What better way to celebrate the release of WooCommerce Subscriptions 2.0 than with a subscriptions-based entrepreneur interview?

John Haji and the team at Gentleman’s Box have spent the last couple of years building a successful subscription box business for today’s gentleman.

John has tirelessly pursued his vision of a carefully curated Gentleman’s Box since first conceiving the idea in 2013. In the process he’s built an impressive list of brand partners featured in each month’s box, as well as a partnership with GQ Magazine.

Read on to learn more about the Gentleman’s Box business, their inspiration, advice, and plans for the future.

Kirby: Could you start by telling me the story of how the Gentleman’s Box came to be?

John: Sure. Prior to the Gentleman’s Box, I worked in the automotive business for roughly nine years.

A friend of mine had been subscribed to the infamous Birchbox for women. She was showing it to me one day—ranting and raving—and I just really loved the concept of receiving a package on a monthly basis with all these great products. Products of discovery, so that you can learn about new brands and new things to use.

I was really interested in fashion, so I kind of built off that concept and idea to form the Gentleman’s Box. Rather than delivering samples on a monthly basis that essentially give you a one-or-two time use, I thought about twisting that concept and putting in more tangible items of greater value.

I developed that idea while working at the dealership for maybe my last year. I did a lot of cold calling with vendors and built up a portfolio to get myself ready to leave the dealership and start full-time.

Kirby: So you started it in 2013?

John: I developed the idea in 2013 and worked on it for almost a year. It was October of 2014 that I left the dealership and our official launch was November 1st of 2014.

Kirby: What should a new subscriber expect to receive in a typical Gentleman’s Box?

John: We find typically that subscribers expect at least two essentials that they can get great use out of, and that’s why we always put a pair of socks in. We do that every month, because we know that every gentleman can use a plethora of different styled socks and designs.

Then we find that a lot of our subscribers like the idea of getting a tie. The tie and the socks alone exceed the value of the $25 they are actually spending. Everything else, whether it’s a pocket square or a grooming product, maybe a lapel, they just add to the value of the box.

At the same time, we like to provide a variety of items that you can incorporate into your normal gentleman’s lifestyle. So there will be months where we offer items like whisky stones, passport cases and stuff like that. We try to encompass the entire lifestyle of being a gentleman.

Kirby: What has been your favourite monthly theme so far?

John: I guess my favourite box, for multiple reasons, would be the September box (which is the one we just finished wrapping up).

The theme around that was the Suit and Tie. Most people will get that we honoured Justin Timberlake that month. In many interviews and shots of him you’ll see that he’s wearing a black bow tie. During one concert he said on stage that every gentleman should own a bow tie. That’s one of the reasons why we put in a bow tie. Then the pocket square, the lapel, and the laces we put in really just complemented it, in terms of the style. It was a good combination.

It was also our first month redesigning the box. We went from having a much larger box that carried the GQ magazine in it to a much smaller, sleek, slim design. We took the magazine out. Rather than it coming in the box every month it now gets shipped directly to the subscriber. At the beginning of the month, they receive a magazine and it acts as a reminder that their Gentleman’s Box is on the way. It also gives them all of the month to enjoy the content of the magazine.

Launching that in September really resonated well with a lot of our subscribers and we got a lot of positive feedback.

Kirby: How did you find the suppliers for the products that go into the boxes?

John: For the majority of the year prior to launching the box, day in day out, I was cold calling and emailing vendors to build a portfolio. That was about establishing relationships early on.

A lot of the brands that we work with have given suggestions of other brands, and then you come across a lot of brands through social media, the web and talking and working with other people.

We’ve built quite a portfolio of brands that we work with. Many of them offer a line of products. So maybe we’ll use a tie one month and then reach back out to them three months later and say: “The tie was a success, let’s work on a pocket square.” We don’t have too much trouble figuring out which products to use because we have such a large portfolio of brands that we work with.

Kirby: How does the partnership with GQ Magazine work?

John: When we first started out, my business partner and I were at his house and we had this little box that we had fashioned with tape and a piece of cardboard. We were envisioning the idea of this box and on his end table was a magazine. It was GQ.

I said to myself: “Well GQ stands for Gentlemen’s Quarterly, and we’re the Gentleman’s Box. How cool would it be if at the same time as receiving all these great products they can try and experience, subscribers can also read up on the latest trends in fashion?”

So I went online and searched the company’s profile. I think I emailed 30-40 people from GQ magazine. One person happened to be in the Detroit satellite office, which is about 20 minutes away from where we live. They invited us out.

We brought over the box that we had fashioned with tape and we pitched the idea of featuring the magazine in the box. At first they were hesitant. They passed it on to their HQ in New York who were like: “Oh no, we don’t think it’s a good fit.” They were concerned about whether we were going to hit our projections.

But we were persistent about it. “We’re going to hit the numbers, we’re going to hit the thousands.” I think this was in October or November of 2014 and we were like: “We’re sure to hit 500 by the end of the year.” Eventually they took a gamble.

We met with them in January in 2015 and worked out the partnership to feature the magazine in the box every month. Initially they wanted to mail it out to all the subscribers separately, but we just thought that it would be better value putting it in the box. Slowly we found out that the subscribers love receiving the magazine early on in the month so that they can enjoy it for the entire month rather than just half the month.

