ago. That shift caught a lot of operators off guard, and I will be honest, it caught me too. When AI assistants started pulling answers directly from search results instead of sending traffic to websites, our organic click-through rates dropped in Q1 of 2025. We were still ranking well on Google. We just were not getting the visits we used to get from those same rankings. The problem was that our content was written to rank, not to be quoted or cited.
So, we made one specific change. We stopped writing content that chased keywords and started writing content that answered real questions in plain, direct language. We wrote the kind of answers a knowledgeable store employee would give someone standing right in front of them. The results showed up fast. Roughly 30% of our new email subscribers in 2025 said they found us through an AI recommendation and not through a Google search or paid social. ChatGPT and Perplexity were pointing people our way because our content gave them something worth quoting.
We reorganized our product pages and buying guides so the most useful information sits in clear, short sentences near the top of each page. AI tools pull from content that is easy to read and well-organized. Hiding your best information inside long paragraphs will cost you traffic in ways you will not even notice until it is already gone. Most operators are still building for a version of search that no longer exists.

5. What do you do to turn first‑time buyers into repeat customers and advocates? Are there specific experiences, content, or community touches that work especially well for you?

Brad Jackson: Most brands spend everything getting the first sale and almost nothing keeping it. That mistake cost me months of growth I did not need to lose. The fix started right after checkout. Instead of a generic order confirmation, we send a personal message within 24 hours that ties the purchase back to the idea of an earned moment. The message ends with one question. We ask what they were celebrating.
Customers who replied to that email bought again at a rate roughly 60% higher than those who did not. That one question did more for our retention than any loyalty program we ever tested. The in-store experience is the second piece. You see, the store is not just a place to sell cigars. It is where customers tell us things they would never type into a survey. They tell us what they want, what they miss and what they expect from us next. That feedback has shaped more product decisions than any analytics tool we use.
We also built a loyal following through email rather than social media. Every month we send a genuine letter about what we are working on, what we are learning and what is coming next. Our unsubscribe rate sits below two percent because people actually read it. Repeat customers come from moments that make someone feel known.

6. If you had to write a short playbook for an ecommerce founder one stage behind you, what would you double down on over the next 12 months – and what would you stop doing entirely?

Brad Jackson: Many founders in their early stages of building a startup are overwhelmed with responsibilities, and that was definitely true for me as well; however, by trying to handle everything on my own, I wasted approximately 6 months of runway that I should have had available to continue building my business. Clearly, the most important area of focus for me would be to create an email list of customers. Your email list is the only true asset in your business because, once established, you own it forever. So, you need to treat it as the most valuable asset your company has. While we achieved a 40% open rate and were able to do so without sending more emails, we were able to achieve these results by carefully selecting who we added to the email list at the time of signup.

Another very important area of focus would be the relationships that you develop with your suppliers or vendors. Unfortunately, many founders overlook the potential for their vendors and instead treat their vendor relationships like a transactional relationship and fail to take advantage of the benefits that they can gain from having a strong partnership with their supplier. At After Action Cigars, we were able to renegotiate our supplier agreement to reduce our packaging costs by 18% over the previous year and added net-45 payment terms. The negotiations with our supplier generated a greater improvement to our profit margins than the three months of marketing expenditures had generated.
In summary, the main keys to success in your business are as follows: Own your relationships with your customers, protect your margins and don’t try to add things to your business until the things you’re currently doing are already successful.