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“I want to start a company selling boxers with pockets,” my soon-to-be business partner Jack Ambrose told me over coffee in June of 2019.

I think some wires in my brain crossed. I was 100% in.

I’m now co-founder and co-CEO of Jambys, a company specializing in those aforementioned (unisex) boxers with pockets, as well as several other highly comfortable variations of what we like to call performance inactivewear that which you wear at home while relaxing, resting, and recharging.

When we started designing the product in June 2019, we were mainly focused on the fabric. It was all we spent time on. It had to be the perfect combination of softness, thickness, and breathability. We landed on a special MicroModal fabric knitted in a French Terry — think plush bathrobe mixed with fancy underwear.

We didn’t have any fundraising or, really, an idea on how to get it. We decided to self-finance a small test launch to see how the product would do out in the wild.

Keeping the test launch simple and local (or so we thought), we didn’t run ads. I photographed six friends in the four samples we had ready four days before launch. A few days before, we used our personal Instagrams and email accounts to ask friends to help spread the word for our “launch.” And then we got lucky. In the first five days, we sold over one thousand boxers. About 10% of those orders shared the same last names as Jack and I, but still. We were so excited!

That moment was great, but the moment I knew we’d made something special was when our friends received the product and started texting us about it. It turns out quite a few of them initially thought boxers with pockets would be a bit of a gimmick. But joke’s on them because they didn’t want to take them off when they put the boxers on!

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Marketing starts at the product level

Right out of college, I worked as an editorial assistant at GQ Magazine. Several years later, I transitioned to Wealthsimple’s marketing team and eventually stepped into freelance writing and photography for small DTC brands and large tech companies.

Jack and I had no product development or business operations experience, but I could write and shoot, and he could hustle to learn about everything else. Both of those skills deeply inform my current work – conceptualizing, writing, and shooting most of the ads we do for Jambys.

In my past work, I was handed a finished product and asked to make it look like something worth buying. With Jambys, we wanted to make sure that the marketing process started at the earliest product development level, which was easy enough for us because, at the time, the whole company was just us two.

Our strategy boiled down to this: figure out how to make your product stand out in the market from the very beginning. Don’t just assume it will just because it’s good quality.

For us, we established a brand point of view that also worked as a design framework. Jambys was going to be for the home and the home only. That structure felt a little bit inhibiting, but once we leaned into it, we found that it made it much easier to create new products that didn’t look or feel like all of the “multi-functional” apparel already out there. We weren’t sexy or sleepy or sleek. We wanted to be fun and make you feel good about what you were doing at home — not guilty or lazy.

The design question was: how would clothes change if they were only for home? The clothes most Americans wear at home were designed for something else, like basketball shorts, sweatpants, or yoga pants.

This led us to ask:

• What do people do at home?
  They mostly sit and lay down, meaning clothes for home needed to not scrunch up or get too tight when sitting.

• What’s the temperature like at home?
  Somewhere between 60 and 80 degrees, choosing a material that worked comfortably with that temperature range was important.

• Would these clothes need to hold up to societal conventions for dressing in public?
  Nope! For the Jambys, we got to create a super unique fabric that was soft, breathable, and stretchy because it didn’t also have to be wearable at happy hour or yoga.

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Building an experience: what does the customer want?

Time at home is important, and Jambys main goal is to make it as enjoyable, comfortable, and fulfilling as it can be. The clothes make up the first part of that goal, and the enriching activities and experiences done while wearing those clothes round out the second.

Even though there are limitless things to do at home, the options can feel overwhelming and paralyzing. So we created Downtime Magazine, an internet magazine (read: blog) filled with interesting reads and recommendations for our customers or non-customers to find something fun and chill to do at home.

Ultimately, the customer (or potential customer) is at the center of every decision made at Jambys. We want to continue building trust and engagement with our brand, and one way we do that is by having a 77-day no-questions-asked guarantee to de-risk trying out our product. 

Listening to our customers and letting their feedback guide and adjust the following steps are another way we build trust. We iterate on our products and ideas until we find the ones that resonate most with our customer base. I know that sounds like the most boring approach ever. But everything else gets easier if we keep it at the top of our minds every day. Jack and I read every review that comes in, and we reply to everyone that’s lower than 5 stars to see what we can learn.

We keep the focus on fun, even though we know there’s currently a bigger audience for gray-on-gray loungewear. And the internet makes that possible. Is there an entire neighborhood that wants to invest in stretchy high-quality loungewear? No. But are there a couple dozen people in every neighborhood who do that we can reach through the internet? Absolutely. The internet allows boutique brands a special kind of proliferation and growth they likely wouldn’t see without it – that of niche interests being shared by a city’s worth of people who all happen to live in different places.

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Risking upfront conversions in favor of long-term customer gain

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There’s so much data available now that it’s tempting to think you’re looking at the complete picture. But the majority of reactions and thoughts about your brand still aren’t being captured.

I read somewhere that tangible marketing number has a negative intangible, which is a good guide. For example, you could have two ads with the same 3% conversion rate — sounds like they have the same effect, right? No way. 

We’ll have to use our intuition to know what the other 97% thought. Some of them may forever think less of your brand because of whatever content was in the ad they saw. Those who bought a product may end up returning it and never coming back because they didn’t feel the ad was honest in its representation of the product. The numbers tell you something, but not everything. We try and run through the website and every ad each week to make sure we’re presenting ourselves the right way.

On the website, we risk upfront conversion because we know a unique experience will strengthen everyone's experience with Jambys. We make jokes and try new things visually and make our CTAs something other than “SHOP NOW.” It might drop the conversion rate a little upfront, but we’re okay with that because of the relationship we create with the customer. 

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Tips for those curious about how to market their brand

Here are five tips for those interested in a unique approach to brand marketing:

1. You don’t have to have your entire vision planned out right away. 

While it’s important to have a baseline concept for your brand and what you want it to be for your customers, allow yourself to take your time in figuring out the details. Let the customer response guide your brand’s direction.

2. Niche is good. 

Avoid attempting to appeal to everyone. If there are a few diehard fans of your product, I guarantee you the internet can help you find a whole lot more. Fill a space that has yet to be filled.

3. Design your product for the specific purpose you want it to have, rather than trying to add a marketing spin after it’s already been created (i.e., the world does not need another pair of normal grey cotton sweatpants marketing themselves as extremely special.)

You’d be surprised at how often this happens. Quality products still need a selling point, and that shouldn’t come after the fact. The earliest DTC brands sold you on reduced prices. The next generation needs to bring something new to the table because the old competitors are online now, too.

4. Ask yourself how you can deepen the customer’s experience of your brand. 

What have they enjoyed that you can expand on? How can you make life more fun for them? Jambys’ answer was to create Downtime Magazine as a way to keep customers engaged and entertained with plenty of suggestions of how to relax in their new house clothes. I found the word “community” to be too abstract, so we just thought: what do people do in Jambys that we could make a little better?

5. Take chances. 

Try new marketing approaches. See how they land with your customers. Ask them for feedback and use it. Just because a customer doesn’t buy immediately doesn’t mean your ad didn’t make a positive impression on them. The next time they think about comfy loungewear, they might remember the brand that made them laugh for the first time in a while.

Note: this is a heck of a lot easier if you don’t go exclusively through an ad agency in your earliest days. No hate on agencies; some of them make much better work than we ever could on our own. But when you’re first starting, you’ll move 10x faster working on your own or with a trusted freelancer to shape your brand and first ads. And when you do bring on others, you can further develop and polish those ideas that you know work.