It’s been a great partnership.

Kirby: How did you find your first customers? How were you reaching people in the beginning?

John: In the beginning it was word of mouth. When we first started off, a lot of our subscribers were from the midwest and that’s where we’re from. So a lot of it was friends and family.

We branched out through social media shortly after that to promote our brand through Instagram, with other complementary social media Instagram pages, like High Fashion Men and Men’s Fashion Post. We also reach out to a lot of bloggers and bloggers reach out to us.

We have ties to some professional athletes that we send boxes to. And now we’re slowly trying to get into more Facebook advertising and go more indepth with other social media platforms.

We’ve been in holiday gift guides with some of our local news stations and newspapers, and across the nation.

Kirby: When you started out, did you fund it yourself or did you receive some investment?

John: No we’re bootstrapped. My business partner and I funded it in the beginning and we’ve been bootstrapped until today.

Kirby: How many people are on the team now?

John: There are about five people. One of the people that we work with, he’s like our head of marketing and IT. He owns his own IT firm, it’s called Element Five Digital. He’s got a team of his own that he works with as well and essentially you can count them as being his resource in helping us. But more directly in the company, there are about five of us.

Kirby: Can you just tell me about your September partnership with NoMore.org and the Joyful Heart Foundation?

John: I worked with a brand in December, a tie company called Knots Apparel. They’ve lined themselves up with Water for Waslala in Africa. I really loved what they were doing and thought about aligning ourselves with a cause.

With everything you see going on in the NFL and with the football season under play right now, we thought: “What better cause to support?”

The fight against domestic violence and sexual assault fits well with being a gentleman. Obviously a gentleman would never engage himself in any type of domestic violence or sexual assault. So it really sits well with what we stand for.

We reached out to the NoMore organisation. They clearly loved what we were doing and they work with all types of domestic violence causes. So whether it’s the Joyful Heart Foundation or it’s a local charity or foundation within certain states, they encompass all of the organisations in the fight against domestic violence and sexual assault. The Joyful Heart association is really reputable so we reached out to them and they also loved the idea. We lined ourselves up and donated a portion of our profits for the month of September to them.

Kirby: Can you tell me a little bit about your experience using the WooCommerce Subscriptions software to power the boxes?

John: I won’t say it’s been absolutely perfect because obviously when we first started off it was about learning the system and really building it to fit our business.

But it’s really been great, it has everything that we need, we’re able to build out everything the way we want it to be.

Kirby: Early on, did you make any mistakes using the software that you’d like to share with other people so that they can avoid making those same mistakes?

John: When we first started out it was figuring out how to re-bill subscriptions. That was something we had to build on our own to fit our model. There were some annual subscriptions that needed to be coded correctly to allow them to renew. It wasn’t necessarily coded properly. We found there were a handful of orders that didn’t renew, so we had customers that didn’t receive their boxes.

I think the best advice I can give is to make sure that everything is coded properly and tested properly so that you know everything is going to renew with no issues. It’s going to be a learning curve and you’re going to have your ups and downs. It was one of those things that we’ve learned from and overcome.

Kirby: What has been the biggest challenge you’ve faced so far?

John: I think it’s twofold.

Being able to curate a box that will appeal to a majority of the subscribers. You’re not going to be able to please everybody and some people will love it for three or four months and then say: “You know, nothing is wrong with the products in the box, it’s just that the pricing is too high,” or: “I’m done with getting ties and socks, but I love the concept.” And so forth. Being able to provide the variety of items and curate it to really appeal to the masses is challenging.

The second challenge is getting that mass. It is marketing and advertising it well enough to attract as many people as you possibly can.

Kirby: Do you have any advice for other entrepreneurs?

John: I think being persistent is very important in this business. Working day in day out. I wasn’t even a business major in college, this is my first business venture. But you realise that it takes the sacrifice of a lot of your time to do the research and perfect the business.

Then it’s reaching out to as many people as you possibly can and to follow up with them. Never give up. Persuade and negotiate with these people to believe in your brand and believe in what you are building.

Stay persistent, keep yourself motivated and put in the time, because the time will pay off.

Kirby: Last question, what are your plans for the future at Gentleman’s Box?

John: Growing the subscriber base.

One of the things that we talked about last week was bringing more attention to the Groomsmen Gifts. We also intend to open an online store in mid-to-end of October to carry a lot of the products that we feature in our box, as well as other great products from the brands that we work with.

Down the line, I think we would love to customise boxes to the subscriber. They’ll be able to go online and fill out a member profile that really goes into depth of what they like from a grooming standpoint. For instance not everybody has hair, there are some people who are bald. So, with the hair gel, obviously they’ll get no use out of that.

So being able to create a member profile where they can say: “I really love the socks, not so much into bow ties, not so much into skinny ties.” To figure out what a person likes and be able to customise the box to their liking every month is something that we really want to get into and build out.

You can tell that John is really serious about building the Gentleman’s Box business and delivering value to his subscribers. I really admire how persistent he was in finding new brands to partner with and in establishing the partnership with GQ Magazine.

It’ll be great to see how he and the team go at building out their online store, more strongly promoting their Groomsmen’s Gifts (which I think are a great idea!), and adding the ability to customize their box offerings to individual subscribers.